Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

• the present invention relates to a hair cleansing composition.
• Patent Document 1 discloses a foaming composition containing sodium xylene sulfonate as a viscosity modifier, an anionic surfactant, and a foaming agent such as propane or isobutane in specific amounts, and a hair care composition.
• the foam density is adjusted to a specific range.
• Patent Document 2 discloses a composition containing an aromatic sulfonic acid compound such as sulfanilic acid having an amino group or a salt thereof, which straightens or straightens keratin fibers such as hair, and improves ease of handling and We are trying to add smoothness to keratin fibers.
• an aromatic sulfonic acid compound such as sulfanilic acid having an amino group or a salt thereof, which straightens or straightens keratin fibers such as hair, and improves ease of handling and We are trying to add smoothness to keratin fibers.
• hair distortion and shrinkage caused by stimulation of the hair such as ultraviolet rays and heat from a hair dryer, or by aging-related scalp deterioration or changes in pores, can cause stubborn curly hair or frizz.
• stimulation of the hair such as ultraviolet rays and heat from a hair dryer, or by aging-related scalp deterioration or changes in pores
• hair distortion and shrinkage caused by stimulation of the hair can cause stubborn curly hair or frizz.
• Patent Document 1 Japanese Patent Publication No. 2019-505546
• Patent Document 2 Japanese Patent Application Publication No. 2019-73443
• the present invention comprises the following components (A) and (B): (A) Aromatic sulfonic acid or its salt 1% by mass or more and 8% by mass or less (B) Sulfonated raw material olefin having 16 carbon atoms and having an average double bond position of 3.9 or more and 4.4 or less , an internal olefin sulfonic acid having 16 carbon atoms or a salt thereof, and having a pH of 1 or more and less than 5 at 25° C. when made into a 5% by mass aqueous solution. It is something that provides something.
• Patent Document 1 no consideration is given to alleviating curls and frizz in hair, and there is plenty of room for improvement. Furthermore, even with the technique described in Patent Document 2, a certain amount of time is unavoidably required in order to obtain sufficient effects. Therefore, the user still faces an excessive burden when using the device repeatedly every day. As described above, a hair cleanser that can sufficiently alleviate curls and frizz while reducing the burden on the user has not yet been realized.
• the present invention relates to a hair cleansing composition that uses an aromatic sulfonic acid or a salt thereof and exhibits excellent performance from washing to rinsing and after washing when applied to hair.
• a hair cleansing composition can be obtained that can effectively alleviate frizz and frizz in hair even when used for a relatively short time.
• the hair cleansing composition of the present invention curl and frizz in hair can be effectively and quickly alleviated while making it possible to shorten the time required for one use.
• the amount of foaming is sufficient as a hair cleansing agent, and the squeaking of the hair during rinsing after cleaning can be reduced. Therefore, in repeated daily use, it is possible to easily achieve straight, glossy, manageable, and youthful hair while effectively reducing the burden on the user.
• the hair cleansing composition of the present invention contains aromatic sulfonic acid or its salt in an amount of 1% by mass or more and 8% by mass or less as component (A).
• component (A) can effectively and quickly exert the effect of alleviating curls and frizz in hair.
• component (A) for example, one or two selected from benzenesulfonic acid or its salt, naphthalenesulfonic acid or its salt, azulenesulfonic acid or its salt, benzophenonesulfonic acid or its salt, etc.
• component (A) for example, one or two selected from benzenesulfonic acid or its salt, naphthalenesulfonic acid or its salt, azulenesulfonic acid or its salt, benzophenonesulfonic acid or its salt, etc.
• the salts of component (A) include sodium salts, potassium salts, lithium salts, aluminum salts, ammonium salts (NH 4+ ), and organic ammonium salts.
• benzenesulfonic acid or a salt thereof includes, for example, benzenesulfonic acid, o-toluenesulfonic acid, p-toluenesulfonic acid, xylene sulfonic acid, cumenesulfonic acid, ethylbenzenesulfonic acid, 2,4,6 -One or more selected from trimethylbenzenesulfonic acid, salts thereof, and the like.
• naphthalenesulfonic acid or its salt includes, for example, 1- or 2-naphthalenesulfonic acid ( ⁇ - or ⁇ -naphthalenesulfonic acid), 2,7-naphthalenedisulfonic acid, 1,5-naphthalenedisulfonic acid Acid, 2,6-naphthalenedisulfonic acid, 1-naphthol-2-sulfonic acid, 1-naphthol-4-sulfonic acid, 2-naphthol-6-sulfonic acid, 2-naphthol-7-sulfonic acid, 2,3- Dihydroxynaphthalene-6-sulfonic acid, 1,7-dihydroxynaphthalene-3-sulfonic acid, J acid (2-amino-5-naphthol-7-sulfonic acid), 1-amino-2-naphthol-4-sulfonic acid, 1-Naphthylamine-4-sulfonic acid, Broenaz acid (2-a
• the azulenesulfonic acid or its salt includes, for example, guaiazulenesulfonic acid, 1-azulenesulfonic acid, 3-acetyl-7-isopropyl-1-azulenesulfonic acid, 3-(2-hydroxyethyl)- 7-isopropyl-1-azulene sulfonic acid, 3-methyl-7-isopropyl-1-azulene sulfonic acid, 7-isopropyl-1-azulene sulfonic acid, 1,4-dimethyl-7-isopropyl-2-azulene sulfonic acid, Examples include one or more selected from 1,3-azulene disulfonic acid, 3-formyl-4,6,8-trimethyl-1-azulene sulfonic acid, salts thereof, and the like.
• the benzophenonesulfonic acid or its salt includes, for example, o-chlorobenzophenonesulfonic acid, p-chlorobenzophenonesulfonic acid, 2-hydroxybenzophenonesulfonic acid, 4-hydroxybenzophenonesulfonic acid, and 2-aminobenzophenonesulfonic acid. acid, 4-aminobenzophenone sulfonic acid, 2-methylbenzophenone sulfonic acid, 4-methoxybenzophenone sulfonic acid, 4,4'-dimethylbenzophenone sulfonic acid, and salts thereof. .
• component (A) 1 selected from benzenesulfonic acid, naphthalenesulfonic acid, and salts thereof, from the viewpoint of synergistically exerting the effect of alleviating frizz and frizz in hair, together with component (B) described below.
• One or more types are preferable, and one or more types selected from o-toluenesulfonic acid, p-toluenesulfonic acid, 2-naphthalenesulfonic acid, and salts thereof are more preferable.
• the content of component (A) is 1% by mass or more, preferably 1% by mass, in the hair cleansing composition of the present invention, from the viewpoint of effectively and quickly exerting the effect of alleviating frizz and frizz in the hair.
• the content is .5% by mass or more, more preferably 2% by mass or more, and 8% by mass or less, preferably 6% by mass or less, and more preferably 4% by mass or less.
• the content of component (A) in the hair cleansing composition of the present invention is 1% by mass or more and 8% by mass or less, preferably 1.5 to 6% by mass, and more preferably It is 2 to 4% by mass.
• the hair cleansing composition of the present invention has 16 carbon atoms, which is obtained by sulfonating a raw material olefin having 16 carbon atoms and having an average double bond position of 3.9 to 4.4 as component (B). It contains 4% by mass or more and 25% by mass or less of internal olefin sulfonic acid or its salt. That is, the internal olefin sulfonic acid having 16 carbon atoms or its salt as component (B) is a compound obtained by sulfonating a starting material olefin having an average double bond position within a specific and extremely limited range. Specifically, it is a compound obtained by sulfonating a raw material olefin, followed by neutralization and hydrolysis.
• Salts of internal olefin sulfonic acids having 16 carbon atoms which are obtained by sulfonating raw olefins having 16 carbon atoms with an average double bond position of 3.9 to 4.4, include sodium salts, potassium salts, etc.
• Alkali metal salts such as ammonium salts, monoethanolamine salts, diethanolamine salts, triethanolamine salts, 2-aminoethanol salts, and 2-aminomethylpropanediol salts
• basic amino acid salts such as lysine salts and arginine salts
• These internal olefin sulfonates having 16 carbon atoms do not necessarily have to be in salt form from the beginning, and salts produced by neutralization reactions during production may be used.
• salts of internal olefin sulfonic acids having 16 carbon atoms sodium salts, potassium salts, ammonium salts and 2-aminoethanol salts are preferred from the viewpoint of effectively enhancing the effect of alleviating frizz and frizz in hair together with component (A).
• One or more selected from these are preferred, one or two selected from sodium salts and potassium salts are more preferred, sodium salts are even more preferred, and sodium internal olefin sulfonate having 16 carbon atoms is even more preferred.
• the internal olefin sulfonic acid having 16 carbon atoms or its salt as component (B), which is a product obtained from such a raw material olefin having 16 carbon atoms, is mainly a hydroxyalkanesulfonic acid having 16 carbon atoms or a salt thereof (hydroxy form , abbreviation "HAS”) and a C16 olefin sulfonic acid or its salt (olefin body, abbreviation "IOS").
• the raw material olefin having 16 carbon atoms which is the starting material for component (B), has a double bond mainly inside the carbon chain, but the so-called olefin in which the double bond is located at the 1st position of the carbon chain It may also contain a trace amount of ⁇ -olefin.
• ⁇ -sultone is mainly produced, and a part of ⁇ -sultone is converted into ⁇ -sultone and olefin sulfonic acid.
• ⁇ -sultones, ⁇ -sultones, and olefin sulfonic acids are converted into hydroxyalkanesulfonic acids having 16 carbon atoms or salts thereof and olefin sulfonic acids having 16 carbon atoms or salts thereof in the neutralization/hydrolysis step (for example, J. Am. Oil Chem. Soc. 69, 39 (1992)).
• the hydroxy group of the obtained hydroxyalkanesulfonic acid or its salt is located inside the alkane chain, and the double bond of the olefinsulfonic acid or its salt is located inside the olefin chain. Therefore, in this specification, each of these products and mixtures thereof are collectively referred to as component (B), a C16 internal olefin sulfonic acid or a salt thereof.
• the raw material olefin having 16 carbon atoms which forms component (B), the internal olefin sulfonic acid having 16 carbon atoms or its salt by being sulfonated has an average double bond position of 3.9 or more and 4.4 or less. be.
• a raw material olefin having 16 carbon atoms and having such an average double bond position has a broad distribution of double bond positions from the 2nd to 8th positions, including the 1st position, which may be present in trace amounts. Note that the double bond position and its distribution in the raw material olefin can be confirmed by measurement using a gas chromatograph mass spectrometer (abbreviated as "GC-MS").
• each component with different carbon chain length and double bond position is accurately separated using a gas chromatograph analyzer (hereinafter abbreviated as GC), and each component is subjected to a mass spectrometer (abbreviated as "MS").
• GC gas chromatograph analyzer
• MS mass spectrometer
• component (B) is defined based on the value of the average double bond position in the starting material olefin.
• Component (B) used in the present invention is an internal olefin sulfonic acid or a salt thereof obtained from a raw material olefin having the above average double bond position value, that is, a broad double bond distribution, and is The sulfonic acid groups are present in a wide range of positions without being excessively unevenly distributed.
• an internal olefin sulfonic acid having 16 carbon atoms or a salt thereof if the sulfonic acid group is unevenly distributed near the end of the carbon chain, the melting point increases due to the increase in the length of the carbon chain, which may cause precipitation to occur easily.
• the sulfonic acid groups are unevenly distributed closer to the inside of the carbon chain, the foam quality during washing and the feel of the hair during rinsing may be impaired, and the hair washing effect may be reduced.
• the component (B) is an internal olefin sulfonic acid having 16 carbon atoms or its salt obtained from the above-mentioned raw material olefin, the sulfonic acid groups are not unevenly distributed in the carbon chain but are present in broad positions, and the sulfonic acid It consists of a moderate mixture of internal olefin sulfonic acids or salts thereof having various lengths of carbon chains from the bonding position of the group to the end.
• the average double bond position (unit: position, abbreviation "DBP") in the raw material olefin having 16 carbon atoms refers to the average double bond position (unit: position, abbreviation "DBP") of each It means the average value of the double bond positions of the raw material olefin having 16 carbon atoms.
• the average double bond position in the raw material olefin having 16 carbon atoms is a value determined by the following formula (1).
• n is an integer (unit: position) representing the position of the double bond present in the raw material olefin having 16 carbon atoms.
• Cn is , indicates the content (unit: mass %) of a raw material olefin with 16 carbon atoms in which a double bond is present in the n-position.
• the average double bond position in the raw material olefin having 16 carbon atoms forming component (B) is at least 3.9 position, preferably at least 4.0 position, from the viewpoint of ensuring excellent hair washing effect.
• 4.4 or lower preferably 4.3 or lower, more preferably 4.2 or lower.
• the average double bond position in the raw material olefin having 16 carbon atoms is from the 3.9th position to the 4.4th position, preferably from 4.0 to 4.4, more preferably from 4.0 to 4.4. 4.3, more preferably 4.0 to 4.2.
• the content of the raw material olefin having a double bond at the 2nd position is preferably 10% by mass or more, more preferably 15% by mass in the raw material olefin having 16 carbon atoms.
• the content is more preferably 20% by mass or more, preferably 35% by mass or less, more preferably 32% by mass or less, and even more preferably 24% by mass or less.
• the content of the raw material olefin having a double bond at the 2nd position is preferably 10 to 35% by mass, more preferably 15 to 35% by mass, in the raw material olefin having 16 carbon atoms.
• the content is 32% by mass, more preferably 20 to 24% by mass.
• the content of the raw material olefin having a double bond at position 3 is preferably 10% by mass or more, more preferably 14% by mass or more in the raw material olefin having 16 carbon atoms. It is more preferably 16% by mass or more, preferably 30% by mass or less, more preferably 24% by mass or less, and even more preferably 19% by mass or less.
• the content of the raw material olefin having a double bond at position 3 is preferably 10 to 30% by mass, more preferably 14 to 30% by mass, in the raw material olefin having 16 carbon atoms. The content is 24% by mass, more preferably 16 to 19% by mass.
• the content of the raw material olefin having a double bond at the 4th position is preferably 10% by mass or more, more preferably 15% by mass or more in the raw material olefin having 16 carbon atoms. It is more preferably 17% by mass or more, preferably 30% by mass or less, more preferably 25% by mass or less, and still more preferably 19% by mass or less.
• the content of the raw material olefin having a double bond at the 4th position is preferably 10 to 30% by mass, more preferably 15 to 30% by mass, in the raw material olefin having 16 carbon atoms. The content is 25% by mass, more preferably 17 to 19% by mass.
• the content of the raw material olefin having a double bond at the 5th position is preferably 5% by mass or more, more preferably 10% by mass or more in the raw material olefin having 16 carbon atoms.
• the content is more preferably 13% by mass or more, preferably 25% by mass or less, more preferably 19% by mass or less, and even more preferably 15% by mass or less.
• the content of the raw material olefin having a double bond at the 5th position is preferably 5 to 25% by mass, more preferably 10 to 25% by mass, in the raw material olefin having 16 carbon atoms.
• the content is 19% by mass, more preferably 13 to 15% by mass.
• the content of the raw material olefin having a double bond at the 6th position is preferably 5% by mass or more, more preferably 7% by mass or more in the raw material olefin having 16 carbon atoms.
• the content is more preferably 11% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, and still more preferably 13% by mass or less.
• the content of the raw material olefin having a double bond at the 6th position is preferably 5 to 20% by mass, more preferably 7 to 20% by mass, in the raw material olefin having 16 carbon atoms.
• the content is 15% by mass, more preferably 11 to 13% by mass.
• the total content of raw material olefins having a double bond at the 7th or 8th position is preferably 5% by mass or more, more preferably 7% by mass or more in the raw material olefin having 16 carbon atoms. It is at least 12% by mass, more preferably at least 12% by mass, preferably at most 25% by mass, even more preferably at most 22% by mass, even more preferably at most 16% by mass.
• the total content of the raw material olefin having a double bond at the 7th or 8th position is preferably 5 to 25% by mass in the raw material olefin having 16 carbon atoms, and more preferably Preferably it is 7 to 22% by weight, more preferably 12 to 16% by weight.
• the mass ratio of the content of the raw material olefin with a double bond in the 3rd to 5th positions to the content of the raw material olefin with a double bond in the 6th to 8th positions is preferably 1.0 or more, more preferably 1.3 or more, still more preferably 1.7 or more, and preferably 4.0 or less. , more preferably 3.5 or less, still more preferably 2.2 or less.
• the mass ratio (raw material Olefin position 3 to 5 /raw material olefin position 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. It is.
• the content of the raw material olefin having a double bond at the 1st position ( ⁇ -olefin), which may be unavoidably present, is preferably 5.0 mass by mass in the raw material olefin having 16 carbon atoms. %, more preferably less than 3.0% by mass, still more preferably less than 2.5% by mass, or the raw material olefin having 16 carbon atoms preferably does not contain ⁇ -olefin.
• the above-mentioned raw material olefin having 16 carbon atoms is obtained by isomerizing (double bond transfer) a raw material olefin ( ⁇ -olefin) having a double bond in the 1st position, which is produced by a dehydration reaction of an alcohol having 16 carbon atoms.
• a solid acid catalyst such as alumina is preferably 0.5 parts by mass or more, more preferably 2 parts by mass or more, preferably 15 parts by mass or less, more preferably 15 parts by mass or less, per 100 parts by mass of 1-hexadecanol. 10 parts by weight or less, preferably 0.5 to 15 parts by weight, more preferably 2 to 10 parts by weight.
• the mixture is stirred preferably at 220°C or higher, more preferably 260°C or higher, preferably 350°C or lower, and preferably 220 to 350°C, more preferably 260 to 350°C, preferably for 1 hour or more.
• the isomerization reaction is more preferably carried out for 3 hours or more, preferably 30 hours or less, more preferably 10 hours or less, and more preferably 1 to 30 hours, more preferably 3 to 10 hours.
• the internal olefin sulfonic acid having 16 carbon atoms or its salt as component (B), which is obtained by sulfonating the raw material olefin having 16 carbon atoms the internal olefin sulfonic acid or its salt has a sulfonic acid group at the 1st to 4th positions.
• the content of salt in component (B) is preferably 40% by mass or more, more preferably 50% by mass or more, still more preferably 55% by mass or more, and preferably 75% by mass or less. , more preferably 70% by mass or less, still more preferably 68% by mass or less.
• the content of the salt thereof in component (B) is preferably 40% by mass or more and 75% by mass or less, more preferably 50 to 70% by mass, and even more preferably 55 to 68% by mass.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• the content of sodium internal olefin sulfonate in which a sulfonic acid group is present at the 1st to 4th positions in the sodium internal olefin sulfonate having 16 carbon atoms The same applies to the above.
• the content of the internal olefin sulfonic acid or its salt in which the sulfonic acid group is present at the 2-position is preferably 10% by mass in component (B). % or more, more preferably 13% by mass or more, still more preferably 17% by mass or more, preferably 35% by mass or less, more preferably 30% by mass or less, even more preferably 25% by mass. It is as follows.
• the content of the internal olefin sulfonic acid or salt thereof having a sulfonic acid group at the 2-position is preferably The content is 10% by mass or more and 35% by mass or less, more preferably 13 to 30% by mass, and even more preferably 17 to 25% by mass.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• the content of sodium internal olefin sulfonate in which the sulfonic acid group is present at the 2-position in the sodium internal olefin sulfonate having 16 carbon atoms is also as described above. It is similar to
• the content of the internal olefin sulfonic acid or its salt in which the sulfonic acid group is present at the 3-position is preferably 5% by mass in component (B). % or more, more preferably 11% by mass or more, still more preferably 15% by mass or more, preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 20% by mass. It is as follows.
• the content of the internal olefin sulfonic acid or salt thereof having a sulfonic acid group at the 3-position is preferably The content is 5% by mass or more and 30% by mass or less, more preferably 11 to 25% by mass, and even more preferably 15 to 20% by mass.
• component (B) is a sodium internal olefin sulfonate having 16 carbon atoms
• the content of sodium internal olefin sulfonate in which a sulfonic acid group is present at the 3-position in the sodium internal olefin sulfonate having 16 carbon atoms is also as described above. It is similar to
• the content of the internal olefin sulfonic acid or its salt having a sulfonic acid group at the 4-position in the component (B) is preferably 15% by mass. % or more, more preferably 18% by mass or more, still more preferably 19% by mass or more, preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 23% by mass. It is as follows.
• the content of the internal olefin sulfonic acid or salt thereof having a sulfonic acid group at the 4-position is preferably The content is 15% by mass or more and 30% by mass or less, more preferably 18 to 25% by mass, and even more preferably 19 to 23% by mass.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• the content of sodium internal olefin sulfonate in which the sulfonic acid group is present at the 4-position in the sodium internal olefin sulfonate having 16 carbon atoms is also as specified above. It is similar to
• the content of the internal olefin sulfonic acid or salt thereof having a sulfonic acid group at the 1-position is preferably as follows: less than 5.0% by mass, more preferably less than 3.0% by mass, even more preferably less than 2.5% by mass, or the component (B) is an internal olefin sulfonic acid having 16 carbon atoms or a salt thereof. It is preferable that the sulfonic acid group does not contain an internal olefin sulfonic acid or a salt thereof in which the sulfonic acid group is present at the 1-position.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• the content of the sodium internal olefin sulfonate in which the sulfonic acid group is present at the 1-position in the sodium internal olefin sulfonate having 16 carbon atoms is also as described above. It is preferable not to contain an internal sodium olefin sulfonate which is similar to or in which the sulfonic acid group is present in the 1-position.
• the mass ratio between the content of hydroxyl form (HAS) and the content of olefin form (IOS) (hydroxy form/olefin form) is determined by the productivity. From the viewpoint of improvement and impurity reduction, the ratio is preferably 50/50 to 100/0, more preferably 60/40 to 100/0, even more preferably 70/30 to 100/0, and still more preferably The ratio is 75/25 to 100/0, and more preferably 75/25 to 95/5.
• the mass ratio (hydroxy body/olefin body) is determined based on the HPLC-MS peak area obtained by separating the hydroxy body and olefin body from component (B) by HPLC and subjecting each to MS.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• HAS sodium internal olefin sulfonate having 16 carbon atoms
• IOS olefin body
• component (B) Since the internal olefin sulfonic acid having 16 carbon atoms or its salt as component (B) is obtained by sulfonating the raw material olefin, unreacted raw material olefin and inorganic compounds remain in the component (B). There is a possibility. It is preferable that the content of these components is small. The same applies when component (B) is sodium internal olefin sulfonate having 16 carbon atoms.
• the content of unreacted raw material olefin in component (B) is preferably less than 5.0% by mass, more preferably 3.0% by mass. It is less than .0% by weight, more preferably less than 1.5% by weight, and even more preferably less than 1.0% by weight.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• the content of unreacted raw material olefin in the sodium internal olefin sulfonate having 16 carbon atoms is the same as above.
• the content of the inorganic compound in component (B) is preferably less than 7.5% by mass, more preferably 5.0% by mass. %, more preferably less than 3.0% by weight, even more preferably less than 2.0% by weight, and even more preferably less than 1.6% by weight.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms
• the content of the inorganic compound in the sodium internal olefin sulfonate having 16 carbon atoms is also the same as above.
• the content of component (B) is 4% by mass or more and 25% by mass or less in the hair cleansing composition of the present invention, from the viewpoint of effectively and quickly exerting the effect of alleviating frizz and frizz in the hair.
• the content is preferably 20% by mass or less, more preferably 18% by mass or less, and even more preferably 16% by mass or less.
• the content of component (B) in the hair cleansing composition of the present invention is 4% by mass or more and 25% by mass or less, preferably 4 to 20% by mass, more preferably 4 to 20% by mass.
• the content is 18% by mass, more preferably 4 to 16% by mass.
• the total content ((A) + (B)) of the content of component (A) and the content of component (B) is determined from the viewpoint of more effectively and quickly exerting the effect of alleviating curls and frizz in the hair.
• the hair cleansing composition of the present invention preferably 5% by mass or more, more preferably 8% by mass or more, still more preferably 10% by mass or more, preferably 30% by mass or less, More preferably it is 25% by mass or less, and still more preferably 20% by mass or less.
• the total content ((A)+(B)) of the content of component (A) and the content of component (B) is preferably 5 to 30% in the hair cleansing composition of the present invention. It is preferably 8 to 25% by mass, and even more preferably 10 to 20% by mass.
• the mass ratio ((A)/(B)) between the content of component (A) and the content of component (B) is determined from the viewpoint of more effectively and quickly exerting the effect of alleviating frizz and frizz in hair. From the viewpoint of generating a sufficient amount of foam as a cleaning agent and also reducing the squeaking of the hair during rinsing after washing, it is preferably 0.05 or more, more preferably 0.08 or more, and even more preferably is 0.13 or more, even more preferably 0.15 or more, preferably 2 or less, more preferably 1.5 or less, still more preferably 1.0 or less, even more preferably It is 0.8 or less.
• the mass ratio ((A)/(B)) between the content of component (A) and the content of component (B) is preferably 0.05 or more and 2 or less, more preferably 0.08 to 2. 1.5, more preferably 0.13 to 1.0, even more preferably 0.15 to 0.8.
• the internal olefin sulfonic acid having 16 carbon atoms or its salt as component (B) can be obtained by reacting the above-mentioned raw material olefin having 16 carbon atoms with sulfur trioxide to sulfonate the raw material olefin. It can be obtained by sulfonating, neutralizing, and then hydrolyzing. More specifically, the amount of sulfur trioxide used when sulfonating the raw material olefin is as follows: Preferably it is 0.8 mol or more, more preferably 0.9 mol or more, and still more preferably 0.95 mol or more.
• the amount of sulfur trioxide used when sulfonating the raw material olefin is preferably 1.2 mol or less, more preferably 1.2 mol or less, from the economical viewpoint and from the viewpoint of suppressing unnecessary coloration of component (B). is 1.1 mol or less, more preferably 1.05 mol or less.
• the amount of sulfur trioxide used when sulfonating the raw material olefin is preferably 0.8 to 1.2 mol, more preferably 0.9 to 1.1 mol, per 1 mol of the raw material olefin. and more preferably 0.95 to 1.05 mol.
• the reaction temperature when sulfonating the raw material olefin is preferably 0°C or higher from the viewpoint of preventing coagulation of sulfur trioxide and component (B), and from the viewpoint of suppressing unnecessary coloring of component (B). , preferably 50°C or lower.
• the reaction temperature when sulfonating the raw material olefin is preferably 0 to 50°C.
• an alkali compound such as sodium hydroxide, potassium hydroxide, ammonia, 2-aminoethanol, etc.
• the amount of the alkali compound added is preferably 1.0 mole or more per mole of sulfonic acid group, from the viewpoint of suppressing the formation of impurities such as raw material olefins and inorganic salts, and from the viewpoint of improving reactivity. More preferably, the amount is 1.03 moles or more. Further, the amount of the alkali compound added is preferably 2.5 times or less by mole per mole of sulfonic acid group, from the viewpoint of economic efficiency and from the viewpoint of suppressing the formation of impurities such as raw material olefins and inorganic salts.
• the temperature at which the sulfonated raw material olefin and the alkaline compound are mixed and the reaction temperature are preferably 40°C or lower from the viewpoint of suppressing the formation of impurities such as internal olefins and inorganic salts due to side reactions.
• the temperature is more preferably 35°C or lower, further preferably 30°C or lower, still more preferably 25°C or lower, and from the viewpoint of improving reactivity, preferably 0°C or higher, more preferably 10°C or lower. °C or higher, more preferably 15°C or higher, and still more preferably 20°C or higher.
• the temperature and reaction temperature when mixing the sulfonated raw material olefin and the alkali compound are preferably 0 to 40°C, more preferably 10 to 35°C, and even more preferably 15 to 30°C. , and more preferably 20 to 25°C.
• the reaction temperature in the hydrolysis performed after neutralization is preferably 120°C or higher, more preferably 140°C or higher, and even more preferably 160°C or higher in the presence of water, from the viewpoint of improving reactivity.
• the reaction temperature in hydrolysis is preferably 220°C or lower, more preferably 180°C or lower, from the viewpoint of suppressing decomposition of the product.
• the reaction temperature in hydrolysis is preferably 120 to 220°C, more preferably 140 to 180°C, even more preferably 160 to 180°C. From the viewpoint of completing the reaction, the reaction time for hydrolysis is preferably 30 minutes or more, more preferably 45 minutes or more.
• the reaction time for hydrolysis is preferably 240 minutes or less, more preferably 180 minutes or less, still more preferably 120 minutes or less, and even more preferably 90 minutes. It is as follows.
• the reaction time for hydrolysis is preferably 30 to 240 minutes, more preferably 45 to 180 minutes, even more preferably 45 to 120 minutes, and even more preferably 45 to 90 minutes. These reactions can be performed sequentially. Further, after the reaction is completed, it can be purified by extraction, washing, etc.
• component (B) is sodium internal olefin sulfonate having 16 carbon atoms and the sodium internal olefin sulfonate having 16 carbon atoms is obtained, the same as above applies.
• the hair cleansing composition of the present invention may further contain one or more selected from fatty acid polyoxyethylene sorbitan ester and polyoxyethylene alkyl ether.
• the number of carbon atoms in the fatty acid residue of the fatty acid polyoxyethylene sorbitan ester is preferably 8 or more, more preferably 10 or more, preferably 18 or less, and more preferably 14 or less.
• the average number of moles of ethyleneoxy groups added in the fatty acid polyoxyethylene sorbitan ester is preferably 5 or more, more preferably 10 or more, preferably 50 or less, and more preferably 30 or less.
• R 1 -O-(CH 2 CH 2 -O) m -H...(2) R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 8 or more carbon atoms and 18 or less carbon atoms, and m represents a number of 5 or more and 50 or less as an average value.
• the number of carbon atoms in R 1 is preferably 10 or more, more preferably 12 or more, and preferably 16 or more, from the viewpoint of effectively and quickly alleviating curl and frizz in the hair. or less, more preferably 14 or less.
• such fatty acid polyoxyethylene sorbitan esters include polyoxyethylene sorbitan monolaurate (e.g., polysorbate 20), polyoxyethylene sorbitan monopalmitate (e.g., polysorbate 40), and polyoxyethylene sorbitan monostearate (e.g., polysorbate 40).
• polysorbate 60) and polyoxyethylene monooleate e.g, polysorbate 80.
• polyoxyethylene sorbitan monolaurate and polyoxyethylene sorbitan monopalmitate are preferred, and polyoxyethylene sorbitan monolaurate is more preferred, from the viewpoint of rapidly increasing the effect of alleviating frizz and frizz in hair.
• polyoxyethylene alkyl ether polyoxyethylene (5) lauryl ether, polyoxyethylene (23) lauryl ether, polyoxyethylene (7) cetyl ether, polyoxyethylene (13) cetyl ether, polyoxyethylene ( 12) Stearyl ether and polyoxyethylene (13) oleyl ether.
• polyoxyethylene lauryl ether and polyoxyethylene cetyl ether are preferred, and polyoxyethylene lauryl ether is more preferred, from the viewpoint of rapidly increasing the effect of alleviating frizz and frizz in hair.
• the content of one or more selected from these fatty acid polyoxyethylene sorbitan esters and polyoxyethylene alkyl ethers is determined in the hair cleanser composition of the present invention from the viewpoint of rapidly increasing the effect of alleviating frizz and frizz in hair.
• the product preferably 0.1% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, preferably 15% by mass or less, and more preferably is 12% by mass or less, more preferably 10% by mass or less.
• the content of one or more selected from these fatty acid polyoxyethylene sorbitan esters and polyoxyethylene alkyl ethers is preferably 0.1 to 15% by mass in the hair cleansing composition of the present invention.
• the content is more preferably 0.2 to 12% by mass, and even more preferably 0.5 to 10% by mass.
• the hair cleansing composition of the present invention can further contain a basic amino acid. Thereby, it is possible to exert an effective and rapid effect of alleviating curls and frizz in the hair.
• a basic amino acid include arginine, lysine, histidine, guanidine, and the like. Among these, arginine is preferred from the viewpoint of effectively and quickly increasing the effect of alleviating curls and frizz in hair.
• the content of basic amino acids is preferably 0.5% by mass or more, more preferably 0.5% by mass or more in the hair cleansing composition of the present invention, from the viewpoint of effectively and quickly increasing the effect of alleviating frizz and frizz in hair. is 1.0% by mass or more, preferably 15% by mass or less, more preferably 12% by mass or less, and even more preferably 10% by mass or less.
• the content of basic amino acids in the hair cleansing composition of the present invention is preferably 0.5 to 15% by mass, more preferably 1.0 to 12% by mass, and even more preferably It is 1.0 to 10% by mass.
• the hair cleansing composition of the present invention preferably further contains water. Thereby, each component of the hair cleansing composition can be dispersed or dissolved well, and the permeability into the hair can be promoted.
• water include ion exchange water and distilled water.
• the content of water in the hair cleansing composition of the present invention is preferably 10% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more, and preferably 95% by mass or more. % by mass or less.
• the water content in the hair cleansing composition of the present invention is preferably 10 to 95% by mass, more preferably 30 to 95% by mass, and even more preferably 50 to 95% by mass. be.
• the content of fatty acids or salts thereof is limited in order to maintain an excellent effect of alleviating frizz and frizz in the hair and to avoid loss of storage stability.
• fatty acids or salts thereof include fatty acids having 8 or more and 22 or less carbon atoms or salts thereof.
• fatty acid salts include sodium salt, potassium salt,
• examples include inorganic salts selected from magnesium salts and ammonium salts, and organic amine salts such as monoethanolamine salts, diethanolamine salts, and triethanolamine salts.
• the content of such fatty acids or salts thereof in the hair cleansing composition of the present invention is preferably 2.5% by mass or less, more preferably 1.5% by mass or less, and still more preferably 0.5% by mass or less. It is 1% by mass or less.
• the content of the fatty acid having 14 carbon atoms or the salt thereof in the total amount of the fatty acid or salt thereof is preferably is less than 80% by mass, more preferably less than 50% by mass, even more preferably less than 20% by mass.
• the hair cleansing composition of the present invention may contain other components that are usually blended in hair cleansers, within a range that does not impede the effects of the present invention.
• Such ingredients include, for example, surfactants other than the above ingredients, antioxidants, oils, anti-dandruff agents, vitamins, bactericidal agents, anti-inflammatory agents, preservatives, chelating agents, humectants, pearl agents, ceramides, Examples include fragrances, ultraviolet absorbers, pH adjusters, and the like.
• the hair cleansing composition of the present invention has a pH of 1 or more and less than 5 at 25° C. when made into a 5% by mass aqueous solution. Thereby, the penetration of the ingredients contained in the hair cleansing composition of the present invention into the hair can be effectively and efficiently promoted.
• the pH at 25°C is such that the ingredients contained in the hair cleansing composition of the present invention permeate into the hair effectively and efficiently. From the viewpoint of promotion, it is 1 or more, preferably 2 or more, more preferably 3 or more, less than 5, preferably 4.5 or less, and more preferably 4 or less.
• the pH at 25°C is 1 or more and less than 5, preferably 2 to 4.5, more preferably 3 to 4.5. It is 4.
• the pH at 25° C. when the hair cleansing composition of the present invention is made into a 5% by mass aqueous solution specifically means a value measured by the method described in Examples.
• the hair cleansing composition of the present invention is extremely useful as a composition for suppressing curl and/or frizz of hair.
• the hair cleansing composition of the present invention specifically, for example, after applying the hair cleansing composition of the present invention to the hair, the hair is rinsed. All you have to do is implement the method. More specifically, the hair cleansing composition of the present invention may be first placed on the palms of the hands and lathered appropriately by rubbing both hands together, and then applied to the hair.
• the amount of the hair cleansing composition of the present invention applied to hair is preferably 0.2 g or more and 50 g or less per 100 g of hair per application.
• the hair may be washed using the palm of the hand or a tool such as a brush.
• the time required for rinsing the hair after applying the hair cleansing composition to the hair is such that the hair cleansing composition of the present invention can effectively and quickly sufficiently alleviate frizz and frizz in the hair. Therefore, the time is preferably 1 minute or more, and may be 10 minutes or less, and further may be 5 minutes or less.
• the present invention further discloses the following hair cleansing composition.
• Component (A) is preferably one or more selected from benzenesulfonic acid or its salt, naphthalenesulfonic acid or its salt, azulenesulfonic acid or its salt, benzophenonesulfonic acid or its salt, etc.
• the salt of component (A) is a sodium salt, a potassium salt, a lithium salt, an aluminum salt, an ammonium salt (NH 4+ ), or an organic ammonium salt. Cleaning composition.
• Component (B) is preferably one or more selected from alkali metal salts, organic amine salts, and basic amino acid salts, more preferably sodium salts, potassium salts, ammonium salts, and 2-amino acid salts. Any of the above [1] to [4], which is one or more selected from ethanol salts, more preferably one or two selected from sodium salts and potassium salts, and even more preferably sodium salts.
• the content of component (A) in the hair cleansing composition of the present invention is preferably 1.5% by mass or more, more preferably 2% by mass or more, and preferably 6% by mass.
• the hair cleansing composition according to any one of [1] to [5] above, which has a content of no more than 4% by mass, more preferably no more than 4% by mass. [7] Any one of [1] to [6] above, wherein the content of component (B) is preferably 20% by mass or less, more preferably 18% by mass or less, and even more preferably 16% by mass or less. 1. Hair cleansing composition. [8] The mass ratio ((A)/(B)) between the content of component (A) and the content of component (B) is preferably 0.05 or more, more preferably 0.08 or more.
• the hair cleansing composition according to any one of [1] to [7] above, which is even more preferably 0.8 or less.
• the pH at 25°C when made into a 5% by mass aqueous solution is preferably 2 or more, more preferably 3 or more, and less than 5, preferably 4.5 or less, and more preferably is 4 or less, the hair cleansing composition according to any one of [1] to [8] above.
• the content of one or more selected from fatty acid polyoxyethylene sorbitan ester and polyoxyethylene alkyl ether is preferably 0.1% by mass or more in the hair cleansing composition of the present invention.
• the hair cleansing composition is more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, preferably 15% by mass or less, more preferably 12% by mass or less, and even more preferably 10% by mass. % or less, the hair cleansing composition of [10] above.
• the hair cleansing composition according to any one of [1] to [11] above, further containing a basic amino acid.
• the content of basic amino acids in the hair cleansing composition of the present invention is preferably 0.5% by mass or more, more preferably 1.0% 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.
• a method for suppressing curl and/or frizz of hair which comprises applying the hair cleansing compositions of [1] to [12] above to hair and then rinsing the hair. [15] After applying the hair cleansing compositions of [1] to [12] above to the hair, use for rinsing the hair to suppress curl and/or frizz of the hair.
• Methods for measuring various physical properties (i) Method for measuring the double bond position of the raw material olefin The double bond position of the raw material olefin was measured by gas chromatography (hereinafter abbreviated as GC). Specifically, the raw material olefin was reacted with dimethyl disulfide to form a dithionated derivative, and then each component was separated by GC. As a result, the double bond position of the raw material olefin was determined from each peak area.
• the equipment and analysis conditions used for the measurement are as follows.
• GC device product name: HP6890, manufactured by HEWLETT PACKARD
• column product name: Ultra-Alloy-1HT capillary column 30 m x 250 ⁇ m x 0.15 ⁇ m, manufactured by Frontier Lab
• detector hydrogen flame ion detector (FID) )
• injection temperature 300°C detector temperature 350°C
• each internal olefin sulfone is determined according to the bonding position of the sulfonic acid group.
• the acid sodium content was measured by high performance liquid chromatography/mass spectrometry (HPLC-MS). Specifically, hydroxy compounds to which sulfonic acid groups are bonded were separated by high-performance liquid chromatography (HPLC), and each was subjected to mass spectrometry (MS) for identification. As a result, each content was determined from the HPLC-MS peak area.
• HPLC device product name: Agilent Technologies 1100, manufactured by Agilent Technologies
• column product name: L-column ODS 4.6 x 150 mm, manufactured by Japan Chemical Evaluation and Research Institute
• sample preparation 1000-fold dilution with methanol
• Eluent A water added with 10mM ammonium acetate
• eluent B methanol added with 10mM ammonium acetate
• MS device product name: Agilent Technologies 1100MS SL (G1946D), Agilent Technologies ), MS detection (anion detection m/z60-1600, UV240nm)
• GC device product name: Agilent Technologies 6850, manufactured by Agilent Technologies
• column product name: Ultra-Alloy-1HT capillary column 15 m x 250 ⁇ m x 0.15 ⁇ m, manufactured by Frontier Labs
• detector hydrogen flame ion detector
• injection temperature 300°C detector temperature 350°C
• He flow rate 3.8mL/min
• the obtained crude alkene internal olefin was transferred to a distillation flask and distilled at 136 to 160° C./4.0 mmHg to obtain a raw material olefin a1 having 16 carbon atoms and having an olefin purity of 100%.
• the double bond distribution of the obtained raw material olefin a1 was as follows: 1.8% by mass at C1 position, 21.8% by mass at C2 position, 18.7% by mass at C3 position, 18.6% by mass at C4 position, and 14.3% by mass at C5 position.
• the mass %, the C6 position was 11.4 mass %
• the total of C7 and C8 positions was 13.6 mass %
• the average double bond position was 4.17.
• the obtained crude alkene internal olefin was transferred to a distillation flask and distilled at 148 to 158° C./0.5 mmHg to obtain a raw material olefin b6 having 18 carbon atoms and having an olefin purity of 100%.
• the double bond distribution of the obtained raw material olefin b6 was as follows: 1.8% by mass at the C1 position, 26.4% by mass at the C2 position, 21.1% by mass at the C3 position, 17.5% by mass at the C4 position, and 11.7% by mass at the C5 position.
• the mass percentage was 8.3% by mass at C6 position, 5.9% by mass at C7 position, the total of C8 and C9 positions was 7.4% by mass, and the average double bond position was 4.00.
• Table 1 shows the physical property values of the obtained raw material olefins b1 to b6.
• Production of sodium internal olefin sulfonate B1 having 16 carbon atoms The raw material olefin b1 obtained in Production Example b1 was placed in a thin film sulfonation reactor having an external jacket, and sulfur trioxide gas was used under the condition that cooling water at 10°C was passed through the outer jacket of the reactor. A sulfonation reaction was performed. The SO 3 /internal olefin molar ratio during the sulfonation reaction was set at 1.01.
• the obtained sulfonated product was mixed with an alkaline aqueous solution prepared with sodium hydroxide (alkaline agent) in an amount of 1.04 moles relative to the theoretical acid value, and neutralized continuously at 30° C. for 1 hour.
• the obtained neutralized product was heated in an autoclave at 170° C. for 1 hour to perform hydrolysis, thereby obtaining sodium internal olefin sulfonate B1 having 16 carbon atoms.
• the content of the raw material olefin contained in the obtained sodium internal olefin sulfonate B1 having 16 carbon atoms was 0.4% by mass, and the content of inorganic compounds was 0.39% by mass.
• Table 2 shows the physical property values of the obtained sodium internal olefin sulfonates B1 to B6.
• Hair cleansing compositions having the compositions shown in Tables 3 and 4 were prepared by a conventional method using the obtained sodium internal olefin sulfonates B1 to B6 as needed. Specifically, component (A), component (B), an appropriate amount of water, and other components as necessary are placed in a beaker, heated to 60 to 80°C, mixed, and cooled to room temperature. Water was replenished to obtain each hair cleansing composition. Using the obtained hair cleansing composition, the following operations 1) to 7) are carried out, assuming short-term hair care that is repeated daily, to improve the effect of alleviating frizz and frizz in the hair and foaming upon application. The amount and the degree to which the hair does not creak during rinsing were evaluated. The results are shown in Tables 3 and 4.
• ⁇ Habit Reduction Rate 1) Place curled Caucasian hair (manufactured by Kerling International Haarfabrik, European-natural hair favour curly 30-35 cm) on a flat board and cut it out at the point of inflection when viewed from above (hereinafter referred to as C curl). This was immersed in ion-exchanged water for 20 minutes, and then allowed to stand at 20° C. and 50% RH for 24 hours or more. 2) C-curl hair was placed on a 1 mm graph paper and photographed from above, and the obtained image was used to compare the C-curl hair to an arc, and the diameter D 0 of a circle inscribed in the arc was measured. 3) Next, C curl hair was immersed in a hair cleansing composition at 40° C.
• ⁇ Foaming amount during application After wetting a bundle of 20 g of Japanese women's hair (approximately 15 to 20 cm) with water, take 1 g of the resulting hair cleansing composition in your hands and ensure that the hair cleansing composition is sufficiently distributed over the hair. I moved my hands to shampoo. The amount of bubbles generated at this time was evaluated by three expert panelists according to the following evaluation criteria, and the average value was determined. ⁇ Evaluation criteria 5: Much 4: Somewhat much 3: Neutral 2: Somewhat less 1: Fewer
• ⁇ Evaluation criteria 5 Hair does not squeak until the end of rinsing 4: Hair squeaks after 3/4 of the time from the beginning of rinsing to the end 3: Half the time from the beginning of rinsing to the end of rinsing 2: Hair starts to creak after 1/4 of the time from the beginning of rinsing to the end of rinsing. 1: Hair starts to squeak from the beginning of rinsing.

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