JP5265282B2 - Skin cosmetics - Google Patents

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JP5265282B2
JP5265282B2 JP2008241867A JP2008241867A JP5265282B2 JP 5265282 B2 JP5265282 B2 JP 5265282B2 JP 2008241867 A JP2008241867 A JP 2008241867A JP 2008241867 A JP2008241867 A JP 2008241867A JP 5265282 B2 JP5265282 B2 JP 5265282B2
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俊雄 引間
稔 佐々木
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Kao Corp
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Description

本発明は、特に美白効果に優れ、さらには優れた肌荒れ防止効果及び美肌効果を発現し、同時に保存安定性にも優れた皮膚化粧料に関する。   The present invention relates to a skin cosmetic that is particularly excellent in a whitening effect, further exhibits an excellent rough skin prevention effect and a beautiful skin effect, and at the same time has excellent storage stability.

従来より、肌のしみやそばかす等の予防や治療を目的とする化粧料には、L−アスコルビン酸やその誘導体、アルブチン等のハイドロキノン誘導体、コウジ酸等のピロン類が配合されている。これらの物質は、メラニン生成の抑制、生成したメラニンの淡色漂白作用等の効果を有し、美白効果を有する物質として広く知られている。しかし、これらの物質は、例えばL−アスコルビン酸およびその誘導体の場合、保存安定性が不十分であったり、紫外線による炎症防止効果が十分に認められないことが多い。またハイドロキノン誘導体は安全性が十分でないなどの問題がある。この様にメラニンの生成抑制効果、メラニンの淡色漂白作用、炎症防止効果、安全性等、総合的に優れた美白を目的とした化粧料を得ることは困難であった。   Conventionally, cosmetics intended for the prevention and treatment of skin spots, freckles and the like have been blended with L-ascorbic acid and derivatives thereof, hydroquinone derivatives such as arbutin, and pyrones such as kojic acid. These substances have effects such as inhibition of melanin production and light color bleaching of the produced melanin, and are widely known as substances having a whitening effect. However, in the case of L-ascorbic acid and its derivatives, for example, these substances often have insufficient storage stability and the inflammation preventing effect due to ultraviolet rays is not sufficiently observed. Hydroquinone derivatives also have problems such as insufficient safety. As described above, it has been difficult to obtain a cosmetic material that is comprehensively excellent in whitening, such as a melanin production inhibitory effect, a light-color bleaching action of melanin, an anti-inflammatory effect, and safety.

一方、特定のビフェニル化合物にはチロシナーゼ活性阻害効果やメラニン生成抑制効果があることが知られている(特許文献1、特許文献2)。しかし、これらを単独で配合した場合、その美白効果は十分に満足できるものではなかった。また、これらの特定ビフェニル化合物は、特に紫外線照射に対する安定性に問題があり、製剤化において大きな課題となっていた。   On the other hand, it is known that specific biphenyl compounds have a tyrosinase activity inhibitory effect and a melanin production inhibitory effect (Patent Documents 1 and 2). However, when these were blended alone, the whitening effect was not fully satisfactory. Moreover, these specific biphenyl compounds have a problem in stability to ultraviolet irradiation in particular, and have been a big problem in formulation.

特開平6−145040号公報JP-A-6-145040 特開平7−25743号公報JP 7-25743 A

上記事情において、安定、かつ安全で、優れた美白効果を発現することができる皮膚化粧料が求められていた。即ち、本発明の目的は、安定、かつ安全で、優れた美白効果を発現することのできる皮膚化粧料を提供することにある。   In the above circumstances, there has been a demand for a skin cosmetic that is stable and safe and that can exhibit an excellent whitening effect. That is, an object of the present invention is to provide a skin cosmetic that is stable and safe and can exhibit an excellent whitening effect.

本発明者は鋭意研究した結果、特定構造を有するビフェニル化合物と共に、ユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)から得られる抽出エキスを含有する皮膚化粧料が、保存安定性に優れ、紫外線によるメラニン生成を抑制すると共にメラニン色素の排泄を促し、相乗的に優れた美白効果を発現し、さらには表皮の乾燥を防ぎ、皮膚の代謝を促進するなど、優れた肌荒れ防止効果及び美肌効果を発現することを見出し、本発明を完成するに至った。   As a result of intensive research, the inventor of the present invention has a storage stability that includes a biphenyl compound having a specific structure and an extract obtained from Saxifragaceae (Bergenia crassifolia (Linne) Fritsch). Excellent anti-rough skin effect, such as suppressing the production of melanin by ultraviolet rays and promoting the excretion of melanin pigment, synergistically showing excellent whitening effect, further preventing epidermis drying and promoting skin metabolism And it discovered that the skin-beautifying effect was expressed, and came to complete this invention.

即ち本発明は、下記一般式(1)又は(2)で表されるビフェニル化合物から選ばれる少なくとも1種と、ユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)から得られる抽出エキスを含有することを特徴とする皮膚化粧料である。   That is, the present invention provides an extract obtained from at least one selected from the biphenyl compounds represented by the following general formula (1) or (2) and from Saxifragaceae (Bergenia crassifolia (Linne) Fritsch). It is a skin cosmetic characterized by containing an extract.

Figure 0005265282
(式中、Rは水素原子又は炭素数2〜10のアシル基を表す。)
Figure 0005265282
(In the formula, R represents a hydrogen atom or an acyl group having 2 to 10 carbon atoms.)

Figure 0005265282
(式中、Rは水素原子又は炭素数2〜10のアシル基を表す。)
Figure 0005265282
(In the formula, R represents a hydrogen atom or an acyl group having 2 to 10 carbon atoms.)

本発明の皮膚化粧料は、特定構造式で表されるビフェニル化合物とユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)から得られる抽出エキスを含有することにより、保存安定性に優れ、紫外線によるメラニン生成を抑制すると共にメラニン色素の排泄を促し、相乗的に優れた美白効果を発現し、さらには表皮の乾燥を防ぎ、皮膚の代謝を促進するなど、優れた肌荒れ防止効果及び美肌効果を発現する。   The skin cosmetic composition of the present invention contains a biphenyl compound represented by a specific structural formula and an extract obtained from Saxifragaceae Azahaiwa Chinese cabbage (Bergenia crassifolia (Linne) Fritsch), thereby improving storage stability. Excellent, suppresses the production of melanin by ultraviolet rays and promotes the excretion of melanin pigment, synergistically exhibits an excellent whitening effect, further prevents epidermis drying, promotes skin metabolism, etc. Expresses skin benefits.

以下、本発明の実施に形態を詳述する。本発明で使用される一般式(1)、(2)で表されるビフェニル化合物のうち、Rが水素原子のものは、従来公知の方法に従って合成することができる(ジャーナル オブ オーガニック ケミストリィ、第28巻、1048頁、1963年;日本科学会誌、第87巻、第6号、603頁、1966年)。その他、モクレン科ホウノキ属植物の樹皮から得られるマグノロールを水素添加することによって得ることも可能である。   Hereinafter, embodiments of the present invention will be described in detail. Among the biphenyl compounds represented by the general formulas (1) and (2) used in the present invention, those in which R is a hydrogen atom can be synthesized according to a conventionally known method (Journal of Organic Chemistry, No. 28). (Volume 1048, 1963; Journal of the Japan Society of Science, Vol. 87, No. 6, 603, 1966). In addition, it can also be obtained by hydrogenating magnolol obtained from the bark of a magnoliaceae plant.

また、本発明で使用される一般式(1)、(2)で表されるビフェニル化合物のうち、Rがアシル基のアシル化誘導体は、従来公知のアシル化反応、例えばピリジン存在下で無水脂肪酸又は酸クロライドと反応させることにより製造することができる。   Among the biphenyl compounds represented by the general formulas (1) and (2) used in the present invention, acylated derivatives in which R is an acyl group are conventionally known acylation reactions, for example, anhydrous fatty acids in the presence of pyridine. Or it can manufacture by making it react with an acid chloride.

本発明の皮膚化粧料は、これら特定のビフェニル化合物の少なくとも1種を含有する。本発明の皮膚化粧料におけるこれらビフェニル化合物の含有量は、皮膚化粧料の総量を基準として、0.0001〜20質量%が好ましく、更に好ましくは0.001〜5質量%、特に好ましくは0.01〜2質量%である。これら範囲であれば、本発明の効果をより有効に発現させることが可能である。   The skin cosmetic of the present invention contains at least one of these specific biphenyl compounds. The content of these biphenyl compounds in the skin cosmetic of the present invention is preferably 0.0001 to 20% by mass, more preferably 0.001 to 5% by mass, and particularly preferably 0.001% by mass based on the total amount of the skin cosmetic. 01 to 2% by mass. Within these ranges, the effects of the present invention can be expressed more effectively.

本発明では、ユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)から得られる抽出エキスを使用する。抽出エキスは、厚葉岩白菜の植物体を材料として、公知の抽出方法により抽出することにより製造することができる。抽出溶媒としては、通常用いられるものであれば特に限定は無いが、水、エタノール、プロパノール等の低級アルコール、グリセリン、プロピレングリコール、1,3−ブチレングリコール等の多価アルコール、その他の極性溶媒又はそれらの混液のような親水性溶媒を用いたほうがより効果の高い抽出物が得られるため、好ましく用いられる。   In the present invention, an extract obtained from the saxifragaceae Atsubaiwa Chinese cabbage (Bergenia crassifolia (Linne) Fritsch) is used. The extracted extract can be produced by extracting with a known extraction method using a plant of Atsubaiwa Chinese cabbage as a material. The extraction solvent is not particularly limited as long as it is usually used, but water, lower alcohols such as ethanol and propanol, polyhydric alcohols such as glycerin, propylene glycol and 1,3-butylene glycol, other polar solvents or It is preferable to use a hydrophilic solvent such as a mixed solution because an extract with higher effect can be obtained.

具体的には、ユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)の根茎を、水或いはグリセリン中で温浸し、濾別して得られた抽出液を使用することができる。   Specifically, an extract obtained by digesting and filtering the rhizomes of Saxifragaceae Azaiwaiwa Chinese cabbage (Bergenia crassifolia (Linne) Fritsch) in water or glycerin can be used.

本発明の皮膚化粧料における厚葉岩白菜から得られる抽出エキスの含有量は、作用効果或いは当該皮膚化粧料の剤型等により適宜調整されるものであるが、皮膚化粧料の全量を基準として、固形分換算で通常0.0001質量%〜3質量%の範囲が好適であり、0.001〜1質量%の範囲が特に好適である。これら範囲であれば、本発明の効果をより有効に発現させることが可能である。   The content of the extract extracted from Atsuba Ichika in the skin cosmetics of the present invention is appropriately adjusted depending on the action effect or the dosage form of the skin cosmetics, but based on the total amount of the skin cosmetics Usually, the range of 0.0001% by mass to 3% by mass in terms of solid content is preferable, and the range of 0.001 to 1% by mass is particularly preferable. Within these ranges, the effects of the present invention can be expressed more effectively.

本発明の皮膚化粧料には、上記原料の他に、色素、香料、防腐剤、界面活性剤、抗酸化剤、保湿剤などを、本発明の目的を達成する範囲内で適宜配合することができる。   In addition to the above-mentioned raw materials, the skin cosmetic of the present invention may be appropriately blended with pigments, fragrances, preservatives, surfactants, antioxidants, moisturizers and the like within the scope of achieving the object of the present invention. it can.

本発明の皮膚化粧料の剤型としては、クリーム、乳液、化粧水、パックなどが挙げられる。例えば乳液等の場合、油相及び水相をそれぞれ加熱溶解したものを乳化分散して冷却する通常の方法により製造することができる。   Examples of the dosage form of the skin cosmetic of the present invention include creams, emulsions, lotions and packs. For example, in the case of an emulsion or the like, it can be produced by an ordinary method of emulsifying and cooling an oil phase and an aqueous phase, which are dissolved by heating, and then cooling.

以下、実施例により本発明の実施の形態を詳述するが、本発明はこれら実施例に限定されるものではない。尚、実施例におけるビフェニル化合物1は上記一般式(1)においてRが水素原子であるビフェニル化合物を、ビフェニル化合物2は上記一般式(2)においてRが水素原子であるビフェニル化合物を意味する。   Hereinafter, the embodiments of the present invention will be described in detail by way of examples, but the present invention is not limited to these examples. The biphenyl compound 1 in the examples means a biphenyl compound in which R is a hydrogen atom in the general formula (1), and the biphenyl compound 2 means a biphenyl compound in which R is a hydrogen atom in the general formula (2).

製造例(厚葉岩白菜抽出エキスの製造)
厚葉岩白菜の根茎50gを水250mLに温度40〜50℃で温浸して濾別した後、再び残渣を同様に温浸することを数回繰り返し、抽出液1.5Lを得た。これを減圧濃縮した残留物に精製水を100mL加え、1週間熟成した後、不溶物を濾別した。この抽出液を再び減圧濃縮し、次いで濃グリセリンを加えて抽出液のグリセリン含有量が40質量%になるように調整し、固型分含量が3.2質量%の抽出溶液を得た。この抽出溶液を厚葉岩白菜抽出エキスとしてとして、以下の実施例、比較例で使用した。
Production Example (Manufacture of Atsuba Rock Chinese Cabbage Extract)
After 50 g of rhizomes of Atsuba Ichigo cabbage were digested in 250 mL of water at a temperature of 40 to 50 ° C. and filtered, the residue was again digested in the same manner several times to obtain 1.5 L of an extract. 100 mL of purified water was added to the residue concentrated under reduced pressure, and the mixture was aged for 1 week, and then insoluble matters were filtered off. This extract was concentrated again under reduced pressure, and then concentrated glycerin was added to adjust the glycerin content of the extract to 40% by mass to obtain an extract solution having a solid content of 3.2% by mass. This extract solution was used in the following Examples and Comparative Examples as an extract of Atsuiwaiwa Chinese cabbage.

次に、皮膚色明度回復試験、荒れ肌改善効果の評価、官能テスト(美肌効果)、保存安定性試験の方法について説明する。   Next, skin color lightness recovery test, evaluation of rough skin improvement effect, sensory test (skin-beautifying effect), and storage stability test will be described.

試験法1(皮膚色明度回復試験)
被験者20名の背部皮膚にUV−B領域の紫外線を最小紅斑量の2倍量照射し皮膚の黒化を惹起させた。試料塗布部位と非塗布部位を設定して、黒化後の各々部位における基準明度(V0値、V0'値)を測定した。引き続いて塗布部位には、評価試料を1日2回、15週間連続塗布した。塗布開始から3、6、9、12、15週間後に塗布部位、非塗布部位それぞれの皮膚明度(Vn値、Vn'値)を測定し、下記の判定基準にしたがって皮膚色の回復の程度を評価点として表した。尚、皮膚の明度(マンセル表色系V値)は高速
分光色彩計で測定して得られたX値、Y値、Z値より算出した。下記実施例では、皮膚色明度の回復を、被験者20名ついての塗布3週間後の評価点の平均値で評価した。
Test Method 1 (Skin Color Lightness Recovery Test)
The back skin of 20 subjects was irradiated with UV rays in the UV-B region twice the minimum erythema amount to induce skin darkening. The sample application part and the non-application part were set, and the standard brightness (V0 value, V0 ′ value) in each part after blackening was measured. Subsequently, the evaluation sample was continuously applied to the application site twice a day for 15 weeks. After 3, 6, 9, 12, and 15 weeks from the start of application, the skin brightness (Vn value, Vn ′ value) of each application site and non-application site was measured, and the degree of skin color recovery was evaluated according to the following criteria. Expressed as a point. The lightness of the skin (Munsell color system V value) was calculated from the X value, Y value, and Z value obtained by measurement with a high-speed spectral colorimeter. In the following examples, the recovery of skin color brightness was evaluated by the average value of the evaluation scores 3 weeks after application for 20 subjects.

(判定基準)
評価点 塗布部位、非塗布部位間の明度回復値の差
―――――――――――――――――――――――――――
5 ΔV−ΔV'≧0.12
4 0.12>ΔV−ΔV'≧0.08
3 0.08>ΔV−ΔV'≧0.04
2 0.04>ΔV−ΔV'≧0
1 0>ΔV−ΔV'
―――――――――――――――――――――――――――
ΔV ;塗布部位の明度の回復値(Vn−V0)
ΔV';非塗布部位の明度の回復値(Vn'−V0')
(Criteria)
Evaluation point Difference in lightness recovery value between applied and non-applied sites ―――――――――――――――――――――――――――
5 ΔV−ΔV ′ ≧ 0.12
4 0.12> ΔV−ΔV ′ ≧ 0.08
3 0.08> ΔV−ΔV ′ ≧ 0.04
2 0.04> ΔV−ΔV ′ ≧ 0
1 0> ΔV−ΔV ′
―――――――――――――――――――――――――――
ΔV: Lightness recovery value at the application site (Vn−V0)
ΔV ′: Lightness recovery value of non-application site (Vn′−V0 ′)

試験法2(荒れ肌改善効果の評価)
下脚に荒れ肌を有する中高年20名を被験者とし、左側下脚試験部位に1日2回約1gの評価試料を4週間連続塗布させた。右側下脚には何も塗布せず対照とした。試験開始前及び終了後に下脚の皮膚の荒れ状態(皮膚乾燥度)を下記の判定基準により判定した。連続塗布前後での試験部位の判定結果を比較し、皮膚乾燥度が2段階以上改善された場合(例えば;+→−,++→±)を「有効」、1段階改善された場合を「やや有効」、変化がなかった場合を「無効」とした。試験結果は「有効」「やや有効」となった被験者の人数で示した。
Test Method 2 (Evaluation of rough skin improvement effect)
20 middle-aged and elderly people with rough skin on the lower leg were subjects, and about 1 g of an evaluation sample was applied to the left lower leg test site twice a day for 4 weeks. No control was applied to the lower right leg as a control. The roughness of the lower leg skin (skin dryness) was determined before and after the test according to the following criteria. Compare the test results of the test site before and after continuous application. When the skin dryness is improved by two or more levels (for example, + →-, ++ → ±) is “effective”, when it is improved by one level, “slightly” “Valid”, and “No” when there was no change. The test result was shown by the number of subjects who became “effective” and “slightly effective”.

(皮膚の荒れの判定基準)
判定 荒れの状態
――――――――――――――――――
− 正常
± 軽微乾燥、落屑なし
+ 乾燥、落屑軽度
++ 乾燥、落屑中等度
+++ 乾燥、落屑顕著
(Criteria for rough skin)
Judgment Rough condition ――――――――――――――――――
-Normal ± Minor dryness, no desquamation + Drying, minor desquamation ++ Drying, moderate desquamation ++++

試験法3(官能テスト)
被験者20名が試料を10日間連用した後の試料の特性を評価した。評価は、平滑性、美白効果、弾力性のアンケート項目に対し、「美白効果が感じられた」、「皮膚が滑らかになった」、「皮膚に張りが生じた」と回答した人数で示した。
Test method 3 (Sensory test)
Twenty subjects evaluated the characteristics of the sample after 10 days of continuous use of the sample. The evaluation was based on the number of respondents who answered that “whitening effect was felt”, “skin became smooth”, or “skin became stretched” for questionnaire items on smoothness, whitening effect, and elasticity. .

試験法4(保存安定性試験)
本発明の化粧料を太陽光下に8時間曝露した後の変色について、下記基準にて評価した。
Test method 4 (storage stability test)
The discoloration after the cosmetic of the present invention was exposed to sunlight for 8 hours was evaluated according to the following criteria.

(判定基準)
判定 変色の程度
――――――――――――
○ 変色なし
△ 若干の変色
× 著しく変色
(Criteria)
Judgment Degree of discoloration ――――――――――――
○ No discoloration △ Slight discoloration × Remarkably discoloration

実施例1〜2、比較例1〜8(スキンクリーム)
ユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)から得られる抽出エキスとビフェニル化合物を表1、2の組成において配合し、下記の調製方法に基づいてスキンクリームを調製した。各々について前記の各種試験を実施した。
Examples 1-2, Comparative Examples 1-8 (skin cream)
Extract extracts obtained from Saxifragaceae Azahaiwa Chinese cabbage (Bergenia crassifolia (Linne) Fritsch) and a biphenyl compound were blended in the compositions shown in Tables 1 and 2, and a skin cream was prepared based on the following preparation method. The various tests described above were performed for each.

(表1)

Figure 0005265282
(Table 1)
Figure 0005265282

(表2)

Figure 0005265282
(Table 2)
Figure 0005265282

(調製方法)
(A)、(B)成分それぞれを70℃にて均一に溶解し、(A)を攪拌しながら(B)を(A)に注入して乳化分散した後、攪拌しながら温度50℃まで冷却し、次に(C)成分を加え、さらに攪拌しながら温度30℃まで冷却して調製する。
(Preparation method)
Each component (A) and (B) is uniformly dissolved at 70 ° C., and (B) is poured into (A) while emulsifying and dispersing while stirring (A), and then cooled to 50 ° C. with stirring. Next, component (C) is added, and the mixture is further cooled to 30 ° C. with stirring.

(特性)
試験結果を表2に示す。本発明の実施例1〜2のスキンクリームは、いずれも前記諸試験において良好な結果を示した。一方、比較例1〜8のスキンクリームは、十分な効果が認められず、本発明の実施例に比べて劣っていた。
(Characteristic)
The test results are shown in Table 2. The skin creams of Examples 1 and 2 of the present invention all showed good results in the various tests. On the other hand, the skin creams of Comparative Examples 1 to 8 were inferior to the examples of the present invention because sufficient effects were not recognized.

実施例3(スキンローション)
表3の組成により本発明のスキンローションを下記の製法によって調製した。
組成
Example 3 (skin lotion)
The skin lotion of the present invention was prepared according to the following method according to the composition shown in Table 3.
composition

(表3)

Figure 0005265282
(Table 3)
Figure 0005265282

(調製方法)
(A)、(B)の各成分をそれぞれ混合溶解し、(B)を(A)に加えて混合攪拌した後、さらに(C)成分を加えて混合攪拌して調製した。
(Preparation method)
The components (A) and (B) were mixed and dissolved, and (B) was added to (A) and mixed and stirred, and then the component (C) was further added and mixed and stirred.

(特性)
この実施例3のスキンローションは、前記諸試験において良好な結果を示した。
(Characteristic)
The skin lotion of Example 3 showed good results in the above tests.

以上記載の如く、本発明により、特に美白効果に優れ、さらには優れた肌荒れ防止効果及び美肌効果を発現し、さらには保存安定性に優れた皮膚化粧料を提供することができる。   As described above, according to the present invention, it is possible to provide a skin cosmetic that is particularly excellent in whitening effect, further exhibits excellent skin roughness prevention effect and skin beautifying effect, and is excellent in storage stability.

Claims (1)

下記一般式(1)又は(2)で表されるビフェニル化合物から選ばれる少なくとも1種と、ユキノシタ科(Saxifragaceae)厚葉岩白菜(Bergenia crassifolia (Linne) Fritsch)から得られる抽出エキスを含有することを特徴とする皮膚化粧料。
Figure 0005265282
(式中、Rは水素原子又は炭素数2〜10のアシル基を表す。)
Figure 0005265282
(式中、Rは水素原子又は炭素数2〜10のアシル基を表す。)
It contains at least one selected from the biphenyl compounds represented by the following general formula (1) or (2) and an extract obtained from Saxifragaceae Atsuba Iwanaku (Bergenia crassifolia (Linne) Fritsch) Skin cosmetics characterized by.
Figure 0005265282
(In the formula, R represents a hydrogen atom or an acyl group having 2 to 10 carbon atoms.)
Figure 0005265282
(In the formula, R represents a hydrogen atom or an acyl group having 2 to 10 carbon atoms.)
JP2008241867A 2008-09-19 2008-09-19 Skin cosmetics Expired - Fee Related JP5265282B2 (en)

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US9000231B2 (en) * 2011-12-20 2015-04-07 Colgate-Palmolive Company Processes for making magnolol and derivatives thereof
KR101868692B1 (en) * 2016-09-20 2018-06-18 가천대학교 산학협력단 Composition for skin whitening and wrinkle improvement, prevention or treatment of skin aging comprising biphenyl dimethyl dicarbosylate

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JPH0859452A (en) * 1994-08-26 1996-03-05 Kanebo Ltd Skin cosmetic
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