JPH0692295B2 - External skin preparation - Google Patents
External skin preparationInfo
- Publication number
- JPH0692295B2 JPH0692295B2 JP62056049A JP5604987A JPH0692295B2 JP H0692295 B2 JPH0692295 B2 JP H0692295B2 JP 62056049 A JP62056049 A JP 62056049A JP 5604987 A JP5604987 A JP 5604987A JP H0692295 B2 JPH0692295 B2 JP H0692295B2
- Authority
- JP
- Japan
- Prior art keywords
- skin
- external preparation
- water
- amide derivative
- surfactant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 19
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 description 32
- -1 alkali metal salt Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 9
- 210000000434 stratum corneum Anatomy 0.000 description 9
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 206010013786 Dry skin Diseases 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003908 antipruritic agent Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 210000000736 corneocyte Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000037312 oily skin Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- 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
- A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/007—Preparations for dry skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Birds (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Genetics & Genomics (AREA)
- Dermatology (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は皮膚外用剤、更に詳しくは特定のアミド誘導体
を含有し、角層の水分保持力を高め、肌あれを改善する
ことができる皮膚外用剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention contains an external preparation for skin, more specifically a specific amide derivative, which enhances the water-retaining power of the stratum corneum and improves skin roughness. Regarding external preparations.
従来、肌にうるおいを与え、肌を柔軟にするには、角質
層の水分が重要であることが知られている。そして、当
該水分の保持は、角質層に含まれている水溶性成分、す
なわち遊離アミノ酸、有機酸、尿素又は無機イオンによ
るものであるとされ、これらの物質は単独であるいは組
合せて薬用皮膚外用剤あるいは化粧料に配合して、肌あ
れの改善又は予防の目的で使用されている。It has been known that moisture in the stratum corneum is important in order to moisturize and soften the skin. The retention of water is said to be due to the water-soluble components contained in the stratum corneum, that is, free amino acids, organic acids, urea or inorganic ions, and these substances may be used alone or in combination for the external preparation for medicated skin. Alternatively, it is used in cosmetics for the purpose of improving or preventing skin roughness.
また、これとは別に水と親和性が高い多くの保湿性物質
が開発され、同様の目的で使用されている。In addition to this, many moisturizing substances having high affinity with water have been developed and used for the same purpose.
しかしながら、これらの保湿性物質は、皮膚に適用した
場合、その作用は、皮膚角質層上にあつて水分を角質に
供給するというもので、しかもその効果は一時的であ
り、根本的に角質層の水分保持能力を改善し、肌あれを
本質的に予防あるいは治癒させるというものではなかつ
た。However, when these moisturizing substances are applied to the skin, the action is to provide water on the stratum corneum of the skin to supply water to the stratum corneum, and the effect is temporary, and basically the stratum corneum is It did not improve the water-retaining capacity of the skin and essentially prevent or cure the rough skin.
斯かる実情において、本発明者らは上記問題点を解決す
べく鋭意研究を行なつたところ、次の一般式（Ｉ） 〔式中、R1は炭素数８〜26の直鎖若しくは分岐鎖の飽和
若しくは不飽和の炭化水素基、R2は炭素数９〜25の直鎖
若しくは分岐鎖の飽和若しくは不飽和の炭化水素基、R3
はＨ、CH3、PhCH2、(CH3)2CH、(CH3)2CHCH2、C2H5(CH3)CHCH
2、HOCH2、CH3(HO)CH、CH3SCH2CH2、YOCOCH2、YOCOCH2CH2、 （ＹはＨ、Li、Na、Ｋを示す）、ＸはＯまたはCH2を示
す〕 で表わされるアミド誘導体が角質層の水分保持能力を根
本的に改善する効果を奏すること、そしてこのアミド誘
導体に界面活性剤を併用するとその効果を更に増大でき
ることを見出し、本発明を完成した。Under such circumstances, the present inventors have conducted diligent research to solve the above-mentioned problems, and found that the following general formula (I) Wherein, R 1 represents a straight chain or a saturated or unsaturated hydrocarbon group branched, R 2 is a hydrocarbon, saturated or unsaturated linear or branched 9 to 25 carbon atoms 8 to 26 carbon atoms Base, R 3
Is H, CH 3 , PhCH 2 , (CH 3 ) 2 CH, (CH 3 ) 2 CHCH 2 , C 2 H 5 (CH 3 ) CHCH
2 , HOCH 2 , CH 3 (HO) CH, CH 3 SCH 2 CH 2 , YOCOCH 2 , YOCOCH 2 CH 2 , (Y represents H, Li, Na, K), X represents O or CH 2 ] and the effect of fundamentally improving the water-retaining ability of the stratum corneum, and the amide derivative It was found that the effect can be further increased by using a surfactant together with the present invention, and the present invention has been completed.
すなわち本発明は、前記式（Ｉ）で表わされるアミド誘
導体を含有する皮膚外用剤、並びに前記式（Ｉ）で表わ
されるアミド誘導体及び界面活性剤を含有する皮膚外用
剤を提供するものである。That is, the present invention provides a skin external preparation containing the amide derivative represented by the formula (I), and a skin external preparation containing the amide derivative represented by the formula (I) and a surfactant.
本発明で使用される式（Ｉ）で表わされるアミド誘導体
は、たとえば特開昭48-72118号に示される如き公知の方
法により、次に示される反応式に従つて製造される。The amide derivative represented by the formula (I) used in the present invention is produced by a known method as shown in JP-A-48-72118 according to the reaction formula shown below.
（式中、R1、R2、R3及びＸは前記と同じ意味を有し、Ｚは
アルカリ金属又はエステル残基を示す） すなわち、グリシジルエーテル〔（III）式中、Ｘ＝
Ｏ〕又はα−オレフインエポキシド誘導体〔（III）式
中、Ｘ＝CH2〕にアミノ酸のアルカリ金属塩もしくはエ
ステルを反応せしめて化合物（II）となし、次いでこれ
をアシル化してアミド誘導体（Ｉ）を製造する。 (In the formula, R 1 , R 2 , R 3 and X have the same meanings as described above, and Z represents an alkali metal or ester residue.) That is, glycidyl ether [in the formula (III), X =
O] or α-olefin epoxide derivative [wherein X = CH 2 ] is reacted with an alkali metal salt or ester of an amino acid to form a compound (II), which is then acylated to form an amide derivative (I). To manufacture.
アミノ酸としては、グリシン、アラニン、フエニルアラ
ニン、バリン、ロイシン、イソロイシン、セリン、メチ
オニン、アスパラギン酸、グルタミン酸、ヒスチジン、
トリプトフアン等が挙げられ、そのアルカリ金属塩とし
てはLi,Na,K塩等が、またエステルとしてはメチル、エ
チル、ｎ−プロピル、iso−プロピル、ブチル等の低級
アルキルエステルあるいはフエニルエステル、ベンジル
エステル等が挙げられる。Amino acids include glycine, alanine, phenylalanine, valine, leucine, isoleucine, serine, methionine, aspartic acid, glutamic acid, histidine,
Tryptophan and the like can be mentioned, as the alkali metal salt thereof, Li, Na, K salts and the like, and as the ester, lower alkyl ester such as methyl, ethyl, n-propyl, iso-propyl, butyl or the like, phenyl ester, benzyl ester. Etc.
アミド誘導体（Ｉ）の本発明皮膚外用剤への配合量は、
特に制限されないが、通常乳化型の皮膚外用剤の場合に
は全組成の0.001〜50重量％（以下単に％で示す）、特
に0.1〜20％が好ましく、またスクワレン等の液状炭化
水素を基剤とする油性の皮膚外用剤の場合には１〜50
％、特に５〜25％が好ましい。The compounding amount of the amide derivative (I) in the external preparation for skin of the present invention is
Although not particularly limited, in the case of an emulsion type external preparation for skin, 0.001 to 50% by weight (hereinafter simply indicated by%) of the total composition, particularly 0.1 to 20% is preferable, and a liquid hydrocarbon such as squalene is used as a base. 1 to 50 for oily skin external preparations
%, Especially 5 to 25% is preferable.
また、本発明に用いられる界面活性剤としては、非イオ
ン界面活性剤、陰イオン界面活性剤、両性界面活性剤の
何れをも使用できるが、就中特に非イオン界面活性剤が
好適である。Further, as the surfactant used in the present invention, any of a nonionic surfactant, an anionic surfactant and an amphoteric surfactant can be used, but the nonionic surfactant is particularly preferable.
非イオン界面活性剤としては、例えばポリオキシエチレ
ンアルキルエーテル、ポリオキシエチレンアルキルフエ
ニルエーテル、ポリオキシエチレン脂肪酸エステル、ソ
ルビタン脂肪酸エステル、ポリオキシエチレンソルビタ
ン脂肪酸エステル、脂肪酸モノグリセライド、グリセリ
ルエーテル等が挙げられる。その中でも、次の一般式
（IV） （式中、R4は炭素数８〜24のアルキル基を示す）で表わ
されるグリセリルエーテル、就中R4が次式（Ｖ） （式中、ｐは４〜10の整数、ｑは５〜11の整数を示し、
ｐ＋ｑ＝11〜17でｐ＝７、ｑ＝８を頂点とする分布を有
する） で表わされるものが特に好ましい。Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid monoglyceride, glyceryl ether and the like. Among them, the following general formula (IV) (Wherein, R 4 represents an alkyl group having 8 to 24 carbon atoms) glyceryl ether represented by, inter alia R 4 have the following formula (V) (In the formula, p represents an integer of 4 to 10, q represents an integer of 5 to 11,
and a distribution represented by p + q = 11 to 17 with p = 7 and q = 8 at the vertices) is particularly preferable.
界面活性剤の本発明皮膚外用剤への配合量は、全組成の
0.01〜20％、特に0.1〜５％が好ましい。The amount of the surfactant added to the external preparation for skin of the present invention is the same as that of the entire composition.
0.01 to 20%, especially 0.1 to 5% is preferable.
本発明の皮膚外用剤は、その使用形態において、薬用皮
膚外用剤と化粧料に大別される。The external preparation for skin of the present invention is roughly classified into a medicated external preparation for skin and a cosmetic in its use form.
薬用皮膚外用剤としては、例えば薬効成分を含有する各
種軟膏剤を挙げることができる。軟膏剤としては、油性
基剤をベースとするもの、油／水、水／油型の乳化系基
剤をベースとするもののいずれであつてもよい。油性基
剤としては、特に制限はなく、例えば植物油、動物油、
合成油、脂肪酸、及び天然又は合成のグリセライド等が
挙げられる。また薬効成分としては、特に制限はなく、
例えば鎮痛消炎剤、鎮痒剤、殺菌消毒剤、収斂剤、皮膚
軟化剤、ホルモン剤等を必要に応じて適宜使用すること
ができる。Examples of the external medicated skin preparation include various ointments containing medicinal components. The ointment may be either one based on an oily base, one based on oil / water, or one based on an emulsion base of water / oil type. The oily base is not particularly limited, for example, vegetable oil, animal oil,
Examples include synthetic oils, fatty acids, and natural or synthetic glycerides. The medicinal component is not particularly limited,
For example, an analgesic anti-inflammatory agent, an antipruritic agent, a bactericidal disinfectant, an astringent agent, an emollient agent, a hormone agent and the like can be appropriately used as necessary.
また、化粧料として使用する場合は、必須成分の他に化
粧料成分として一般に使用されている油分、保湿剤、紫
外線吸収剤、アルコール類、キレート剤、pH調整剤、防
腐剤、増粘剤、色素、香料等を任意に組合せて配合する
ことができる。When used as a cosmetic, in addition to the essential components, oils commonly used as cosmetic components, moisturizers, UV absorbers, alcohols, chelating agents, pH adjusters, preservatives, thickeners, A dye, a fragrance, etc. can be arbitrarily combined and blended.
化粧料としては、種々の形態、例えば水／油、油／水型
乳化化粧料、クリーム、化粧乳液、化粧水、油性化粧
料、口紅、フアウンデーシヨン、皮膚洗浄剤、ヘアート
ニツク、整髪剤、養毛剤、育毛剤等の皮膚化粧料とする
ことができる。As the cosmetics, various forms such as water / oil, oil / water emulsion cosmetics, creams, lotions, lotions, oily cosmetics, lipsticks, foundations, skin cleansers, hair nicks, hair styling agents, It can be used as a skin cosmetic such as a hair nourishing agent or a hair restorer.
本発明皮膚外用剤における式（Ｉ）で示されるアミド誘
導体の作用機構の詳細は完全には解明されていないが、
これが角質細胞間に脂質膜を再構築して角質層の水分保
持機能を発揮するものと考えられる。Although the details of the mechanism of action of the amide derivative represented by the formula (I) in the external preparation for skin of the present invention have not been completely elucidated,
It is considered that this reconstructs the lipid membrane between the corneocytes and exerts the water retaining function of the stratum corneum.
本発明皮膚外用剤は、このような作用を有するアミド誘
導体（Ｉ）を含有するものであるため、肌あれに対して
優れた改善及び予防効果を発揮することができる。Since the external preparation for skin of the present invention contains the amide derivative (I) having such an action, it can exert an excellent improving and preventing effect on the rough skin.
次に、実施例を挙げて本発明を更に説明する。 Next, the present invention will be further described with reference to examples.
実施例１ 下記第１表に示すアミド化合物Ia〜Imとワセリンとをア
ミド化合物／ワセリン＝1/3の割合で混合し、それぞれ
について下記方法により皮膚コンダクタンス及び肌あれ
について評価した。その結果を第２表に示す。Example 1 Amide compounds Ia to Im shown in Table 1 below and vaseline were mixed at a ratio of amide compound / vaseline = 1/3, and skin conductance and skin roughness were evaluated by the following methods. The results are shown in Table 2.
（試験方法） 冬期に頬部に肌あれを起こしている20〜50才の女性10名
を被験者とし、左右の頬に異なる皮膚外用剤を２週間塗
布する。２週間の塗布が終了した翌日に次の項目につき
試験を行なつた。(Test method) Ten women aged 20 to 50 who have rough skin on the cheeks in winter are used as test subjects, and different skin external preparations are applied to the left and right cheeks for 2 weeks. On the day after the application for two weeks was completed, the following items were tested.
（１）皮膚コンダクタンス 37℃の温水にて洗顔後、温度20℃、湿度40％の部屋で20
分間安静にした後、角質層の水分含有量を皮膚コンダク
タンスメータ（IBS社製）にて測定した。コンダクタン
ス値は値が小さいほど皮膚は肌あれし、５以下ではひど
い肌あれである。一方この値が20以上であれば肌あれは
ほとんど認められない。(1) Skin conductance After washing the face with warm water of 37 ℃, in a room with temperature of 20 ℃ and humidity of 40%, 20
After resting for a minute, the water content of the stratum corneum was measured with a skin conductance meter (IBS). The smaller the conductance value is, the rougher the skin is, and when the conductance value is 5 or less, the skin is severely rough. On the other hand, if this value is 20 or more, almost no rough skin is observed.
（２）肌あれスコア 肌あれを肉眼で観測し、下記基準により判定した。スコ
アは平均値で示した。(2) Rough skin score Rough skin was observed with the naked eye and judged according to the following criteria. The score is shown as an average value.
実施例２ 実施例１で得たアミド化合物Ia〜Imを用いて下記第３表
に示す組成の皮膚外用剤（乳化化粧料）を製造し、その
肌あれ改善効果を実施例１と同様の方法により評価し
た。結果を第４表に示す。 Example 2 Using the amide compounds Ia to Im obtained in Example 1, a skin external preparation (emulsified cosmetic) having the composition shown in Table 3 below was produced, and the skin roughening improving effect was the same as in Example 1. It was evaluated by. The results are shown in Table 4.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 31/40 7431−4Ｃ 31/415 7431−4Ｃ // Ｃ０７Ｃ 233/47 7106−4Ｈ 233/49 7106−4Ｈ Ｃ０７Ｄ 209/20 9284−4Ｃ 233/64 １０６ (72)発明者 芋川 玄爾 栃木県宇都宮市氷室町1022−89 (72)発明者 高石 尚武 栃木県宇都宮市氷室町1022−24 (56)参考文献 特開 昭47−43596（ＪＰ，Ａ) 特開 昭48−8805（ＪＰ，Ａ) 特開 昭62−228048（ＪＰ，Ａ) 特開 昭63−192703（ＪＰ，Ａ) 特開 昭63−216852（ＪＰ，Ａ)─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical display location A61K 31/40 7431-4C 31/415 7431-4C // C07C 233/47 7106-4H 233/49 7106-4H C07D 209/20 9284-4C 233/64 106 (72) Inventor Genji Imokawa 1022-89 Himurocho, Utsunomiya City, Tochigi Prefecture (72) Innovator Naotaka Takaishi 1022-24 Himurocho, Utsunomiya City, Tochigi Prefecture (56) References JP-A-47-43596 (JP, A) JP-A-48-8805 (JP, A) JP-A-62-228048 (JP, A) JP-A-63-192703 (JP, A) JP-A-63 -216852 (JP, A)
Claims (2)
若しくは不飽和の炭化水素基、R2は炭素数９〜25の直鎖
若しくは分岐鎖の飽和若しくは不飽和の炭化水素基、R3
はＨ、CH3、PhCH2、(CH3)2CH、(CH3)2CHCH2、C2H5(CH3)CHCH
2、HOCH2、CH3(HO)CH、CH3SCH2CH2、YOCOCH2、YOCOCH2CH2、 （ＹはＨ、Li、Na、Ｋを示す）、ＸはＯまたはCH2を示
す〕 で表わされるアミド誘導体を含有する皮膚外用剤。1. The following general formula (I): Wherein, R 1 represents a straight chain or a saturated or unsaturated hydrocarbon group branched, R 2 is a hydrocarbon, saturated or unsaturated linear or branched 9 to 25 carbon atoms 8 to 26 carbon atoms Base, R 3
Is H, CH 3 , PhCH 2 , (CH 3 ) 2 CH, (CH 3 ) 2 CHCH 2 , C 2 H 5 (CH 3 ) CHCH
2 , HOCH 2 , CH 3 (HO) CH, CH 3 SCH 2 CH 2 , YOCOCH 2 , YOCOCH 2 CH 2 , (Y represents H, Li, Na, K), X represents O or CH 2 ], and an external preparation for skin containing an amide derivative.
囲第１項記載の皮膚外用剤。2. The external preparation for skin according to claim 1, which further contains a surfactant.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62056049A JPH0692295B2 (en) | 1987-03-11 | 1987-03-11 | External skin preparation |
| ES92115766T ES2077948T3 (en) | 1987-03-06 | 1988-03-02 | PREPARATION FOR EXTERNAL SKIN CARE. |
| EP88103177A EP0282816B1 (en) | 1987-03-06 | 1988-03-02 | External skin care preparation |
| EP92115766A EP0534286B1 (en) | 1987-03-06 | 1988-03-02 | External skin care preparation |
| DE88103177T DE3884021T2 (en) | 1987-03-06 | 1988-03-02 | External skin care preparation. |
| DE3854275T DE3854275T2 (en) | 1987-03-06 | 1988-03-02 | External skin care preparation. |
| US07/163,835 US4985547A (en) | 1987-03-06 | 1988-03-03 | External skin care preparation |
| US07/546,276 US5028416A (en) | 1987-03-06 | 1990-06-29 | External skin care preparation |
| US07/584,739 US5071971A (en) | 1987-03-06 | 1990-09-19 | External skin care preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62056049A JPH0692295B2 (en) | 1987-03-11 | 1987-03-11 | External skin preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63222107A JPS63222107A (en) | 1988-09-16 |
| JPH0692295B2 true JPH0692295B2 (en) | 1994-11-16 |
Family
ID=13016227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62056049A Expired - Lifetime JPH0692295B2 (en) | 1987-03-06 | 1987-03-11 | External skin preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0692295B2 (en) |
-
1987
- 1987-03-11 JP JP62056049A patent/JPH0692295B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63222107A (en) | 1988-09-16 |
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