2005 ANNUAL SCIENTIFIC MEETING 193 DEVELOPMENT OF THE NOVEL PLANT-DERIVED LANOLIN SUBSTITUTE AND ITS COSMETIC APPLICATIONS Abstract Yukihiro Ohashi and Katsunori Myojo Nippon Fine Chemical Co., Ltd., Tokyo, Japan We have developed Bis-behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate (oligomer ester) as a novel plant-derived lanolin or adsorption refined lanolin substitute with very pale color (GH=l), low odor, and excellent stability. It is an oligomer type phytosterol ester in a paste form synthesized only from plant-derived materials. This oligomer ester has excellent lanolin-like properties such as high water holding capability (200%), excellent moisturizing effect in human use tests, excellent gloss in makeup products (superior to lanolin and adsorption refined lanolin) coming from its high refractive index (approx. 1.475 at 60 °C), high pigment dispersing ability, excellent foam-stabilizing ability and moisturizing effect in cleansing products and shampoos, emulsion stabilizing effect, skin affinity, etc. And this oligomer ester is much more stable against oxidation than lanolin and adsorption refined lanolin in CDM test. So this oligomer ester is useful for make-up products, cleansing products, skincare products, and haircare products. Introduction Lanolin has been used as a cosmetic ingredient for a long time because of its good properties such as water holding capability, skin affinity, gloss coming from high refractive index, pigment dispersing ability, and so on. But lanolin has also some problems (not so good color, odor, and oxidation stability). The properties of lanolin are mainly due to its characteristic composition profiles, that is, complicated mixed esters consisted of extremely many kinds of fatty acids and alcohols, including sterols and branched fatty acids / alcohols, and high molecular weight. In this investigation, we have attempted to develop a new lipid having similar properties to lanolin (and adsorption refined lanolin) only from plant-derived raw materials. Therefore we have designed in consideration of the above composition profiles of lanolin and synthesized Bis-behenyl/isostearyl/ phytosteryl dimer dilinoleyl dimer dilinoleate (oligomer ester Figure l) from hydrogenated dimer acid, dimerdiol, behenyl alcohol, isostearyl alcohol, and phytosterol as a novel plant-derived lanolin without the problems of lanolin [I]. RJ-OCO-Rl(-COO-R2-0CO-Rl)n-COO-RJ RI: Dimer acid residue, R2: Dimerdiol residue. R3 Phytosterol, Behenyl / lsostearyl alcohol residue Figure 1: Molecular structure of the oligomer ester Physical properties of the oligomer ester Bis-behenyl/isostearyl/ phytosteryl dimer dilinoleyl dimer dilinoleate (oligomer ester) has excellent lanolin-like properties. It's a paste ester with a melting point near the body temperature (approx. 38 °C) and a thixotropic flow like lanolin. It also has high water holding capability (200%, Figure 2), high refractive index (approx. 1.475 at 60 °C) and excellent spread gloss in model lipsticks (superior to lanolin and adsorption refined lanolin, Figure 3), high pigment dispersing ability (very low flow point and wet point, , Figure 4), and good skin affinity, which are very similar to lanolin. On the other hand, the color (GH=l) and odor of the oligomer ester are superior to those of lanolin. And the oligomer esters is much more stable against oxidation (induction period 48hr) than lanolin and adsorption refined lanolin (8hr)) in CDM test (temp: l20°C, air:20L/hr, Figure 5). Features of the oligomer ester in cosmetic products The oligomer ester has excellent effects in cosmetic products. The oligomer ester showed excellent moisturizing effect in human use tests (in vivo water sorption-desorption test [2] after 4-week-application of the oligomer ester cream, skin conductance (approx. 2.5 times, Figure 6) and water holding capacity were extremely improved and skin barrier function was improved), emulsion stabilizing effect, and excellent foam-stabilizing ability (superior to lanolin, Figure 7) and moisturizing effect (skin conductance) in cleansing products and shampoos. So this oligomer ester is considered to be useful for make-up products (especially high gloss

194 JOURNAL OF COSMETIC SCIENCE lipsticks and moisturizing foundations), cleansing products, skincare products (especially emollient creams and UV care cosmetics), and haircare products (especiaUy shampoo and rinse-off and leave-on hair conditioners for damaged hair). l 400 -� :S 300 U 200 I :a 0 ::c l00 ... I 0 UII 60 50 � 40 'i 30 [ 20 10 0 Ollgo1111r Lanolin Ad1orptlon Altrol■tum eater l'lflned Control Petrolatum Lanolin Oligomer lanolin ester Figure 2: Water ,,olding capability Figure 3: Spread gloss of model lipsticks Pigment good� Dispersing ____,. bad Ability 'i 100 A orption -- --7 re ned lanolin Flow Point(g/lOOg of1102) 0 l00 200 JOO Mineral Oil Oligmier ester Lamlin Adsorption refinedlmolin 1PM OliwOil Figure 4: Dispersing ability to 1itanium dioixide 600 � j 500 .g 4 00 ----------------1 8 3001----�l....Jtcle�� .!:l � 2001--------;1,__----:;a,�--------l ·! 100 1-------1 �- = ====-1 i:r:= 0 Initial 4 Weeks Figure 6: Skin conductance in ,,uman use test (Skincare cream) References 80 cg 1/L•rnl ... • ii! 60 s 40 -.t- � ;I 20 Oligomerester 0 0 6 12 18 Time (hr) Figure 5: Oxidation stability (CDM Test) 25 a 20 !. ! 15 ,! ! 10 .. 1111 · = 5 0 Squalme Luolin Oligomer Blank ester (no oil) Figure 7: Foam stabilizing ability (Body soap) I) Ueda T, Yamamoto Y, Rashida M, Yamaguchi T, Katsura M, Ohashi Y, Okumura M, Japan Patent No. JP 2004-256515-A. 2) Tagami H, Kanamaru Y, Inoue K, Suehisa S, Inoue F, Iwatsuki K, Yoshikuni K, Yamada M, J Investigative Dermatology, 78, 425 ( 1982). 24