JPS63183518A - Composition for hair - Google Patents

Composition for hair

Info

Publication number
JPS63183518A
JPS63183518A JP22749487A JP22749487A JPS63183518A JP S63183518 A JPS63183518 A JP S63183518A JP 22749487 A JP22749487 A JP 22749487A JP 22749487 A JP22749487 A JP 22749487A JP S63183518 A JPS63183518 A JP S63183518A
Authority
JP
Japan
Prior art keywords
hair
group
formula
composition
compound
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.)
Pending
Application number
JP22749487A
Other languages
Japanese (ja)
Inventor
Keikichi Sugiyama
圭吉 杉山
Koji Takada
康二 高田
Ikuo Yamamoto
山本 郁雄
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lion Corp filed Critical Lion Corp
Publication of JPS63183518A publication Critical patent/JPS63183518A/en
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362Polycarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • A61K8/553Phospholipids, e.g. lecithin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/606Nucleosides; Nucleotides; Nucleic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63Steroids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Cosmetics (AREA)

Abstract

PURPOSE:To obtain a composition for hair capable of promoting melanin formation, preventing and improving gray hair by external use to scalp, containing, a nucleic acid-related substance such as adenosine 3',5'-cyclic-phosphate compound, etc., and flavin adenine dinucleotide, etc. CONSTITUTION:A composition for hair containing 0.01-2% nucleic acid-related substance selected from a compound having a basis skeleton shown by formula I, flavin adenine dinucleotide and a salt thereof. The composition is applied to scalp, activates melanoctye, promotes melanin formation, can prevent and improve gray hair. A compound shown by formula II (R1-R3 are H, 1-22C acyl or alkyl; X1 and X2 are H, halogen, thio-containing group, amino or OH; M1 is H or salt-forming cation) is preferable as the compound shown by formula I and adenosine 3',5'-cyclic-phosphate wherein R1-R3, X1 and X2 are all H may be cited.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、頭皮に外用することにより、毛根のメラノサ
イトを活性化し、メラニン生成を促進して白髪を防止、
改善することができる毛髪用組成物、例えばヘアトニッ
クなどに関するものである。
[Detailed Description of the Invention] [Industrial Application Field] The present invention is applied externally to the scalp to activate melanocytes in the hair roots, promote melanin production, and prevent gray hair.
It relates to hair compositions, such as hair tonics, which can be improved.

〔従来の技術〕[Conventional technology]

育毛・養毛剤についてはこれまでに数多くの開発がなさ
れているが、白髪の防止、改善効果を有する毛髪化粧料
については、開発結果の報告が極めて少ないのが現状で
ある。このうち、特開昭60−1747’05号には、
ビタミンD3及びその誘導体を利用することが記載され
ている。しかしながら、この方法には、 (i)使用するビタミンD3及びその誘導体が、空気中
では極めて不安定で酸化されやすいために製剤化が困難
であり、外用剤として連用した場合、十分な効果を発揮
し得ない、 (ii)ビタミンD、及びその誘導体は、ビタミンD過
剰症、即ち、高カルシウム血症の症状(食欲不振、嘔吐
、便秘、体重減少、成長停止等)を起こす恐れがあり、
安全性の上の疑念がある、等の問題があり、該公開公報
記載の技術は実用性に乏しかった。
Although a large number of hair growth and tonics have been developed to date, there are currently very few reports on the development results of hair cosmetics that have the effect of preventing or improving gray hair. Among them, JP-A-60-1747'05 has
The use of vitamin D3 and its derivatives has been described. However, this method has the following drawbacks: (i) Vitamin D3 and its derivatives used are extremely unstable in the air and easily oxidized, making it difficult to formulate formulations; however, when used continuously as an external preparation, it is not sufficiently effective; (ii) Vitamin D and its derivatives may cause symptoms of hypervitaminosis D, that is, hypercalcemia (anorexia, vomiting, constipation, weight loss, growth arrest, etc.);
There were problems such as doubts about safety, and the technology described in the publication was not practical.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

従って、本発明は、頭皮に外用することにより、優れた
白髪防止、改善効果を発揮し、皮膚に対する安全性が極
めて高い毛髪用組成物を提供することを目的とする。
Therefore, an object of the present invention is to provide a hair composition that exhibits excellent gray hair prevention and improvement effects when applied externally to the scalp and is extremely safe for the skin.

〔問題点を解決するための手段〕[Means for solving problems]

本発明は、生体内の各組織、細胞に微量に存在し、種々
の調節機能、生理作用を有する特定核酸関連物質及びそ
の誘導体を化粧料基材に含有させると上記問題点を有効
に解決できるとの知見に基づいてなされたものである。
The present invention can effectively solve the above problems by incorporating specific nucleic acid-related substances and derivatives thereof, which exist in trace amounts in each tissue and cell in the living body and have various regulatory functions and physiological effects, into a cosmetic base material. This was done based on the knowledge that

すなわち、本発明は、下記[I]式で示される基本骨格
を有する化合物、フラビンアデニンジヌクレオチド及び
その塩からなる群から選ばれる少なくとも1種の核酸関
連物質を含有することを特徴とする毛髪用組成物を提供
する。
That is, the present invention provides a hair product containing at least one nucleic acid-related substance selected from the group consisting of a compound having a basic skeleton represented by the following formula [I], flavin adenine dinucleotide, and salts thereof. A composition is provided.

本発明では、上記一般式〔■〕で表わされる骨格を分子
内に有する限りどのような化合物をも使用することがで
きるが、これらのうち下記一般式〔■〕で表わされる化
合物を用いるのが好ましい。
In the present invention, any compound can be used as long as it has a skeleton represented by the above general formula [■] in the molecule, but among these, the compound represented by the following general formula [■] is preferred. preferable.

(式〔■〕中、R1、R2、R3は、水素、炭素数1〜
22、好ましくは1〜15のアシル基又は炭素数1〜2
2、好ましくは1〜15のアルキル基であり、Xl、X
2は、水素、臭素、沃素、塩素、弗素などのハロゲン、
メルカプト基、炭素数1〜4のチオアルキル基、4−ク
ロロフェニルチオ基、チオベンジル基等のチオ含有基、
アミノ基、炭素数1〜4のアミノアルキル基又は水酸基
である。又、Ml は、水素や塩形成カチオン、例えば
ナトリウム、カリウム、リチウムなどのアルカリ金属、
トリス(ヒドロキシメチル)アミノメタンを示す。尚、
アシル基、アルキル基にはハロゲン等の置換基があって
もよく、芳香族環を含んでいてもよい。また、二塩基酸
由来のアシル基でもよい。) 上記一般式〔■〕で表わされる化合物には、アデノシン
3’、5’−環状一リン酸(式中、R1、R2、R3、
xl、x2、MIがいずれも水素の化合物;以下cAM
Pと略称する。)、その特定の誘導体及びその塩が包含
される。
(In formula [■], R1, R2, R3 are hydrogen, carbon number 1-
22, preferably 1 to 15 acyl group or carbon number 1 to 2
2, preferably an alkyl group of 1 to 15, Xl, X
2 is halogen such as hydrogen, bromine, iodine, chlorine, fluorine,
Thio-containing groups such as mercapto group, thioalkyl group having 1 to 4 carbon atoms, 4-chlorophenylthio group, thiobenzyl group,
They are an amino group, an aminoalkyl group having 1 to 4 carbon atoms, or a hydroxyl group. Ml also represents hydrogen, salt-forming cations, such as alkali metals such as sodium, potassium, and lithium;
Indicates tris(hydroxymethyl)aminomethane. still,
The acyl group and the alkyl group may have a substituent such as a halogen, and may contain an aromatic ring. Alternatively, it may be an acyl group derived from a dibasic acid. ) The compound represented by the above general formula [■] includes adenosine 3',5'-cyclic monophosphate (in the formula, R1, R2, R3,
A compound in which xl, x2, and MI are all hydrogen; hereinafter referred to as cAM
It is abbreviated as P. ), certain derivatives thereof and salts thereof.

次に、これらの化合物及びフラビンアデニンジヌクレオ
チド(以下FADと略称する。)及びその塩について詳
しく説明する。
Next, these compounds, flavin adenine dinucleotide (hereinafter abbreviated as FAD), and salts thereof will be explained in detail.

一般式[IDで表わされる化合物 本発明で用いるcAMPは、生体内において、各種ホル
モン作用の調節機能を有する生理的に重要な物質であり
、すでに生化学試薬、心臓薬として利用されている。
Compound represented by the general formula [ID] cAMP used in the present invention is a physiologically important substance that has the ability to regulate various hormone actions in vivo, and has already been used as a biochemical reagent and a cardiac drug.

現在、工業的には醗酵法または合成法で製造されている
が、さらに細胞膜透過性が改善された、あるいは生体内
での安定性が向上された各種誘導体も市販されている。
Currently, they are produced industrially by fermentation or synthesis methods, but various derivatives with improved cell membrane permeability or in vivo stability are also commercially available.

本発明で用いる一般式〔■〕で表わされる化合物として
、具体的には、表−1に示される化合物とそれらのナト
リウム塩、カリウム塩、リチウム塩等の1種又は2種以
上の混合物が例示される。
Specific examples of the compound represented by the general formula [■] used in the present invention include one or a mixture of two or more of the compounds shown in Table 1 and their sodium salts, potassium salts, lithium salts, etc. be done.

なお、表−1において用いたc p phsは、4−ク
ロロフェニルチオ基を表わす(以下、同じ)。
Note that c p phs used in Table 1 represents a 4-chlorophenylthio group (the same applies hereinafter).

これらの化合物のうち、式〔■〕中のR1−R3、xl
、X2のすべてが水素でない化合物が好ましい。さらに
、R,、R3は水素またはアシル基、R2、xlは水素
、x2は水素、ハロゲン、チオ含有基、アミン基または
水酸基であるものが好ましい。これらのうち、特に好ま
しいのは、X2が水素の場合には、R+ SRaのいず
れか一方または両方ともがアシル基であって、該アシル
基がモノカルボン酸由来のものについては、炭素数5〜
15のものが好ましく、ジカルボン酸由来のものについ
ては、炭素数2〜15のものが好ましい。
Among these compounds, R1-R3, xl in formula [■]
, X2 are all not hydrogen. Furthermore, it is preferable that R,, R3 are hydrogen or an acyl group, R2 and xl are hydrogen, and x2 is hydrogen, a halogen, a thio-containing group, an amine group, or a hydroxyl group. Among these, when X2 is hydrogen, one or both of R+SRa is an acyl group, and when the acyl group is derived from a monocarboxylic acid, it is particularly preferable that the acyl group has 5 to 5 carbon atoms.
Those having 15 carbon atoms are preferred, and those derived from dicarboxylic acids are preferably those having 2 to 15 carbon atoms.

また、X2がハロゲン、チオ含有基、アミノ基または水
酸基の場合には、R,、R3は水素または炭素数1〜1
5のアシル基であるものが好ましい。
In addition, when X2 is a halogen, a thio-containing group, an amino group, or a hydroxyl group, R, R3 is hydrogen or has 1 to 1 carbon atoms.
5 is preferably an acyl group.

FAD及びその塩 FADは、酸化還元酵素の補酵素として、生体内で有機
化合物の酸化全般に関与する重要な物質として知られて
いる。そして、FADは、医薬品原料として皮膚炎、ア
レルギー性疾患、口内炎、脚気の治療、さらに目薬の有
効成分等として広く用いられている。
FAD and its salt FAD are known as important substances that are involved in the general oxidation of organic compounds in vivo as coenzymes of oxidoreductases. FAD is widely used as a pharmaceutical raw material in the treatment of dermatitis, allergic diseases, stomatitis, and beriberi, and as an active ingredient in eye drops.

現在、FADは工業的に醗酵法または合成法で製造され
ており、容易に入手することが可能である。
Currently, FAD is produced industrially by fermentation or synthesis, and is easily available.

尚、FADの塩も本発明では使用可能であり、具体的に
はFADナトリウム塩(FAD  ・2Na) 、FA
Dカリウム塩(FAD  ・2K)などが例示される。
Note that salts of FAD can also be used in the present invention, specifically FAD sodium salt (FAD 2Na), FA
Examples include D potassium salt (FAD 2K).

本発明では、必須成分とする前記核酸関連物質を頭皮に
直接族することにより、白髪防止、改善効果を発揮する
という、従来知られていなかった効果を利用するもので
あり、毛髪用組成物中に任意の濃度で配合できる。通常
は、製品形態、使用頻度にもよるが、各種毛髪用組成物
中にo、 o o i〜5重量%(以下、%と略する。
The present invention takes advantage of the hitherto unknown effect of preventing and improving gray hair by directly applying the nucleic acid-related substance as an essential ingredient to the scalp. Can be blended at any concentration. Usually, depending on the product form and frequency of use, various hair compositions contain o, o o i to 5% by weight (hereinafter abbreviated as %).

)程度、好ましくは0.01〜2%配合するのがよい。), preferably 0.01 to 2%.

本発明の組成物には、上記の必須成分に加えて他の薬剤
成分として、例えばビタミンA1ビタミンB6 、ビタ
ミンE1パントテン酸、ビオチン等のビタミン類、メチ
オニン、システィン、シスチン、チロシン等のアミノ酸
類、サリチル酸、ヒノキチオール、レゾルシン、トリク
ロロカルバニリド等の殺菌剤、エチニルエストラジオー
ル、プロゲステロン等のホルモン類等を配合することが
でき、好ましくは、毛髪用組成物中0.0001〜3%
添加するのがよい。
In addition to the above-mentioned essential ingredients, the composition of the present invention includes other pharmaceutical ingredients, such as vitamins such as vitamin A1, vitamin B6, vitamin E1, pantothenic acid, and biotin; amino acids such as methionine, cysteine, cystine, and tyrosine; Bactericidal agents such as salicylic acid, hinokitiol, resorcinol, trichlorocarbanilide, etc., hormones such as ethinyl estradiol, progesterone, etc. can be blended, and preferably 0.0001 to 3% in the hair composition.
It is good to add it.

さらに、油分、水、界面活性剤、保湿剤、低級アルコー
ル、増粘剤、酸化防止剤、キレート剤、pH調整剤、防
腐剤、香料、色素等通常化粧料に用いられる原料が配合
可能である。具体的には、油分としては、オリーブ油、
ホホバ油、硬化油等の油脂類、鯨ロウ、蜜ロウ、ラノリ
ン等のロウ類、流動パラフィン、セレシン、スクワラン
等の炭化水素類、ステアリン酸、オレイン酸等の脂肪酸
類、セタノール、ステアリルアルコール、ラノリンアル
コール、ヘキシルデカノール等のアルコール類、ミリス
チン酸イソプロピル、ステアリン酸ブチル等のエステル
類等である。油分を毛髪用組成物中0.5〜85%含有
させるのがよい。また、界面活性剤としては、ステアリ
ン酸ナトリウム、セチル硫酸ナトリウム、ポリオキシエ
チレンラウリルエーテルリン酸、N−アシルグルタミン
酸ナトリウム等のアニオン界面活性剤、塩化ステアリル
ジメチルベンジルアンモニウム、塩化ステアリルトリメ
チルアンモニウム等のカチオン界面活性剤、塩酸アルキ
ルアミノエチルグリシン液、レシチン等の両性界面活性
剤、モノステアリン酸グリセリン、モノステアリン酸ソ
ルビタン、ショ糖脂肪酸エステル、モノステアリン酸プ
ロピレングリコール、ポリオキシエチレンオレイルエー
テル、モノステアリン酸ポリエチレングリコール、モノ
パルミチン酸ポリオキシエチレンソルビクン、ポリオキ
シエチレンヤシ脂肪酸モノエタノールアミド、ポリオキ
シエチレンポリオキシプロピレングリコール、ポリオキ
シエチレンヒマシ油、ポリオキシエチレンラノリン等の
非イオン界面活性剤等を例示することができる。界面活
性剤を毛髪用組成物中0.1〜15%含有させるのがよ
い。さらに、保湿剤としては、グリセリン、1.3−ブ
チレングリコール、プロピレングリコール等を、低級ア
ルコールとしては、エタノール、インプロパツール等を
、増粘剤としては、ポリエチレングリコール、カルボキ
シメチルセルロースナトリウム等を、酸化防止剤として
は、ジブチルヒドロキシトルエン、ブチルヒドロキシア
ニソール、没食子酸プロピル等を、キレート剤としては
、エデト酸ニナトリウム、エタンヒドロキシジホスフェ
ート等を、pH調整剤としては、クエン酸、クエン酸ナ
トリウム、ホウ酸、ホウ砂、リン酸−水素ナトリウム等
を、防腐剤としては、パラオキシ安息香酸メチル、パラ
オキシ安息香酸エチノペデヒドロ酢酸、サリチル酸、安
息香酸等をそれぞれ例示することができる。なお、任意
成分は、これらに限定されるものではない。上記必須成
分と任意成分を適当に配合することにより、ヘアトニッ
ク、クリーム、ローション、乳液、軟膏等外用できる剤
型のものであればいずれでもよく、種々の製品形態で用
いることができる。
Furthermore, raw materials commonly used in cosmetics such as oil, water, surfactants, humectants, lower alcohols, thickeners, antioxidants, chelating agents, pH adjusters, preservatives, fragrances, and pigments can be added. . Specifically, the oils include olive oil,
Oils and fats such as jojoba oil and hydrogenated oils, waxes such as spermaceti wax, beeswax, and lanolin, hydrocarbons such as liquid paraffin, ceresin, and squalane, fatty acids such as stearic acid and oleic acid, cetanol, stearyl alcohol, and lanolin. These include alcohols, alcohols such as hexyldecanol, and esters such as isopropyl myristate and butyl stearate. It is preferable that the hair composition contains oil in an amount of 0.5 to 85%. Examples of surfactants include anionic surfactants such as sodium stearate, sodium cetyl sulfate, polyoxyethylene lauryl ether phosphate, and sodium N-acylglutamate, and cationic surfactants such as stearyldimethylbenzylammonium chloride and stearyltrimethylammonium chloride. Active agent, alkylaminoethylglycine hydrochloride solution, amphoteric surfactant such as lecithin, glycerin monostearate, sorbitan monostearate, sucrose fatty acid ester, propylene glycol monostearate, polyoxyethylene oleyl ether, polyethylene glycol monostearate Examples include nonionic surfactants such as polyoxyethylene sorbicun monopalmitate, polyoxyethylene coconut fatty acid monoethanolamide, polyoxyethylene polyoxypropylene glycol, polyoxyethylene castor oil, and polyoxyethylene lanolin. can. The surfactant is preferably contained in the hair composition in an amount of 0.1 to 15%. Furthermore, as humectants, glycerin, 1,3-butylene glycol, propylene glycol, etc. are used, as lower alcohols, ethanol, inpropatol, etc. are used, as thickeners, polyethylene glycol, carboxymethyl cellulose sodium, etc., and oxidized As inhibitors, dibutylhydroxytoluene, butylhydroxyanisole, propyl gallate, etc. are used. As chelating agents, disodium edetate, ethane hydroxy diphosphate, etc. are used. As pH adjusters, citric acid, sodium citrate, boron, etc. are used. Examples of preservatives include methyl paraoxybenzoate, etinopedehydroacetic acid paraoxybenzoate, salicylic acid, and benzoic acid. Note that the optional components are not limited to these. By appropriately blending the above-mentioned essential components and optional components, it can be used in a variety of product forms, including hair tonics, creams, lotions, emulsions, ointments, etc., as long as they can be used externally.

具体的には、ヘアトニックとしては、上記必須成分0.
01〜2%、低級アルコール40〜98%、薬剤成分0
〜3%、保湿剤0〜15%、精製水0〜60%、香料 
微量を含有する組成物があげられ、ヘアクリームとして
は、上記必須成分0.01〜2%、油分20〜80%、
界面活性剤0.5〜15%、保湿剤0〜15%、精製水
15〜80%、防腐剤微量を含有する組成物が例示され
る。また、乳液としては、上記必須成分0.01〜2%
、油分5〜30%、界面活性剤0.5〜15%、保湿剤
0〜15%、精製水50〜95%、防腐剤 微量を含有
する組成物が例示される。
Specifically, the hair tonic contains 0.0% of the above essential ingredients.
01-2%, lower alcohol 40-98%, drug ingredients 0
~3%, moisturizer 0-15%, purified water 0-60%, fragrance
Examples include compositions containing trace amounts of the above essential ingredients, 0.01 to 2% of the above essential ingredients, 20 to 80% of oil content,
An example is a composition containing 0.5 to 15% surfactant, 0 to 15% humectant, 15 to 80% purified water, and a trace amount of preservative. In addition, as an emulsion, 0.01 to 2% of the above essential ingredients
Examples include compositions containing 5 to 30% oil, 0.5 to 15% surfactant, 0 to 15% humectant, 50 to 95% purified water, and a trace amount of preservative.

本発明で用いられる核酸関連物質が、外用により白髪防
止、改善効果を示す作用の詳細は不明であるが頭皮毛根
の毛球部に存在するメラノサイトを活性化してメラニン
生成を促進し、生成したメラニン顆粒が毛母細胞に取り
込まれることにより、白髪防止、改善効果が発揮され、
さらには、毛母細胞の賦活化等により養毛・育毛作用も
発揮されるものと推定される。
The details of the effect of the nucleic acid-related substance used in the present invention on preventing and improving gray hair when applied externally are unknown, but it activates melanocytes present in the hair bulb of the scalp hair roots to promote melanin production, resulting in the production of melanin. By incorporating the granules into hair matrix cells, it has the effect of preventing and improving gray hair.
Furthermore, it is presumed that it also exhibits hair nourishing and restoring effects by activating hair matrix cells.

また、本発明の核酸関連物質は、本来生体内に広く存在
するものであることから、安全性は極めて高いが、念の
ため安全性について確認したところ、急性毒性、皮膚刺
激性、皮膚感作性等の点で実用上特に問題は認められな
かった。
In addition, the nucleic acid-related substance of the present invention is extremely safe because it is widely present in living organisms. No practical problems were observed in terms of performance, etc.

〔発明の効果〕〔Effect of the invention〕

本発明によれば、頭皮に外用することにより、優れた白
髪防止、改善効果を発揮し、皮膚に対する安全性が極め
て高い毛髪化粧料が提供される。
According to the present invention, there is provided a hair cosmetic that exhibits excellent gray hair prevention and improvement effects when applied externally to the scalp and is extremely safe for the skin.

本発明によれば、養毛・育毛効果も上記効力に加えて、
発揮される。
According to the present invention, in addition to the above-mentioned effects, hair nourishing and hair growth effects are also achieved.
Demonstrated.

゛ 従って本発明の毛髪用組成物は、毛髪に適用するた
めの種々の形態、例えばヘアトニック、クリーム、ロー
ション、乳液、軟膏、ヘアトリートメント、ヘアコンデ
ィショナー等の毛髪化粧料等、外用できる剤型のものと
して種々の形態で幅広く使用できる。
Therefore, the hair composition of the present invention can be applied to hair in various forms, such as hair tonics, creams, lotions, emulsions, ointments, hair treatments, hair conditioners, and other hair cosmetics, and externally applicable formulations. It can be used widely in various forms.

次に、実施例により本発明を説明する。Next, the present invention will be explained by examples.

なお、実施例においては以下の略号を用いた。In addition, the following abbreviations were used in the examples.

MB:モノブチリル MH:モノヘキサノイル MO=モノオクタノイル MS:モノサクシニル DAニジアセチル DBニジブチリル DM=ジマロニル DSニジサクシニル CβPhS:4−クロロフェニルチオ また、cAMP誘導体の置換基の位置は次のように示し
た。
MB: monobutyryl MH: monohexanoyl MO = monooctanoyl MS: monosuccinyl DA nidiacetyl DB nidibutyryl DM = dimalonyl DS nidisuccinyl CβPhS: 4-chlorophenylthio Further, the positions of the substituents of the cAMP derivative are shown as follows.

N6 :R,またはR2が水素以外の場合の結合位置を
示す。
N6: Indicates the bonding position when R or R2 is other than hydrogen.

0”:R3が水素以外の場合の結合位置を示す。0'': Indicates the bonding position when R3 is other than hydrogen.

8:X2が水素以外の場合の結合位置を示す。8: Shows the bonding position when X2 is other than hydrogen.

〔実施例〕〔Example〕

実施例1 エタノールに香料を加えて均一に溶解した。これとは別
に、精製水に他の成分を加えて均一に溶解した溶液を調
製しておき、ここに前記エタノール溶液を加えてヘアト
ニックを調製した。表−2に組成を示すが、表中の数値
は配合量(重量%)である(以下同じ)。
Example 1 A fragrance was added to ethanol and dissolved uniformly. Separately, a solution was prepared by adding other ingredients to purified water and uniformly dissolved therein, and the ethanol solution was added thereto to prepare a hair tonic. The composition is shown in Table 2, and the numerical values in the table are the blending amount (% by weight) (the same applies hereinafter).

表−2 上記ヘアトニックを、白髪のある20名の男女(30〜
60才)に1日2回(朝・夜)、連続3力月間、本発明
品と比較例のそれぞれをハーフ・ヘッド法で左右頭皮に
別々に使用させ、塗布部位の状態を、試験前後で比較し
、白髪防止、改善効果を調べた。結果を次に示す。
Table 2 The above hair tonic was applied to 20 men and women with gray hair (30~
(60 years old) twice a day (morning and evening) for 3 consecutive months, the product of the present invention and the comparative example were used separately on the left and right scalp using the half-head method, and the condition of the application site was observed before and after the test. We compared the results and investigated their effectiveness in preventing and improving gray hair. The results are shown below.

表−3 表−3の結果から、N6.0” −DBcAMP−Na
を配合した本発明のヘアトニックは、無添加のヘアトニ
ックと比較して、白髪の量を少なくすることができ、顕
著な白髪防止・改善効果を示すことがわかる。
Table-3 From the results of Table-3, N6.0''-DBcAMP-Na
It can be seen that the hair tonic of the present invention containing the above can reduce the amount of gray hair compared to a hair tonic without additives, and exhibits a remarkable effect of preventing and improving gray hair.

なお、上記ヘアトニックの3力月間の使用中及び使用後
においても、皮膚の状態に異常な症状は特に認められな
かった。
In addition, no abnormal symptoms were observed in the skin condition during or after using the hair tonic for three months.

N6. O” −DBcAMP−Naの安全性にツイテ
試験を行った。試験項目と結果をまとめて表−4に示す
N6. A tweet test was conducted to check the safety of O''-DBcAMP-Na. The test items and results are summarized in Table 4.

表−4の結果からN6. O” −DBcAMP −N
aの安全性は極めて高いことが確認された。
From the results in Table-4, N6. O”-DBcAMP-N
It was confirmed that the safety of a was extremely high.

実施例2 表−5に示す成分1〜5及び成分6〜10を別々に80
℃にて加熱溶解した後、両者を混合乳化し、冷却中に、
成分11を加え、さらに均一に分散して、毛髪用乳液を
調製した。尚、表中、Tはエチレンオキシドの平均付加
モル数を示す(以下、同じ)。
Example 2 Components 1 to 5 and components 6 to 10 shown in Table 5 were separately prepared at 80%
After heating and dissolving at ℃, the two were mixed and emulsified, and while cooling,
Component 11 was added and further uniformly dispersed to prepare a hair emulsion. In addition, in the table, T indicates the average number of added moles of ethylene oxide (the same applies hereinafter).

表−5 実施例1と同様にして前記乳液の白髪防止、改善効果を
調べた。結果を表−6に示す。
Table 5 In the same manner as in Example 1, the effect of the milky lotion on preventing and improving gray hair was investigated. The results are shown in Table-6.

表−6 表−6の結果から、FAD  ・2Naを配合した本発
明の乳液を使用した場合は、無添加の乳液を使用した場
合に比べて、白髪の量が少なく、顕著な白髪防止、改善
効果を示した。
Table 6 From the results in Table 6, when using the emulsion of the present invention containing FAD/2Na, the amount of gray hair was smaller than when using an additive-free emulsion, and there was significant prevention and improvement of gray hair. It was shown to be effective.

なお、上記乳液の3力月間の使用中及び使用後において
も、皮膚の状態に異常な症状は特に認められなかった。
In addition, no abnormal skin symptoms were observed during or after using the emulsion for three months.

さらに、同じ乳液を用いて以下のように養毛効果につい
ても試験を行った。
Furthermore, the same emulsion was also tested for hair growth effect as described below.

即ち、C57ブラツクマウス6匹を1群とし、マウスの
腹部両側から背部にかけて刺毛し、片側に本発明の乳液
を、もう一方には比較例を毎日1回、連続2週間塗布し
た。そして、1週間毎に刺毛部に生えてきた毛の長さを
それぞれ測定して養毛効果を比較した。結果を表−7に
示す。尚、表2 °を 中の数値は毛の長さくmm)を(平均値上標準偏差)で
示したものである。
That is, six C57 black mice were made into one group, hairs were pricked from both sides of the abdomen to the back of the mice, and the emulsion of the present invention was applied to one side and the comparative example was applied once a day for two consecutive weeks for two consecutive weeks. Then, the length of hair that grew in the pricked area was measured every week to compare the hair growth effects. The results are shown in Table-7. The numerical values in Table 2 are the hair length (mm) expressed as the standard deviation above the average value.

表−7 表−7の結果から明らかなように、FAD  ・2Na
を配合した本発明の乳液は、無添加の乳液と比較して著
しい養毛効果を示した。
Table 7 As is clear from the results in Table 7, FAD ・2Na
The emulsion of the present invention containing the above showed a remarkable hair-nourishing effect compared to the emulsion without additives.

FAD  ・2Naの安全性について実施例1と同じ方
法で実験したところ、皮膚刺激等の問題点は全く認めら
れず、安全性は極めて高いことが確認された。
When testing the safety of FAD 2Na using the same method as in Example 1, no problems such as skin irritation were observed, and it was confirmed that the safety was extremely high.

実施例3 表−8に示す成分1〜6及び成分7〜10を別々に80
℃で加熱溶解した後混合乳化し、冷却中に成分11を加
え、均一に分散して表−8に示すヘアクリームを調製し
た。
Example 3 Components 1 to 6 and components 7 to 10 shown in Table-8 were separately prepared at 80%
After heating and dissolving at ℃, the mixture was mixed and emulsified, and while cooling, component 11 was added and uniformly dispersed to prepare the hair cream shown in Table 8.

実施例1と同様にして、ヘアクリームの白髪防止、改善
効果を調べた。結果を表−9に示す。
In the same manner as in Example 1, the effect of the hair cream on preventing and improving gray hair was investigated. The results are shown in Table-9.

表−9 表−9の結果からN6. O” −DScAMP−Na
を配合した本発明のクリームを使用した場合は、無添加
のクリームを使用した場合に比べて、白髪の量が少なく
、顕著な白髪防止、改善効果を示した。
Table-9 From the results of Table-9, N6. O”-DScAMP-Na
When the cream of the present invention containing the following was used, the amount of gray hair was smaller than when using a cream without additives, and it showed a remarkable effect of preventing and improving gray hair.

なお、上記クリームの3力月間の使用中及び使用後にお
いても、皮膚の状態に異常な症状は特に認められなかっ
た。又、N6.0” −DScAMP−Naの安全性に
ついて実施例1と同じ方法で実験したところ、皮膚刺激
等の問題点は全く認められず、安全性は極めて高いこと
が確認された。
Furthermore, during and after using the above cream for three months, no abnormal symptoms were observed in the condition of the skin. Furthermore, when the safety of N6.0"-DScAMP-Na was tested in the same manner as in Example 1, no problems such as skin irritation were observed, and it was confirmed that the safety was extremely high.

実施例4 表−10に示す成分1〜4及び成分5〜9を別々に混合
溶解した後、成分5〜9の溶液を撹拌しながら、ここに
成分1〜4の溶液を添加し、表−10に示す毛髪用乳液
を調製した。
Example 4 After separately mixing and dissolving components 1 to 4 and components 5 to 9 shown in Table 10, the solution of components 1 to 4 was added thereto while stirring the solution of components 5 to 9, and the solution of components 1 to 4 was added to the solution shown in Table 1. A hair emulsion shown in No. 10 was prepared.

実施例1と同様にして、乳液の白髪防止、改善効果を調
べた。結果を表−11に示す。
In the same manner as in Example 1, the effect of the emulsion on preventing and improving gray hair was investigated. The results are shown in Table-11.

表−11 表−11の結果からO” −MSc、AMP−Naを配
合した本発明の乳液を使用した場合は、無添加の乳液を
使用した場合に比べて、白髪の量が少なく、顕著な白髪
防止、改善効果を示した。
Table 11 From the results in Table 11, when using the emulsion of the present invention containing O"-MSc and AMP-Na, the amount of gray hair was less and more noticeable than when using an additive-free emulsion. It has been shown to be effective in preventing and improving gray hair.

なお、上記乳液の3力月間の使用中及び使用後において
も、皮膚の状態に異常な症状は特に認められなかった。
In addition, no abnormal skin symptoms were observed during or after using the emulsion for three months.

又、O” −MScAMP−Naの安全性について実施
例1と同じ方法で実験したところ、皮膚刺激等の問題点
は全く認められず、安全性は極めて高いことが確認され
た。
Furthermore, when testing the safety of O''-MScAMP-Na using the same method as in Example 1, no problems such as skin irritation were observed, and it was confirmed that the safety was extremely high.

実施例5 表−12に示す組成のヘアクリームを調製し、実施例1
と同様にして、白髪防止、改善効果を調べた。結果を表
−13に示す。
Example 5 A hair cream having the composition shown in Table 12 was prepared, and Example 1
In the same manner as above, the effect of preventing and improving gray hair was investigated. The results are shown in Table-13.

表−13 表−13の結果から、N6−MBcAMP−Naを配合
した本発明のヘアクリームを使用した場合は、無添加の
ヘアクリームを使用した場合に比べて、白髪の量が少な
く、顕著な白髪防止、改善効果を示した。      
      “ なお、上記ヘアクリームの3力月間の使用中及び使用後
においても、皮膚の状態に異常な症状は特に認められな
かった。又、N6−MBcAMP−Naの安全性につい
て実施例1と同じ方法で実験したところ、皮膚刺激等の
問題点は全く認められず、安全性は極めて高いことが確
認された。
Table 13 From the results in Table 13, when using the hair cream of the present invention containing N6-MBcAMP-Na, the amount of gray hair was less and more noticeable than when using additive-free hair cream. It has been shown to be effective in preventing and improving gray hair.
“In addition, no abnormal symptoms were observed in the skin condition during or after using the above hair cream for 3 months.In addition, the safety of N6-MBcAMP-Na was tested using the same method as in Example 1. When tested, no problems such as skin irritation were observed, confirming that the product is extremely safe.

実施例6 実施例3で用いたN6. O” −DScAMl”Na
の代りに、8−BrcAMt’Na、 8−C12cA
MP−Na、 8−Cjl! PhScAMP・Na、
 8−3fl8−3flcA、 8−OHc8−0Hc
A、 O” −MB−8−BrcAMP・NaまたはN
6.0” −D^−8−NH2CAMP−Naを配合し
たヘアトニックを調製し、実施例1と同様にして評価し
たところ、実施例3とほぼ同等の白髪防止、改善効果が
得られた。
Example 6 N6. used in Example 3. O”-DScAMl”Na
instead of 8-BrcAMt'Na, 8-C12cA
MP-Na, 8-Cjl! PhScAMP・Na,
8-3fl8-3flcA, 8-OHc8-0Hc
A, O”-MB-8-BrcAMP・Na or N
A hair tonic containing 6.0"-D^-8-NH2CAMP-Na was prepared and evaluated in the same manner as in Example 1. As a result, almost the same gray hair prevention and improvement effect as in Example 3 was obtained.

実施例7 エタノールに他の成分を順次加えて均一に溶解し、ヘア
トニックを調製した。組成を表−14に示す。
Example 7 A hair tonic was prepared by sequentially adding other ingredients to ethanol and uniformly dissolving them. The composition is shown in Table-14.

表−14 実施例1と同様にして、前記ヘアトニックの白髪防止、
改善効果を調べた。結果を表−15に示す。
Table 14 In the same manner as in Example 1, the hair tonic was used to prevent gray hair,
The improvement effect was investigated. The results are shown in Table-15.

表−15 表−15の結果から、FAD・2Naを配合した本発明
のヘアトニックを使用した場合は、無添加のヘアトニッ
クを使用した場合に比べて、白髪の量が少なく、顕著な
白髪防止、改善効果を示した。
Table 15 From the results in Table 15, when using the hair tonic of the present invention containing FAD/2Na, the amount of gray hair was smaller than when using the hair tonic without additives, and there was significant prevention of gray hair. , showed an improvement effect.

なお、上記ヘアトニックの3力月間の使用中及び使用後
においても、皮膚の状態に異常な症状は特1こδ忍めら
れなかった。
Furthermore, even during and after using the above hair tonic for three months, I could not bear any unusual symptoms in my skin condition.

実施例8 実施例7で用いたFAD・2Naの代りに、Na−MS
cAMl”Na、%N6−MHcAMP−Na、 0”
 −MOcAMP−NaまたはNa、 O”−DMcA
Mt’Naを配合したヘアトニックを調製し、実施例1
と同様にして評価したところ、実施例7とほぼ同等の白
髪防止、改善効果が得られた。
Example 8 Instead of FAD・2Na used in Example 7, Na-MS
cAMl”Na, %N6-MHcAMP-Na, 0”
-MOcAMP-Na or Na, O”-DMcA
A hair tonic containing Mt'Na was prepared and Example 1
When evaluated in the same manner as in Example 7, almost the same gray hair prevention and improvement effects as in Example 7 were obtained.

Claims (2)

【特許請求の範囲】[Claims] (1)下記〔 I 〕式で示される基本骨格を有する化合
物、フラビンアデニンジヌクレオチド及びその塩からな
る群から選ばれる少なくとも1種の核酸関連物質を含有
することを特徴とする毛髪用組成物。 ▲数式、化学式、表等があります▼・・・・・・〔 I
(1) A hair composition comprising at least one nucleic acid-related substance selected from the group consisting of a compound having a basic skeleton represented by the following formula [I], flavin adenine dinucleotide, and salts thereof. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・〔I
]
(2)〔 I 〕式で示される基本骨格を有する化合物が
、下記一般式〔II〕で表わされるアデノシン3′,5′
−環状−リン酸化合物である特許請求の範囲第(1)項
記載の毛髪用組成物。 ▲数式、化学式、表等があります▼・・・・・・〔II〕 (式〔II〕中、R_1、R_2、R_3は、水素、炭素
数1〜22のアシル基または炭素数1〜22のアルキル
基であり、X_1およびX_2は、水素、ハロゲン、チ
オ含有基、アミノ基、アミノアルキル基または水酸基で
あり、M_1は、水素または塩形成カチオンを示す。)
(2) The compound having the basic skeleton represented by the formula [I] is adenosine 3',5' represented by the following general formula [II]
- The hair composition according to claim (1), which is a cyclic phosphoric acid compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・[II] (In the formula [II], R_1, R_2, R_3 are hydrogen, an acyl group having 1 to 22 carbon atoms, or an acyl group having 1 to 22 carbon atoms. is an alkyl group, X_1 and X_2 are hydrogen, halogen, thio-containing group, amino group, aminoalkyl group or hydroxyl group, and M_1 represents hydrogen or a salt-forming cation.)
JP22749487A 1986-09-18 1987-09-10 Composition for hair Pending JPS63183518A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP22021186 1986-09-18
JP61-220211 1986-09-18

Publications (1)

Publication Number Publication Date
JPS63183518A true JPS63183518A (en) 1988-07-28

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Country Link
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995001773A1 (en) * 1993-07-07 1995-01-19 Trustees Of Boston University Stimulation of tanning by dna fragments
US6103689A (en) * 1994-08-31 2000-08-15 Trustees Of Boston University Methods of inducing hair growth and coloration
US6867179B1 (en) 1994-08-31 2005-03-15 Trustees Of Boston University Methods of inducing hair growth and coloration
US7196055B2 (en) 1994-08-31 2007-03-27 Trustees Of Boston University Inhibition of apoptosis in keratinocytes by a ligand of p75 nerve growth factor receptor
JP2009534334A (en) * 2006-04-21 2009-09-24 ディーエスエム アイピー アセッツ ビー.ブイ. Use of opioid receptor antagonists
JP2010229071A (en) * 2009-03-26 2010-10-14 Kose Corp Oil-based solid hair cosmetic

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2077725A1 (en) * 1970-02-10 1971-11-05 Lapinet Eugene Adenosine phosphoric acid - to stimulate cellular function of the ski
DE2139183A1 (en) * 1971-08-05 1973-02-15 Lingner Werke Gmbh Sustained action cosmetic and/or pharm compsns - contg addns of cyclic adenosine-monophosphoric acid
JPS6245527A (en) * 1985-08-21 1987-02-27 Shiseido Co Ltd Preventive and remedy for gray hair

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2077725A1 (en) * 1970-02-10 1971-11-05 Lapinet Eugene Adenosine phosphoric acid - to stimulate cellular function of the ski
DE2139183A1 (en) * 1971-08-05 1973-02-15 Lingner Werke Gmbh Sustained action cosmetic and/or pharm compsns - contg addns of cyclic adenosine-monophosphoric acid
JPS6245527A (en) * 1985-08-21 1987-02-27 Shiseido Co Ltd Preventive and remedy for gray hair

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995001773A1 (en) * 1993-07-07 1995-01-19 Trustees Of Boston University Stimulation of tanning by dna fragments
US5470577A (en) * 1993-07-07 1995-11-28 Trustees Of Boston University Stimulation of tanning by DNA fragments or single-stranded DNA
US5532001A (en) * 1993-07-07 1996-07-02 Trustees Of Boston University Stimulation of tanning by DNA fragments or single-stranded DNA
US5580547A (en) * 1993-07-07 1996-12-03 Trustees Of Boston University Stimulation of tanning by DNA fragments or single-stranded DNA
US5643556A (en) * 1993-07-07 1997-07-01 Trustees Of Boston University Stimulation of tanning by DNA fragments or single-stranded DNA
US6103689A (en) * 1994-08-31 2000-08-15 Trustees Of Boston University Methods of inducing hair growth and coloration
US6867179B1 (en) 1994-08-31 2005-03-15 Trustees Of Boston University Methods of inducing hair growth and coloration
US7196055B2 (en) 1994-08-31 2007-03-27 Trustees Of Boston University Inhibition of apoptosis in keratinocytes by a ligand of p75 nerve growth factor receptor
JP2009534334A (en) * 2006-04-21 2009-09-24 ディーエスエム アイピー アセッツ ビー.ブイ. Use of opioid receptor antagonists
JP2010229071A (en) * 2009-03-26 2010-10-14 Kose Corp Oil-based solid hair cosmetic

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