JP4528892B2 - Soap with a whitening agent, bathing agent, fiber treatment agent, fiber - Google Patents

Description

[0001]
BACKGROUND OF THE INVENTION
  The present invention contains a whitening agent.StoneThis relates to saponification, bathing agents, fiber treatment agents and fibers.
[0002]
[Prior art]
  Undecylenic acid is an unsaturated fatty acid having 11 carbon atoms, and as an ingredient contained in human skin, it plays the main role in the cleansing action of the skin. Industrially, it is obtained by thermal decomposition of castor oil. Antifungal action is known, and glycerin ester of undecylenic acid is used as an antibacterial agent as an external medicine (Patent Document 1). Recently, trehalose esters have been developed as antibacterial agents (Patent Document 2 and Patent Document 3). So far, we have developed enzyme-catalyzed esterification technology for sugars such as trehalose and fatty acids such as undecylenic acid.
  Natural products such as arbutin and kojic acid having tyrosinase inhibitory activity are often used as whitening agents in the field of cosmetics and the like (for example, see Non-Patent Documents 1, 2, 3 and 4). However, the tyrosinase inhibitory action of undecylenic acid or a salt thereof, or an ester derivative thereof has never been known so far, and these compounds are used as a skin whitening agent, soap, bathing agent, fiber treatment agent and fiber as a whitening agent. There are no examples of blending and using them.
[0003]
[Patent Document 1]
JP 2002-114669 A
[Patent Document 2]
Japanese Patent Laid-Open No. 2001-278752
[Patent Document 3]
JP-A-5-137994
[Non-Patent Document 1]
Pharmaceutical Journal, 112 (4), pp. 276-282, 1992
[Non-Patent Document 2]
Pharmaceutical Journal, 115 (8), pp. 626-632, 1995
[Non-Patent Document 3]
Bioindustry, 11 (4), 206, 1994
[Non-Patent Document 4]
Biosci. Biotech. Biochem. 61, 11, pp. 1926-1928, 1997.
[0004]
[Problems to be solved by the invention]
  It is an object of the present invention to provide a skin external preparation, a soap, a bath agent, a fiber treatment agent, and a fiber containing a whitening agent having an excellent whitening effect.
[0005]
[Means for Solving the Problems]
  According to the present invention, the following whitening agent is contained.StoneSoaps, bathing agents, fiber treatment agents and fibers are provided.
  (1) The following general formula (2)
[Chemical formula 5]
  S- (OH)_q-1OOC- (CH₂)₈-CH = CH₂(2)
  (Wherein S- (OH)_q-1Represents a whitening agent composed of an undecylenic acid derivative represented by the monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded thereto from a monosaccharide. 0.001 to 20.0% by massFor whiteningSoap.
  (2) The following general formula (2)
[Chemical 6]
  S- (OH)_q-1OOC- (CH₂)₈-CH = CH₂(2)
  (Wherein S- (OH)_q-1Represents a whitening agent composed of an undecylenic acid derivative represented by a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded thereto from a monosaccharide. 0.001 to 20.0% by massFor whiteningBath additive.
  (3) The following general formula (2)
[Chemical 7]
  S- (OH)_q-1OOC- (CH₂)₈-CH = CH₂(2)
  (Wherein S- (OH)_q-1Is a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded thereto from a monosaccharide) and a whitening agent comprising an undecylenic acid derivative represented by 0.001 to 20.0% by massFor whiteningFiber treatment agent.
  (4) The following general formula (2)
[Chemical 8]
  S- (OH)_q-1OOC- (CH₂)₈-CH = CH₂(2)
  (Wherein S- (OH)_q-1Is a monosaccharide and a whitening agent composed of an undecylenic acid derivative represented by a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded thereto. 0.001 to 20.0% by massFor whiteningfiber.
[0006]
DETAILED DESCRIPTION OF THE INVENTION
  Erasure
[0007]
  In the general formula (2), S- (OH)_q-1Is a carbohydrate S- (OH) to which q hydroxyl groups are bonded._qThe carbohydrate residue which remove | excluded the one hydroxyl group from is shown.
  The number q of hydroxyl groups bonded to the saccharide is not particularly limited, but is usually 1 or more, preferably 2 to 20, and more preferably 2 to 10.
  Carbohydrate S- (OH)_qHas a simple sugarKindCan be mentioned.
[0008]
  Examples of monosaccharides include hexoses such as glucose, fructose, mannose, galactose, fucose, and rhamnose, and pentoses such as arabinose, xylose, ribose, and lyxose.
[0009]
  Erasure
[0010]
  Erasure
[0011]
  S- (OH)_q-1Preferred carbohydrates that give are monosaccharides and disaccharides. More preferred are glucose, mannose, galactose, sucrose, maltose, trehalose, uridine, and thymine riboside.
[0012]
  Erasure
[0013]
  Erasure
[0014]
  Erasure
[0015]
  Erasure
[0016]
  Erasure
[0017]
  Erasure
[0018]
  Erasure
[0019]
  Erasure
[0020]
  Erasure
[0021]
  Erasure
[0022]
  The soap, bathing agent, fiber treatment agent, and fiber of the present invention are characterized by containing a whitening agent as an active ingredient. In this case, as the whitening agent, at least one selected from undecylenic acid derivatives represented by the general formula (2) is used.
  In the skin external preparation, soap, bathing agent, fiber treatment agent, and fiber of the present invention, the content of the whitening agent is 0.001 to 20.0% by mass, preferably 0.01 to 10% by mass.
[0023]
  Erasure
[0024]
  Contains whitening agent of the present inventionSoapThe bathing agent, the fiber treatment agent and the fiber exhibit a high whitening effect due to the whitening agent contained therein.
[0025]
【Example】
  Next, the present invention will be described in detail by examples.
[0026]
  (Example of whitening agent production)
  Production Example 1
  (Method for synthesizing 10-undecylenic acid sodium salt)
  10 g of undecylenic acid (5 g, 23.8 mmol) was added to 10 ml of an aqueous solution in which 1.23 g of NaOH (23.8 mmol) was dissolved, and the mixture was stirred for 1 hour. The reaction solution was lyophilized to obtain 11 g of white crystals [sodium 10-undecylenate] (Compound I).
[0027]
  Production Example 2
  400 mg of alkaline protease derived from Bacillus bacteria (Bioplace SP-10; manufactured by Nagase ChemteX) in 30 ml of DMF solution containing 5.7 g (15 mmol) of trehalose dihydrate and 3.2 g (15 mmol) of vinyl undecylenate The mixture was added and reacted at 35 ° C. for 10 days. The reaction solution was filtered to remove the enzyme, methanol and water were added, the aqueous layer was washed several times with hexane, the aqueous layer was concentrated, and the product was purified by silica gel chromatography (ethyl acetate: methanol = 85: 15). Was isolated. In this way, 3.0 g of colorless powdery product [trehalose 6-undecylenate] (compound II) was obtained (yield 60%). The structure was confirmed by NMR.
[0028]
  NMR apparatus: Jeol JNM-EX270, 67.8 MHz¹³C-NMR: δ 93.35 (C1), 71.61 (C2), 72.89 (C3), 71.61 (C4), 72.62 (C5), 60.87 (C6), 93.24 ( C1 ′) 71.52 (C2 ′), 72.83 (C3 ′), 70.17 (C4 ′), 69.71 (C5 ′), 63.13 (C6 ′) 172.87 (C═O) 24.5, 28.31, 28.49, 28.56, 28.75, 33.23, 33.59 (CH₂), 138.85 (CH =), 114.67 (CH₂=). Anal. Calcd for C₂₃H₄₀O₁₂(508.27): C, 54.34; H, 7.95, Found: C, 52.78; H, 8.04
  Melting point: 146-147 ° C
[0029]
  Production Example 3
  1 g of actinomycete-derived alkaline protease (ALP-901; manufactured by Toyobo Co., Ltd.) was added to 100 ml of a DMF solution containing 10.3 g (30 mmol) of sucrose and 25.2 g (120 mmol) of vinyl undecylenate and reacted at 35 ° C. for 7 days. did. The reaction solution was treated in the same manner as in Production Example 1 to obtain 9.5 g of a colorless powdery product [sucrose 1'-undecylenic acid ester] (Compound III) (yield 64%). The structure was confirmed by NMR.
[0030]
  ¹³C-NMR: δ 92.15 (C1), 71.43 (C2), 72.97 (C3), 69.87 (C4), 72.83 (C5), 60.54 (C6), 62.29 ( C1 ′), 102.23 (C2 ′), 76.62 (C3 ′), 73.34 (C4 ′), 82.79 (C5 ′), 61.96 (C6 ′), 172.42 (C = O), 24.50, 28.31, 28.49, 28.54, 28.75, 33.23, 33.57 (CH₂), 138.87 (CH =), 114.67 (CH₂=). Anal. Calcd for C₂₃H₄₀O₁₂(508.63): C, 54.31; H, 7.94, Found: C, 53.89; H, 8.05
  Melting point: 114-116 ° C
[0031]
  Production Example 4
  1 g of actinomycete-derived alkaline protease (ALP-901; manufactured by Toyobo Co., Ltd.) was added to 100 ml of a DMF solution containing 10.8 g (60 mmol) of glucose and 25.2 g (120 mmol) of vinyl undecylenate and reacted at 35 ° C. for 7 days. did. The reaction solution was treated in the same manner as in Production Example 1 to obtain 10.0 g of a colorless powdery product [glucose 6-undecylenate] (Compound IV) (yield 48%). The structure was confirmed by NMR.
[0032]
  ¹³C-NMR: δ 92.33 (C1), 70.61 (C2), 72.94 (C3), 72.24 (C4), 69.19 (C5), 63.9 (C6), 172.94 ( C = O), 24.51, 28.32, 28.49, 28.54, 28.79, 28.75, 33.24, 33.52 (CH₂), 138.83 (CH =), 114.63 (CH₂=). Anal. Calcd for C₁₇H₃₀O₇(346.47): C, 58.92; H, 8.75, Found: C, 59.22; H, 8.78.
  Melting point: 119-121 ° C
[0033]
  Production Example 5
  1 g of lipase derived from Pseudomonas cepacia (Lipase PS; manufactured by Amano Enzyme) was added to 100 ml of a diisopropyl ether solution containing 4.3 g (35.2 mmol) of 1-phenylethanol and 12.8 g (104.9 mmol) of vinyl 10-undecylenate. And reacted at 35 ° C. for 7 days. The reaction solution was filtered to remove the enzyme, then diisopropyl ether was distilled off, and the product was isolated by silica gel chromatography (hexane: ethyl acetate = 9: 1). In this way, 3.8 g of colorless and transparent liquid [phenyl-1-yl-10-undecylenic acid ester] (Compound V) was obtained. (Yield 25%).
[0034]
  ¹³C-NMR: δ 141.68, 128.47, 127.83, 126.03 (C₆H₅), 72.25 (CO), 22.2 (CH₃), 172.95 (C = O), 24.5, 28.31, 28.47, 28.53, 28.78, 28.74, 33.24, 33.52 (CH₂), 138.82 (CH =), 114.61 (CH₂=) Anal. Calcd for C₁₉H₂₈O₂(288.17): C, 79.19; H, 9.72, Found: C, 79.21; H, 9.85.
[0035]
  Production Examples 6-12
  Examples of 10-undecylenic acid ester obtained by the enzymatic method of Production Example 2 are shown in the following table.
[0036]
[Table 1]
[0037]
  [Evaluation of Tyrosinase Inhibitory Activity]
  The tyrosinase inhibitory activity of the undecylenic acid derivative was measured by a method using proline (Analytical Biochemistry, 179, 375-381, 1989). 40 μl of 0.749 M L-proline dissolved in 0.1 M phosphate buffer at pH 7.5, 40 μl of 0.037 M 1,2-dihydroxybenzene, various undecylenic acid derivative solutions obtained in Example 1 1.41 ml was stirred in an absorbance cuvette. Next, 10 μl of 350 μg / ml tyrosinase (mushroom derived, SIGMA) solution was added, and the change in absorbance was measured at 525 nm for 10 seconds with stirring. The results are shown in Table 2.
[0038]
[Table 2]
[0039]
  From the results of Table 2, it is confirmed that the whitening agent used in the present invention exhibits an equivalent tyrosinase inhibitory activity effect compared to kojic acid, and exhibits an excellent whitening effect.
[0040]
  (Example)
  Below, based on the Example and reference example of this invention, it demonstrates still in detail. All blending amounts are expressed in mass% unless otherwise specified.
[0041]
  Reference example 1
  (cream)
  (A) Component composition (%)
  (1) stearic acid: 6.0, (2) stearyl alcohol: 3.0, (3) isopropyl myristate: 18.0, (4) glycerol monostearate ester: 3.0, (5) propylene glycol: 10.0, (6) 10-undecylenic acid: 10.0, (7) caustic potash: 0.2, (8) ethylenediaminetetraacetic acid tetrasodium salt: 0.01, (9) tocopherol acetate: 0.1, ( 10) Appropriate amount of butylparaben, (11) Perfume; Appropriate amount, (12) Ion-exchanged water: remaining
  (B) Manufacturing method
  (12) was dissolved by adding (5), (7) and (8) and kept at 70 ° C. (aqueous phase). The other components were mixed and dissolved by heating and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase and pre-emulsified at 70 ° C. Next, the mixture was uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain a cream.
[0042]
  Reference example 2
  (cream)
  (A) Component composition (%)
  (1) stearic acid: 5.0, (2) sorbitan monostearate ester: 2.5, (3) sorbitan monostearate ester: 1.5, (4) arbutin: 7.0, (5) hydrogen sulfite Sodium: 0.03, (6) Propylene glycol: 10.0, (7) 10-Undecylenic acid sodium salt (Compound I): 1.0, (8) Glycerin trioctanoate: 10.0, (9) Squalene: 5.0, (10) Octyl paradimethylaminobenzoate: 3.0, (11) Disodium salt of ethylenediaminetetraacetic acid: 0.01, (12) Ethylparaben: 0.3, (13) Fragrance: appropriate amount (14) Ion-exchanged water: remaining
  (B) Manufacturing method
  (6) and (11) were added to (14) and dissolved, and kept at 70 ° C. (aqueous phase). The other components were mixed and dissolved by heating and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase and pre-emulsified at 70 ° C. Next, the mixture was uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain a cream.
[0043]
  Reference example 3
  (cream)
  (A) Component composition (%)
  (1) Stearyl alcohol: 7.5, (2) Stearic acid: 1.5, (3) Hydrogenated lanolin: 2.0, (4) Squalane: 5.0, (5) 2-Octyldodecyl alcohol: 6 0.0, (6) Cetyl ether: 3.0, (7) Glycerol monostearate: 2.0, (8) Propylene glycol: 5.0, (9) Placenta extract: 0.1, (10) Hyaluron Sodium acid: 0.1, (11) Octylcinnamate: 4.0, (12) Trehalose 6-O-10-undecylenic acid (Compound III): 0.5, (13) Ethylenediaminetetraacetic acid disodium salt: 0 .03, (14) ethyl paraben: 0.3, (15) fragrance: appropriate amount (16) ion-exchanged water: remaining
  (B) Manufacturing method
  (16) was dissolved by adding (8) and (13) and kept at 70 ° C. (aqueous phase). The other components were mixed and dissolved by heating and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase and pre-emulsified at 70 ° C. Next, the mixture was uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain a cream.
[0044]
  Reference example 4
  (cream)
  (A) Component composition (%)
  (1) stearic acid: 6.5, (2) sorbitan monostearate: 2.0, (3) sorbitan monostearate: 1.5, (4) propylene glycol: 10.0, (5) sucrose 1'-O-10-undecylenic acid ester (Compound III): 0.5, (6) Glycerin trioctanoate: 10.0, (7) Squalene: 5.0, (8) Sodium hyaluronate: 1. 0, (9) Ethylenediaminetetraacetic acid trisodium salt: 0.01, (10) Glucose: 0.5, (11) Ascorbic acid glucoside: 5.0, (12) Ethylparaben: 0.3, (13) Fragrance : Appropriate amount, (14) Ion exchange water: Residual
  (B) Manufacturing method
  (14) was dissolved by adding (4) and (9) and kept at 70 ° C. (aqueous phase). The other components were mixed and dissolved by heating and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase and pre-emulsified at 70 ° C. Next, the mixture was uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain a cream.
[0045]
  Reference Example 5
  (Milky lotion)
  (A) Component composition (%)
  (1) stearic acid: 2.0, (2) cetyl alcohol: 1.5, (3) petrolatum: 5.0, (4) decamethylcyclopentasiloxane: 1.0, (5) liquid paraffin: 10. 0, (6) POE (10) monooleate: 2.0, (7) polyethylene glycol (PEG 1500): 3.0, (8) triethanolamine: 1.0, (9) sodium hyaluronate: 0 .05, (10) glucose 6-O-10-undecylenate (compound IV): 1.0, (11) carboxyvinyl polymer: 0.05, (12) ascorbic acid glucoside: 3.0, (13) Sodium bisulfite: 0.01, (14) Ethylparaben: 0.3, (15) Fragrance: appropriate amount (16) Ion exchange water: remaining
  (B) Manufacturing method
  (11) was dissolved in a small amount of (16) (phase A), and (7), (8) and (13) were added to the remaining (16), dissolved by heating and kept at 70 ° C. (water phase) . The other components were mixed, heated and melted and kept at 70 ° C. (oil phase), and the oil phase was added to the aqueous phase and pre-emulsified. Next, Phase A was added and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain an emulsion.
[0046]
  Reference Example 6
  (Milky lotion)
  (A) Component composition (%)
  (1) Cetyl alcohol: 1.0, (2) Silicone compound: 2.0, (3) Liquid paraffin (medium viscosity): 3.0, (4) Propylene glycol: 5.0, (5) Glycerin: 2 0.0, (6) 4-methoxy-4-tert-butylbenzoylmethane: 3.5, (7) ethanol: 15.0, (8) carboxyvinyl polymer: 0.3, (9) potassium hydroxide: appropriate amount (10) Preservative: appropriate amount, (11) Placenta extract: 5.0 (12) Phenyl-1-yl-10-undecylenate (Compound V): 3.0, (13) Ion-exchanged water: remaining
  (B) Manufacturing method
  The placenta extract was dissolved by heating in (13) and (7), and (4) the following water-soluble components were dissolved and kept at 70 ° C. (aqueous phase). Other oil components were mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer. After emulsification, the emulsion was cooled to 30 ° C. while stirring well to obtain an emulsion.
[0047]
  Reference Example 7
  (Milky lotion)
  (A) Component composition (%)
  (1) stearic acid: 2.5, (2) cetyl alcohol: 1.0, (3) petrolatum: 5.0, (4) liquid paraffin: 10.0, (5) monooleate: 2.0 (6) Polyethylene glycol (PEG 1500): 3.0, (7) Triethanolamine: 1.0, (8) Glycerol alpha mono 10-undecylenate (Compound VI): 1.0, (9) Glycyrrhizic acid : 0.5, (10) amino acid: 0.3, (11) carboxyvinyl polymer: 0.05, (12) sodium bisulfite: 0.01, (13) arbutin: 3.0, (14) ethyl paraben : 0.3, (15) Fragrance: appropriate amount, (16) ion-exchanged water: remaining
  (B) Manufacturing method
  Dissolve (11) in a small amount of (16) (phase A), add (6), (7) and (12) to the remaining (16), dissolve by heating and maintain at 70 ° C. (aqueous phase) . The other components were mixed, heated and melted and kept at 70 ° C. (oil phase), and the oil phase was added to the aqueous phase and pre-emulsified. Next, Phase A was added and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain an emulsion.
[0048]
  Reference Example 8
  (Milky lotion)
  (A) Component composition (%)
  (Oil phase)
  Stearyl alcohol: 2.0, squalene: 2.0, petrolatum: 2.5, deodorized liquid lanolin: 1.5, evening primrose oil: 2.0, isopropyl myristate: 5.0, glycerin monooleate: 2.0 Hydrogenated castor oil: 2.0, tocopherol acetate: 0.05, 10-undecylenate glycerol (compound IV): 1.0, tranexamic acid: 5.0, ethyl paraben: 0.2, butyl paraben: 0. 1, perfume: appropriate amount
  (Water phase)
  Glycerin: 5.0, sodium hyaluronate: 0.01, carboxyvinyl polymer: 0.2, potassium hydroxide: 0.2, sodium bisulfite: 0.01, purified water: residue
  (B) Bookbinding
  The oil phase part and the water phase part were each dissolved at 70 ° C., the oil phase part was mixed with the water phase part, emulsified with an emulsifier, and then cooled to 30 ° C. with a heat exchanger to obtain an emulsion.
[0049]
  Reference Example 9
  (jelly)
  (A) Component composition (%)
  (1) 95% ethanol: 10.0, (2) dipropylene glycol: 12.5, (3) oleyl ether: 2.0, (4) carboxyvinyl polymer: 1.0, (5) arbutin: 0.0. 5, (6) Sodium bisulfite: 0.03, (7) Hexanediol mono 10-undecylenate (Compound VIII): 5.0, (8) Caustic soda: 0.15, (9) L-arginine: 0 1, (10) 2-hydroxy-4-methoxybenzophenone: sodium sulfonate: 0.05, (11) methylparaben: 0.2, (12) ethylenediaminetetraacetic acid trisodium salt: 0.05, (13) perfume : Appropriate amount, (14) ion-exchanged water: remaining
  (B) Bookbinding
  (4) was uniformly dissolved in (14) (aqueous phase). (3) was dissolved in (1) and added to the aqueous phase.
  Further, other components were added, and finally (8) and (9) were added to neutralize and thicken to obtain a jelly.
[0050]
  Reference Example 10
  (Cosmetic liquid)
  (A) Component composition (%)
  (Phase A)
  95% ethanol: 10.0, octyldodecanol: 1.1, methyl paraben: 0.2, pantotenyl ethyl ether: 0.1, butanediol mono 10-undecylenate (Compound IX): 1.0
  (Phase B)
  Potassium hydroxide: 0.1,
  (Phase C)
  Glycerin: 5.0, Dipropylene glycol: 10.0, Sodium bisulfite: 0.03, Carboxyvinyl polymer: 0.2, Tranexamic acid: 3.0, Purified water: Residue
  (B) Bookbinding
  The A phase and the C phase were uniformly dissolved, and the A phase was added to the C phase and solubilized. Next, phase B was added and dissolved to obtain a serum.
[0051]
  Reference Example 11
  (pack)
  (A) Component composition (%)
  (Phase A) Dipropylene glycol: 6.0, hydrogenated castor oil: 5.0
  (Phase B) benzyl alcohol 10-undecylenic acid (Compound X): 0.5, olive oil: 5.0, tocopherol acetate: 0.2, ethyl paraben: 0.2, perfume: appropriate amount
  (Phase C) Polyvinyl alcohol (degree of saponification 90, degree of polymerization 2000): 13.0, ethanol: 7.0, arbutin: 3.0, sodium bisulfite: 0.03, purified water: residue
  (B) Manufacturing method
  A phase, B phase, and C phase were uniformly dissolved, and after adding B phase to A phase and solubilizing, this was added to C phase and filled to obtain a pack.
[0052]
  Reference Example 12
  (Peel-off type pack)
  (A) Component composition (%)
  (Alcohol phase)
  95% ethanol: 10.0, oleyl alcohol ether: 2.0, 2-hydroxy-4-methoxybenzophenone: 3.5, preservative: appropriate amount, fragrance: appropriate amount, 7-O-10-undecylenic acid ester (compound XI ): 3.0
  (Water phase)
  Tranexamic acid: 2.0, polyvinyl alcohol: 12.0, glycerin: 3.0, polyethylene glycol (PEG 1500): 1.0, ion-exchanged water: residual
  (B) Manufacturing method
  Prepare an aqueous phase at 80 ° C and cool to 50 ° C. Subsequently, the alcohol phase prepared at room temperature was added and mixed uniformly and allowed to cool to obtain a peel-off type pack.
[0053]
  Reference Example 13
  (Solid foundation)
  (A) Component composition (%)
  (1) Talc: 43.1, (2) Kaolin: 15.0, (3) Sericite: 10.0, (4) Zinc flower: 7.0, (5) Titanium dioxide: 3.8, (6 ) Yellow iron oxide: 2.9, (7) Black iron oxide: 0.2, (8) Squalane: 8.0, (9) Isostearic acid: 4.0, (10) Sorbitan monooleate: 3.0 (11) Isocetyl octanoate: 2.0, (12) 2- (10-undecylenoyl) -3-butinoic acid (Compound XII): 1.0, (13) Preservative: appropriate amount, (14) Fragrance : Appropriate amount
  (B) Manufacturing method
  (1)-(7) powder components are sufficiently mixed with a blender, (8)-(11) oily components, (12), (13), (14) are added to this and kneaded well. And molded into a solid foundation.
[0054]
  Reference Example 14
  [Emulsification foundation (cream type)]
  (A) Component composition (%)
  (Powder part) Titanium dioxide: 10.1, sericite: 5.4, kaolin: 3.0, yellow iron oxide: 0.8, black iron oxide: 0.2
  (Oil phase) Decamethylcyclopentasiloxane: 11.5, liquid paraffin: 4.5, polyoxyethylene-modified dimethylpolysiloxane: 4.0
  (Aqueous phase) Purified water: 50.0, 1,3-butylene glycol: 4.5, trehalose 6-O-undecylenate (compound II): 1.0, tranexamic acid: 2.0, sorbitan sesquioleic acid Ester: 3.0, preservative: appropriate amount, fragrance: appropriate amount
  (B) Manufacturing method
  After the aqueous phase is heated and stirred, the powder part sufficiently mixed and pulverized is added and homomixed. Furthermore, after adding the heat-mixed oil phase and carrying out a homomixer process, it added the fragrance | flavor, stirring, and cooled to room temperature, and obtained the emulsion type foundation.
[0055]
  Reference Example 15
  (Lotion)
  (A) Component composition (%)
  Ethanol: 8.0, 1,3-butylene glycol: 5.0, oleyl alcohol ether: 1.8, sucrose 1′-O-undecylenate (compound III): 0.5, magnesium ascorbate: 3.0 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid sodium salt: 0.1, sodium pyrrolidonecarboxylate: 0.5, pullulan: 0.05, jojoba oil: 0.5, caustic potash: 0.015, ethylenediamine tetra Acetic acid trisodium salt: 0.01, fragrance: 0.1, ion-exchanged water: remaining amount
  (B) Manufacturing method
  The above ingredients were stirred and mixed to obtain a skin lotion.
[0056]
  Reference Example 16
  (lotion)
  (A) Component composition (%)
  (1) Purified water: 40.0, (2) Dipropylene glycol: 5.0, (3) 1,3-butylene glycol: 10.0, (4) Polyethylene glycol (PEG 400): 10.0, (5 ) Ethyl alcohol: 20.0, (6) hydrogenated castor oil: 3.0, (7) octyl paramethoxycinnamate: 1.0, (8) glucose 6-O-undecylenate (compound IV): 1 0.0, (9) Arbutin: 4.0, (10) Sodium bisulfite: 0.03, (11) Ascorbic acid glucoside: 5.0, (12) Triethanolamine: 5.0, (13) Fragrance: Appropriate amount
  (B) Manufacturing method
  (6), (7) and (13) are dissolved in (5) (alcohol phase). On the other hand, (8) and (9) were dissolved in ethanol in advance, and another polyhydric alcohol was added to (1) and dissolved sufficiently (aqueous phase). The alcohol phase was added to the aqueous phase and stirred well to obtain a lotion.
[0057]
  Reference Example 17
  (Lotion)
  (A) Component composition (%)
  Glycerol alpha mono 10-undecylenate (compound VI): 0.5, placenta: 0.2, hydroquinone-β-D- (N-acetylglucosamine): 0.1, dimethyl myristylamine oxide: 0.01, ethanol : 9.0, oleyl ether: 1.0, ascorbic acid glucoside: 5.0, preservative: appropriate amount, fragrance: appropriate amount, purified water: residual
  (B) Manufacturing method
  The above ingredients were stirred and mixed to obtain a skin lotion.
[0058]
  Reference Example 18
  (lotion)
  (A) Component composition (%)
  Ethyl alcohol: 55.0, hydrogenated castor oil ether: 2.0, antioxidant: appropriate amount, preservative: appropriate amount, fragrance: appropriate amount, ethylene glycol 10-undecylenate (compound VII): 5.0, kojic acid: 3.0, sodium hexametaphosphate: appropriate amount, ion-exchanged water: remaining
  (B) Manufacturing method
  Each of the above components was stirred and mixed to obtain a lotion.
[0059]
  Reference Example 19
  (lotion)
  (A) Component composition (%)
  (Alcohol phase) 95% ethanol: 55.0, hydrogenated castor oil: 2.0, antioxidant: appropriate amount, preservative: appropriate amount, hexanediol mono 10-undecylenate (compound VII): 1.0
  (Aqueous phase) Dipropylene glycol: 5.0, sodium hexametaphosphate: appropriate amount, ion-exchanged water: remaining
  (B) Manufacturing method
  According to a conventional method, an alcohol phase and an aqueous phase were prepared and solubilized to obtain a lotion.
[0060]
  Reference Example 20
  (Cold cream)
  (A) Component composition (%)
  Solid paraffin: 5.0, beeswax: 10.0, petrolatum: 15.0, liquid paraffin: 41.0, glycerin monostearate: 2.0, sorbitan monolaurate: 2.0, ascorbic acid phosphate Magnesium: 2.0, 4-methoxy-4-tert-butylbenzoylmethane: 3.5, soap powder: 0.1, borax: 0.2, butanediol mono 10-undecylenate (Compound IX): 3, Ion-exchanged water: residue, fragrance: appropriate amount, preservative: appropriate amount, antioxidant: appropriate amount (B)
  Each of the above components was stirred and mixed to obtain a cold cream.
[0061]
  Reference Example 21
  (Soap)
  Soap (beef tallow: palm oil = 65: 35): 91.6, 10-undecylenic acid: 3.0, palmitic acid: 4.0, glycerin: 1.0, titanium oxide: 0.3, EDTA: 0.00. 03, EHDP: 0.07 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0062]
  Reference Example 22
  (Soap)
  Soap (beef tallow: palm oil = 60: 40): 93.2, 10-undecylenic acid sodium salt: 3.0, PEG # 600: 2.0, titanium oxide: 0.2, EHDP: 0.3, fragrance 1.3 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0063]
  Example 23
  (Soap)
  Soap (palm oil: palm kernel oil = 70: 30): 90.48, trehalose 6-O-10 undecylenic acid (compound II): 5.0, allantoin: 0.2, palmitic acid: 4.0, 2, 4,4′-trichloro-2′-hydroxydiphenyl ether 0.2, EDTA: 0.02, EHDP: 0.1 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0064]
  Example 24
  (Soap)
  Soap (beef tallow: palm oil = 65: 35): 91.6, sucrose 1′-O-10-undecylenate (compound III): 3.0, palmitic acid: 4.0, glycerin: 1.0, Titanium oxide: 0.3, EDTA: 0.03, EHDP: 0.07 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0065]
  Example 25
  (Soap)
  Soap (beef tallow: palm oil = 60: 40): 93.2, glucose 6-O-10-undecylenate (compound IV): 3.0, PEG # 600: 2.0, titanium oxide: 0.2 , EHDP: 0.3, Fragrance 1.3 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0066]
  Reference Example 26
  (Soap)
  Soap (palm oil: palm kernel oil = 70: 30): 90.48, phenyl-1-yl-10-undecylenate (compound V): 5.0, allantoin: 0.2, palmitic acid: 4.0 2,4,4′-trichloro-2′-hydroxydiphenyl ether 0.2, EDTA: 0.02, EHDP: 0.1 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0067]
  Reference Example 27
  (Soap)
  Soap (beef tallow: palm oil = 65: 35): 91.6, glycerol α-mono 10-undecylenate (compound VI): 3.0, palmitic acid: 4.0, glycerin: 1.0, titanium oxide: 0.3, EDTA: 0.03, EHDP: 0.07 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0068]
  Reference Example 28
  (Soap)
  Soap (beef tallow: palm oil = 60: 40): 93.2, ethylene glycol 10-undecylenate (compound VII): 3.0, PEG # 600: 2.0, titanium oxide: 0.2, EHDP: 0.3, Fragrance 1.3 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0069]
  Reference Example 29
  (Soap)
  Soap (palm oil: palm kernel oil = 70: 30): 90.48, hexanediol mono 10-undecylenate (compound VIII): 5.0, allantoin: 0.2, palmitic acid: 4.0, 2, 4,4′-trichloro-2′-hydroxydiphenyl ether 0.2, EDTA: 0.02, EHDP: 0.1 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0070]
  Reference Example 30
  (Soap)
  Soap (beef tallow: palm oil = 65: 35): 91.6, butanediol mono 10-undecylenate (compound IV): 3.0, palmitic acid: 4.0, glycerin: 1.0, titanium oxide: 0.3, EDTA: 0.03, EHDP: 0.07 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0071]
  Reference Example 31
  (Soap)
  Soap (beef tallow: palm oil = 60: 40): 93.2, benzyl alcohol 10-undecylenate (compound X): 3.0, PEG # 600: 2.0, titanium oxide: 0.2, EHDP: 0.3, Fragrance 1.3 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0072]
  Reference Example 32
  (Soap)
  Soap (palm oil: palm kernel oil = 70: 30): 90.48, kojic acid 7-O-10-undecylenic acid ester (compound XI): 5.0, allantoin: 0.2, palmitic acid: 4.0 2,4,4′-trichloro-2′-hydroxydiphenyl ether 0.2, EDTA: 0.02, EHDP: 0.1 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0073]
  Reference Example 33
  (Soap)
  Soap (beef tallow: palm oil = 65: 35): 91.6, 2- (10-undecylenoyl) -3-butinoic acid (compound XII): 3.0, palmitic acid: 4.0, glycerin: 1.0 , Titanium oxide: 0.3, EDTA: 0.03, EHDP: 0.07 (%)
  The above ingredients were mixed with stirring to obtain a soap.
[0074]
  Reference Example 34
  (Bath additive)
  Sodium sulfate: 45, sodium bicarbonate: 53, 10-undecylenic acid: 1, fragrance: 1 (%), pigment: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0075]
  Reference Example 35
  (Bath additive)
  Sodium sulfate: 45, sodium hydrogen carbonate: 51, 10-undecylenic acid sodium salt (compound I): 3, fragrance: 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0076]
  Example 36
  (Bath additive)
  Sodium sulfate: 45, sodium bicarbonate: 52, trehalose 6-O-10-undecylenic acid (Compound II): 2, fragrance: 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0077]
  Example 37
  (Bath additive)
  Sodium sulfate: 40, sodium bicarbonate: 57, sucrose 1'-O-10-undecylenic acid ester (compound III): 2, fragrance: 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0078]
  Example 38
  (Bath additive)
  Sodium sulfate: 44, sodium bicarbonate: 52, glucose 6-O-10-undecylenate (compound IV): 3, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0079]
  Reference Example 39
  (Bath additive)
  Sodium sulfate: 45, sodium bicarbonate: 53, phenyl-1-yl-10-undecylenate (Compound V): 1, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0080]
  Reference Example 40
  (Bath additive)
  Sodium sulfate: 50, sodium hydrogen carbonate: 47, glycerol α-mono 10-undecylenate (compound VI): 2, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0081]
  Reference Example 41
  (Bath additive)
  Sodium sulfate: 49, sodium hydrogen carbonate 49: ethylene glycol 10-undecylenate (compound VII): 1, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0082]
  Reference Example 42
  (Bath additive)
  Sodium sulfate: 50, sodium bicarbonate: 48, hexanediol mono 10-undecylenate (Compound VIII): 1, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0083]
  Reference Example 43
  (Bath additive)
  Sodium sulfate: 49, sodium hydrogen carbonate: 49, butanediol mono 10-undecylenate (compound IV): 1, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0084]
  Reference Example 44
  (Bath additive)
  Sodium sulfate: 48, sodium bicarbonate: 50, benzyl alcohol 10-undecylenate (compound X): 1, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0085]
  Reference Example 45
  (Bath additive)
  Sodium sulfate: 51, sodium bicarbonate: 47, kojic acid 7-O-10-undecylenic acid ester (compound XI): 1, fragrance 1 (%), dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0086]
  Reference Example 46
  (Bath additive)
  Sodium sulfate: 52, sodium hydrogen carbonate: 48, 2- (10-undecylenoyl) -3-butinoic acid (Compound XII): 1, fragrance 1, dye: appropriate amount
  The above components were stirred and mixed to obtain a bath agent.
[0087]
  Reference examples 47 and 48Examples 49-51, Reference Examples 52-59
  Table 3 shows the component composition (%) of the fiber treatment agent.
[0088]
[Table 3]
[0089]
  The above components were stirred at 60 ° C. to obtain an emulsion fiber treatment agent.
[0090]
  Reference Examples 60-61, Examples 60-62, Reference Examples 64-72
  (fiber)
  The fiber treatment agent obtained in Examples 60 to 72 was used and adsorbed on commercially available fibers.
  Table 4 shows specific examples of fibers containing a whitening agent.
[0091]
[Table 4]
[0092]
  1 g of fiber was infiltrated into 100 g of each treatment agent, dehydrated and dried at 100 ° C.
[0093]
【The invention's effect】
  The present inventionStoneSapon, bathing agent, fiber treatment agent, and fiber exhibit a high whitening effect because the whitening agent contained therein has a high tyrosinase inhibitory action.

Claims (4)

The following general formula (2)
[Chemical 1]
_{S- (OH) q-1 OOC-} (CH 2) 8 -CH = CH 2 (2)
(In the formula, S- (OH) _q-1 represents a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded to a monosaccharide from the monosaccharide). A whitening soap containing a whitening agent comprising an acid derivative in an amount of 0.001 to 20.0% by mass based on the total amount of soap. The following general formula (2)
[Chemical 2]
_{S- (OH) q-1 OOC-} (CH 2) 8 -CH = CH 2 (2)
(In the formula, S- (OH) _q-1 represents a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded to a monosaccharide from the monosaccharide). A bath agent for whitening comprising a whitening agent comprising an acid derivative in an amount of 0.001 to 20.0% by mass relative to the total amount of the bath agent. The following general formula (2)
[Chemical 3]
_{S- (OH) q-1 OOC-} (CH 2) 8 -CH = CH 2 (2)
(Wherein S- (OH) _q-1 represents a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded to a monosaccharide from the monosaccharide) A whitening fiber treatment agent comprising 0.001 to 20.0% by mass of a whitening agent comprising an acid derivative with respect to the total amount of the fiber treatment agent. The following general formula (2)
[Formula 4]
_{S- (OH) q-1 OOC-} (CH 2) 8 -CH = CH 2 (2)
(In the formula, S- (OH) _q-1 represents a monosaccharide residue obtained by removing one of q (q: an integer of 1 or more) hydroxyl groups bonded to a monosaccharide from the monosaccharide). A whitening fiber containing a whitening agent comprising an acid derivative in an amount of 0.001 to 20.0% by mass based on the total amount of the fiber.