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Skin cosmetic

A technology for cosmetic materials and compounds, applied in cosmetics, skin diseases, cosmetic preparations, etc., can solve the problems of insufficient solubility of bisphenol compounds, limited use range, poor permeability, etc., and achieves excellent melanin production inhibition effect, easy application, No skin irritation effect

Inactive Publication Date: 2009-04-29
KAO CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this bisphenol compound has insufficient solubility and high crystallinity, so when it is blended into drugs, non-drugs, and cosmetics, the range of use of preparations is limited.
In addition, since the bisphenol compound has high polarity, there are also problems such as poor penetration into the skin.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0035] Anhydrous tetrahydrofuran was added to 5.0 g of 2,2'-dihydroxy-5,5'-di-n-propylbiphenyl (hereinafter referred to as "propyl bisphenol") used as a raw material for cosmetics, and stirred under ice cooling. Then, 1.0 ml of pyridine and 6.0 g of acetyl chloride were sequentially added, and after 4 hours, post-treatment was carried out according to the usual method to obtain 5.2 g of crude product.

[0036] The obtained product was separated by silica gel column chromatography [mobile phase: ethyl acetate / n-hexane (1:5)] using silica gel 60N (100-210μm) manufactured by Kanto Chemical Co., Ltd., and 3.0 g of monochromate were obtained as light yellow oils. Acetate and 1.9g diacetyl.

[0037] use 1 H-NMR (400MHz, CDCl 3 ) Confirm the obtained monoacetyl and diacetyl of propyl bisphenol ( figure 1 ,figure 2). The obtained NMR signal is shown below.

[0038] (Monoacetyl)

[0039]

[0040] [δ(ppm); 0.94(m, 6H), 1.63(m, 4H), 1.99(s, 3H), 2.51(t, J=7.5Hz, 2H), 2.59(t, J=7.5Hz, 2H) ...

preparation example 2

[0045] According to Preparation Example 1, anhydrous tetrahydrofuran was added to 2.2 g of propyl bisphenol and stirred under ice cooling. Then 0.5ml of pyridine and about 3.5ml of propionyl chloride were added successively, and after 4 hours, the post-treatment was carried out according to the usual method to obtain 2.2g of crude product.

[0046] The crude product was separated by silica gel column chromatography [mobile phase: ethyl acetate / n-hexane (1:4)] using silica gel 60N (100-210 μm) manufactured by Kanto Chemical Co., Ltd. to obtain 1.47 g of dipropylene as a colorless oily substance Acylate.

[0047] use 1 H-NMR (400MHz, CDCl 3 ) The obtained dipropionyl product of propyl bisphenol was confirmed (Figure 3). The obtained NMR signal is shown below.

[0048] (Dipropionyl)

[0049]

[0050] [δ(ppm); 0.93(t, J=7.2Hz, 6H), 0.98(t, J=7.6Hz, 6H), 1.64(q, J=7.2Hz, 4H), 2.28(q, J=7.2Hz , 4H), 2.59 (t, J = 7.2 Hz, 4H), 7.02 (d, J = 8.4 Hz, 2H), 7.08 (s, 2H), 7.16 (dd, J = 2.0, 8...

preparation example 3

[0052] According to Preparation Example 1, anhydrous tetrahydrofuran was added to 1.0 g of propyl bisphenol, and the mixture was stirred under ice cooling. Then 0.5ml of pyridine and about 2.5ml of octanoyl chloride were added successively, and after 4 hours, after treatment according to the usual method, 1.5g of crude product was obtained.

[0053] The crude product was separated by silica gel column chromatography [mobile phase: ethyl acetate / n-hexane (1:10)] using silica gel 60N (100-210μm) manufactured by Kanto Chemical Co., Ltd. to obtain 1.25 g of monooctane as a pale yellow oily substance Acylate.

[0054] use 1 H-NMR (400MHz, CDCl 3 ) The monooctanoyl compound of the obtained propyl bisphenol was confirmed (Figure 4). The obtained NMR signal is shown below.

[0055] (Monoctanoyl)

[0056]

[0057] [δ(ppm); 0.85-0.97(m, 9H), 1.14-1.26(m, 8H), 1.41(q, J=7.2Hz, 2H), 1.58-1.69(m, 4H), 2.27(t, J =7.2Hz, 2H), 2.49-2.63 (m, 4H), 6.87-6.91 (m, 2H), 7.02-7.07 (m, 2H), 7.23-7.25 (...

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Abstract

The present invention provides a skin cosmetic having an excellent whitening effect to inhibit skin tanning by ultraviolet rays and having high safety. The skin cosmetic product includes a melanogenesis inhibitor comprising as an active ingredient an acylated biphenol compound represented by the following general formula (1): wherein R1 and R2 are each a hydrogen atom or an acyl group having 2 to 10 carbon atoms, provided that both R1 and R2 are not hydrogen atoms; and R3 and R4 are each a hydrogen atom or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms.

Description

Technical field [0001] The present invention relates to a skin cosmetic with excellent whitening effect and high safety, which suppresses skin darkening caused by ultraviolet rays. Background technique [0002] If the skin is exposed to ultraviolet rays, the skin will be affected in various ways. That is, the active oxygen, lipid peroxide, etc., generated in the skin due to ultraviolet exposure can cause inflammation and cause great damage to the skin tissue. The damage causes the skin to lose its moisturization, luster, texture, etc., and if the damage damages the dermis, wrinkles, etc. are formed, which may cause light aging. In addition, active oxygen generated by ultraviolet rays or various factors released from skin cells due to its influence can increase the activity of tyrosinase in melanocytes. Tyrosine is oxidized by tyrosinase in melanocytes to produce melanin that affects skin color. Therefore, it is believed that if ultraviolet rays activate tyrosinase, melanin will b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K8/37A61Q19/02
CPCA61K8/37A61Q19/02A61P17/00
Inventor 杉田淳中原道夫池本毅
Owner KAO CORP
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