JP2014114233A - 皮膚外用剤 - Google Patents
皮膚外用剤 Download PDFInfo
- Publication number
- JP2014114233A JP2014114233A JP2012268901A JP2012268901A JP2014114233A JP 2014114233 A JP2014114233 A JP 2014114233A JP 2012268901 A JP2012268901 A JP 2012268901A JP 2012268901 A JP2012268901 A JP 2012268901A JP 2014114233 A JP2014114233 A JP 2014114233A
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- Prior art keywords
- serine
- compound
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- skin
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Images
Abstract
Description
<1> 下記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩と、2)アドバンスド・グリケーション・エンドプロダクツ(AGEs:Advanced glycation end-products)分解剤とを含有する、皮膚外用剤。
(1)
[式中、R1は、無置換又は置換基を有する芳香族基を表し、R2は、水素原子、炭素数1〜4の直鎖又は分岐のアルキル基、炭素数1〜4の直鎖又は分岐のアルキル鎖を有するアシル基を表し、R3は、水素原子、炭素数1〜4の直鎖又は分岐のアルキル基を表す。]
<7> 前記AGEs分解剤が、下記の植物より得られる植物抽出物より選択される1種又は2種以上である、<1>〜<6>の何れかに記載の皮膚外用剤。
(植物)マメ科ゲンゲ属に属する植物、モクセイ科オリーブ属に属する植物、ユキノシタ科ユキノシタ属に属する植物、バラ科ポテンチラ属に属する植物、バラ科キジムシロ属に属する植物、マメ科アスパラトゥス属に属する植物、バラ科シモツケソウ属に属する植物、キク科ヨモギ属に属する植物
<8> 前記のマメ科ゲンゲ属、モクセイ科オリーブ属、ユキノシタ科ユキノシタ属、バラ科ポテンチラ属、バラ科キジムシロ属、マメ科アスパラトゥス属、バラ科シモツケソウ属、キク科ヨモギ属に属する植物が、マメ科ゲンゲ属レンゲソウ、モクセイ科オリーブ属オリーブ、ユキノシタ科ユキノシタ属ユキノシタ、バラ科ポテンチラ属トルメンチラ、バラ科ポテンチラ属ミヤマキンバエ、バラ科キジムシロ属カワラサイコ、マメ科アスパラトゥス属ルイボス、バラ科シモツケソウ属シモツケソウ、キク科ヨモギ属ヨモギである、<7>に記載の皮膚外用剤。
<9> 前記AGEs分解剤が、皮膚角層中AGEsの分解作用を有する、<1>〜<8>の何れかに記載の皮膚外用剤
<10> 前記AGEs分解剤を、皮膚外用剤全量に対し0.0001質量%〜10質量%含有する、<1>〜<9>の何れかに記載の皮膚外用剤。
<11> 化粧料(但し、医薬部外品を含む)である、<1>〜<10>の何れかに記載の皮膚外用剤。
<12> 美白用である、<1>〜<11>の何れかに記載の皮膚外用剤。
本発明の皮膚外用剤は、1)前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩と、2)AGEs分解剤とを含有することを特徴とし、優れた色素沈着予防又は改善作用を有する。本発明の皮膚外用剤の必須成分である前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩は、AGEs分解剤と共に皮膚外用剤に含有させることにより、前記一般式(1)に表される化合物が有するメラニン産生抑制作用が効果的に増強され、優れた色素沈着予防又は改善作用を発揮する。また、前記一般式(1)に表される化合物は、高い安全性及び安全性、取り分け、皮膚感作性、皮膚刺激性などに対する高い安全性、原体及び製剤中における高い安定性を有する。さらに、前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩は、セリン誘導体であり市販の原料より安価に製造出来るほか、化粧品など皮膚外用剤を製造する際に使用される汎用基剤に対する溶解性、取り分け、水又は低級アルコ−ル、多価アルコ−ル等の極性基剤に対する溶解性に優れ、多様な形態の製剤を作製することが可能である。
メイラード糖化反応は、加熱によりアミノ酸と還元糖が褐色の色素を生成する反応である。メイラード反応は、還元糖のカルボニル基及びアミノ酸のアミノ基がシッフ塩基を形成した後、エナミノールを経由し、アマドリ転位により安定なアマドリ化合物を生成する初期段階と、それ以降の、脱水、加水分解、炭素間の開裂により、α−ジカルボニル化合物を生成し、その後、α−ジカルボニル化合物、シッフ塩基、アマドリ化合物の分解、脂質過酸化反応由来のアルデヒド、糖の自動酸化及び分解などによりAGEsが生成する後期段階に分類することが出来る。AGEsは、前記のメイラード糖化反応の結果生じる生成物の総称であり、単一の化合物を意味するものではない。また、メイラード反応は、最終生成物のAGEs生成に至る過程において、生体内蛋白質と分子内又は分子間の無秩序な架橋構造を形成することにより、皮膚の色調のくすみ、弾力性、肌の肌理等の美肌、美白的な要因に深く関与する。また、皮膚中に存在するAGEsの内、真皮AGEsを分解する成分は、メイラード糖化反応を抑制することにより、くすみなどの色素沈着を予防又は改善する作用が存する。しかしながら、真皮AGEsを分解する成分を用いたとしても、紫外線暴露による色素沈着に対する予防又は改善効果、取り分け、治りの難いしみ、くすみ、炎症、肌荒れ症状を伴う色素沈着に対する予防又は改善効果は満足のいくものではなかった。本発明の皮膚外用剤は、AGEs分解剤、取り分け、角層AGEs分解作用(表皮AGEs分解作用)を有するAGEs分解剤と、前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩と共に皮膚外用剤に含有させることにより、前記の色素沈着症状に対する予防又は改善効果に優れる皮膚外用剤を提供することが出来る。
オリーブの葉3(kg)に50%エタノール水溶液5Lを加え、2時間加熱環流し、濾過によって不溶物を取り除き減圧濃縮し、本発明のオリーブより得られる植物抽出物を44(g)得た。
ユキノシタの葉3.5(kg)に50%エタノール水溶液6Lを加え、2時間加熱環流し、濾過によって不溶物を取り除き減圧濃縮し、本発明のユキノシタより得られる植物抽出物を41(g)得た。
バラ科ポテンチラ属トルメンチラの全草の乾燥物100(g)を、細切した後、500(mL)の50%エタノール水溶液を加えて3時間、加熱還流し、冷却後濾過にて不溶物を取り除いた後、減圧濃縮し、ついで凍結乾燥し、植物抽出物1を得た。しかる後に、植物抽出物1に200(mL)の水と200(mL)の酢酸エチルを加え、液液抽出を行い、酢酸エチル相をとり、減圧濃縮し、本発明のバラ科ポテンチラ属トルメンシラより得られる植物抽出物を得た。
バラ科キジムシロ属カワラサイコの全草の乾燥物100(g)を、細切した後、500(mL)の50%エタノール水溶液を加えて3時間、加熱還流し、冷却後濾過にて不溶物を取り除いた後、減圧濃縮し、ついで凍結乾燥し、植物抽出物2を得た。しかる後に、植物抽出物2に200(mL)の水と200(mL)の酢酸エチルを加え、液液抽出を行い、酢酸エチル相をとり、減圧濃縮し、本発明のバラ科キジムシロ属カワラサイコより得られる植物抽出物を得た。
バラ科ポテンチラ属ミヤマキンバイの全草の乾燥物100(g)を、細切した後、500(mL)の50%エタノール水溶液を加えて3時間、加熱還流し、冷却後濾過にて不溶物を取り除いた後、減圧濃縮し、ついで凍結乾燥し、植物抽出物3を得た。しかる後に、植物抽出物3に200(mL)の水と200(mL)の酢酸エチルを加え、液液抽出を行い、酢酸エチル相をとり、減圧濃縮し、本発明のバラ科ポテンチラ属ミヤマキンバイより得られる植物抽出物を得た。
マメ科アスパラトゥス属ルイボスの葉の乾燥物100(g)を、細切した後、500(mL)の50%エタノール水溶液を加えて3時間、加熱還流し、冷却後濾過にて不溶物を取り除いた後、減圧濃縮し、ついで凍結乾燥し、抽出物4を得た。しかる後に、抽出物4に200(mL)の水と200(mL)の酢酸エチルを加え、液液抽出を行い、酢酸エチル相をとり、減圧濃縮し、本発明のマメ科アスパラトゥス属ルイボスより得られる植物抽出物を得た。
バラ科ポテンチラ属シモツケソウの全草の乾燥物100(g)を、細切した後、500(mL)の50%エタノール水溶液を加えて3時間、加熱還流し、冷却後濾過にて不溶物を取り除いた後、減圧濃縮し、ついで凍結乾燥し、抽出物5を得た。しかる後に、抽出物5に200(mL)の水と200(mL)の酢酸エチルを加え、液液抽出を行い、酢酸エチル相をとり、減圧濃縮し、本発明のバラ科シモツケソウ属シモツケソウより得られる植物抽出物を得た。
キク科ヨモギ属ヨモギの全草の乾燥物100(g)を、細切した後、500(mL)の50%エタノール水溶液を加えて3時間、加熱還流し、冷却後濾過にて不溶物を取り除いた後、減圧濃縮し、ついで凍結乾燥し、抽出物6を得た。しかる後に、抽出物6に200(mL)の水と200(mL)の酢酸エチルを加え、液液抽出を行い、酢酸エチル相をとり、減圧濃縮し、本発明のキク科ヨモギ属ヨモギより得られる植物抽出物を得た。
マメ科ゲンゲ属レンゲソウの全草及び種子の乾燥物1(kg)を細断し、10(L)のエタノール溶液を加え、50℃以下の温度にて一晩浸漬した後、濾過にて不溶物を除去することにより、エタノール溶液抽出物である抽出物を得た。
22mM 1−フェニル−1,2−プロパンジオン/メタノ−ル+0.1M リン酸緩衝液(pH7.4) 1(mL)と、本発明の植物抽出物(モクセイ科オリーブ属オリ−ブより得られる植物抽出物、ユキノシタ科ユキノシタ属ユキノシタより得られる植物抽出物、バラ科ポテンチラ属トルメンチラより得られる植物抽出物、バラ科キジムシロ属カワラサイコより得られる植物抽出物、バラ科ポテンチラ属ミヤマキンバイより得られる植物抽出物、マメ科アスパラトゥス属ルイボスより得られる植物抽出物、バラ科シモツケソウ属シモツケソウより得られる植物抽出物、キク科ヨモギ属ヨモギより得られる植物抽出物、マメ科ゲンゲ属レンゲソウより得られる植物抽出物) 1×10−3(w/w%)を混合し、37℃で10時間反応させ、安息香酸の量をHPLCにて定量した。
(HPLC条件)
分析条件 検出器 :紫外吸光光度計(測定波長:260nm)
カラム :東ソー TSK−ODS80TsQA
カラム温度:室温
移動層 :氷酢酸2(g)/アセトニトリル 500(mL)+エデト酸二ナトリウム溶液(1→250) 500(mL)
流量:1(mL)/min.
以下の試験材料を用い、AGEs分解作用評価を実施した。
AGE−BSA:グルコースと牛血清アルブミン(BSA)を37℃で12週間以上インキュベートし、PD−10 columns(Amersham Biosciences 17−0851−01)にて余分なグルコ−スを除いたもの、1次抗体 :Anti-Albumin、Bovine Serum、Rabbit−Poly ROCKLAND 201−41331/20000、2次抗体 :Goat anti−rabbit IgG horseradish peroxidase conjugate BioRAD 170−6515 1/10000、基質 :TMB solution Wako 546−01911
(手順)
Type I コラーゲンコートした96穴マイクロプレート(Bio Coat 35 4407)に10(μg/mL)のAGE-BSAを100μL加え、1.0μg(AGE-BSA/well) 37℃にて4時間静置した後、0.05%Tween20/PBS(−)にて3回洗浄(マイクロミキサー上で室温、3分間振とうし)、PBS(−)に溶解した濃度(1×10−3%)の試料を100(μL)加え、37℃で10時間以上反応させる。その後、0.05%Tween20/PBS(−)にて3回洗浄し、1次抗体を各wellに100μL/well加え、室温で30分間静置する。0.05%Tween20/PBS(−)にて3回洗浄し、2次抗体を100(μL/well)入れ、室温30分間静置する。0.05%Tween20/PBS(−)にて3回洗浄し、TMBを100(μL/well)加え、室温15分反応させる。1N塩酸を100(μL/well)入れ、反応を止め、450nmの吸光度を測定する。AGEsの量を変え、検量線を引き、この検量線より残存AGEs量を定量した。残存AGEsを添加したAGEsより減じ、添加したAGEsで除し、100を乗じてAGEs分解率を算出した。
角層中のAGEsは次のようにして検出できる。皮膚より市販の粘着テープ等を利用してテープストリッピングにより角層採取を行い、溶剤で半日処理して粘着テ−プ部分を除去する。得られた角層に対して免疫組織染色を行い、染色された角層標本を顕微鏡下で観察する。結果を図1に示す。前記溶剤としては、有機溶媒、特にキシレンが好ましく例示できる。免疫組織染色の条件として、一次抗体(anti AGE monocronal antibody(mouse) TransGenic KH001)、ビオチン化2次抗体(Biotin-Rabbit Anti Mouse IGg conjugate ZYMED 81-6740)、ABC 試薬(R.T.U VECTASTAIN Elite ABC REAGENT BECTOR PK-7100)、AEC基質(ENVISION kit/HRP(AEC) Dako K3464)が好ましく例示できる。対照として、70%エタノール溶液に浸漬した角層標本を用意した。角層標本を、100mMグルコースを溶解した70%エタノール溶液に浸漬する。また、本発明のAGEs分解剤であるマメ科ゲンゲ属レンゲソウより得られる植物抽出物 0.1%共存下、非共存下で、37度で8日間放置後、AGEsを検知した。マメ科ゲンゲ属レンゲソウより得られる植物抽出物の非共存下においては、対照と比較して明らかに反応部位が多く、グルコースによりAGEsが産生したことがわかった。マメ科ゲンゲ属レンゲソウより得られる植物抽出物 0.1%共存下では、非共存下に比べて明らかに反応部位が少なく、マメ科ゲンゲ属レンゲソウより得られる植物抽出物がヒト角層中におけるAGEsの産生抑制作用を有することがわかった。この度合いは、標識の存在面積比によって定量化することができるし、該標識の存在割合は、後述の如く、スコアなどで簡便に数値化できる。
本発明の皮膚外用剤は、1)前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩と、2)AGEs分解剤を含有することを特徴とする。また、本発明の皮膚外用剤は、優れた色素沈着予防又は改善作用を有する。本発明の皮膚外用剤の製造方法は、前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩と、2)AGEs分解剤を含有するものであれば、両成分の含有量やその他の構成については特に限定されず、調製方法も特に限定されない。
以下の表1及び表2に示す処方に従って、本発明の皮膚外用剤である化粧料(ローション1〜4)を作製した。即ち、処方成分を80℃に加熱し、攪拌し、溶解させ、攪拌冷却した後、化粧料(ローション1〜4)を得た。同様に、表1の処方成分中の「本発明の前記一般式(1)に表される化合物」を「水」に置換した比較例1、「本発明のAGEs分解剤」を「水」に置換した比較例2、「本発明の前記一般式(1)に表される化合物」及び「本発明のAGEs分解剤」を共に「水」に置換した比較例3を作製した。また、「本発明の前記一般式(1)に表される化合物」及び「本発明のAGEs分解剤」の化粧料(ローション)における含有量変化は、「水」の含有量を調整することにより全体として100質量%となる様に調整した。
実施例1に記載の方法に従い製造した化粧料(ローション1〜4)及び比較例1〜3を用い、色素沈着抑制効果を調べた。自由意思で参加したパネラ−の背部に、試験初日(1日目)に1.5cm×1.5cmの試験部位を設け、試験部位の皮膚明度(L*値)を色彩色差計(CR-300、コニカミノルタ株式会社)にて測定した。試験初日に皮膚明度を測定した後、試験部位に最少紅斑量の2倍量(2MED)の紫外線を1回照射した。紫外線照射終了直後より1日3回、14日連続して、各試験部位に各検体(ローション1〜4及び比較例1〜3)を50μL塗布した。塗布終了24時間後(15日目)に色彩色差計(CR-300、コニカミノルタ株式会社)にて各試験部位の皮膚明度(L*値)を測定し、試験初日のL*値から15日目のL*値を引いたΔL*値を算出した。L*値は大きいほど皮膚明度が高いことを示す。そのため、ΔL*値が小さいほど、試験初日のL*値と15日目のL*値との差が小さく、色素沈着が抑制されたと判断することができる。結果を表3に示す。本発明の皮膚外用剤であるローション1〜4は、比較例3と比べてΔL*値が小さく、優れた色素沈着抑制効果を有することが分かる。また、比較例1及び比較例2も、比較例3と比べてΔL*値が小さく、色素沈着抑制作用が認められたが、その効果はローション1〜4に比較し弱かった。これにより、本発明の皮膚外用剤である化粧料(ローション1〜4)は、優れた色素沈着に対する予防又は改善効果を示すことが分かる。
表4及び表5に記載の処方に従い油中水乳化剤型の化粧料(クリーム1〜3)を作製した。即ち、イ、ロ、ハの成分をそれぞれ80℃に加温し、イの中にニを加えて溶解させ、混練してゲルを形成させ、これにロを加え希釈し、これに攪拌下徐々にハを加えて乳化し、攪拌冷却し、本発明の皮膚外用剤である化粧料(クリーム1〜3)を作製した。同様に、表4の処方成分中の「本発明の前記一般式(1)に表される化合物」を「水」に置換した比較例4、「本発明のAGEs分解剤」を「水」に置換した比較例5、「本発明の前記一般式(1)に表される化合物」及び「本発明のAGEs分解剤」を共に「水」に置換した比較例6を作製した。
実施例3に記載の方法に従い製造した化粧料(クリーム1及び2)及び比較例4〜6に関し、実施例2に記載の試験方法に従い色素沈着抑制効果を評価した。結果を表6に示す。本発明の皮膚外用剤である化粧料(クリーム1及び2)は、比較例4〜6と比べてΔL*値が小さく、優れた色素沈着に対する予防又は改善効果を有することが分かる。
Claims (12)
- 前記一般式(1)に表される化合物が、N−(p−メチルベンゾイル)セリン(化合物1)、N−(p−エチルベンゾイル)セリン(化合物2)、N−(p−メトキシベンゾイル)セリン(化合物3)、N−(p−フルオロベンゾイル)セリン(化合物4)、N−(p−トリフルオロメチルベンゾイル)セリン(化合物5)、N−(2−ナフトイル)セリン(化合物6)、N−(4−フェニルベンゾイル)セリン(化合物7)、N−(ベンゾイル)セリン(化合物8)、N−(p−メチルベンゾイル)セリン メチルエステル(化合物9)、N−(2−ナフトイル)セリン メチルエステル(化合物10)、N−ベンゾイル−O−メチルセリン(化合物11)、N−(p−メチルベンゾイル)−O−メチルセリン(化合物12)、N−(p−メチルベンゾイル)−O−アセチルセリン(化合物13)、N−(2−ナフトイル)−O−メチルセリン(化合物14)、その光学異性体及び/又はそれらの薬理学的に許容される塩である、請求項1に記載の皮膚外用剤。
N−(p−メチルベンゾイル)セリン(化合物1)
N−(p−エチルベンゾイル)セリン(化合物2)
N−(p−メトキシベンゾイル)セリン(化合物3)
N−(p−フルオロベンゾイル)セリン(化合物4)
N−(p−トリフルオロメチルベンゾイル)セリン(化合物5)
N−(2−ナフトイル)セリン(化合物6)
N−(4−フェニルベンゾイル)セリン(化合物7)
N−(ベンゾイル)セリン(化合物8)
N−(p−メチルベンゾイル)セリン メチルエステル(化合物9)
N−(2−ナフトイル)セリン メチルエステル(化合物10)
N−ベンゾイル−O−メチルセリン(化合物11)
N−(p−メチルベンゾイル)−O−メチルセリン(化合物12)
N−(p−メチルベンゾイル)−O−アセチルセリン(化合物13)
N−(2−ナフトイル)−O−メチルセリン(化合物14)
- 前記一般式(1)に表される化合物、その光学異性体及び/又はそれらの薬理学的に許容される塩を、皮膚外用剤全量に対し0.001質量%〜10質量%含有する、請求項1〜5の何れか一項に記載の皮膚外用剤。
- 前記AGEs分解剤が、下記の植物より得られる植物抽出物より選択される1種又は2種以上である、請求項1〜6の何れか一項に記載の皮膚外用剤。
(植物)マメ科ゲンゲ属に属する植物、モクセイ科オリーブ属に属する植物、ユキノシタ科ユキノシタ属に属する植物、バラ科ポテンチラ属に属する植物、バラ科キジムシロ属に属する植物、マメ科アスパラトゥス属に属する植物、バラ科シモツケソウ属に属する植物、キク科ヨモギ属に属する植物 - 前記のマメ科ゲンゲ属、モクセイ科オリーブ属、ユキノシタ科ユキノシタ属、バラ科ポテンチラ属、バラ科キジムシロ属、マメ科アスパラトゥス属、バラ科シモツケソウ属、キク科ヨモギ属に属する植物が、マメ科ゲンゲ属レンゲソウ、モクセイ科オリーブ属オリーブ、ユキノシタ科ユキノシタ属ユキノシタ、バラ科ポテンチラ属トルメンチラ、バラ科ポテンチラ属ミヤマキンバエ、バラ科キジムシロ属カワラサイコ、マメ科アスパラトゥス属ルイボス、バラ科シモツケソウ属シモツケソウ、キク科ヨモギ属ヨモギである、請求項7に記載の皮膚外用剤。
- 前記AGEs分解剤が、皮膚角層中AGEsの分解作用を有する、請求項1〜8の何れか一項に記載の皮膚外用剤
- 前記AGEs分解剤を、皮膚外用剤全量に対し0.0001質量%〜10質量%含有する、請求項1〜9の何れか一項に記載の皮膚外用剤。
- 化粧料(但し、医薬部外品を含む)である、請求項1〜10の何れか一項に記載の皮膚外用剤。
- 美白用である、請求項1〜11の何れか一項に記載の皮膚外用剤。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014114234A (ja) * | 2012-12-10 | 2014-06-26 | Pola Chem Ind Inc | 皮膚外用剤 |
JP2019127443A (ja) * | 2018-01-22 | 2019-08-01 | 株式会社アンズコーポレーション | 乳化化粧料、及び乳化化粧料の製造方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003261432A (ja) * | 2002-03-07 | 2003-09-16 | Noevir Co Ltd | 皮膚外用剤 |
JP2011011981A (ja) * | 2009-06-30 | 2011-01-20 | Pola Chemical Industries Inc | 化粧料 |
WO2011074643A1 (ja) * | 2009-12-16 | 2011-06-23 | ポーラ化成工業株式会社 | 色素沈着予防又は改善剤 |
JP2011246353A (ja) * | 2010-05-22 | 2011-12-08 | Pola Chemical Industries Inc | 皮膚外用剤 |
JP2014114234A (ja) * | 2012-12-10 | 2014-06-26 | Pola Chem Ind Inc | 皮膚外用剤 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003261432A (ja) * | 2002-03-07 | 2003-09-16 | Noevir Co Ltd | 皮膚外用剤 |
JP2011011981A (ja) * | 2009-06-30 | 2011-01-20 | Pola Chemical Industries Inc | 化粧料 |
WO2011074643A1 (ja) * | 2009-12-16 | 2011-06-23 | ポーラ化成工業株式会社 | 色素沈着予防又は改善剤 |
JP2011246353A (ja) * | 2010-05-22 | 2011-12-08 | Pola Chemical Industries Inc | 皮膚外用剤 |
JP2014114234A (ja) * | 2012-12-10 | 2014-06-26 | Pola Chem Ind Inc | 皮膚外用剤 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014114234A (ja) * | 2012-12-10 | 2014-06-26 | Pola Chem Ind Inc | 皮膚外用剤 |
JP2019127443A (ja) * | 2018-01-22 | 2019-08-01 | 株式会社アンズコーポレーション | 乳化化粧料、及び乳化化粧料の製造方法 |
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