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Table of Content

    22 September 2014, Volume 44 Issue 9 Previous Issue    Next Issue
    Basic research
    Synthesis and surface activity of alcohol ether propionate surfactants
    WANG Jun, YANG Xu-zhao, MIAO Jin-hui, ZOU Wen-yuan, CHEN Xiang
    2014, 44 (9):  481-485.  doi: 10.13218/j.cnki.csdc.2014.09.107
    Abstract ( 276 )   PDF (880KB) ( 330 )  
    Four kinds of fatty alcohol ether propionate were synthesized via addition and saponification with fatty alcohol (octanol,decanol and dodecanol),fatty alcohol polyoxyethylene ether (AEO7) and tert-butyl acrylate as raw materials.Structure of the products was characterized by FTIR,1HNMR and ESI-MS methods.The addition reaction parameters were optimized via a series of experiments as follows:n(fatty alcohol (AEO7)):n(tert-butyl-acrylate):n(sodium methoxide)=1:3:0.02;reaction temperature,50 ℃;reaction time,6 h.The products show good surface activity.With increasing of the carbon chain length,their cmc,γcmc and Amin decreases while Γmax and pc20 increases.However,the results were reversed as the fatty alcohol molecules are ethoxylated.
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    Lecture of science and technology
    Performance and applications of surfactants (Ⅸ) Solubilization function of surfactants and applications
    ZHOU Ya-wen, LIU Jing-wei, ZHAO Li, XU Bao-cai, LIU Hong-qin
    2014, 44 (9):  486-489.  doi: 10.13218/j.cnki.csdc.2014.09.108
    Abstract ( 666 )   PDF (841KB) ( 785 )  
    Expression way and mechanism of surfactant solubilization were introduced.Applications of surfactant solubilization in surfactant-enhanced remediation (SER),micellar-enhanced ultrafiltration (MEUF) and pharmaceutical preparation were summarized.The SER application applied in the treatment of organic pollutant,the mechanism and influencing factors of SER application as well as application for solubilization of insoluble or sparingly soluble drugs were discussed in details.Their development outlooks were prospected.
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    Development and application
    Properties of ethoxylated Guerbet hexadecyl alcohol
    HUANG Cheng-bin, LI Qiu-xiao, LI Ming
    2014, 44 (9):  490-493.  doi: 10.13218/j.cnki.csdc.2014.09.109
    Abstract ( 505 )   PDF (861KB) ( 521 )  
    A series of ethoxylated Guerbet hexadecyl alcohol GAEOn (n=7,9,11,13,15) were synthesized by ethoxylating Guerbet hexadecyl alcohol.The surface activities and application performance were measured in comparison with that of fatty alcohol polyoxyethylene ether AEO9(using the mixture of n-dodecanol and n-tetradecanol as raw material) and AEO15 (using n-hexadecanol as raw material).With appropriate EO number,GAEOn could show good surface activity,wetting power,emulsifying performance and detergency,while its foaming power is low.
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    Chemical modification of azelaic acid and tyrosinase inhibition activity of the modified product
    LI Yang, YANG Zi-jia, ZHU Jun, DONG Yin-mao
    2014, 44 (9):  494-496.  doi: 10.13218/j.cnki.csdc.2014.09.110
    Abstract ( 424 )   PDF (775KB) ( 409 )  
    Intermediates,ethyl azelaoyl di-alaninate,di-valinatee and di-leucinatee were prepared via the improved Schotten-Bauman condensation with azelaoyl di-chloride and the corresponding amino acid hydrochloride as starting materials.Then the intermediates were hydrolyzed with sodium hydroxide solution and the products sodium salts of corresponding azelaoyl amino acids were obtained.Structures of the products were characterized by 1HNMR and LC-MS.Inhibition ratio of the products on tyrosinase activity was investigated,and compared with that of potassium azelaoyl di-glycine.The results showed that,their water solubility increased significantly and all of the products display strong inhibition effect on the activity of tyrosinase.The inhibition ratio increases as the raise of mass concentration of the products.Comparing with potassium azelaoyl di-glycine,when the inhibition ratio reaches 50%,the mass concentration (IC50) of sodium azelaoyl di-alanine as well as sodium azelaoyl di-valine is 6.5 g·L-1,while that (IC50) of potassium azelaoyl di-glycine is 15 g·L-1.Obviously,at low mass concentrations,inhibiting effect on tyrosinase activity of sodium azelaoyl di-alanine and sodium azelaoyl di-valine is comparatively stronger.
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    Preparation and skin care function of silanol hyaluronic acid compound
    LI Yan, CHEN Jian-ying, WANG Xiao-mei, LIU Xia, CHEN Qian-qian, LING Pei-xue
    2014, 44 (9):  497-500.  doi: 10.13218/j.cnki.csdc.2014.09.111
    Abstract ( 325 )   PDF (809KB) ( 374 )  
    Silanol hyaluronic acid compound (SHAC) was synthesized from sodium hyaluronate and chlorodimethylsilane suspended in organic phase using tetrabutylammonium iodide as catalyst.The product compound was precipitated by adding ethyl acetate to the filtrate of the reaction product mixture.The skin irritation,cytotoxicity and skin care effect of SHAC product were investigated.In test for back of rabbits that smeared with SHAC of mass fraction 1%,all the cumulative score for erythema and hydropsy is zero.It denotes that SHAC has no skin irritation.IC50 of SHAC is higher than 5 g·L-1 that is much higher than 1.5 g·L-1,which is the EU standard criteria for no cytotoxicity.It shows that SHAC exhibits no cytotoxicity.Under environment of air relative humidy 65% and 30%,the moisture content of pig skin after smeared with SHAC achieves (49±2.16)% and (45±2.27)% respectively,which is better than that smeared with sodium hyaluronate that is widely used as humectant.The survival rate of keratinocyte that acted with 0.001 g·L-1 mass concentration of SHAC achieves (106.0±6.2)% that is no significant differences as comparing with that acted by epidermal growth factor (EGF).
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    Action of N-acetyl-L-cystein for resisting human skin fibroblast damage induced by H2O2
    WANG Feng-lou, ZHU Li-ping, MA Xia
    2014, 44 (9):  501-503.  doi: 10.13218/j.cnki.csdc.2014.09.112
    Abstract ( 294 )   PDF (784KB) ( 356 )  
    Action of N-acetyl-L-cystein (NAC) for resisting damage of human skin fibroblast (HSF) induced by H2O2 was studied.Results of experiments for cell survival ratio and cell positive ratio showed that under low mass concentration (50-100 mg·L-1) of NAC,there is no obvious cell toxicity;and under mass concentration of 200~800 mg·L-1,cell proliferation is promoted;while under higher mass concentration (1 000 mg·L-1),the growth of HSF is inhibited obviously.Positive ratio of blank group,H2O2 group,H2O2 (500 μmol·L-1)+NAC (100 mg·L-1) group and H2O2 (500 μmol·L-1)+NAC (200 mg·L-1) group is 39.90%,69.57%,45.29% and 36.60% respectively.NAC can decrease the cell positive ratio obviously and resist the cell damage induced by H2O2.
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    Selection and sunscreen effect evaluation of UV-absorbing ingredients extracted from some kinds of tree leaves and fruit pomaces
    WANG Chun-xiao, DONG Li, LI Chun-yi, ZHANG Yan
    2014, 44 (9):  504-507.  doi: 10.13218/j.cnki.csdc.2014.09.113
    Abstract ( 278 )   PDF (806KB) ( 387 )  
    Leaves of six kinds of tree that planted extensively in south China as well as fruit pomaces of 5 kinds of conventional fruit were selected to be extracted with 50%(vol) ethanol aqueous solution under ultrasonic wave assistance.The extracts were blended based upon their UV absorbing spectra and to be used in formulating sunscreen creams.Test results showed that in case the mass concentration is 0.2 g·L-1,average UV absorbance of the leaves of mango tree achieves 1.248 while that of both orange pomaces and grape pomaces achieves near or more than 1.0.The blend was formulated in accordance with m(grape pomaces) : m(orange pomaces) :m(mango tree leaves) = 1:4:5,and blend dosage in the sunscreen cream product is 10 mL of extract blend in 100 g of cream base.The product displays good sunscreening efficacy.
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    Synthesis of rosamusk fragrance ester
    SHEN De-li, MU Min, HE Xin, LIU Yu-ping, TIAN Hong-yu, SUN Bao-guo
    2014, 44 (9):  508-511.  doi: 10.13218/j.cnki.csdc.2014.09.114
    Abstract ( 322 )   PDF (774KB) ( 517 )  
    Firstly,intermediate 1-(3,3-dimethylcyclohexyl)ethyl formate was prepared with dihydromycene and formic acid as starting materials and concentrate sulfuric acid as catalyst.Then the intermediate was saponified by a methanol solution of sodium hydroxide to obtain 1-(3,3-dimethylcyclohexyl) ethanol.The latter was further reacted with acetic anhydride in presence of p-toluenesulfonic acid as catalyst to prepare the targeted product rosamusk fragrance ester.Influences of mole ratio of materials,reaction time and reaction temperature on yield of the product were investigated in order to optimize the synthetic conditions.The structures of intermediate and product were characterized by means of IR,GC-MS,1HNMR and 13CNMR,while the odor characteristic of the targeted product was evaluated.The results showed that all the designed reaction steps were carried out in order and the yield of the targeted product achieves 91.1%.The odor evaluation result indicated that the targeted product displays a mild wood fragrance,rose fragrance,fruit fragrance,sweet fragrance as well as a flavor of geranium,herb and musk.
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    Synthesis and spectroscopic property of 6-phenylazo-coumarin- 3-ethyl formate catalyzed by potassium carbonate
    ZENG Yu-cai, LIU Xiao-ling, LI Lan
    2014, 44 (9):  512-516.  doi: 10.13218/j.cnki.csdc.2014.09.115
    Abstract ( 285 )   PDF (848KB) ( 507 )  
    5-Phenylazo salicylaldehyde (1) was prepared by successive diazotization and coupling reaction,starting from aniline.Effect of pH of the reaction medium on product yield of coupling reaction was investigated.When pH=9,the yield can achieve 95.7%.6-Phenylazo-coumarin-3-ethyl formate (2) was synthesized with 1 and diethyl malonate using K2CO3 as catalyst under solvent-free condition.Effects of dosage of the catalyst,reaction time and mole ratio of the reactants on the yield were investigated.Results indicated that yield of 2 achieves 82.5% under conditions as:5 mmol of 1;mole ratio of 1 to ethyl malonate 1:2; dosage of K2CO3 0.05 mmol and reaction time 15 min.Structure of the product was characterized by FTIR, 1HNMR and 13CNMR.UV absorption spectra and fluorescence emission spectra of the product 2 in various solvents were tested and observed.Results showed that as increase of polarity of the solvent used,the product displays positive solvatochromism and Stokes shifts of the product becomes bigger.
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    Synthesis of 6,7-dimethoxycoumarin
    LIU Xian-ming, TANG Xiao-fang
    2014, 44 (9):  517-520.  doi: 10.13218/j.cnki.csdc.2014.09.116
    Abstract ( 469 )   PDF (803KB) ( 493 )  
    First intermediate,4,5-dimethoxysalicylaldehyde was synthesized by demethylation of 2,4,5-trimethoxybenzaldehyde with boron tribromide.The yield is about 64%.Then second intermediate 4,5-dimethoxy-2-hydroxy ethyl phenylacrylate was prepared from the first intermediate by reaction with ethyl malonate and the yield is about 79%.Finally the targeted product 6,7-dimethoxycoumarin was synthesized from the second intermediate via cyclization with thionyl chloride and yield is about 51%.All the intermediates and product were characterized by 1HNMR and MS.The results showed that the targeted intermediates and product were prepared as required.
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    Reviews
    Applications of viscoelastic surfactant in oilfield
    LI Xia-qing, ZHANG Chi, ZHANG Gui-cai, GE Ji-jiang, WANG Zong-sheng
    2014, 44 (9):  521-524.  doi: 10.13218/j.cnki.csdc.2014.09.117
    Abstract ( 257 )   PDF (879KB) ( 559 )  
    Based on the composition structure of viscoelastic surfactant (VES),micelle change mechanism of VES was described.Through wide investigations on present situation of VES in Chinese and foreign oilfields,mechanisms and applications of separate types of VES in clear fracturing fluid,self-diverting acid and some other techniques were systematically introduced.Moreover,existing problems were summarized and studied.VES has wide application prospects in fracturing,acidizing,tertiary oil recovery,drilling fluid and fluids drag-reducing transportation because of its special micellar structure and rheological property.At the end,working emphases and research trends in this field were proposed.
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    Progress in development of paint removing agents used in graffito removal technology
    GAO Quan, YU Qian, WEN Wu, GAO Min, YU Lin, LI Yong-feng
    2014, 44 (9):  525-528.  doi: 10.13218/j.cnki.csdc.2014.09.118
    Abstract ( 358 )   PDF (766KB) ( 454 )  
    Conventional chemical paint removing agents used in graffito removal technology were summarized.Main ingredients,paint removing efficacy,corrosion to the substrate of solvent-based and alkaline paint removal agents,influencing factors on stripping effect of benzyl alcohol type and ester type paint removal agents,as well as toxic effects to human body of methylene chloride type and N-methyl pyrrolidone type of paint removal agents were reviewed.Comparison of advantages and disadvantages of various paint removers were described,and new development of environment-friendly paint removers were indicated.
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    Analytical methods and testing
    Determination of 23 kinds of phthalic ester in cosmetics by UPLC-MS/MS
    YU Jian, XU Yong, ZHENG Rong, LIU Chang, WANG Ke
    2014, 44 (9):  529-533.  doi: 10.13218/j.cnki.csdc.2014.09.119
    Abstract ( 250 )   PDF (819KB) ( 393 )  
    A method for determination of 23 kinds of phthalic ester in cosmetics simultaneously by UPLC-MS/MS was established.Various types of cosmetics were extracted and purified by different methods.MRM mode was used to qualitatively identify the 23 target compounds and isotope internal standards were used to quantify by calibration curves.In the range of 0.01-1.0 mg·L-1,the linearity of the method is good and the correlation coefficients are over 0.998.The LOD of the method ranges within 0.003-0.095 μg·g-1.The average recovery of the method ranges within 86.1%-100.5% (n=9) and the RSD ranges within 0.74%-3.23%.Methodology experiment displayed that the reproducibility,precision and stability of the method are good.
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    Determination of 14 kinds of heavy metal in detergent product by ICP-MS method
    YE Jia-mei, WU Bei-lei, LIN Zhen-xing, LUO Chuan, WANG Hao
    2014, 44 (9):  534-538.  doi: 10.13218/j.cnki.csdc.2014.09.120
    Abstract ( 288 )   PDF (804KB) ( 331 )  
    A method for the determination of 14 kinds of heavy metal in detergent product by ICP-MS was established.The samples were pretreated with microwave digestion.Pressure control was adopted to monitor the digestion process and to examine the digestion conditions.Effects of the amount of sample used,composition of digestion system,digestion temperature and time on the digestion result were investigated.Selection of parameters used as well as the internal standard element for the ICP-MS system was optimized.The detection limits of this method range within 0.002-0.362 μg·L-1.The relative standard deviations are less than 10%.The spiked recoveries are 90.8%-109.6%.
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