油酸甾醇酯液晶的合成、微胶囊化及其防晒配方应用

doi:10.3969/j.issn.2097-2806.2025.11.006

Abstract

Abstract:

This study reports the synthesis of oleic acid sterol ester with liquid crystalline properties and its enhanced stability and UV-blocking performance through microencapsulation. Oleic acid sterol ester was synthesized via the esterification of phytosterol and oleic acid, whose structure was characterized using Fourier-transform infrared spectroscopy （FTIR） and mass spectrometry （MS）. Its liquid crystalline behavior was confirmed via the polarized optical microscopy （POM）, thermogravimetric analysis （TGA）, differential scanning calorimetry （DSC）, wide-angle X-ray scattering （WAXS）, and small-angle X-ray scattering （SAXS）. UV absorption tests were conducted to assess the UV-blocking performance of the oleic acid sterol ester liquid crystals. To improve the stability of its liquid crystalline structure, the oleic acid sterol ester was encapsulated into microcapsules through the emulsion polymerization. SPF measurements were performed on the sunscreen formulations containing liquid crystal microcapsules. The oleic acid sterol ester displayed cholesteric liquid crystalline behavior and strong UVA absorption, which indicates its suitability as a natural UV absorber. Microencapsulation further enhanced its stability and UV-blocking properties. SPF testing showed that the formulations with microcapsules achieved an SPF value of 7.01, which surpasses the nano titanium dioxide （SPF=6.23） and significantly outperform the unencapsulated liquid crystal formulations （SPF=2.65）. This study highlights the potential of microencapsulated oleic acid sterol ester as a novel UV absorber in the sunscreen formulations, offers the enhanced stability and effective UV protection, and showcases its application potential in the innovative cosmetic products.

Key words: phytosterol, liquid crystals, microencapsulation, UV absorption, sunscreen formulations, SPF testing

CLC Number:

TQ658

Xuze Liu, Chang Xu, Liangliang Lin, Hujun Xu. Synthesis and microencapsulation of oleic acid sterol ester liquid crystals for its application in sunscreen formulations[J].China Surfactant Detergent & Cosmetics, 2025, 55(11): 1408-1418.

Figures/Tables 14

Fig.1

Tab.1

Fig.2

Fig.3

Fig.4

Fig.5

Fig.6

Fig.7

Fig.8

Fig.9

Fig.10

Fig.11

Tab.2

Fig.12

References 34

[1]	Chen L, Wang J X, Wu X W, et al. Boosting the effectiveness of UV filters and sunscreen formulations using photostable, non-toxic inorganic platelets[J]. Chemical Communications, 2024, 8: 1039-1042.
[2]	Najafabadi A H, Soheilifar M H, Masoudi-Khoram N. Exosomes in skin photoaging: biological functions and therapeutic opportunity[J]. Cell Communication and Signaling, 2024, 22 (1) : 32.
[3]	Shin S H, Lee Y H, Rho N K, et al. Skin aging from mechanisms to interventions: focusing on dermal aging[J]. Frontiers in Physiology, 2023, 14: 1195272. doi: 10.3389/fphys.2023.1195272
[4]	Karmali R A, Safai B. Ultraviolet-evoked prostaglandin biosynthesis in varying stages of keratinocyte differentiation in guinea pig skin[J]. Prostaglandins Leukotrienes and Medicine, 1984, 15 (3) : 277-286. doi: 10.1016/0262-1746(84)90127-6
[5]	Poon F, Kang S, Chien A L. Mechanisms and treatments of photoaging[J]. Photodermatology, Photoimmunology & Photomedicine, 2015, 31 (2) : 65-74.
[6]	Jin S G, Padron F, Pfeifer G P. UVA radiation, DNA damage, and melanoma[J]. ACS Omega, 2022, 7 (37) : 32936-32948. doi: 10.1021/acsomega.2c04424
[7]	Mu J, Chen H, Ye M, et al. Acacetin resists UVA photoaging by mediating the SIRT3/ROS/MAPKs pathway[J]. Journal of Cellular and Molecular Medicine, 2022, 26 (16) : 4624-4628. doi: 10.1111/jcmm.v26.16
[8]	Hoang M, Qureshi A, Oancea E, et al. Furocoumarins potentiate UVA-induced DNA damage in skin melanocytes[J]. Biochemical And Biophysical Research Communications, 2023, 684: 149066. doi: 10.1016/j.bbrc.2023.09.094
[9]	Wakefield G, Stott J. Photostabilization of organic UV-absorbing and anti-oxidant cosmetic components in formulations containing micronized manganese-doped titanium oxide[J]. International Journal of Cosmetic Science, 2006, 57 (5) : 385-395.
[10]	Kullberg S A, Hylwa S A. The versatile UV absorber drometrizole: Expanding from the realm of cosmetics to feminine sanitary products[J]. Contact Dermatitis, 2020, 83 (6).
[11]	Sahoo D K, Mohanty P, Biswal H S, et al. Conformers influence on UV-absorbance of avobenzone[J]. Journal of Photochemistry and Photobiology A: Chemistry, 2024, 453: 115671. doi: 10.1016/j.jphotochem.2024.115671
[12]	Liu H M, Ma X Y, Zhao Y H. Preparation of liquid crystal emulsion and its application in cosmetics[J]. China Surfactant Detergent & Cosmetics, 2022, 52 (7) : 762-769.
[13]	Zhao Y, Shi Z, Lang T, et al. Research of nanofibres loaded with ultraviolet absorber to increase the wavewidth of cholesteric liquid crystals[J]. Optical Materials, 2023, 137: 113545. doi: 10.1016/j.optmat.2023.113545
[14]	Pathak G, Hegde G, Prasad V. Octadecylamine-capped CdSe/ZnS quantum dot dispersed cholesteric liquid crystal for potential display application: Investigation on photoluminescence and UV absorbance[J]. Liquid Crystals, 2021, 48 (4) : 579-587. doi: 10.1080/02678292.2020.1799085
[15]	Rapalli V K, Waghule T, Hans N, et al. Insights of lyotropic liquid crystals in topical drug delivery for targeting various skin disorders[J]. Journal of Molecular Liquids, 2020, 315: 113771. doi: 10.1016/j.molliq.2020.113771
[16]	Puglia C, Bonina F. In vivo spectrophotometric evaluation of skin barrier recovery after topical application of soybean phytosterols[J]. International Journal of Cosmetic Science, 2008, 31: 217-224.
[17]	Rocha V Z, Ras R T, Gagliardi A C, et al. Effects of phytosterols on markers of inflammation: A systematic review and meta-analysis[J]. Atherosclerosis, 2016, 248: 76-83. doi: 10.1016/j.atherosclerosis.2016.01.035 pmid: 26987068
[18]	Shen M, Yuan L, Zhang J, et al. Phytosterols: Physiological functions and potential application[J]. Foods, 2024, 13 (11) : 1754.
[19]	Vigne S, Pot C. Implication of oxysterols and phytosterols in aging and human diseases[J]. Implication of Oxysterols and Phytosterols in Aging and Human Diseases, 2023: 231-260.
[20]	Zhang S, Yang Y, Xing H, et al. Synthesis of phytosteryl oleate using composite catalysts[J]. CIESC Journal, 2015, 66 (8) : 3078-3083.
[21]	Meng X, Pan Q, Yang T. Synthesis of phytosteryl esters by using alumina-supported zinc oxide (ZnO/Al₂O₃) from esterification production of phytosterol with fatty acid[J]. Journal of the American Oil Chemists’ Society, 2011, 88 (1) : 143-149. doi: 10.1007/s11746-010-1654-2
[22]	Pastarnokienė L, Potapov E, Makuška R, et al. Optimization of microencapsulation of polyaspartic acid ester into UV curable epoxy-acrylate resin using Taguchi method of experimental design[J]. Journal of Applied Polymer Science, 2024, 141 (15) : e55216.
[23]	Xu D, Yang R. Efficient preparation and characterization of paraffin-based microcapsules by emulsion polymerization[J]. Journal of Applied Polymer Science, 2019, 136 (21) : 47552.
[24]	Wang L, Liu S, Luo S, et al. Advances in the preparation and application of liquid crystal microcapsules[J]. Liquid Crystals, 2024, 51 (11) : 1792-1823. doi: 10.1080/02678292.2024.2364789
[25]	Althaqafi K A, Satterthwaite J, AlShabib A, et al. Synthesis and characterisation of microcapsules for self-healing dental resin composites[J]. BMC Oral Health, 2024, 24 (1) : 109.
[26]	Zhang Y R, Liu D, Zhang Y, et al. Preparation of SiO₂-encapsulated TiO₂ composite nanoparticles and evaluation of the sunscreen performance[J]. China Surfactant Detergent & Cosmetics, 2022, 52 (1) : 28-34.
[27]	Jiang Z J. Consistency of sunscreen SPF values measured by in vivo and in vitro methods[J]. China Surfactant Detergent & Cosmetics, 2019, 49 (4) : 234-237.
[28]	Liu Z P, He X Z, Cong Y H, et al. Synthesis and characterization of two series of pressure-sensitive cholesteric liquid crystal elastomers with optical properties[J]. Liquid Crystals, 2020, 47 (1) : 143-153. doi: 10.1080/02678292.2019.1642524
[29]	Labeeb A M, Ward Y A, Fikry M. Thermal control of tunable photonic optical bandgaps in different cholesteric liquid crystals mixtures[J]. Journal of Molecular Liquids, 2021, 340: 117179. doi: 10.1016/j.molliq.2021.117179
[30]	den Adel R, Heussen P C M, Bot A. Effect of water on self-assembled tubules in β-sitosterol+γ-oryzanol-based organogels[J]. Journal of Physics: Conference Series. IOP Publishing, 2010, 247 (1) : 012025.
[31]	Hsiao B S, Chu B, Burger C. Synchrotron X-Ray scattering of polymer nanocomposites[J]. Synchrotron Radiation News, 2002, 15 (5) : 20-34.
[32]	Zhang J, Dong B, Zheng L, et al. Lyotropic liquid crystalline phases formed in ternary mixtures of 1-cetyl-3-methylimidazolium bromide/p-xylene/water: A SAXS, POM, and rheology study[J]. Journal of Colloid and Interface Science, 2008, 321 (1) : 159-165. doi: 10.1016/j.jcis.2008.01.020 pmid: 18294647
[33]	Hong H J, Nasrollahi A, Park S Y. Transparent UV-blocking photonic film based on reflection of cholesteric liquid crystals[J]. Journal of Molecular Liquids, 2021, 344: 117739. doi: 10.1016/j.molliq.2021.117739
[34]	Qu C, Wang Q, Zhang X, et al. Excellent ultraviolet-blocking properties of chiral nematic liquid crystals[J]. Photochemistry and Photobiology, 2024, 100 (1) : 33-40. doi: 10.1111/php.v100.1

	w/%
	Formulation A		Formulation B		Formulation C		Formulation D
Phase A	Stearic acid	8	Stearic acid	8	Stearic acid	8	Stearic acid	8
	Stearyl alcohol	3	Stearyl alcohol	3	Stearyl alcohol	3	Stearyl alcohol	3
	liquid crystal microcapsules	5	Oleic acid sterol ester	5	Nano titanium dioxide	5	Glyceryl monostearate	1.5
	Glyceryl monostearate	1.5	Glyceryl monostearate	1.5	Glyceryl monostearate	1.5	Glyceryl monostearate	1.5
Phase B	Glycerol	10	Glycerol	10	Glycerol	10	Glycerol	10
Phase B	Water	72.5	Water	72.5	Water	72.5	Water	77.5

Synthesis and microencapsulation of oleic acid sterol ester liquid crystals for its application in sunscreen formulations

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 14

References 34

Related Articles 4

Metrics

Comments

Recommended 10

[1]	Wang Xiaokang, Chen Wen, Zhang Taijun, Yin Zhigang, Gu Yulong, Li Tao. Research and application prospect of phytosterols （esters） [J]. China Surfactant Detergent & Cosmetics, 2023, 53(4): 445-452.
[2]	XI Qi,YAN Yong-li,ZHANG Yang. Progress in the formation of lyotropic liquid crystals in non-aqueous solvent [J]. China Surfactant Detergent & Cosmetics, 2019, 49(12): 817-823.
[3]	WANG Li-jun. Extraction of Ampelopsis grossedentata seed oil by aqueous enzymatic method and its microencapsulation [J]. China Surfactant Detergent & Cosmetics, 2015, 45(2): 99-102.
[4]	ZHANG Ying, LIN Feng, RAO Chang-quan, MO Wei-huan. Studies on sunscreen efficacy of chlorogenic acid in Flos lonicerae [J]. China Surfactant Detergent & Cosmetics, 2014, 44(8): 448-451.