Methods for treating keratin substances

Abstract

This invention relates to a method for treating keratinous substances, comprising the following steps (I) and (II) in sequence. Step (I): applying a cleaning agent composition (A) to the keratinous substance, wherein the cleaning agent composition (A) contains an internal olefin sulfonic acid or its salt (a) obtained by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5. Step (II): applying a conditioning agent composition (B) containing a cationic surfactant (b) to the keratinous substance.

Description

Technical Field

[0001] This invention relates to a method for processing keratin. Prior Technology

[0002] Internal olefin sulfonates are known as anionic surfactants, possessing various carbon numbers. Because of their excellent performance as anionic surfactants, internal olefin sulfonates are used in cleansing compositions for keratinous substances such as skin and hair.

[0003] For example, Japanese Patent Application Publication No. 2015-27975 (Patent Document 1) discloses a skin or hair cleanser composition containing an internal olefin sulfonate with a carbon number of 12 to 24 and a cationic polymer or an amphoteric polymer, which can impart good foam persistence and rinsing properties, combability during hair rinsing, softness of hair after rinsing and towel drying, and a moisturizing feeling on the skin. Japanese Patent Application Publication No. 2015-178467 (Patent Document 2) discloses a composition that can be used as a cleaning product, which contains a mixture of sulfonates and at least one foaming enhancer or foaming agent, and has good foaming properties and a good skin feel after use. The sulfonate mixture contains an internal olefin sulfonate having 16 carbon atoms and an internal olefin sulfonate having 18 carbon atoms in a specific mass ratio. International Publication No. 2017 / 098637 (Patent Document 3) discloses a surfactant composition containing a specific amount of an internal olefin sulfonate having 16 to 18 carbon atoms, a specific amount of an α-olefin sulfonic acid having 12 to 14 carbon atoms, and water. This surfactant composition contains a high concentration of an internal olefin sulfonate having 16 to 18 carbon atoms, which can exhibit excellent foaming and cleaning properties, and can ensure good shelf life and flowability. Summary of the Invention

[0004] This invention relates to the following. [1] A method for treating keratinous material, comprising the following steps (I) and (II) in sequence: Step (I): Applying the cleaning agent composition (A) to a keratin substance, wherein the cleaning agent composition (A) contains an internal olefin sulfonic acid or its salt (a) obtained by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5; Step (II): Applying the conditioning composition (B) containing the cationic surfactant (b) to the above-mentioned keratin substance. [2] A cosmetic kit for treating keratin substances includes a cleansing composition (A) and a conditioning composition (B) containing a cationic surfactant (b), wherein the cleansing composition (A) contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 or more and 4.5 or less. [3] A composition for treating keratin material, which is applied to keratin material before a conditioning composition (B) containing a cationic surfactant (b), and contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 or more and 4.5 or less. Implementation

[0005] Patent Document 1 discloses that if a cationic polymer or an amphoteric polymer is formulated into a cleansing composition for skin or hair, in addition to the basic cleansing properties, it can also impart a pleasant feel to the skin or hair. However, when using only the cleansing composition, there is room for improvement in imparting sufficient conditioning effects to keratinous substances such as skin and hair, and in making those conditioning effects last. For example, regarding hair, by applying a conditioning treatment to washed hair, one can achieve improved smoothness and softness during rinsing, reduced tangling during rinsing, and neater hair after drying. Furthermore, from the perspective of shortening hair care time, it is also desirable to improve the drying speed of washed hair. However, even with conditioning treatments to impart these effects to hair washed with the previous detergent composition, there is a problem that the conditioning effect is lost if the hair is washed again subsequently.

[0006] The objective of this invention is to provide a treatment method for keratin substances such as skin and hair, which can impart sufficient conditioning effects to the treated keratin substances, especially improving the lubricity and softness of the hair during rinsing, the non-tangling during rinsing, the drying speed, and the neatness of the hair after drying, and thus the conditioning effect is also excellent in its longevity.

[0007] The inventors have discovered that a method for treating keratinous substances comprising the following steps in sequence can solve the above-mentioned problems: applying a cleaning agent composition containing a specific internal olefin sulfonic acid or its salt to the keratinous substance; and applying a conditioning agent composition containing a cationic surfactant to the keratinous substance.

[0008] According to the present invention, a method for treating keratin substances is provided, which imparts sufficient conditioning effects to the treated keratin substances, especially improving the lubricity and softness of the hair during rinsing, the non-tangling during rinsing, the drying speed, and the neatness of the hair after drying, thereby also providing excellent long-lasting conditioning effects.

[0009] <Definition> In this invention, "containing ingredient X" is considered to have the same meaning as "blended with ingredient X". In this invention, "keratin material" includes, for example, skin, hair, or nails. Keratin material that is the target of the processing method of this invention is preferably skin or hair, and more preferably hair. In this invention, "conditioning effect" refers to the conditioning effect of keratin substances after washing with the detergent composition. For example, when the keratin substance is hair, the conditioning effect on hair refers to the effect of improving the lubricity and softness of the hair during rinsing, reducing tangling during rinsing, improving drying speed, and enhancing the neatness of the hair after drying. Furthermore, "persistence of conditioning effect" means that even if the keratin substance treated with the method of this invention is further washed, the above-mentioned conditioning effect is not lost and continues. Moreover, in the following description, the above-mentioned effects of this invention will also be collectively referred to as "conditioning effect and its persistence (enhancing effect)".

[0010] Methods for treating keratinous substances The keratin material treatment method of the present invention comprises the following steps (I) and (II) in sequence. Hereinafter, the keratin material treatment method of the present invention will be referred to simply as "the treatment method of the present invention". Step (I): Applying the cleaning agent composition (A) to a keratin substance, wherein the cleaning agent composition (A) contains an internal olefin sulfonic acid or its salt (a) obtained by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5. Step (II): Applying the conditioning composition (B) containing the cationic surfactant (b) to the above-mentioned keratin substance. The processing method of the present invention, by having the above-described structure, imparts a sufficient conditioning effect to the treated keratin material, improves the lubricity and softness of the hair during rinsing after washing, and improves the non-tangling during rinsing, drying speed, and neatness of the hair after drying, thereby also having excellent long-lasting conditioning effect.

[0011] The reason for achieving the above-mentioned effects by means of the processing method of the present invention is not clear, but it is speculated as follows. The internal olefin sulfonic acid or its salt (a) used in this invention (hereinafter also referred to as "component (a)") is obtained by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5. The detergent composition (A) containing component (a) exhibits excellent cleaning properties. If the detergent composition (A) is applied to keratinous material in step (I) for cleaning, a cleaning effect is achieved, while component (a) remains on the surface of the keratinous material. Subsequently, if a conditioning composition (B) containing a cationic surfactant (b) (hereinafter also referred to as "component (b)") is applied to the aforementioned keratinous material in step (II), component (a) present on the surface of the keratinous material interacts ionicly with component (b) in the conditioning composition (B) to form a complex, which remains on the surface of the keratinous material. Since this complex is a readily hydrated gel, excellent conditioning effects can be observed in this invention through the formation of this complex.

[0012] <Step (I)> In step (I), a cleaning composition (A) is applied to a keratinous substance. This cleaning composition (A) contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5. The cleaning composition (A), by containing component (a), exhibits excellent cleaning properties. Furthermore, after applying the cleaning composition (A) to the keratinous substance in step (I), it is then fed into step (II), whereby the complex formed by components (a) and (b) adsorbs onto the surface of the keratinous substance, imparting a sufficient conditioning effect and its persistence to the treated keratinous substance.

[0013] (Cleaning composition (A)) The cleaning composition (A) used in step (I) contains, as component (a), an internal olefin sulfonic acid or its salt formed by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5, based on the viewpoints of exhibiting excellent cleaning properties, imparting conditioning effects to treated keratin substances and their persistence.

[0014] [Internal olefin sulfonic acid or its salt (a) obtained by sulfonating a raw olefin with an average double bond position of 3.9 to 4.5] The internal olefin sulfonic acid or its salt, which is component (a), is obtained by sulfonating a starting olefin with an average double bond position of 3.9 to 4.5. That is, the internal olefin sulfonic acid or its salt, which is component (a), is a compound obtained by sulfonating a starting olefin with an average double bond position within a specific range. Specifically, it is a compound obtained by neutralizing and hydrolyzing the starting olefin after sulfonation.

[0015] Examples of salts of internal olefin sulfonates include: alkali metal salts such as sodium and potassium salts; organic amine salts such as ammonium salts, monoethanolamine salts, diethanolamine salts, triethanolamine salts, 2-aminoethanol salts, and 2-aminomethylpropanediol salts; and basic amino acid salts such as lysine salts and arginine salts. These internal olefin sulfonates do not necessarily need to be in salt form initially; they can also be salts generated through a neutralization reaction during the manufacturing process. Among them, as a salt of internal olefin sulfonate, based on the viewpoints of exhibiting excellent cleaning properties, imparting conditioning effects and their persistence to treated keratin substances, and ease of manufacture, it is preferably selected from one or more of the group consisting of sodium salt, potassium salt, ammonium salt and 2-aminoethanol salt, more preferably selected from one or more of the group consisting of sodium salt and potassium salt, and even more preferably sodium salt, that is, even more preferably sodium internal olefin sulfonate.

[0016] Furthermore, the component (a) of the product obtained from this raw material olefin is an internal olefin sulfonic acid or its salt, which is mainly a mixture of hydroxyalkyl sulfonic acid or its salt (hydroxyl body, abbreviated as "HAS") and olefin sulfonic acid or its salt (olefin body, abbreviated as "IOS").

[0017] Furthermore, regarding the starting material olefins used as the starting material for component (a), the double bonds are primarily located within the carbon chain, but there are also cases where trace amounts of double bonds are located at the 1-position of the carbon chain, i.e., so-called α-olefins. If the starting material olefin is sulfonated, β-sulfonolactones are mainly generated, and some β-sulfonolactones are converted into γ-sulfonolactones and olefin sulfonic acids, which are then converted into hydroxyalkyl sulfonic acids or their salts and olefin sulfonic acids or their salts in the neutralization and hydrolysis steps (e.g., J. Am. Oil Chem. Soc. 69, 39 (1992)). Also, the hydroxyl groups of the resulting hydroxyalkyl sulfonic acids or their salts are located within the alkane chain, and the double bonds of the olefin sulfonic acids or their salts are located within the olefin chain. Therefore, in this specification, the various products and mixtures thereof are collectively referred to as the internal olefin sulfonic acid or its salt of component (a).

[0018] From the viewpoint of achieving excellent cleaning properties and imparting conditioning effects and persistence to treated keratin substances, the carbon number of component (a) and raw material olefin is preferably 12 or more, more preferably 14 or more, and even more preferably 16 or more; furthermore, it is preferably 24 or less, more preferably 22 or less, even more preferably 20 or less, and even more preferably 18 or less. Furthermore, the carbon number of component (a) and raw material olefin is preferably 12 to 24, more preferably 14 to 22, even more preferably 14 to 20, and even more preferably 16 to 18.

[0019] The average double bond position of the starting olefin forming component (a) is between 3.9 and 4.5. The average double bond position indicates that the starting olefin with this value has a relatively wide double bond distribution, including possibly trace amounts of the 1 position. Furthermore, the positions and distribution of double bonds in the raw olefin can be confirmed by gas chromatography-mass spectrometry (GC-MS). Specifically, a gas chromatography analyzer (hereinafter referred to as GC) accurately separates components with different carbon chain lengths and double bond positions, and then samples each component to a mass spectrometer (MS). The double bond positions can be identified by analyzing the GC peak areas of each component.

[0020] On the other hand, regarding component (a) obtained by sulfonating the starting olefin, the more located the sulfonic acid group introduced by sulfonation is within the carbon chain, the more difficult it is to separate. Therefore, there is currently no definitive analytical method. However, it is reasonably presumed that the position of the sulfonic acid group in component (a) roughly corresponds to the position of the double bond in the starting olefin, exhibiting a relatively wide distribution including the 1 position without excessive unevenness. Therefore, in this invention, component (a) is identified based on the average double bond position value in the starting olefin.

[0021] The component (a) used in this invention is an internal olefin sulfonic acid or its salt obtained from a raw material olefin having the aforementioned average double bond position value, i.e., a relatively wide double bond distribution. The sulfonic acid groups in the carbon chain are not excessively unevenly distributed, but rather exist in a wider range of positions. If component (a) is obtained from the aforementioned raw material olefin, the sulfonic acid groups in the carbon chain are not excessively unevenly distributed, but rather exist in a wider range of positions. Internal olefin sulfonic acids or their salts of various lengths from the sulfonic acid group bonding position to the terminal carbon chain are moderately mixed, thereby maintaining excellent cleaning effect and exhibiting good low-temperature storage stability. Furthermore, the average double bond position (unit: position) in the raw material olefins refers to the average double bond position of each raw material olefin present in the total amount of raw material olefins, which is obtained by the following formula (1).

[0022] [Number 1] (In formula (1), x is y / 2 when the carbon number of the raw material olefin is even (y is the carbon number of the raw material olefin), and (y-1) / 2 when the carbon number of the raw material olefin is odd. n represents the integer position of the double bond in the raw material olefin (unit: position). Cn represents the content of the raw material olefin with double bonds at position n out of 100% by mass (unit: mass%).

[0023] From the viewpoint of ensuring good low-temperature storage stability, the average double bond position in the raw material olefin forming component (a) is 3.9 or higher, preferably 4.0 or higher, and more preferably 4.1 or higher. Furthermore, from the viewpoint of ensuring excellent cleaning effect, the average double bond position in the raw material olefin is 4.5 or lower, preferably 4.4 or lower, and more preferably 4.3 or lower. Moreover, the average double bond position in the raw material olefin is 3.9 to 4.5, preferably 4.0 to 4.4, and more preferably 4.1 to 4.3.

[0024] Furthermore, the content of the raw material olefin with the double bond at the 2-position is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, and preferably 35% by mass or less, more preferably 32% by mass or less, and even more preferably 24% by mass or less. Moreover, the content of the raw material olefin with the double bond at the 2-position is preferably 10 to 35% by mass, more preferably 15 to 32% by mass, and even more preferably 20 to 24% by mass.

[0025] The content of the feed olefin with the double bond at the 3-position is preferably 10% by mass or more, more preferably 14% by mass or more, and even more preferably 16% by mass or more, and preferably 30% by mass or less, more preferably 24% by mass or less, and even more preferably 19% by mass or less. Furthermore, the content of the feed olefin with the double bond at the 3-position is preferably 10 to 30% by mass, more preferably 14 to 24% by mass, and even more preferably 16 to 19% by mass.

[0026] The content of the feed olefin with the double bond at position 4 is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 17% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 19% by mass or less. Furthermore, the content of the feed olefin with the double bond at position 4 is preferably 10 to 30% by mass, more preferably 15 to 25% by mass, and even more preferably 17 to 19% by mass.

[0027] The content of the feed olefin with the double bond at the 5-position is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 13% by mass or more, and preferably 25% by mass or less, more preferably 19% by mass or less, and even more preferably 15% by mass or less. Furthermore, the content of the feed olefin with the double bond at the 5-position is preferably 5 to 25% by mass, more preferably 10 to 19% by mass, and even more preferably 13 to 15% by mass.

[0028] The content of the raw material olefin with the double bond at position 6 is preferably 5% by mass or more, more preferably 7% by mass or more, and even more preferably 11% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 13% by mass or less. Furthermore, the content of the raw material olefin with the double bond at position 6 is preferably 5 to 20% by mass, more preferably 7 to 15% by mass, and even more preferably 11 to 13% by mass.

[0029] When the raw material olefin includes a raw material olefin with 16 or more carbon atoms, the total content of the raw material olefin with a double bond position of 7 or more is preferably 5% by mass or more, more preferably 7% by mass or more, and even more preferably 12% by mass or more, and preferably 25% by mass or less, more preferably 22% by mass or less, and even more preferably 16% by mass or less. Furthermore, when the raw material olefin includes a raw material olefin with 16 or more carbon atoms, the total content of the raw material olefin with a double bond position of 7 or more is preferably 5 to 25% by mass, more preferably 7 to 22% by mass, and even more preferably 12 to 16% by mass.

[0030] When the raw material olefin includes a raw material olefin with 16 or more carbon atoms, the mass ratio of the content of the raw material olefin with double bonds at positions 3 to 5 to the content of the raw material olefin with double bonds at positions 6 to 8 (raw material olefin 3 to 5 positions / raw material olefin 6 to 8 positions) is preferably 1.0 or more, more preferably 1.3 or more, and more preferably 1.7 or more, and more preferably 4.0 or less, more preferably 3.5 or less, and more preferably 2.2 or less. Furthermore, when the raw material olefin includes a raw material olefin with 16 or more carbon atoms, the mass ratio of the content of the raw material olefin with double bonds at positions 3 to 5 to the content of the raw material olefin with double bonds at positions 6 to 8 (raw material olefin 3 to 5 positions / raw material olefin 6 to 8 positions) is preferably 1.0 to 4.0, more preferably 1.3 to 3.5, and more preferably 1.7 to 2.2.

[0031] The content of α-olefins (with double bonds at position 1) in the raw material olefins that may inevitably exist is preferably less than 5.0% by mass, more preferably less than 3.0% by mass, and even more preferably less than 2.5% by mass, and even more preferably does not contain α-olefins.

[0032] Furthermore, the aforementioned raw material olefin can be obtained by isomerizing (double bond migration) a raw material olefin (α-olefin) with a double bond position of 1-position generated by the dehydration reaction of an alcohol. Specifically, relative to 100 parts by mass of 1-alkanol, the amount of solid acid catalyst such as alumina is preferably 0.5 parts by mass or more, more preferably 2 parts by mass or more, and preferably 15 parts by mass or less, more preferably 10 parts by mass or less, and preferably 0.5 to 15 parts by mass, more preferably 2 to 10 parts by mass. Subsequently, the isomerization reaction is carried out with stirring at a temperature preferably above 220°C, more preferably above 260°C and more preferably below 350°C, and more preferably between 220 and 350°C, more preferably between 260 and 350°C, for at least 1 hour, more preferably at least 3 hours and more preferably less than 30 hours, more preferably less than 10 hours, and more preferably between 1 and 30 hours, more preferably between 3 and 10 hours. The above-mentioned olefin feedstock can be obtained by appropriately distilling the product after the reaction.

[0033] The content of sulfonic acid or its salt in component (a) having a sulfonic acid group present at the 1st to 4th position is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 55% by mass or more, and preferably 75% by mass or less, more preferably 70% by mass or less, and even more preferably 68% by mass or less. Furthermore, the content of sulfonic acid or its salt in component (a) having a sulfonic acid group present at the 1st to 4th position is preferably 40 to 75% by mass, more preferably 50 to 70% by mass, and even more preferably 55 to 68% by mass.

[0034] The content of alkene sulfonic acid or its salt containing the sulfonic acid group at the 2-position in component (a) is preferably 10% by mass or more, more preferably 13% by mass or more, and even more preferably 17% by mass or more, and preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less. Furthermore, the content of alkene sulfonic acid or its salt containing the sulfonic acid group at the 2-position in component (a) is preferably 10 to 35% by mass, more preferably 13 to 30% by mass, and even more preferably 17 to 25% by mass.

[0035] The content of olefin sulfonic acid or its salt with the sulfonic acid group present at the 3-position in component (a) is preferably 5% by mass or more, more preferably 11% by mass or more, and even more preferably 15% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less. Furthermore, the content of olefin sulfonic acid or its salt with the sulfonic acid group present at the 3-position in component (a) is preferably 5 to 30% by mass, more preferably 11 to 25% by mass, and even more preferably 15 to 20% by mass.

[0036] The content of alkene sulfonic acid or its salt containing a sulfonic acid group at the 4-position in component (a) is preferably 15% by mass or more, more preferably 18% by mass or more, and even more preferably 19% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 23% by mass or less. Furthermore, the content of alkene sulfonic acid or its salt containing a sulfonic acid group at the 4-position in component (a) is preferably 15 to 30% by mass, more preferably 18 to 25% by mass, and even more preferably 19 to 23% by mass.

[0037] Furthermore, the content of sulfonic acid or its salt in an internal olefin sulfonic acid with a sulfonic acid group present at the 1 position in component (a) is preferably less than 5.0% by mass, more preferably less than 3.0% by mass, and even more preferably less than 2.5% by mass, and even more preferably does not contain sulfonic acid or its salt in an internal olefin sulfonic acid with a sulfonic acid group present at the 1 position.

[0038] The mass ratio (hydroxyl body / olefin body) of the hydroxyl body (HAS) to the olefin body (IOS) in component (a) is preferably 50 / 50 to 100 / 0, more preferably 60 / 40 to 100 / 0, further preferably 70 / 30 to 100 / 0, further preferably 75 / 25 to 100 / 0, and further preferably 75 / 25 to 95 / 5, based on the viewpoint of improving productivity and reducing impurities. Furthermore, the mass ratio (hydroxyl body / olefin body) is determined by separating the hydroxyl body and olefin body from component (a) using HPLC (High Performance Liquid Chromatography), feeding each onto MS (Mass Spectrometer), and calculating based on the peak areas obtained from the HPLC-MS (High Performance Liquid Chromatography-Mass Spectrometer) results.

[0039] Since component (a) is obtained by sulfonating raw olefins, it may contain unreacted raw olefins and inorganic compounds. It is preferable to have a lower content of these components.

[0040] The content of unreacted raw material olefins in component (a) is preferably less than 5.0% by mass, more preferably less than 3.0% by mass, and even more preferably less than 1.5% by mass, and even more preferably less than 1.0% by mass.

[0041] The content of inorganic compounds in component (a) is preferably less than 7.5% by mass, more preferably less than 5.0% by mass, even more preferably less than 3.0% by mass, even more preferably less than 2.0% by mass, and even more preferably less than 1.6% by mass.

[0042] Component (a) is obtained by sulfonating the above-mentioned raw material olefin with sulfur trioxide. Specifically, it can be obtained by sulfonating the raw material olefin, neutralizing it, and then hydrolyzing it. More specifically, the amount of sulfur trioxide used during the sulfonation of the aforementioned raw material olefin, from the viewpoint of increasing the yield of component (a) and improving reactivity, is preferably 0.8 mol or more, more preferably 0.9 mol or more, and even more preferably 0.95 mol or more, relative to 1 mol of the raw material olefin. Furthermore, from the viewpoint of economy and inhibiting unnecessary coloring of component (a), the amount of sulfur trioxide used is preferably 1.2 mol or less, more preferably 1.1 mol or less, and even more preferably 1.05 mol or less. Moreover, the amount of sulfur trioxide used relative to 1 mol of the raw material olefin is preferably 0.8 to 1.2 mol, more preferably 0.9 to 1.1 mol, and even more preferably 0.95 to 1.05 mol. From the viewpoint of preventing the solidification of sulfur trioxide and component (a) during the sulfonation of the above-mentioned raw material olefins, the reaction temperature is preferably above 0°C, and from the viewpoint of inhibiting unnecessary coloring of component (a), it is preferably below 50°C. Furthermore, the reaction temperature during the sulfonation of the raw material olefins is preferably between 0°C and 50°C.

[0043] During the neutralization process, basic compounds such as sodium hydroxide, potassium hydroxide, ammonia, and 2-aminoethanol are reacted. Among these, sodium hydroxide is preferred from the viewpoint that it is readily available as a sodium salt component (a). The amount of the basic compound added is preferably at least 1 mol relative to 1 mol of sulfonic acid, and more preferably at least 1.03 mol, from the viewpoint of suppressing the formation of impurities such as olefins or inorganic salts in the raw materials, and from the viewpoint of improving reactivity. Furthermore, the amount of the basic compound added is preferably at least 2.5 mol, more preferably at least 2.0 mol, and even more preferably at least 1.5 mol, from the viewpoint of economy and suppressing the formation of impurities such as olefins or inorganic salts in the raw materials. Furthermore, the amount of the alkaline compound added relative to 1 mole of sulfonic acid group is preferably 1.00 to 2.5 moles, more preferably 1.03 to 2.0 moles, and even more preferably 1.03 to 1.5 moles. From the viewpoint of suppressing the formation of internal impurities such as olefins or inorganic salts caused by side reactions, the temperature at which the sulfonated olefin feedstock is mixed with the basic compound during the neutralization process, and the reaction temperature, are preferably below 40°C, more preferably below 35°C. From the viewpoint of improving reactivity, the temperature is preferably above 0°C, more preferably above 10°C, further preferably above 15°C, and even more preferably above 20°C. Furthermore, the temperature at which the sulfonated olefin feedstock is mixed with the basic compound, and the reaction temperature, are preferably 0~40°C, more preferably 10~35°C, further preferably 15~35°C, and even more preferably 20~35°C.

[0044] From the viewpoint that the presence of water enhances reactivity, the reaction temperature during hydrolysis after neutralization is preferably 120°C or higher, more preferably 140°C or higher, and even more preferably 160°C or higher. Furthermore, from the viewpoint of inhibiting the decomposition of the products, the reaction temperature during hydrolysis is preferably 220°C or lower, more preferably 180°C or lower. Moreover, the reaction temperature during hydrolysis is preferably 120~220°C, more preferably 140~180°C, and even more preferably 160~180°C. From the perspective of ensuring the completion of the reaction, the reaction time during hydrolysis is preferably 30 minutes or more, more preferably 45 minutes or more. Furthermore, from the perspective of improving productivity, the reaction time during hydrolysis is preferably 240 minutes or less, more preferably 180 minutes or less, further preferably 120 minutes or less, and further preferably 90 minutes or less. Moreover, the reaction time during hydrolysis is preferably 30 to 240 minutes, more preferably 45 to 180 minutes, further preferably 45 to 120 minutes, and further preferably 45 to 90 minutes. These reactions can be carried out continuously. After the reaction is completed, purification can be performed by extraction, washing, or other methods.

[0045] The content of component (a) in the cleaning composition (A) is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, further preferably 0.3% by mass or more, further preferably 0.5% by mass or more, further preferably 1.0% by mass or more, further preferably 2.0% by mass or more, further preferably 5.0% by mass or more, further preferably 8.0% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, further preferably 20% by mass or less, further preferably 18% by mass or less, and further preferably 14% by mass or less, based on the viewpoints of exhibiting excellent cleaning properties, imparting conditioning effects to treated keratin substances and their persistence. Furthermore, the content of component (a) in the cleaning agent composition (A) is preferably 0.1 to 30% by mass, more preferably 0.2 to 30% by mass, even more preferably 0.3 to 25% by mass, even more preferably 0.5 to 25% by mass, even more preferably 1.0 to 20% by mass, even more preferably 2.0 to 20% by mass, even more preferably 5.0 to 18% by mass, even more preferably 8.0 to 14% by mass.

[0046] [Catonic polymers] The cleaning composition (A) may contain a cationic polymer, based on the viewpoint of further improving the feel of the treated hair. Here, "cationic polymer" means a polymer having cationic groups or exhibiting cationic properties when dissolved in water.

[0047] Examples of such cationic polymers include one or more selected from the group consisting of cationic polygalactomannan, cationic hydroxyalkyl cellulose, diallyl quaternary ammonium salt polymers, copolymers containing methacrylamide propyltrimethylammonium chloride, and cross-linked cationic polymers. As a cationic polygalactomannan, for example, one or more can be selected from the group consisting of cationic guar gum, cationic tara gum, and cationic locust bean gum. As a cationic hydroxyalkyl cellulose, for example, one or more can be selected from the group consisting of cationic hydroxyethyl cellulose and cationic hydroxypropyl cellulose. Examples of diallyl quaternary ammonium salt polymers include, for example, one or more selected from the group consisting of polydiallyl dimethyl ammonium chloride, diallyl dimethyl ammonium chloride / acrylic acid copolymer, diallyl dimethyl ammonium chloride / acrylic acid / acrylic acid copolymer, and diallyl dimethyl ammonium chloride / acrylic acid / acrylic acid copolymer. As a copolymer containing methacrylamide propyltrimethylammonium chloride, examples include one or more copolymers selected from the group consisting of acrylic acid / methyl acrylate / methacrylamide propyltrimethylammonium chloride copolymer and acrylic acid / acrylamide / methacrylamide propyltrimethylammonium chloride copolymer. Examples of cross-linked cationic polymers include, for example, N,N-dimethylaminoethyl methacrylate diethyl sulfate / N,N-dimethylacrylamide / polyethylene glycol dimethacrylate copolymer. Of the above, as a cationic polymer, from the viewpoint of further improving the feel of the treated hair, it is preferable to select one or more from the group consisting of cationic hydroxyalkyl cellulose and cross-linked cationic polymers, more preferably cationic hydroxyalkyl cellulose, and even more preferably cationic hydroxyethyl cellulose.

[0048] When the cleaning agent composition (A) contains a cationic polymer, the content of the cationic polymer in the cleaning agent composition (A), from the viewpoint of improving the feel of the treated hair, is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and even more preferably 0.1% by mass or more. Furthermore, from the viewpoint of the treatment properties of the cleaning agent composition (A), it is preferably 10% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less. Moreover, the content of the cationic polymer in the cleaning agent composition (A) is preferably 0.01 to 10% by mass, more preferably 0.05 to 3% by mass, and even more preferably 0.1 to 1% by mass.

[0049] [Electrolytes] From the viewpoint of enabling component (a) to more effectively adhere to the surface of keratinous material and impart better conditioning effect and its persistence to the treated keratinous material, the cleaning composition (A) preferably contains an electrolyte. If the cleaning composition (A) containing electrolyte is applied to the keratinous material and then washed with water, the electrolyte concentration in the composition decreases, and component (a) is more easily adsorbed onto the surface of the keratinous material. In this invention, "electrolyte" refers to a salt compound that undergoes ion dissociation in water. Examples of electrolytes include sodium chloride, potassium chloride, magnesium chloride, sodium citrate, potassium benzoate, ammonium chloride, sodium carbonate, dipotassium phosphate, and monoethanolamine sulfate. One of these electrolytes may be used alone or in combination with two or more of them. Of the above, from the perspectives of water solubility, the more effective adsorption of the complex formed by components (a) and (b) onto the surface of keratin, the better conditioning effect and its sustainability on the treated keratin, and economic efficiency, the electrolyte is preferably an inorganic salt, more preferably one or more selected from the group consisting of sodium chloride, potassium chloride, and magnesium chloride, and even more preferably one or more selected from the group consisting of sodium chloride and potassium chloride, and even more preferably sodium chloride.

[0050] When the cleaning agent composition (A) contains electrolytes, the electrolyte content in the cleaning agent composition (A) is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and more preferably 0.3% by mass or more, and preferably 10% by mass or less, more preferably 5% by mass or less, more preferably 3% by mass or less, and more preferably 1% by mass or less. Furthermore, the electrolyte content in the cleaning agent composition (A) is preferably 0.1 to 10% by mass, more preferably 0.1 to 5% by mass, more preferably 0.2 to 3% by mass, and more preferably 0.3 to 1% by mass.

[0051] [Aqueous media] From the viewpoints of dispersing component (a), adjusting the cleaning composition (A) to a desired dosage form, and improving treatability, it is preferable that the cleaning composition (A) contains an aqueous medium. Examples of aqueous media include: water; lower alcohols such as ethanol and isopropanol; and low molecular weight diols and triols with 6 or fewer carbon atoms, such as 1,3-butanediol, glycerol, ethylene glycol, propylene glycol, and dipropylene glycol. One of these can be used alone, or two or more can be used in combination. Among these, water is preferred as a mediator when sulfonating a raw olefin to obtain component (a).

[0052] When the cleaning agent composition (A) contains an aqueous medium, from the viewpoints of dispersing component (a), adjusting the cleaning agent composition (A) to the desired dosage form, and improving treatability, the content of the aqueous medium in the cleaning agent composition (A) is preferably 30% by mass or more, more preferably 50% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, and preferably 99.4% by mass or less.

[0053] [Other ingredients] Furthermore, the cleaning agent composition (A) may also contain other ingredients such as pH adjusters, surfactants other than ingredient (a), antioxidants, higher alcohols, oils, aromatic alcohols, vitamins, bactericides, anti-inflammatory agents, anti-dandruff agents, preservatives, chelating agents, moisturizers, pearlescent agents, ceramides, fragrances, and ultraviolet absorbers.

[0054] (Method for manufacturing cleaning composition (A)) The cleaning composition (A) can be manufactured by conventional methods. For example, it can be manufactured by mixing the formulation (a) and other ingredients as needed using a known stirring device.

[0055] (Application method of cleaning composition (A)) As a method for applying the cleaning agent composition (A) to the keratin material in step (I), examples include: applying, spraying, or casting the cleaning agent composition (A) onto the keratin material; impregnating the keratin material with the cleaning agent composition (A); etc. Among these, applying the cleaning agent composition (A) onto the keratin material is preferred. The keratinous substance to which the cleaning agent composition (A) is applied can be either dry or wet.

[0056] There is no particular limitation on the amount of keratin-based cleaning composition (A) used. For example, when the keratin is hair, from the viewpoint of hair cleansing properties, the bath ratio of cleaning composition (A) to the dry weight of the applied hair (mass of cleaning composition (A) / dry weight of the applied hair) is preferably 0.005 or more, more preferably 0.01 or more, and even more preferably 0.05 or more, and preferably 20 or less, more preferably 15 or less, and even more preferably 12 or less. Furthermore, the bath ratio of cleaning composition (A) to the dry weight of the applied hair (mass of cleaning composition (A) / dry weight of the applied hair) is preferably 0.005 to 20, more preferably 0.01 to 15, and even more preferably 0.05 to 12. The hair to which the cleaning agent composition (A) is applied may be the entire hair or a portion thereof.

[0057] After applying the cleaning agent composition (A) to the keratin material, it is preferable to perform a cleaning operation according to the type and location of the keratin material. The cleaning operation may involve applying the cleaning agent composition (A) evenly to the surface of the keratin material or causing the cleaning agent composition (A) to foam on the surface of the keratin material. After applying the cleaning composition (A) to keratinous materials or after performing the above-mentioned cleaning operation, it is preferable to rinse the cleaning composition with water, warm water, or the like. After rinsing off the cleaning agent composition (A), the keratin material can be used directly in step (II) without drying, or it can be temporarily dried before use in step (II). When the keratin material is hair, it can be dried, for example, by towel drying, air drying, or forced drying using a hair dryer. These drying methods can also be combined.

[0058] <Step (II)> In step (II), the conditioning agent composition (B) containing cationic surfactant (b) is applied to the above-mentioned keratin material. In the treatment method of the present invention, by sequentially performing steps (I) and (II), the treated keratin material can be given a conditioning effect and its persistence.

[0059] (Conditioning agent composition (B)) The conditioning composition (B) used in step (II) contains a cationic surfactant as an ingredient (b) from the viewpoint of imparting conditioning effects and their persistence to the treated keratin material.

[0060] [Catonic surfactants (b)] Examples of cationic surfactants (b) (hereinafter also referred to as "component (b)") used in conditioning composition (B) include (i) alkyl trimethylammonium salts, (ii) alkoxyalkyl trimethylammonium salts, (iii) dialkyl dimethylammonium salts, (iv) alkylamide alkyl trimethylammonium salts, (v) alkyl dimethylamine and its salts, (vi) alkoxyalkyl dimethylamine and its salts, and (vii) alkylamide alkyl dimethylamine and its salts, etc., and one or more of these may be used.

[0061] Examples of (i) alkyltrimethylammonium salts include alkyltrimethylammonium salts having an alkyl group having a preferred carbon number of 12 or more and 22 or less, and more preferably a carbon number of 16 or more and 20 or less. Specifically, examples include cetyltrimethylammonium chloride (cetyltrimethylammonium chloride), stearyltrimethylammonium chloride (stearyltrimethylammonium chloride), benzyltrimethylammonium chloride, etc. As an (ii) alkoxyalkyltrimethylammonium salt, examples include alkoxyalkyltrimethylammonium salts having an alkoxy group preferably having 12 or more carbon atoms and 16 or more carbon atoms and 20 or less carbon atoms. Specifically, examples include stearoxypropyltrimethylammonium chloride, stearoxyethyltrimethylammonium chloride, stearoxyhydroxypropyltrimethylammonium chloride, etc. As (iii) dialkyl dimethyl ammonium salt, examples include dialkyl dimethyl ammonium salts having an alkyl group having a preferred carbon number of 12 or more and 22 or less, and more preferably a carbon number of 16 or more and 20 or less. Specifically, examples include distearate dimethyl ammonium chloride. As an (iv) alkyl amide alkyl trimethylammonium salt, examples include alkyl amide alkyl trimethylammonium salts in which the number of carbon atoms in the alkyl group of the alkyl amide portion is preferably 11 to 21 and more preferably 13 to 19. Specifically, examples include palmitamide propyltrimethylammonium chloride (palmitamide propyltrimethylammonium chloride).

[0062] (v) Alkyl dimethylamine, (vi) alkoxy alkyl dimethylamine, and (vii) alkyl amide alkyl dimethylamine react with acids to form tertiary amine salts, which become cationic surfactants. (v) The alkyl group in alkyl dimethylamine and its salt, and (vi) The alkoxy group in alkoxy alkyl dimethylamine and its salt preferably have 12 or more and 22 or less carbon atoms, and more preferably 16 or more and 20 or less carbon atoms. (vii) In alkyl amides, alkyl dimethylamines and their salts, the alkyl group of the alkyl amide portion preferably has 11 to 21 carbon atoms, and more preferably 15 to 19 carbon atoms.

[0063] The amines (v) to (vii) can be reacted with the acid beforehand to form a salt, which is then formulated into the conditioning agent composition (B). Alternatively, they can be directly formulated into the conditioning agent composition (B) in amine form, thereby incorporating the acid into the conditioning agent composition (B) and forming a salt in the composition. Therefore, the above-mentioned amines and their salts are defined here as cationic surfactants. Furthermore, their content is calculated based on the mass of the above-mentioned amines.

[0064] Salts of amines (v) to (vii) can be exemplified by salts obtained from organic or inorganic acids. Examples of organic acids include: monocarboxylic acids such as acetic acid and propionic acid; dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid, fumaric acid, and phthalic acid; polycarboxylic acids such as polyglutamic acid; hydroxycarboxylic acids such as glycolic acid, lactic acid, hydroxyacrylic acid, glyceric acid, malic acid, tartaric acid, and citric acid; and acidic amino acids such as glutamic acid and aspartic acid. Examples of inorganic acids include, for example, hydrochloric acid, sulfuric acid, and phosphoric acid. Among these, organic acids are preferred, and more preferably, one or more acids selected from the group consisting of dicarboxylic acids, hydroxycarboxylic acids, and acidic amino acids. As dicarboxylic acids, one or more acids selected from the group consisting of maleic acid and succinic acid are preferred. As hydroxycarboxylic acids, one or more acids selected from the group consisting of glycolic acid, lactic acid, and malic acid are preferred. As an acidic amino acid, glutamic acid is preferred.

[0065] Examples of (v) alkyl dimethylamines and their salts include N,N-dimethylbenzylamine, N,N-dimethylstearylamine, and their organic acid salts, with preferred examples being lactate of N,N-dimethylbenzylamine and glycolate of N,N-dimethylstearylamine.

[0066] Examples of (vi) alkoxyalkyl dimethylamines and their salts include N,N-dimethyl-3-hexadecyloxypropylamine, N,N-dimethyl-3-octadecyloxypropylamine, and their organic acid salts, with N,N-dimethyl-3-hexadecyloxypropylamine or its salts, and N,N-dimethyl-3-octadecyloxypropylamine (stearoyloxypropyl dimethylamine) or its salts.

[0067] Examples of (vii) alkyl amides and their salts include N-[3-(dimethylamino)propyl]betaine, N-[3-(dimethylamino)propyl]stearylamine, and their organic acid salts, with preferred examples being the lactate of N-[3-(dimethylamino)propyl]betaine and the glycolate of N-[3-(dimethylamino)propyl]stearylamine.

[0068] Of the above, as a cationic surfactant (b), from the viewpoint of imparting conditioning effects and their persistence to the treated keratin material, it is preferably selected from one or more of the group consisting of (i) alkyltrimethylammonium salts and (vi) alkoxyalkyldimethylamines and their salts, more preferably selected from one or more of the group consisting of cetyltrimethylammonium chloride (chlorinated cetyltrimethylammonium), stearyltrimethylammonium chloride (chlorinated stearyltrimethylammonium), benzyltrimethylammonium chloride, and N,N-dimethyl-3-octadecyloxypropylamine and their salts.

[0069] The content of component (b) in the conditioning agent composition (B), from the viewpoint of imparting a conditioning effect and its persistence to the treated keratin, is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, more preferably 1.0% by mass or more, more preferably 2.0% by mass or more, more preferably 3.0% by mass or more, and preferably 25% by mass or less, more preferably 20% by mass or less, more preferably 15% by mass or less, and more preferably 10% by mass or less. Furthermore, the content of component (b) in the conditioning agent composition (B) is preferably 0.1 to 25% by mass, more preferably 0.5 to 20% by mass, more preferably 1.0 to 20% by mass, more preferably 2.0 to 15% by mass, more preferably 2.0 to 10% by mass, and more preferably 3.0 to 10% by mass.

[0070] [Higher alcohols] The conditioning composition (B) may contain higher alcohols, based on the viewpoint of further enhancing the feel of the treated hair. The number of carbon atoms in higher alcohols is preferably 12 or more and 22 or less. Examples of such higher alcohols include cetyl alcohol, oleyl alcohol, stearyl alcohol, isostearyl alcohol, 2-octyldodecanool, myristyl alcohol, betaine alcohol, cetearyl alcohol, etc., and one of these alcohols may be used alone or in combination of two or more of these alcohols.

[0071] When the conditioning agent composition (B) contains higher alcohols, the content of higher alcohols in the conditioning agent composition (B), from the viewpoint of further improving the feel of the treated hair, is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, and even more preferably 3.0% by mass or more, and preferably 15% by mass or less, more preferably 12% by mass or less, and even more preferably 10% by mass or less. Furthermore, the content of higher alcohols in the conditioning agent composition (B) is preferably 1.0 to 15% by mass, more preferably 2.0 to 12% by mass, and even more preferably 3.0 to 10% by mass.

[0072] [Aqueous media] From the perspective of dispersing component (b), adjusting the conditioner composition (B) to the desired dosage form, and improving processability, it is preferable to contain an aqueous medium. Examples of aqueous media include: water; lower alcohols such as ethanol and isopropanol; and low molecular weight diols and triols with 6 or fewer carbon atoms, such as 1,3-butanediol, glycerol, ethylene glycol, propylene glycol, and dipropylene glycol. One of these can be used alone, or two or more can be used in combination. Among these, water is preferred as the aqueous media.

[0073] When the conditioning agent composition (B) contains an aqueous medium, from the viewpoint of dispersing component (b), adjusting the conditioning agent composition (B) to the desired dosage form, and improving processability, the content of the aqueous medium in the conditioning agent composition (B) is preferably 30% by mass or more, more preferably 50% by mass or more, more preferably 70% by mass or more, more preferably 75% by mass or more, and preferably 99.9% by mass or less, more preferably 95% by mass or less.

[0074] [Other ingredients] Furthermore, the conditioning composition (B) may also contain, for example, the aforementioned organic or inorganic acids, other pH adjusters, surfactants other than component (b), antioxidants, oils, aromatic alcohols, vitamins, bactericides, anti-inflammatory agents, anti-dandruff agents, preservatives, chelating agents, moisturizers, pearlescent agents, ceramides, fragrances, ultraviolet absorbers, and other ingredients.

[0075] (Method for manufacturing conditioner composition (B)) The conditioning composition (B) can be manufactured by conventional methods. For example, it can be manufactured by mixing the conditioning ingredients (b) and other ingredients as needed using a known stirring device.

[0076] (Application method of conditioning composition (B)) As a method for applying the conditioning composition (B) to the keratin substance in step (II), examples include: applying, spraying, or casting the conditioning composition (B) onto the keratin substance; impregnating the keratin substance with the conditioning composition (B); etc. Among these, applying the conditioning composition (B) onto the keratin substance is preferred. The keratin material to which the conditioning agent composition (B) is applied can be dry or wet. Based on the viewpoint of directly applying the keratin material treated in step (I) to step (II), and from the viewpoint of efficiently forming a complex and imparting conditioning effects and their persistence to the treated keratin material, it is preferred to apply the keratin material in a wet state.

[0077] There are no particular limitations on the amount of keratin-based conditioning agent composition (B) used. For example, when the keratin is hair, from the viewpoint of improving conditioning effect and its lasting effect, the ratio of the conditioning agent composition (B) to the dry weight of the applied hair (mass of conditioning agent composition (B) / dry weight of the applied hair) is preferably 0.005 or more, more preferably 0.01 or more, and even more preferably 0.05 or more, and preferably 20 or less, more preferably 15 or less, and even more preferably 12 or less. Furthermore, the ratio of the conditioning agent composition (B) to the dry weight of the applied hair (mass of conditioning agent composition (B) / dry weight of the applied hair) is preferably 0.005 to 20, more preferably 0.01 to 15, and even more preferably 0.05 to 12.

[0078] After applying the conditioning agent composition (B) to the keratin material, it is preferable to perform the following steps: apply the conditioning agent composition (B) evenly to the surface of the keratin material and then rinse with water, warm water, etc. From the perspective of improving conditioning effects and their lasting effects, after applying the conditioning agent composition (B) to keratinous substances and before rinsing, a step can be performed where the conditioning agent composition (B) is left on. The placement time is preferably 3 minutes or more, more preferably 5 minutes or more. Furthermore, from the perspective of treatment efficiency, the placement time is preferably 30 minutes or less.

[0079] Furthermore, in the processing method of the present invention, steps (I) and (II) can be performed sequentially, preferably by repeating the series of treatments of washing in step (I) and conditioning in step (II). By repeating the series of treatments of steps (I) and (II), the complex formed by components (a) and (b) accumulates on the surface of the keratin material, thereby further enhancing the conditioning effect and its persistence. There is no particular limitation on the number of times the series of treatments of steps (I) and (II) are repeated, usually more than twice, but from the viewpoint of enhancing the conditioning effect and its persistence, as well as the viewpoint of the simplicity of the process, it is preferable to repeat more than three times, and more preferably more than five times.

[0080] [Cosmetic Set for Keratin Treatment] The present invention provides a cosmetic kit for treating keratin substances (hereinafter also referred to as "cosmetic kit"), which comprises a cleansing composition (A) and a conditioning composition (B) containing a cationic surfactant (b). The cleansing composition (A) contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 or more and 4.5 or less. The cosmetic kit of the present invention, by sequentially applying a cleansing agent composition (A) and a conditioning agent composition (B) to keratin substances, can impart a conditioning effect and its persistence to the treated keratin substances.

[0081] The preferred forms of the cleansing agent composition (A), conditioning agent composition (B), and the like constituting the cosmetic kit of the present invention are the same as described above. Furthermore, both the cleansing agent composition (A) and the conditioning agent composition (B) can be applied to keratin substances by means of the same processing method as described above for the present invention.

[0082] [Composition for Keratin Treatment] Furthermore, the present invention provides a composition for treating keratin substances, which is applied to keratin substances before a conditioning composition (B) containing a cationic surfactant (b), and contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 or more and 4.5 or less. The keratin material treatment composition of the present invention, when applied to keratin material before the conditioning agent composition (B), can form a complex of component (a) and component (b) on the surface of the keratin material, thereby imparting a conditioning effect and its persistence to the treated keratin material. The preferred forms of component (a), conditioning agent composition (B), and the like are the same as described above.

[0083] The keratin treatment composition containing component (a) is a composition applied to keratin substances prior to the conditioning composition (B), and can be a cleansing composition. Other examples of keratin treatment compositions include hair conditioner compositions, conditioning compositions, and repairing compositions for keratin substances. From the viewpoint of improving conditioning effects and their sustained effectiveness, the keratin treatment composition is preferably a cleansing composition, and more preferably the aforementioned cleansing composition (A).

[0084] The present invention will further disclose the following regarding the above-described embodiments. <1> A method for treating keratinous substances, comprising the following steps (I) and (II) in sequence: Step (I): Applying the cleaning agent composition (A) to a keratin substance, wherein the cleaning agent composition (A) contains an internal olefin sulfonic acid or its salt (a) obtained by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5; Step (II): Applying the conditioning composition (B) containing the cationic surfactant (b) to the above-mentioned keratin substance. <2> like <1> The method for processing keratinous substances described herein, wherein the carbon number of the aforementioned component (a) is preferably 12 to 24, more preferably 14 to 22, further preferably 14 to 20, and further preferably 16 to 18. <3> like <1> or <2> In the described method for processing keratin substances, the average double bond position in the aforementioned raw material olefin is preferably 4.0 to 4.4, and more preferably 4.1 to 4.3. <4> like <1> to <3> In any of the methods for processing keratin substances described herein, the content of the raw material olefin with the double bond position at position 2 is preferably 10-35% by mass, more preferably 15-32% by mass, and even more preferably 20-24% by mass. <5> like <1> to <4> In any of the methods for processing keratin substances described herein, the content of the raw material olefin with the double bond position at the 3-position is preferably 10-30% by mass, more preferably 14-24% by mass, and even more preferably 16-19% by mass. <6> like <1> to <5> In any of the methods for processing keratin substances described herein, the content of the raw material olefin with the double bond position at position 4 is preferably 10-30% by mass, more preferably 15-25% by mass, and even more preferably 17-19% by mass. <7> like <1> to <6> In any of the methods for processing keratin substances described herein, the content of the raw material olefin with the double bond position at position 5 is preferably 5 to 25% by mass, more preferably 10 to 19% by mass, and even more preferably 13 to 15% by mass. <8> like <1> to <7> In any of the methods for processing keratin substances described herein, the content of the raw material olefin with the double bond position at position 6 is preferably 5 to 20% by mass, more preferably 7 to 15% by mass, and even more preferably 11 to 13% by mass. <9> like <1> to <8> In any of the methods for processing keratin substances described herein, when the raw material olefin comprises a raw material olefin having 16 or more carbon atoms, the total content of the raw material olefin having a double bond position of 7 or more is preferably 5 to 25% by mass, more preferably 7 to 22% by mass, and even more preferably 12 to 16% by mass. <10> like <1> to <9> In any of the methods for processing keratin substances described herein, when the raw material olefin comprises a raw material olefin having 16 or more carbon atoms, the mass ratio of the content of the raw material olefin with double bond positions at positions 3 to 5 to the content of the raw material olefin with double bond positions at positions 6 to 8 (raw material olefin at positions 3 to 5 / raw material olefin at positions 6 to 8) is preferably 1.0 to 4.0, more preferably 1.3 to 3.5, and even more preferably 1.7 to 2.2.

[0085] <11> like <1> to <10> In any of the methods for processing keratin substances described herein, the content of the α-olefin (with the double bond at position 1) in the aforementioned raw olefin is preferably less than 5.0% by mass, more preferably less than 3.0% by mass, further preferably less than 2.5% by mass, and further preferably not contained. <12> like <1> to <11> The method for processing keratinous material as described in any one of the above components (a) is preferably 40 to 75% by mass, more preferably 50 to 70% by mass, and even more preferably 55 to 68% by mass. <13> like <1> to <12> The method for processing keratinous material as described in any one of the above components (a) is preferably 10 to 35% by mass, more preferably 13 to 30% by mass, and even more preferably 17 to 25% by mass. <14> like <1> to <13> The method for processing keratinous material as described in any one of the above components (a) is preferably 5 to 30% by mass, more preferably 11 to 25% by mass, and even more preferably 15 to 20% by mass. <15> like <1> to <14> The method for processing keratinous material described in any one of the above components (a) is preferably 15 to 30% by mass, more preferably 18 to 25% by mass, and even more preferably 19 to 23% by mass. <16> like <1> to <15> The method for processing keratinous material as described in any one of the above components (a) preferably contains less than 5.0% by mass, more preferably less than 3.0% by mass, further preferably less than 2.5% by mass, and further preferably does not contain sulfonic acid or its salt containing an olefinic group at the 1st position. <17> like <1> to <16> In any of the methods for processing keratin substances described herein, the mass ratio (hydroxyl body / olefin body) of the content of hydroxyl body (HAS) to olefin body (IOS) in the aforementioned component (a) is preferably 50 / 50 to 100 / 0, more preferably 60 / 40 to 100 / 0, further preferably 70 / 30 to 100 / 0, further preferably 75 / 25 to 100 / 0, and further preferably 75 / 25 to 95 / 5. <18> like <1> to <17> The method for treating keratinous substances as described in any one of the above-mentioned methods, wherein the content of the above-mentioned component (a) in the cleaning agent composition (A) is preferably 0.1 to 30% by mass, more preferably 0.2 to 30% by mass, further preferably 0.3 to 25% by mass, further preferably 0.5 to 25% by mass, further preferably 1.0 to 20% by mass, further preferably 2.0 to 20% by mass, further preferably 5.0 to 18% by mass, further preferably 8.0 to 14% by mass. <19> like <1> to <18> The method for treating keratinous substances as described in any one of the following, wherein the cleaning agent composition (A) contains a cationic polymer, preferably one or more selected from the group consisting of cationic polygalactomannan, cationic hydroxyalkyl cellulose, diallyl quaternary ammonium salt polymer, copolymer containing methacrylamide propyltrimethylammonium chloride, and cross-linked cationic polymers, more preferably one or more selected from the group consisting of cationic hydroxyalkyl cellulose and cross-linked cationic polymers, further preferably containing cationic hydroxyalkyl cellulose, and even more preferably containing cationic hydroxyethyl cellulose. <20> like <19> The method for treating keratinous substances described herein, wherein the content of the cationic polymer in the cleaning agent composition (A) is preferably 0.01 to 10% by mass, more preferably 0.05 to 3% by mass, and even more preferably 0.1 to 1% by mass.

[0086] <21> like <1> to <20> The method for treating keratinous substances as described in any one of the above-mentioned cleaning agent compositions (A) further contains an electrolyte, preferably an inorganic salt, more preferably one or more selected from the group consisting of sodium chloride, potassium chloride, and magnesium chloride, further preferably one or more selected from the group consisting of sodium chloride and potassium chloride, and more preferably sodium chloride. <22> like <21> The method for treating keratinous substances described herein, wherein the electrolyte content in the cleaning agent composition (A) is preferably 0.1 to 10% by mass, more preferably 0.1 to 5% by mass, further preferably 0.2 to 3% by mass, and further preferably 0.3 to 1% by mass. <23> like <1> to <22> The method for treating keratinous substances as described in any one of the above-mentioned cleaning agent compositions (A) contains an aqueous medium, preferably containing one or more of the group consisting of water, lower alcohols, low molecular weight diols with 6 or fewer carbon atoms, and triols, and more preferably containing water. <24> like <23> The method for treating keratinous substances described herein, wherein the content of the aqueous medium in the cleaning agent composition (A) is preferably 30% by mass or more, more preferably 50% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, and preferably 99.4% by mass or less. <25> like <1> to <24> In any of the methods for treating keratinous substances described herein, in step (I), when the keratinous substance is hair, the amount of the detergent composition (A) used is preferably 0.005 to 20, more preferably 0.01 to 15, and even more preferably 0.05 to 12, based on the bath ratio of detergent composition (A) to the dry mass of the applied hair (mass of detergent composition (A) / dry mass of the applied hair). <26> like <1> to <25> The method for treating keratinous material described in any one of the methods comprises, in step (I), applying the above-mentioned cleaning agent composition (A) to the keratinous material and then rinsing the cleaning agent composition (A) with water or warm water. <27> like <1> to <27> The method for treating keratin substances as described in any one of the following methods, wherein the aforementioned cationic surfactant (b) is selected from one or more of the group consisting of (i) alkyltrimethylammonium salt, (ii) alkoxyalkyltrimethylammonium salt, (iii) dialkyldimethylammonium salt, (iv) alkylamide alkyltrimethylammonium salt, (v) alkyldimethylamine and its salt, (vi) alkoxyalkyldimethylamine and its salt, and (vii) alkylamide alkyldimethylamine and its salt, and preferably selected from one or more of the group consisting of (i) alkyltrimethylammonium salt and (vi) alkoxyalkyldimethylamine and its salt, more preferably selected from one or more of the group consisting of cetyltrimethylammonium chloride (chlorinated cetyltrimethylammonium), stearyltrimethylammonium chloride (chlorinated stearyltrimethylammonium), benzyltrimethylammonium chloride, and N,N-dimethyl-3-octadecyloxypropylamine and its salt. <28> like <1> to <27> The method for treating keratinous substances as described in any one of the above methods, wherein the content of the above-mentioned cationic surfactant (b) in the above-mentioned conditioning agent composition (B) is preferably 0.1 to 25% by mass, more preferably 0.5 to 20% by mass, further preferably 1.0 to 20% by mass, further preferably 2.0 to 15% by mass, further preferably 2.0 to 10% by mass, and further preferably 3.0 to 10% by mass. <29> like <1> to <28> The method for treating keratinous substances as described in any one of the claims, wherein the conditioning agent composition (B) contains a higher alcohol, preferably a higher alcohol having 12 to 22 carbon atoms, and more preferably one or more selected from the group consisting of cetyl alcohol, oleyl alcohol, stearyl alcohol, isostearyl alcohol, 2-octyldodecanool, myristyl alcohol, betaine alcohol, and cetearyl alcohol. <30> like <29> The method for treating keratin substances described herein, wherein the content of higher alcohols in the above-mentioned conditioning agent composition (B) is preferably 1.0 to 15% by mass, more preferably 2.0 to 12% by mass, and even more preferably 3.0 to 10% by mass.

[0087] <31> like <1> to <30> The method for treating keratinous substances as described in any one of the above-mentioned conditioning agent compositions (B) contains an aqueous medium, preferably containing one or more of the group consisting of water, lower alcohols, low molecular weight diols with 6 or fewer carbon atoms, and triols, and more preferably containing water. <32> like <31> In the described method for treating keratinous substances, the content of the aqueous medium in the above-mentioned conditioning agent composition (B) is preferably 30% by mass or more, more preferably 50% by mass or more, more preferably 70% by mass or more, more preferably 75% by mass or more, and preferably 99.9% by mass or less, more preferably 95% by mass or less. <33> like <1> to <32> The method for treating keratinous material as described in any one of the methods, wherein in step (II) the above-mentioned conditioning agent composition (B) is applied to the keratinous material in a moist state. <34> like <1> to <33> In any of the methods for treating keratinous substances described herein, in step (II), when the keratinous substance is hair, the amount of the conditioning agent composition (B) applied is preferably 0.005 to 20, more preferably 0.01 to 15, and even more preferably 0.05 to 12, based on the bath ratio of the conditioning agent composition (B) to the dry mass of the applied hair (mass of conditioning agent composition (B) / dry mass of the applied hair). <35> like <1> to <34> In any of the methods for treating keratinous substances described herein, in step (II) after applying the above-mentioned conditioning agent composition (B) to the keratinous substance, the conditioning agent composition (B) is rinsed with water or warm water. <36> like <35> The method for treating keratinous material described herein involves, in step (II), applying the above-mentioned conditioning agent composition (B) to the keratinous material and, before rinsing, placing it in a state with the conditioning agent composition (B) applied. <37> like <1> to <36> The method for treating keratinous substances described in any one of the methods repeats the series of treatments of step (I) washing and step (II) conditioning more than twice, and preferably more than three times, and more preferably more than five times. <38> A cosmetic kit for treating keratinous substances comprises a cleansing composition (A) and a conditioning composition (B) containing a cationic surfactant (b). The cleansing composition (A) contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 or more and 4.5 or less. <39> A composition for treating keratin substances, which is applied to keratin substances prior to a conditioning composition (B) containing a cationic surfactant (b), and contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 3.9 to 4.5. <40> like <39> The keratin substance treatment composition described herein, wherein the keratin substance treatment composition containing the above-mentioned component (a) is a keratin substance cleaning agent composition, hair conditioner composition, conditioning agent composition, or repair agent composition. [Example]

[0088] The present invention will now be described with reference to examples, but the invention is not limited to the scope of the examples. Furthermore, the various physical property measurements in the examples were performed using the following methods.

[0089] (i) Method for determining the position of double bonds in raw olefins The double bond positions of the starting olefin were determined by gas chromatography (GC). Specifically, the starting olefin was reacted with dimethyl disulfide to prepare a disulfide derivative, and the components were separated by GC. The double bond positions of the starting olefin were then determined from the peak areas of each component. Furthermore, the apparatus and analytical conditions used for the determination are as follows. GC device: HP6890 manufactured by Hewlett Packard. Column: Ultra-Alloy-1HT capillary column manufactured by Frontier Laboratories, 30 m × 250 μm × 0.15 μm Detector: Flame Ionization Detector (FID) Injection temperature: 300℃ Detector temperature: 350℃ He flow rate: 4.6 mL / min

[0090] (ii) Method for determining the content corresponding to the sulfonic acid group bond positions of the internal olefin sulfonate sodium For sodium sulfonates of internal olefins bonded with sulfonic acid groups, the content of each sodium sulfonate corresponding to the bond position of the sulfonic acid group was determined by high-performance liquid chromatography / mass spectrometry (HPLC-MS). Specifically, the hydroxyl groups bonded with sulfonic acid groups were separated by HPLC, and each was then subjected to mass spectrometry (MS) for identification. The content of each was determined from the HPLC-MS peak area. Furthermore, the apparatus and conditions used for the measurement are as follows. HPLC apparatus: LD20ASXR manufactured by Shimadzu Corporation. Column: ODS Hypersil (registered trademark) manufactured by Thermo Fisher Scientific, 4.6 × 250 mm, particle size: 3 μm Sample preparation: Dilute 1000 times with methanol. Solution A: Water with 10 mM ammonium acetate added Solution B: A solution containing 10 mM ammonium acetate methylacrylonitrile / water = 95 / 5 (v / v) Gradient: 0 minutes (A / B=60 / 40) → 15.1~20 minutes (30 / 70) → 20.1~30 minutes (60 / 40) MS device: "LCMS-2020" manufactured by Shimadzu Corporation. ESI detection: Anion detection m / z = 321.10 (components with 16 or 18 carbon atoms (a)) Column temperature: 40℃ Flow rate: 0.5 mL / min Injection volume: 5 μL

[0091] (iii) Method for determining the mass ratio of hydroxyl body to olefin body The mass ratio of hydroxyl to olefinic groups in the internal sodium olefin sulfonate was determined by HPLC-MS. Specifically, the hydroxyl and olefinic groups were separated by HPLC, and each was then analyzed by MS. The ratio of each group was determined from the HPLC-MS peak areas. Furthermore, the apparatus and conditions used for the measurement are as follows. HPLC apparatus: Agilent Technologies 1100, manufactured by Agilent Technologies. The column is an "L-column ODS 4.6 × 150 mm" manufactured by the Chemical Substance Evaluation and Research Institute (CDERI). Sample preparation: Dilute 1000 times with methanol. Solution A: Water with 10 mM ammonium acetate added Solution B: Methanol with 10 mM ammonium acetate added Gradient: 0 minutes (A / B=30 / 70%) → 10 minutes (30 / 70%) → 55 minutes (0 / 100%) → 65 minutes (0 / 100%) → 66 minutes (30 / 70%) → 75 minutes (30 / 70%) MS device: Agilent Technologies 1100MS SL (G1946D) manufactured by Agilent Technologies. MS detection: Anion detection m / z = 60-1600, UV 240 nm

[0092] (iv) Method for determining the content of olefins in raw materials The content of unreacted olefins in sodium olefin sulfonate was determined by GC. Specifically, ethanol and petroleum ether were added to an aqueous solution of sodium olefin sulfonate, followed by extraction to obtain olefins in the petroleum ether phase. The olefin content was then quantified by the GC peak area. Furthermore, the apparatus and analytical conditions used for the determination are as follows. GC device: Agilent Technologies 6850 manufactured by Agilent Technologies. Column: Ultra-Alloy-1HT capillary column manufactured by Frontier Laboratories, 15 m × 250 μm × 0.15 μm Detector: Flame Ionization Detector (FID) Injection temperature: 300℃ Detector temperature: 350℃ He flow rate: 3.8 mL / min

[0093] (v) Methods for determining the content of inorganic compounds The content of inorganic compounds is determined by potentiometric titration or neutralization titration. Specifically, the content of Na₂SO₄ is quantified by determining the sulfate ion (SO₄²⁻) using potentiometric titration. Furthermore, the content of NaOH is quantified by neutralization titration using dilute hydrochloric acid.

[0094] Manufacturing Example 1 (Manufacturing of Sodium Sulfonate 1 with 16 carbon atoms) [Manufacturing of 16-carbon olefin 1] 7000 g (28.9 moles) of 1-hexadecaneol (product name: Kalcol 6098, manufactured by Kao Corporation) and 350 g (5% by mass relative to the starting alcohol) of γ-alumina (manufactured by STREM Chemicals, Inc.) as a solid acid catalyst were added to a flask equipped with a stirrer. Nitrogen was bubbled into the system at 280°C (7000 mL / min) while stirring, and the reaction was carried out for 8 hours. The alcohol conversion rate was 100% at the end of the reaction. The obtained crude olefin was transferred to a distillation flask and distilled at 136–160 °C / 4.0 mmHg to obtain 16-carbon olefin of 100% purity. The double bond distribution of the obtained olefin was as follows: C1 position 1.8 wt%, C2 position 21.8 wt%, C3 position 18.7 wt%, C4 position 18.6 wt%, C5 position 14.3 wt%, C6 position 11.4 wt%, C7 position 6.8 wt%, and C8 position 6.8 wt% (the total of C7 and C8 positions is 13.6 wt%), with an average double bond position of 4.17.

[0095] [Sulfonation of raw material olefin 1] Raw material olefin 1 was placed in a thin-film sulfonation reactor with an external sleeve. Sulfonation was carried out using sulfur trioxide gas under conditions where cooling water at 10°C was circulated through the external sleeve. The molar ratio of SO3 to internal olefin during the sulfonation reaction was set to 1.01. The resulting sulfonate was mixed with an alkaline aqueous solution prepared using sodium hydroxide (alkali) in an amount equal to 1.04 molars relative to the theoretical acid value, and neutralized continuously at 30°C for 1 hour. The resulting neutralized product was then hydrolyzed in an autoclave at 170°C for 1 hour to obtain sodium sulfonate 1 with 16 carbon atoms. The obtained sodium sulfonate 1 with 16 carbon atoms contained 0.4% by mass of raw material olefin and 0.39% by mass of inorganic compounds.

[0096] The physical properties of the obtained internal olefin sulfonate sodium 1 are shown in Table 1.

[0097] [Table 1] Table 1 Sodium olefin sulfonate Manufacturing Example 1 Raw material olefins 1 Distribution of sulfonic acid groups (quality%) 1 person 2.0 2 people 24.8 3 people 19.1 4 people 22.0 5-9 32.1 total 100.0 Hydroxyl body 83.9 olefin bodies 16.1

[0098] Examples 1-4, Comparative Examples 1-4 (Hair Treatment Methods and Evaluation (1)) (Preparation of cleaning agent compositions and conditioning agent compositions) After preparing the components according to the composition shown in Table 2, mix them until homogeneous to prepare the cleaning agent composition and the conditioning agent composition respectively. The pH of the cleaning agent composition was adjusted to 4.3 at 25°C. Furthermore, the amounts listed in the tables of this embodiment are the effective ingredient amounts (mass %) of each component. (Step (I)) After wetting a 5g bundle of dry hair with warm water at 35-40°C, apply 2g of the cleaning agent composition for each example, lather for 30 seconds, and wash the hair. Then, rinse with running water at 35-40°C for 30 seconds to remove the cleaning agent composition. (Step (II)) For the hair strands treated in step (I), apply 2 g of the conditioning composition for each example and spread evenly. Then, rinse with running water at 35-40°C for 30 seconds to remove the conditioning composition. The above steps (I) to (II) were repeated a total of 5 times for hair treatment. Using 2 g of the cleaning agent composition used in step (I), the treated hair tufts were further cleaned, and the following evaluation criteria were assessed: lubricity during rinsing, softness during rinsing, amount of tangling during rinsing, neatness after towel drying, neatness after drying, drying speed, and persistence of the conditioning effect. The results are shown in Table 2. Furthermore, regarding the lubricity during rinsing, the softness during rinsing, the amount of tangling during rinsing, the neatness after towel drying, and the neatness after drying, the evaluation results of the following benchmark hair strands are set as "score 3" and evaluated in 4 levels. Using 2 g of the cleaning composition of Comparative Example 2, the hair bundle was washed once in the same manner as described above. Then, 2 g of a regular conditioner with the following composition was applied and spread evenly. The hair bundle was rinsed with running water at 40°C for 1 minute. This hair bundle was used as a reference hair bundle. The hair bundle was further washed using 2 g of the cleaning composition of Comparative Example 2, and the following evaluations were made in order of smoothness during rinsing, softness during rinsing, amount of tangling during rinsing, neatness after towel drying, and neatness after drying. [Composition of regular hair conditioner] [(] [quality] [%) Cetyltrimethylammonium chloride (*1) 5.0 Cetyl alcohol (*2) 5.0 Lactic acid 2.0 [water] [] [margin] [] Total 100.0 (*1) "Quartamin 60W" manufactured by Kao Corporation. (*2) "Kalcol 6098" manufactured by Kao Corporation (stock).

[0099] (Lubrication during rinsing) The lubricity of the hair strand surface was evaluated by passing water at 35-40°C over the hair strand after the above treatment, according to the following criteria. 4: Lubricity is higher than the standard hair strand 3: Lubricity is the same as the reference hair strand. 2: Lubrication is slightly inferior to the standard hair strand. 1: I can't feel any lubrication.

[0100] (Softness during rinsing) The hair strands treated with the above-mentioned method were flowed through water at 35~40℃, and the softness of the hair strands was evaluated according to the following criteria. 4: Softness is higher than the standard hair strand 3: Softness is the same as the standard hair strand 2: Slightly less soft than the standard hair strand 1: I can't feel its softness.

[0101] (The amount of hair tangled during rinsing) Pass water at 35-40°C over the treated hair strands and perform a sensory evaluation of the amount of hair tangling during rinsing, according to the following criteria. 4: The number of strands of hair is less than the baseline. 3: The tangled hair strand is the same as the baseline hair strand. 2: Slightly more prone to tangling than the baseline hair strand 1: Clearly, a conflict has arisen.

[0102] (The neatness after being dried with a towel) A sensory evaluation was performed on the neatness of the hair strands after the above treatment was performed by towel drying, according to the following criteria. 4: Easier to tidy up than the standard hair tie 3: The neatness is the same as the reference hair strand. 2: Slightly less even than the baseline hair strand 1: Not neat

[0103] (Uniformity after drying) For the hair strands treated as described above, use a Panasonic EH-NA94 hair dryer (TURBO mode) at a distance of 5 cm from the hair dryer to comb and brush for 4 minutes while drying. The neatness of the hair after complete drying was then assessed using sensory evaluation according to the following criteria. 4: Easier to tidy up than the standard hair tie 3: The neatness is the same as the reference hair strand. 2: Slightly less even than the baseline hair strand 1: Not neat

[0104] (Drying speed) For the hair strands treated as described above, use a Panasonic EH-NA94 hair dryer (TURBO mode) at a distance of 5 cm to comb the hair 20-40 times for 30 seconds while drying. Record the moisture content of the hair every 30 seconds and measure the time taken until the moisture content drops below 0.5%.

[0105] (The duration of the treatment effect) For the hair strands treated as described above, the cleaning agent composition used in each example was used, and step (I) (applying, washing, and rinsing the cleaning agent composition) was repeated only. Each time step (I) was performed, the conditioning effect on the hair strands was evaluated using sensory evaluation, and the number of times the conditioning effect of step (I) on the hair strands treated as described above was evaluated according to the following criteria. 5:5 times or more 4:4 times 3:3 times 2:2 times 1:1 times 0: None

[0106] [Table 2] Table 2 (quality%) Example Comparative example 1 2 3 4 1 2 3 4 Step (I) Cleaning composition (a1) Sodium olefin sulfonate 1*1 12.5 12.5 12.5 12.5 - - - - (a')alkyl sulfate salts*2 - - - - 12.5 12.5 12.5 12.5 Sodium chloride 0.5 0.5 0.5 0.5 0 0 0 0 lactic acid Adjustment amount Adjustment amount Adjustment amount Adjustment amount Adjustment amount Adjustment amount Adjustment amount Adjustment amount water margin margin margin margin margin margin margin margin total 100 100 100 100 100 100 100 100 Step (II) Conditioner Composition (b1) Cetyltrimethylammonium chloride*3 5.0 5.0 (b2) Stearyltrimethylammonium chloride*4 5.0 5.0 (b3) Sulphotrimethylammonium chloride *5 5.0 5.0 (b4) N,N-Dimethyl-3-octadecyloxypropylamine*6 5.0 5.0 Cetyl alcohol*7 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 lactic acid 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 water margin margin margin margin margin margin margin margin total 100 100 100 100 100 100 100 100 Evaluation results Lubrication during rinsing 3 3 4 3 1 1 1 1 Softness during rinsing 3 3 4 3 1 1 1 1 How much hair gets tangled during rinsing 4 4 4 4 1 1 1 1 Neatness after being dried with a towel 4 4 4 4 1 2 1 2 Uniformity after drying 3 3 3 3 1 1 1 1 Drying speed [sec] 150 150 90 120 210 210 210 210 Duration of conditioning effects 5 5 5 5 1 1 1 1

[0107] *1 (a1) Sodium internal olefin sulfonate 1: Sodium internal olefin sulfonate obtained in Manufacturing Example 1 (16 carbons, average double bond position: 4.17) *2 (a') Alkyl sulfate salt: Polyoxyethylene (1) alkyl (C10-16) ether ammonium sulfate, "Emal 125A" manufactured by Kao Corporation. *3 (b1) Cetyltrimethylammonium chloride: "Quartamin 60W" manufactured by Kao Corporation. *4 (b2) Stearyltrimethylammonium chloride: Quartamin 86W manufactured by Kao Corporation. *5 (b3) Sulphotrimethylammonium chloride: "Quartamin 2285E" manufactured by Kao Corporation. *6 (b4)N,N-Dimethyl-3-octadecyloxypropylamine: "Farmin DM E-80" manufactured by Kao Corporation. *7 Cetyl alcohol: Kao Corporation's "Kalcol 6098"

[0108] The above evaluation (1) is a comparison between the use of internal olefin sulfonate sodium in the cleaning composition of step (I) and the use of alkyl sulfate salt instead of internal olefin sulfonate sodium. As shown in Table 2, it can be seen that the method of using sodium internal olefin sulfonate in the cleaning composition of step (I) in Examples 1-4 is more effective than that of Comparative Examples 1-4 in which alkyl sulfate salts are used instead of sodium internal olefin sulfonate in the cleaning composition of step (I).

[0109] Examples 5-12 (Hair treatment methods and evaluation (2)) (Preparation of cleaning agent compositions and conditioning agent compositions) After preparing the components according to the composition shown in Table 3, mix them until homogeneous to prepare the cleaning agent composition and the conditioning agent composition respectively. The pH of the cleaning agent composition was adjusted to 4.3 at 25°C. (Step (I)) After wetting a 5g bundle of dry hair with warm water at 35-40°C, apply 2g of the cleaning agent composition for each example, lather for 30 seconds, and wash the hair. Then, rinse with running water at 35-40°C for 30 seconds to remove the cleaning agent composition. (Step (II)) For the hair strands treated in step (I), apply 2 g of the conditioning composition for each example and spread evenly. Then, rinse with running water at 35-40°C for 30 seconds to remove the conditioning composition. The above steps (I) to (II) were repeated a total of 5 times for hair treatment. Using 2 g of the cleaning agent composition used in step (I), the treated hair tufts were further washed. Following the same order as above, the following were evaluated: lubricity during rinsing, softness during rinsing, amount of tangling during rinsing, neatness after towel drying, neatness after drying, drying speed, and persistence of the conditioning effect. The results are shown in Table 3. Among them, the evaluation results of the above-mentioned benchmark hair strands are set as "score 1" for the lubricity during rinsing, the softness during rinsing, the amount of tangling during rinsing, the neatness after towel drying, and the neatness after drying, and the evaluation results of the hair strands used in Example 9 are set as "score 5", and the evaluation is divided into 5 levels. The same evaluation result as the benchmark hair strand is set as "score 1", the same evaluation result as Example 9 is set as "score 5", the slightly better than the benchmark hair strand is set as "score 2", the slightly worse than Example 9 is set as "score 4", and the middle between score 2 and 4 is set as "score 3".

[0110] [Table 3] Table 3 (quality%) Example 5 6 7 8 9 10 11 12 Step (I) Cleaning composition (a1) Sodium olefin sulfonate*1 0.1 0.1 0.5 0.5 12.5 12.5 15 15 Sodium chloride 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Polyquaternary ammonium salt-10*8 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 water margin margin margin margin margin margin margin margin total 100 100 100 100 100 100 100 100 Step (II) Conditioner Composition (b1) Cetyltrimethylammonium chloride*3 2.5 15 2.5 15 2.5 15 2.5 15 Cetyl alcohol*7 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 lactic acid 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 water margin margin margin margin margin margin margin margin total 100 100 100 100 100 100 100 100 Evaluation results Lubrication during rinsing 3 3 3 3 5 5 5 5 Softness during rinsing 2 3 2 3 5 5 4 5 How much hair gets tangled during rinsing 2 3 3 3 5 5 4 5 Neatness after being dried with a towel 2 3 2 3 5 5 5 4 Uniformity after drying 2 3 2 4 5 5 5 4 Drying speed [sec] 210 180 180 150 120 180 150 90 Duration of conditioning effects 2 3 2 4 5 5 4 4

[0111] *1 (a1) Sodium internal olefin sulfonate 1: Sodium internal olefin sulfonate obtained in Manufacturing Example 1 (16 carbons, average double bond position: 4.17) *3 (b1) Cetyltrimethylammonium chloride: "Quartamin 60W" manufactured by Kao Corporation. *7 Cetyl alcohol: Kao Corporation's "Kalcol 6098" *8 Polytetraammonium Salt-10: O-[2-hydroxy-3-(trimethylammonium)propyl]hydroxyethyl cellulose, manufactured by Kao Corporation as "Caticello L-150"

[0112] The above evaluation (2) is based on a more stringent evaluation criterion than the above evaluation (1), and studies a better range within the scope of the method of the present invention. In Examples 5-12, the content of sodium olefin sulfonate in the cleaning agent composition used in step (I) and the content of cationic surfactant in the conditioning agent composition used in step (II) were changed. As shown in Table 3, it can be seen that the invention is more effective in the cases of Examples 9-12, and preferably Examples 9 and 10. [Industrial Applicability]

[0113] According to the present invention, a method for treating keratin material is provided, which imparts sufficient conditioning effect to the treated keratin material, improves the lubricity and softness of the hair during rinsing, reduces tangling during rinsing, increases drying speed, and improves the neatness of the hair after drying, and the conditioning effect is also excellent in its duration.

Claims

1. A method for treating keratin material, comprising the following steps (I) and (II) in sequence: Step (I): applying a cleaning agent composition (A) to the keratin material, wherein the cleaning agent composition (A) contains an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw material olefin with an average double bond position of 4.0 to 4.4; Step (II): applying a conditioning agent composition (B) containing a cationic surfactant (b) to the keratin material.

2. The method for treating keratinous material as claimed in claim 1, wherein the content of the internal olefin sulfonic acid or its salt (a) in the cleaning agent composition (A) is 0.1% by mass or more and 30% by mass or less.

3. The method for treating keratin substances as claimed in claim 1 or 2, wherein the content of the above-mentioned cationic surfactant (b) in the above-mentioned conditioning agent composition (B) is more than 0.5% by mass and less than 20% by mass.

4. A cosmetic kit for treating keratin substances, comprising a cleansing composition (A) and a conditioning composition (B) containing a cationic surfactant (b), wherein the cleansing composition (A) contains an internal olefin sulfonic acid or a salt thereof having 16 carbons obtained by sulfonating a raw material olefin having an average double bond position of 4.0 to 4.4 positions.

5. A composition for treating keratin substances, comprising an internal olefin sulfonic acid or its salt (a) formed by sulfonating a raw olefin having 16 carbons at an average double bond position of 4.0 to 4.4.