Đang tải... (xem toàn văn)
This proceedings contains the scientific contributions included in the program of the 6 th InternationalConference on Green Technology and Sustainable Development (GTSD2022), which was organized on July2930, 2022 in Nha Trang University, Khanh Hoa Province, Vietnam. The GTSD International Conferenceseries is a prestigious biannual event created to provide an international scientific research forum intechnologies and applications in the field of Green technology and Sustainable development in the Industrialrevolution 4.0. The areas of GTSD include but are not limited to energy engineering, environmentalengineering, education, digital transformation, new materials and solutions for sustainable development,advances in computational intelligence and their applications to the real world and so on.The conference is structurally organized in order to promote the active participation of all attendees andpresenters, via plenary presentation sessions, keynote addresses, interactive workshops and paneldiscussions, to find out how to further contribute to and solve various problems in life and manufacture. Theaim was to further increase the body of knowledge in this specific area by providing a forum to exchangeideas and discuss results.The program committee members of GTSD2022 come from various countries, and the 269 selected papers(out of more than 450 submitted papers) are from 27 countries and from 5 continents. This certainly attests tothe widespread and international importance of the theme of the conference. Each paper was carefullyreviewed on the basis of originality, novelty and rigorousness.We would like to take this opportunity to express our deep appreciation to all authors, participants, keynotespeakers, program committee members, session chairs, organizing committee members, steering committeemembers, as well as the organizers for their great efforts and contributions to making the GTSD2022successful, surging the global care about green technology research for sustainable development.
PROCEEDINGS OF TH 20226 INTERNATIONALCONFERENCE ONGREENTECHNOLOGY ANDSUSTAINABLEDEVELOPMENT (GTSD) July29-30,2022-NhaTrangCity,Vietnam VNUHCM PRESS Proceedings of 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) July 29-30, 2022 - Nha Trang City, Vietnam VNUHCM PRESS 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Table of Contents Editors Preface viii GTSD2022 Organizing Committee ix A Novel Mechanism Design following Augmented Objective with Flexible Energy Control Xuan Phu Do and Van Chi Le Evaluating Green Marketing Trending Determinants by a Text Mining Approach Phan-Anh-Huy Nguyen A Simple Synthesis of Antibacterial and Antifungal ZnO Nanorods Khanh Son Trinh and Vinh Tien Nguyen An Assessment of Complementary Energy of HPFRCs under Tension 15 Duy-Liem Nguyen, Tien-Tho Do, Thi-Ngoc-Han Vuong and H T Tai Nguyen A Study of the Scavenging Process in a Two-stroke Free Piston Linear Engine at Low Velocity Using CFD and DPM 21 Nguyen Huynh Thi, Nguyen Van Trang, Huynh Thanh Cong, Dao Huu Huy, Huynh Van Loc, Truong Hoa Hiep, Ngo Duc Huy and Vo Bao Toan Investigating the Relationship between Workers’ Needs and Commitments to Garment Enterprise 27 Tu Tran Optimization of Aggregates in Concrete Brick with Recycled Materials from Stone 32 Nguyen Thang Xiem, Ho Minh Chau, Tran Doan Hung and Truong Thanh Chung A Comparison on the Flexural Capacity and Dynamic Performance of a Reinforced Concrete Beam and a Steel Beam in a High-rise Building 36 Tham Hong Duong Optimization Model for Biomass Supply Chain Planning: A Case Study in Mekong River Delta – Vietnam 44 Thi-Be-Oanh Cao, Duc Duy Nguyen, Thanh-Tuan Dang and Chia-Nan Wang Developing a Digital Competence Performance Assessment Platform for University Students Based on the DigComp Framework 50 Anh Tho Mai, Thi Kim Oanh Duong and Anh Tuan Ngo The Performance of Geonet Reinforced Straw Rolls as a Flexible Waterbreaker for Riverbank Protection 57 Minh-Duc Nguyen, Le-Nhat-Huy Nguyen and Tran-Phuong-Thao Hua SSD21, Educational Toolbox for Static, Stability, and Dynamic Analysis of Frame 63 Truong Thanh Chung, Le Nguyen Anh Vu, Le Cong Lap and Nguyen Thang Xiem Digital Competence of University Students: A Comparative Study at Three Universities in Vietnam 67 Anh Tho Mai, Quynh Trang Mai and Anh Tuan Ngo i 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Load Capacity Evaluation of Simple Reinforced Concrete Girder Bridges with Considering the Corrosion of Reinforcement and Concrete 75 Tran The Truyen, Tran Thu Minh, Nguyen Dac Duc, Tran Duc Manh and Nguyen Quoc Cuong Effect of Biodegradable and Metallic Mordants on Dyeing Cotton Fabric with Spent Coffee Grounds 80 Tuan Anh Nguyen The Importance of Green Technology for Sustainable Development Education: A Case Study at Lac Hong University 85 Nga Hong Thi Doan and Truong Van Nguyen Unique Competitive Advantages of Vietnam’s Garment Industry in the Sustainable Development Trend 89 Quang-Tri Tran, Thanh-Nhan Nguyen, Tho Alang, Tuyet-Anh Truong, Kim-Chi Le and Nguyen Thi Le Driving Factors of Green Economy for Smart Cities in the Context of Developing Countries 95 Tiep Nguyen, Nghia Hoai Nguyen, Leonie Hallo and Bao Van Pham Impacts of Green Training on Green Competencies of Employees: Empirical Case of Industrial Manufacturers in Dong Nai Parks 101 Thanh-Lam Nguyen, Doan Thi Chuyen, Nguyen Thi Phuong Thao and Doan Van Ly Mathematical Modelling of Combined Infrared and Heat Pump Drying of Squid 107 Pham Van Toan, Phan Nhu Quan, Nguyen Hay and Le Anh Duc Improving the Tensile and Compressive Strength of Cement-Based Materials by Hybrid Electrospun Nanofibers 114 Tri N M Nguyen, Xuan Tung Nguyen, Thanh Toan Dao, Huy Q Nguyen and Jung J Kim Controlling Crystal Morphology via Crystallization Processes, Cases Studied of KDP and Zinc Lactate 118 Tam Le-Minh, Cuong Nguyen Van and Venkata Subbarayudu Sistla A Green Solution for Kitchen Waste Treatment Using Earthworm, Experimental and Mathematical Approaches 122 Tam Le-Minh, Phuong Pham Thi Hong and Nhu Vo Thi Thu Effect of Reinforcement Corrosion on Crack Development in Concrete Under Load 127 Vo Van Nam and Tran The Truyen Study on Synthesizing and Size Controlling of Silver Nanoparticles by Using a System of Two Protectants Trisodium Citrate and Polyvinylpyrrolidone 132 Hien Chuc Mai, Quynh Nguyen Thi Nhu, Thuan Hoang Duc, Du Cao Van, Cuong Ngo Van and Dung Duong Thi Ngoc Study on Chemical Composition and In-vitro Biological Activities of Salvia officinalis L in Lamdong, Vietnam 137 Thao Tran Thach, Cuong Ngo Van and Xuan Nguyen Bang Dynamic Analysis of Plates under Moving Discontinuous Impulsive Load on Viscoelastic Foundation 141 The Tuan Nguyen and Trong Phuoc Nguyen ii 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Isolation and Quantitative Determination of Geniposide from Gardenia jasminoides Ellis Using HighPerformance Liquid Chromatography 147 Vo Thi Nga, Truong Thi Khanh Van and Bui Trung Huu Oxygen-LPG Torch for Thermal Spraying 152 Ngo Thanh Binh, Le Van Canh and Pham Huy Dong Predicting Land Use Change in Buon Ma Thuot City, Dak Lak Province by Integrating GIS and Markov Chain 158 Nguyen Thi Ngoc Quyen, Nguyen Thi Tinh Au, Nguyen Cong Tai Anh and Tran Thi Xuan Phan Dissimilar Friction Stir Welded Lap-joint of Aluminum Alloy 6061 and 316 Stainless Steel 165 Huy Huu Ho, Hao Dinh Duong, Nam Hoai Quach, Thuyen Van Phi, and Tra Hung Tran A Stochastic Half-Car Model for Vibration Analysis with Uncertain Parameters 169 Nguyen Van Thuan Sources of Payment Risks to Contractors in the Vietnam Construction Industry 173 Duong Vuong, Thao Huynh and Phu Tran Pharmacognostic Assessment of Polyscias Fruticosa Leaves in Vietnam 180 Dao Phan Thi Anh, Hue Ha Thi, Trang Le Vu Khanh, Thanh Le Duc, Huong Nguyen Thi Thu and Trieu Ly Hai Alkali-Activated Slag/Sugarcane Bagasse Ash Pastes Cured in Room-Air Ambient and in Saturated Lime Water: A Study on the Compressive Strength and Shrinkage 185 Duc-Hien Le and My Ngoc-Tra Lam Production Efficiency Improvement Using Value Stream Mapping with Simulation: A Case Study in Vietnam 191 Xuan-Quang Bach, Thanh-Tuan Dang and Chia-Nan Wang Study on the Effect of Mixing Ratio of Biodiesel Fuel Made from Animal Fat on Exhaust Emissions of the Fishing Vessel’s Diesel Engines 199 Pham Dinh Trung, Mai Duc Nghia and Ho Duc Tuan A Study on Mechanical Properties of Ca-Alginate Hydrogels 204 Thanh Tan Nguyen, Van Tron Tran, Long Nhut-Phi Nguyen and Nguyen Thi My Le Mechanical Characteristics of PBT Based Blend 208 Hoang-Khang Lu, Ngoc Tran-Nhu Nguyen, Huy Huynh-Nhat Do, Van-Huong Hoang, Van-Thuc Nguyen, Nga Thi-Hong Pham, Van-Tron Tran, Long Nhut-Phi Nguyen and Thanh-Tan Nguyen An Evaluation of Corporation Social Responsibility Performance for Vietnamese Contractors 213 Nguyen Van Minh, Ha Duy Khanh, Soo Yong Kim and Chu Viet Cuong Local Waste Seeds as Organic-Based Coagulant Aids in Water and Wastewater Treatment 218 Nhung Thi-Tuyet Hoang, Anh Thi-Kim Tran and Luu Hong Quang The Implementation of 5C’s in Online-Foreign Language Teaching for Vietnamese Students in the 4.0 Era 222 Chau Le Thi Bao, Nhu Vo Hoang Nhu and Nhi Ho Yen iii 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Antibacterial Activity of Aqueous Extracts from Marine Sponges Found in Vietnam’s Sea 229 Huynh Nguyen Duy Bao and Nguyen Khac Bat Digital Competence of University Students: Developing Information and Data Literacy for IT Students at Ho Chi Minh City University of Technology and Education 233 Anh Tho Mai and Quynh Trang Mai A Simple Design Method for Piled Raft Foundations 239 Tong Nguyen, Nhat Nguyen Le Anh and Dat Nguyen Thanh Evaluating Performance of Petroleum Industry Using Data Envelopment Analysis: A Case Study in Vietnam 247 Kristofer Neal C Imperial, Chia-Nan Wang, Thanh-Tuan Dang and Nguyen Ngoc Hiep Fire Resistance Properties and Geopolymer Coating 254 Van Su Le, Van Vu Nguyen, Artem Sharko, Doan Hung Tran, Petr Louda, Piotr Los, Thang Xiem Nguyen, Stanislaw Mitura and Katarzyna Buczkowska Effects of Intake Air Temperature on Power and Emission Characteristics of the HCCI Engine Fueled with the Blends of 15% Ethanol and 85% Petrol Fuels 259 Minh Xuan Le and Thanh Tuan Nguyen Linear Viscoelastic Characterization of an SMA Mixture Using Dynamic Indirect Tensile Test 263 H T Tai Nguyen, Hong Ha Mai and Van Hien Nguyen Effect of the Limestone Powder Content on the Properties of Alkali–Activated Slag Mortar 268 Tai Tran Thanh, Chung Pham Duy, Tu Nguyen Thanh and Hyug-Moon Kwon The Educational Philosophy of Existentialism with the Development of Personalized Learning for Learners in Massive Open Online Courses (MOOCs) – The Case of Ho Chi Minh City University of Technology and Education 273 Thi Thao Tran, Tran Phuong Thao Hua and Thi Chu Tran Transportation Infrastructure Strategy for Sustainable Development: A Case Study of Vietnam Mekong Delta 281 Le Thu Huyen Study on Behaviour of Short Pile Groups in Soft Ground with Sand Leveling on a Small Scale Model Using Schneebeli Analogue Soil 286 Sy Hung Nguyen and Thi Phuong Huyen Tran Research and Preparation of Thinking Strategies for Quality of Textile and Garment Products Manufactured in Vietnam 292 Nguyen Phuoc Son, Nguyen Ngoc Chau and Nguyen Thi Tuyet Trinh Building Students’ Self-Reliant on Problem-Based Learning by Embedding Mind of Engineering Design Concept at HCMC University of Technology and Education 296 Xuan Tien Vo Modeling and Comprehensive Assessment of Construction Risks: A Perspective of PPP Transportation Projects 300 Ha Duy Khanh, Soo-Yong Kim and Nguyen Van Khoa iv 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Fabrication of Graphene Oxide from the Graphite Rod of a Disposed Battery 305 Huy-Binh Do, Hoang-Trung Huynh, Thien-Trang Nguyen, Van-Cuong Pham, Tien-Luat Nguyen, Anh-Vu Phan-Gia and Maria Merlyne De Souza Design and Optimization of a Compliant Mechanism for Vibration-Assisted Drilling 309 Hai-Thanh Nguyen, Van-Khien Nguyen, Phan-Khanh-Tam Nguyen, Huy-Tuan Pham, Quang-Khoa Dang and Pham Son Minh Eco-friendly Adsorbent Formulated from Rubber Shell Biochar to Remove Chromium (Cr(VI)) from Aqueous Solutions 313 Linh My Nguyen A Study on the Effect of the Shape of the Center Rib on Thermal Resistance on the Dual-Layer Microchannel Heat Sink 317 Hung-Son Dang and Thi-Anh-Tuyet Nguyen Experimental Study of the Effect of Heat Input on Tensile Strength and Microstructure of the Weld using the Orbital TIG Welding Process 321 Thien Tran Ngoc, Ngoc-Huy Dinh, An-Duong Tra, Kha-Duy Doan, Binh-Minh Ngo and Anh-Duc Pham Duc A Study of Customer Satisfaction in Online Food Delivery Service Quality During the Covid-19 Pandemic: Baemin’s Case Study 326 Hong-Xuyen Thi Ho, Ngoc-Tra Tran Thi and Ngoc-Anh Ha Thi Controllable Green Synthesis and Morphological Properties of Gold Nanostar 332 P Quoc-Duy Huynh, Van-Dung Le, Chi-Hien Dang, Radek Fajgar, The-Ha Stuchlikova, Jiri Stuchlik and Thanh-Danh Nguyen Isolation, Selection and Identification of the Probiotic Properties of Lactobacillus spp from Shrimp Ponds in Nhon Trach, Dong Nai 336 Doan Thi Tuyet Le, Le Thi Thu Huong, Phan Pham, Pham Minh Thinh, Vo Thi Lan Chi, Nguyen Phuoc Trung, Huynh Minh Hieu and Do Minh Anh Production of Cheese from Reconstituted Milk and Soy Milk with the Addition of Microbial Transglutaminase 340 Pham Thi Hoan and Trinh Khanh Son Studying the Effect of Biodiesel Blend Ratios Derived from Rubber Seed Oil on the Technical Characteristics of Diesel Engines without Modifying the Structure by Simulation and Experiment 349 Nguyen Manh Cuong and Huynh Phuoc Son Work from Home during the Covid-19 Pandemic: A Qualitative Research with Women Taking Care of Young Children 355 Hien Phan Thi Thanh, Thuy Nguyen Thi Thanh and Tram Nguyen Thi Mai Study on Determining the Freezing Mode of Frozen Fillet Bigeye Tuna (Thunnus obesus) 361 Dzung Tan Nguyen, Linh Khanh Thuy Do, Chuyen Van Hoang and Tuan Thanh Chau Numerical Investigation of the Optimum Operating Condition in Magnetically Confined Plasma with Sheared Slab Ion-Temperature-Gradient Model 367 Thanh Tinh Tran v 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Using Brake and Engine Torque to Control Traction on Either Side of the Drive Wheel 371 Tan Tai Phan and Van Nhu Tran Fatigue Life of Accelerated Corroded Steel Plate 377 Dao Duy Kien, Nguyen Thanh Hung, Nguyen Thi Thu Hao, Nguyen Van Hung and Haidang Phan A Study on Ultrasonic Shear Horizontal Waves in Composite Structures 381 Duy Kien Dao, Hoang Ngoc Quy, Truong Giang Nguyen, Ductho Le, Hoai Nguyen and Haidang Phan Designing and Modeling Pipe Welding Machine 385 Tuong Phuoc Tho, Phan Phuc Khang, Tran Thanh Nhon and Pham Phi Long Investigation of the Mechanical Properties of Lightweight Geopolymer Concrete Using Keramzite as Coarse Aggregate 390 Kiet Tran Tuan, Duc Nguyen Phan, Tuan Le Anh, Khoa Nguyen Tan and An Huynh Thao Researching and Improving the Registration and Treatment Process in Health Care Facility with Lean Principles and Ergonomics Standards 394 Minh-Tai Le Application of Lean and Six Sigma Tools to Improve Productivity and Product Quality at Dien Quang Company, Vietnam 401 Minh Tai Le, Hoang Khang Lu and Nhat Huy Do Huynh Hydrogen Plasma Annealed Gallium and Aluminum co-doped Zinc Oxide Films Applied in Lowemissivity Glass 408 Shang-Chou Chang, Yun-Che Tsai, Huang-Tian Chan, Jian-Liang Lai, Jian-Syun Wu and Wei-Min Wang Study on Pectinase Production by Bacillus subtilis in Molasses and Its Application for Coffee Fermentation 412 Ngan K Le, Duy Q Nguyen, Nhi Y Dinh and Phu H Le Environmental Sustainability: Exploring Managers’ Attitudes and Behaviours at High-End Accommodation Businesses in Vietnam 417 Thanh-Nhan Nguyen, Quang-Tri Tran and Tho Alang Research on Optimal Algorithms Using Experimental Planning to Improve Shoe Production Line Productivity 425 Minh Tai Le, Thi Cam Duyen Doan and Huynh Thao Vy Nguyen Application of Multivariable Linear Regression Algorithm to Support Inventory Management 431 Trung Tin Ngo, Minh Tai Le, Nguyen Kim Thoa Vo and Thanh Nam Luong Ethanol in Gasoline Fuel Blends: Experimental Investigation Effects on Exhaust Emission of the Homogeneous Charge Compression Ignition Engine 437 Minh Xuan Le and Thanh Tuan Nguyen The Impact of the Industrial Revolution 4.0 on Logistics Businesses: A Case in Mekong Delta 441 Ngo Hong Ngoc and Huang Ying Yin vi 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Enhancement in Dielectric Constant of Poly Vinyl Alcohol by Loading of Strontium Titanate for Supercapacitor Applications 447 Anju Yadav, Dinesh Kumar Yadav, Khushbu Meena, Kiran Devat, Narendra Jakhar, Rajesh Sahu, S K Jain and Balram Tripathi Free Vibration Analysis of Smart FG Porous Plates Reinforced by Graphene Platelets Using Isogeometric Approach 451 Lieu B Nguyen and Duc-Thien Pham Free Vibration of MSGT Porous Metal Foam Microplates Using a Moving Kriging Meshfree Approach 459 P T Hung Impacts of Adverse Weather on Mode Choice Behavior: A case study in Hanoi City, Vietnam 469 Binh Nguyen Mai, Thi Anh Hong Nguyen, Akimasa Fujiwara and Canh Do Travel Behavior on Ground Access Mode Choices by Introducing a New City Air Terminal: A Case Study of Vientiane Airport, Laos 474 Komack Keochampa, Canh Do, Akimasa Fujiwara and Thi Anh Hong Nguyen A Study of The Tensile Strength for The Mixing Ratio of Eva in Pa6/Eva Blends 482 Minh-Nhat Nguyen, Quy-Long Nguyen, Ngoc-Thien Tran, Vinh-Tien Nguyen and Minh The-Uyen Tran Cytotoxicity of Isoxazole/Pyrazole Curcuminoids against Human Oral Epidermal Carcinoma-KB Cell Line 486 Hoang Minh Hao, Ho Dung Manh and Vo Thi Nga Modeling of Flow Mixed with Polymers in Open Channel Flow: Application on the Blumenau River in Brazil 491 Walid Bouchenafa, Airton Hoenicke, Bruna Luiza Cunico, Huyen Xuan Dang-Vu and Trong Dang-Vu vii 2022 6th International Conference on Green Technology and Sustainable Development (GTSD A Study of the Tensile Strength for the Mixing Ratio of Eva in PA6/EVA Blends Minh-Nhat Nguyen Faculty of Mechanical Engineering HCMC University of Technology and Education Ho Chi Minh City, Viet Nam 18144272@student.hcmute.edu.vn Quy-Long Nguyen Faculty of Mechanical Engineering HCMC University of Technology and Education Ho Chi Minh City, Viet Nam 18144261@student.hcmute.edu.vn Vinh-Tien Nguyen Faculty of Chemical and Food Technology HCMC University of Technology and Education Ho Chi Minh City, Viet Nam tiennv@hcmute.edu.vn Abstract: The mixing of plastics to create a material that meets the requirements of tensile strength and mechanical properties of the product has been of great interest in recent years The properties of Polyamide (PA6), which is a plastic material with characteristics such as hard, durable, good heat resistance, and corrosion resistance, but its ductility is quite low To compensate for that weakness, mixing PA6 with Ethylene Vinyl Acetate (EVA) - with the properties of a 'rubber' with high ductility and flexibility at low temperatures - is one solution Therefore, in this study, mixtures of EVA and PA6 at 5%-30% (wt) were extruded to make tested samples The results of the EVA/PA6 mixed extruded sample test will include such indicators as Tensile strength, Young's modulus, and Elongation SEM micrographs of fractured surfaces show the particles-dispersed phase morphology of PA6/EVA blends The indicators show that tensile strength decreases with increasing of EVA ratio but has a higher elongation at break, and reach maximum when the ratio of EVA in the blend was 15% The photomicrographs also show the spheres particles can be observed when the EVA percent reaches 15% and more obvious when the percentage of EVA reaches 20-30%, the more spherical particles appear in the blends, the more adhesion ability of the two materials is reduced Keywords: PA6/EVA blends, tensile strength, phase morphology, mixing polymers I INTRODUCTION Polyamide (PA6) or Nylon is a type of plastic widely used in industries, especially the automotive and electronic industries, based on its outstanding features such as high strength and stiffness at high temperatures, and resistance to high-temperature resistance [1-6] Good fatigue and wear resistance, resistance to chemical corrosion and UV rays, and non-toxic to humans [7] Ethylene Vinyl Acetate (EVA) is a copolymer polymer of Ethylene and Vinyl Acetate, which can change properties based on changing the ratio of Vinyl Acetate Copyright © authors This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License Ngoc-Thien Tran Faculty of Mechanical Engineering HCMC University of Technology and Education Ho Chi Minh City, Viet Nam thientn@hcmute.edu.vn Minh The-Uyen Tran Faculty of Mechanical Engineering HCMC University of Technology and Education Ho Chi Minh City, Viet Nam uyentmt@hcmute.edu.vn (VA), the higher the ratio of VA [8-12], the more flexibility Based on the ratio of VA in EVA, it can be divided into types: high VA rate (>60%) called Ethylene Vinyl Acetate rubber; moderate rate of VA (4-30%) is a copolymer with some rubber-like properties, called a thermoplastic elastomer material; low VA ratio ( 128 g/mL) 3,5-bis((E)-3-methoxystyryl)isoxazole (O4): Yield 56% (111.9 mg), yellow solid, C21H21NO3 [333.14 g/mol]; Rf = 0.45 (HEX/EA = 9/1); m.p 102.8 oC; 1H-NMR (500 MHz, CDCl3, ppm): 3.86 (s, OCH3, 6H), 6.95-6.97 (dd, H4,4, 3J (H,H) = 8,0 Hz, 4J (H,H) = 2.5 Hz, 2H), 7.13 (s, H2,2, 2H), 7.22 (d, H6,6, 3J (H,H) = 7.5 Hz, 2H), 7.31 (t, H5,5, 3J (H,H) = 8.0 Hz, 2H), 7.38 (d, H2,6, 3J (H,H) = 15.5 Hz, 2H), 7.73 (d, H1,7, 3J (H,H) = 15.5 Hz, 2H) 13C-NMR (125 MHz, CDCl3, ppm): 55.4 (OCH3), 113.5 (C2,2), 116.4 (H4,4), 120.1 (C2,6), 121.3 H6,6), 129.9 (C5,5), 143.4 (C1,1), 143.4 (C1,7), 160.0 (C3,5) ESI-MS m/z calc for [M+Cl]-: 368.64; found: 368.80 III RESULTS AND DISCUSSION C NMR and MS data (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3methoxyphenyl)hepta-1,4,6-trien-3-one (Cur): Yield 53% (1.95 g), red-orange solid, C21H20O6 [368.13 g/mol]; Rf = 0.31 (n-hexane (HEX)/ethyl acetate (EA) = 3/2); m.p 182.3 oC; 1HNMR (500 MHz, CDCl3): δ = 3.94 (s, OCH3, 6H), 5.79 (s, H4, 1H), 6.57 (d, H1,7, 3J (H,H) = 16.0 Hz, 2H); 6.92 (d, H5,5, 3J (H,H) = 8.0 Hz, 2H), 7.04 (d, H2,2, 3J (H,H) = 1.5 Hz, 2H), 7.10 (dd, H6,6, 3J (H,H) = 8.0 Hz, 3J (H,H) = 2.0 Hz, 2H) 13C-NMR (125 MHz, CDCl3): δ = 56.0 (OCH3), 101.1 (C4), 109.7 (C5,5), 114.8 (C2,2), 121.8 (C6,6), 127.7 (C1,1), 140.5 (C1,7), 146.8 (C3,3), 147.9 (C4,4), 183.3 (C3,5) ppm ESI-MS m/z calc for [M+H]+: 369.14; found: 368.90 3,5-bis((E)-4-fluorostyryl)isoxazole (O5): Yield 41% (76.0 mg), yellow solid, C19H13F2NO [309.10 g/mol]; Rf = 0.46 (HEX/EA = 9/1); m.p 158.6 oC; 1H-NMR (500 MHz, CDCl3, ppm): 5.81 (s, H4, 1H), 7.07 (d, H3,3, 3J (H,H) = 9.0 Hz, 2H), 7.09 (d, H5,5, 3J (H,H) = 8.5 Hz, 2H), 7.53 (d, C2,2, 3J (H,H) = 9.0 Hz, 2H), 7.54 (d, H6,6, 3J (H,H) = 8.5 Hz, 2H), 7.61 (d, H1,7, 3J (H,H) = 16.0 Hz, 2H), 7.63 (d, H2,6, J (H,H) = 15.5 Hz, 2H) 13C-NMR (125 MHz, CDCl3, ppm): 101.7 (C4), 116.0 (C3,3), 116.1 (C5,5), 123.7 (C2,6), 129.9 (C2,2), 129.9 (C6,6), 131.2 (C1,1), 139.3 (C1,7), 162.8 (C4,4), 164.8 (C3,5) ESI-MS m/z calc for [M-H]-: 308.09; found: 307.90 4,4'-((1E,1'E)-isoxazole-3,5-diylbis(ethene-2,1diyl))bis(2-methoxyphenol) (O1): Yield 44% (96.4 mg), white solid, C21H19NO5 [365.13 g/mol]; Rf = 0.34 (HEX/EA = 1:1); m.p 163.6 oC ; 1H-NMR (500 MHz, CDCl3, ppm): δ = 3.95 (s, OCH3, 3H), 3.96 (s, OCH3, 3H), 5.76 (s, Ar-OH, 1H), 5.79 (s, Ar-OH, 1H), 6.41 (s, H4, 1H), 6.79 (d, H6, 3J (H,H) = 16.0 Hz, 1H), 6.91 (d, H5'', 3J (H,H) = 8.0 Hz, 1H), 6.92 (d, H5, 3J (H,H) = 8.0 Hz, 1H), 6.96 (d, H2, 3J (H,H) = 16.5 Hz, 1H), 7.01 (d, H2'', 4J (H,H) = 2.0 Hz, 1H), 7.02 (d, H2, 4J (H,H) = 2.0 Hz, 1H), 7.06-7.08 (dd, H6'',6', 3J (H,H) = 8.0 Hz, J (H,H) = 2.0 Hz, 2H), 7.08 (d, H7, 3J (H,H) = 16.5 Hz, 1H), 7.26 (d, H1, 3J (H,H) = 16.5 Hz, 1H); 13C-NMR (125 MHz, CDCl3, ppm): δ = 55.9 (OCH3), 55.9 (OCH3), 97.6 (C4), 108.2 (C2), 108.8 (C2), 110.9 (C5), 113.8 (C5), 114.6 (C6), 114.8 (C6), 121.5 (C2), 121.6 (C6), 128.2 (C1), 128.5 (C1), 134.8 (C1), 135.6 (C7), 146.7-147.0 (C4,4, C3,3, 4C), 162.2 (C5), 168.5 (C3) ESI-MS m/z calc for [M+H]+: 366.14; found: 366.00 3,5-bis((E)-3-fluorostyryl)isoxazole (O6); Yield 57% (105.7 mg), yellow solid, C19H13F2NO [309.10 g/mol]; Rf = 0.26 (HEX/EA = 9:1); m.p 157.8 oC; 1H-NMR (500 MHz, CDCl3, ppm): 6.50 (s, H4, 1H), 6.94 (d, H6, 3J(H,H) = 16.5 Hz, 1H), 7.01 (m, H4,4, 2H), 7.13 (d, H2, 3J(H,H) = 16.5 Hz, 1H), 7.14 (d, H7, 3J(H,H) = 16.5 Hz, 1H), 7.21 (d, H2, J (H,H) = 1.5 Hz, 1H), 7.23 (d, H2, 4J (H,H) = 1.5 Hz, 1H), 7.28 (d, H6,6, 3J (H,H) = 8.0 Hz, 2H), 7.31 (d, H1, 3J(H,H) = 17.0 Hz, 1H), 7.33 (m, H5,5, 2H); 13C-NMR (125 MHz, CDCl3, ppm): 99.1 (C4), 113.3 – 113.5 (C2,2, 2C), 114.1 (C6), 115.7 – 116.1 (C4,4, 2C), 117.4 (C2), 122.8 – 123.2 (C6,6, 2C), 130.3 – 130.4 (C5,5, 2C), 133.8 (C7), 134.6 (C1), 138.1 (C1,1, 2C), 161.7 (C3), 162.2 (C3), 164.1 (C5), 167.9 (C3) ESI-MS m/z calc for [M+H]+: 310.11; found: 309.90 3,5-di((E)-styryl)isoxazole (O2): Yield 56% (91.7 mg), white solid, C19H15NO [273.12 g/mol]; Rf = 0.43 (HEX/EA = 9:1); m.p 168.3 oC; 1H-NMR (500 MHz, CDCl3, ppm): 7.03 (s, H4, 1H), 7.23 (d, H6, 3J (H,H) = 16.5 Hz, 1H), 7.26 (d, H2, J (H,H) = 16.5 Hz, 2H), 7.30 – 7.38 (m, H2,2, 2H), 7.38 – 7.46 (m, H1,7,6,6,4,4, 6H), 7.67 (dd, H3,3,5,5, 3J (H,H) = 7.5 Hz, 4H); 13C-NMR (125 MHz, CDCl3, ppm): 99.2 (C4), 113.3 (C6), 115.6 (C2), 127.1 (C2,6, 2C), 127.2 (C2,6, 2C), 128.8 (C4), 128.8 (C4), 128.9 (C3,5, 2C), 129.1 (C3,5, 2C), 134.4 (C1), 135.3 (C1), 135.6 (C1), 136.2 (C7), 161.9 (C5), 168.0 (C3) ESI-MS m/z calc for [M+H]+: 274.13; found: 273.90 3,5-bis((E)-2-fluorostyryl)isoxazole (O7): Yield 61% (113.1 mg), yellow solid, C19H13F2NO [309.10 g/mol]; Rf = 0.59 (HEX/EA = 9/1); m.p 120.1 oC; 1H-NMR (500 MHz, CDCl3, ppm): 6.57 (s, H4, 1H), 7.07 (d, H6, 3J (H,H) = 16.5 Hz, 1H), 7.07-7.12 (m, H3,3, 2H), 7.15-7.19 (td, H5,5, 3J (H,H) = 7.5 Hz, 4J (H,H) = 1.0 Hz, 2H), 7.20 (d, H2, 3J (H,H) = 16.5 Hz, 1H); 7.28-7.32 (m, H6,6, 2H), 7.33 (d, H7, 3J (H,H) = 16.5 Hz, 1H); 7.46 (d, H1, 3J (H,H) = 17.0 Hz, 1H); 7.53-7.63 (td, H4,4, 3J (H,H) = 7.5 Hz, 4J (H,H) = 1.5 Hz, 2H); 13C-NMR (125 MHz, CDCl3, ppm): 98.9 (C4), 115.5 (C6), 115.9 (C3), 116.0 (C3), 118.3 (C2), 123.5 (C1, 123.7 3,5-bis((E)-4-methoxystyryl)isoxazole (O3): Yield 48% (95.9 mg), yellow solid, C21H19NO3 [333.14 g/mol]; Rf = 0.28 (HEX/EA = 4:1); m.p 172.2 oC; 1H-NMR (500 MHz, CDCl3, ppm): 3.83 (s, OCH3, 3H), 3.84 (s, OCH3, 3H), 6.41 (s, H4, 487 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) (C1), 124.4 (C5,5), 127.4 (C4), 127.8 (C1), 128.1 (C7), 128.2 (C4) , 130.2 (C6), 130.4 (C6), 159.6-161.9 (C2,2, 2C), 162.1 (C5), 168.3 (C3) ESI-MS m/z calc for [M+H]+: 310.11; found: 309.90 132.6 (C1,1), 147.0 (C3,5), 161.6 (C4), 163.6 (C4) ppm; ESI-MS m/z calc for [M+H]+: 309.12; found: 308.90 3,5-bis((E)-3-fluorostyryl)-1H-pyrazole (P6): Yield 76% (0.14 g), colorless solid, C19H14F2N2 [308.11 g/mol]; Rf = 0.22 (HEX/EA = 7/3); m.p 187.3 oC; 1H-NMR (500 MHz, CDCl3): δ 6.65 (s, H4, 1H), 6.96 (td, 3J (H,H; H-F) = 8.0 Hz, 3J (H,H) = 2.5 Hz, H4,4, 2H), 7.03 (d, 3J (H,H) = 16.5 Hz, H2,6, 2H), 7.11 (d, 3J (H,H) = 16.5 Hz, H1,7, 2H), 7.15 (t, 3J (H,H) = 2.0 Hz, H2, 2H), 7.22 (d, 3J (H,H) = 7.5 Hz, H6,6, 2H), 7.29 (m, H5,5, 2H) ppm; 13C-NMR (125 MHz, CDCl3): δ 101.0 (C4), 112.8-113.0 (C2,2), 114.9-115.1 (C4,4), 118.4 (C2,6), 122.5 (C6,6), 130.2 (C5,5), 130.3 (C1,7), 138.7 (C1,1), 162.2 (C3), 164.1 (C3) ppm; ESI-MS m/z calc for [M+H]+: 309.12; found: 308.90 4,4'-((1E,1'E)-(1H-pyrazole-3,5-diyl)bis(ethene-2,1diyl))bis(2-methoxyphenol) (P1): Yield 73% (0.16 g), redorange powder, C21H20N2O4 [364.14 g/mol]; Rf = 0.46 (HEX/EA = 3/2); m.p 215.3 oC; 1H-NMR (500 MHz, CDCl3MeOD): δ = 3.93 (s, OCH3, 6H), 6.55 (s, H4, 1H), 6.85 (d, 3J (H,H) = 16.0 Hz, H2,6, 2H), 6.88 (d, 3J (H,H) = 8.0 Hz, H5,5, 2H), 6.99 (d, 3J (H,H) = 8.5 Hz, H6,6, 2H), 7.03 (s, H2,2, 2H), 7.04 (d, 3J (H,H) = 16.5 Hz, H1,7, 2H) ppm; 13CNMR (125 MHz, CDCl3-MeOD): δ = 55.8 (OCH3), 99.3 (C4), 108.6 (C2,2), 114.8 (C5,5), 114.9 (C2,6), 120.6 (C6,6), 129.0 (C1,1), 131.2 (C1,7), 146.2 (C4,4), 147.1 (C3,3) ppm; ESI-MS m/z calc for [M+H]+: 365.15; found: 364.9 3,5-bis((E)-2-fluorostyryl)-1H-pyrazole (P7): Yield 81% (0.15 g), colorless solid, C19H14F2N2 [308.11 g/mol]; Rf = 0.32 (HEX/EA = 3/2); m.p 160.2 oC; 1H-NMR (500 MHz, CDCl3): δ 6.72 (s, H4, 1H), 7.05 (m, H3,3, 2H), 7.09 (m, H5,5, 2H), 7.12 (d, 3J (H,H) = 16.5 Hz, H2,6, 2H), 7.22 (m, H6,6, 2H), 7.27 (d, 3J (H,H) = 17.0 Hz, H1,7, 2H), 7.53 (m, H5,5, 2H) ppm; 13C-NMR (125 MHz, CDCl3): δ 100.6 (C4), 115.7115.9 (C3,3), 119.6 (C2,6), 123.8-123.8 (C1,1), 124.2 (C5,5), 124.3-124.4 (C1,1), 127.3 (C4,4), 129.3 (C6,6), 147.1 (C3,5), 159.5 (C2), 161.5 (C2) ppm; ESI-MS m/z calc for [M+H]+ 309.12; found: 308.90 3,5-di((E)-styryl)-1H-pyrazole (P2): Yield 79% (0.13 g), yellow solid, C19H16N2 [272.13 g/mol]; Rf = 0.27 (HEX/EA = 9/1); m.p 161.2 oC; 1H-NMR (500 MHz, CDCl3): δ 6.66 (s, H4, 1H), 7.05 (d, 3J (H,H) = 16.0 Hz, H2,6, 2H), 7.16 (d, 3J (H,H) = 16.0 Hz, H1,7, 2H), 7.27 (t, 3J (H,H) = 7.5 Hz, H44, 2H), 7.31 (t, 3J (H,H) = 7.0 Hz, H3,3,5,5, 4H), 7.47 (d, 3J (H,H) = 7.5 Hz, H2,2,6,6, 4H) ppm; 13C-NMR (125 MHz, CDCl3): δ 100.4 (C4), 116.9 (C2,6), 126.6 (C2,2,6,6), 128.2 (H4,4), 128.7 (C3,3,5,5), 131.9 (C1,7), 136.3 (C1,1), 147.0 (C3,5) ppm; ESI-MS m/z calc for [M+H]+: 273.14; found: 272.90 D Cytotoxicity against KB cancer cell line As summarized in Table 1, phenolic compounds bearing an isoxazole (O1, IC50 = 13.851.17 M) or a pyrazole (P1, IC50 = 3.400.22 M) ring exhibited higher activities than curcumin (IC50 = 3.400.22 M) The presence of isoxazole and pyrazole moiety led to a 2- to 10-fold greater potency toward KB cancer cell line The absence of substituents (-OH and -OCH3) or the presence of para-OCH3 group in phenyl rings showed no anticancer activities It should be noted that the presence of pyrazole scaffold in P2 structure exhibited better anticancer activity with an IC50 of 24.06 μM regardless of the removal of -OH and -OCH3 groups Compound P3 bearing -OCH3 at para-position showed poor anticancer activity when compared with curcumin Structures containing isoxazole/pyrazole ring and meta-substituted -OCH3 group displayed close (O4, IC50 = 34.732.76 M) or lower (P4, IC50 = 51.964.09 M) inhibitory activities respecting to curcumin These observations indicated the effects of isoxazole/pyrazole ring and substituents (nature and position) in aromatic moieties on the inhibitory activities of isoxazole and pyrazole curcuminoids 3,5-bis((E)-4-methoxystyryl)-1H-pyrazole (P3): Yield 69% (0.14 g), yellow solid, C21H20N2O2 [332.15 g/mol]; Rf = 0.42 (HEX/EA = 3/2); m.p 176.1 oC; 1H-NMR (500 MHz, CDCl3): δ = 3.81 (s, OCH3, 6H), 6.57 (s, H4, 1H), 6.86 (d, 3J (H,H) = 8.5 Hz, H3,3,5,5, 4H), 6.88 (d, 3J (H,H) = 16.5 Hz, H2,6, 2H), 7.06 (d, 3J (H,H) = 16.5 Hz, H1,7, 2H), 7.39 (d, 3J (H,H) = 8.5 Hz, H2,2,6,6, 4H) ppm; 13C-NMR (125 MHz, CDCl3): δ = 55.3 (OCH3), 99.6 (C4), 114.2 (C3,3,5,5), 115.3 (C2), 113.9 (C6), 127.8 (C1), 129.3 (C1), 129.3 (C2,2,6,6), 130.8 (C1,7), 159.7 (C4,4) ppm; ESI-MS m/z calc for [M+H]+: 333.16; found: 333.00 3,5-bis((E)-3-methoxystyryl)-1H-pyrazole (P4): Yield 71% (0.14 g), colorless solid, C21H20N2O2 [332.15 g/mol]; Rf = 0.32 (HEX/EA = 7/3); m.p 106.5 oC; 1H-NMR (500 MHz, CDCl3): δ = 3.79 (s, OCH3, 6H), 6.62 (s, H4, 1H), 6.76 (dd, 3J (H,H) = 8.5 Hz, dd, 3J (H,H) = 2.5 Hz, H4,4, 2H), 6.98 (t, 4J (H,H) = 1.5, H2,2, 2H), 7.01 (d, 3J (H,H) = 16.5 Hz, H2,6, 2H), 7.01-7.06 (m, 2H), 7.09 (d, 3J (H,H) = 16.5 Hz, H1,7, 2H), 7.22 (t, 3J (H,H) = 8.0 Hz, H5,5, 2H) ppm; 13C-NMR (125 MHz, CDCl3): δ = 55.2 (OCH3), 100.4 (C4), 111.7 (C2,2), 113.8 (C4,4), 117.8 (C2,6), 119.2 (C6,6), 129.6 (C5,5), 131.0 (C1,7), 137.9 (C1,1), 147.09 (C3,5), 159.9 (C3,3) ppm; ESI-MS m/z calc for [M+3H]+: 335.18; found: 335.00 Table Cytotoxicity against KB of curcumin (Cur), isoxazole (O1-7) and pyrazole (P1-7) curcuminoids MTT viability assay after 72 h, n=3, mean standard deviation (SD), Cpd: compound 3,5-bis((E)-4-fluorostyryl)-1H-pyrazole (P5): Yield 68% (0.12 g), colorless solid, C19H14F2N2 [308.11 g/mol]; Rf = 0.41 (HEX/EA = 7/3); m.p 229.1 oC; 1H-NMR (500 MHz, CDCl3): δ 6.61 (s, H4, 1H), 6.95 (d, 3J (H,H) = 16.5 Hz, H2,6, 2H), 6.99 (t, 3J (H,H) = 8.5 Hz, H5,5, 4H), 7.09 (d, 3J (H,H) = 16.5 Hz, H1,7, 2H), 7.40 (d, 3J (H,H) = 9.0 Hz, H2,2, 2H), 7.40 (d, 3J (H,H) = 9.0 Hz, H6,6, 2H) ppm; 13C-NMR (125 MHz, CDCl3): δ 100.3 (C4), 115.6 (C3,3), 115.8 (C5,5), 117.2 (C2,6), 128.0 (C2,2), 128.1 (C6,6),), 130.0 (C1,7), 488 CPD IC50SD (M) CPD IC50SD (M) Cur 33.352.66 O1 13.851.17 P1 3.400.22 O2 NA P2 24.069.00 O3 NA P3 252.8920.23 O4 34.732.76 P4 51.964.09 O5 207.0516.17 P5 NA O6 NA P6 245.4918.98 O7 NA P7 NA 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) [2] N Sreejayan and M N Rao, “Curcuminoids as potent inhibitors of lipid peroxidation”, J Pharm Pharmacol., vol 46, pp 1013–1016, Dec 1994 [3] K Mehta, P Pantazis, T McQueen, and B B Aggarwal, “Antiproliferative effect of curcumin (diferuloylmethane) against human breast tumor cell lines”, Anticancer Drugs, vol 8, pp 470–481, Jun 1997 [4] V T B Pham, T V Nguyen, H V Nguyen, T T Nguyen, and H M Hoang, “Curcuminoids versus Pyrazole‐Modified Analogues: Synthesis and Cytotoxicity against HepG2 Cancer Cell Line”, ChemistrySelect, vol 5, pp 11681–11684, Oct 2020 [5] A Theppawong et al., “Synthesis of Non ‐ Symmetrical Nitrogen‐Containing Curcuminoids in the Pursuit of New Anticancer Candidates”, ChemistryOpen, vol 8, pp 236–247, Feb 2019 [6] B C Jordan, B Kumar, R Thilagavathi, A Yadhav, P Kumar, and C Selvam, “Synthesis, evaluation of cytotoxic properties of promising curcumin analogues and investigation of possible molecular mechanisms”, Chem Biol Drug Des., vol 91, pp 332–337, Jan 2018 [7] J Sup Shim et al., “Hydrazinocurcumin, a novel synthetic curcumin derivative, Is a potent inhibitor of endothelial cell proliferation”, Bioorg Med Chem., vol 10, pp 2439–2444, Aug 2002 [8] J Das, S Pany, S Panchal, A Majhi, and G M Rahman, “Binding of isoxazole and pyrazole derivatives of curcumin with the activator binding domain of novel protein kinase C,” Bioorg Med Chem., vol 19, pp 6196–6202, Nov 2011 [9] D Simoni et al., “Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cells,” Bioorg Med Chem Lett., vol 18, pp 845–849, Jan 2008 [10] M W Amolins, L B Peterson, and B S J Blagg, “Synthesis and evaluation of electron-rich curcumin analogues”, Bioorg Med Chem., vol 17, pp 360–367, Jan 2009 [11] B E Smart, “Fluorine substituent effects (on bioactivity)”, J Fluor Chem., vol 109, pp 3–11, Jun 2001 [12] M Schlosser and D Michel, “About the ‘physiological size’ of fluorine substituents: Comparison of sensorially active compounds with fluorine and methyl substituted analogues”, Tetrahedron, vol 52, pp 99–108, Jan 1996 [13] F Bray, J Ferlay, I Soerjomataram, R L Siegel, L A Torre, and A Jemal, “Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries”, CA Cancer J Clin., vol 68, pp 394–424, Nov 2018 [14] C.-P Wu, S Ohnuma, and S V Ambudkar, “Discovering natural product modulators to overcome multidrug resistance in cancer chemotherapy”, Curr Pharm Biotechnol., vol 12, pp 609–620, Apr 2011 [15] H M Hoang, N T Vo, and T H Le, “Synthesis of New Isoxazole Analogs of Curcuminoid”, vol 24, pp 2141–2145, Dec 2021 [16] P A Cerutti, “Oxidant stress and carcinogenesis”, Eur J Clin Invest., vol 21, pp 1–5, Feb 1991 [17] T Chuprajob, C Changtam, R Chokchaisiri, W Chunglok, N Sornkaew, and A Suksamrarn, “Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids”, Bioorg Med Chem Lett., vol 24, pp 2839–2844, Jul 2014 [18] S Mishra et al., “Differential apoptotic and redox regulatory activities of curcumin and its derivatives”, Free Radic Biol Med., vol 38, pp 1353–1360, May 2005 [19] M Sökmen and M Akram Khan, “The antioxidant activity of some curcuminoids and chalcones”, Inflammopharmacology, vol 24, pp 81–86, Jun 2016 [20] M Labbozzetta et al., “Lack of nucleophilic addition in the isoxazole and pyrazole diketone modified analogs of curcumin; implications for their antitumor and chemosensitizing activities”, Chem Biol Interact., vol 181, pp 29–36, Sep 2009 As reported, the free radicals are involved in cell damage by attacking DNA strands [16] Considering chemical structure of a para-substituted phenolic motif, the anticancer capacity of curcumin can be attributed to the favorable formation of phenoxyl radical, which is stabilized by a conjugated -system [17,18] In addition, curcumin was found to generate reactive oxygen species (ROS), which are responsible for cell apoptosis [18,19] The ability of curcumin to induce cell apoptosis in cancer cells can be explained through the detoxification mechanism Curcumin is classified as an , -unsaturated ketone, which prone to Michael addition with nucleophiles such as -SH groups of glutathione S-transferases (GSTs) In other words, curcumin is an inhibitor of detoxification enzymes GSTs through Michael addition reaction [20-22] Note that isoxazole/pyrazole cyclization leads to a more rigid structure and elimination of keto-enol tautomerism In other words, curcumin sensitizes to Michael donors while the isoxazole/pyrazole analogs are not taken the detoxification mechanism into account However, the replacement of diketone group in curcumin by isoxazole/pyrazole ring (O1, P1) resulted in significant anticancer activities against KB cancer cell line These observations are similar to the reported results, in which the anticancer activities of isoxazole and pyrazole curcuminoids were increased due to their improved solubility and stability when compared to curcumin [4,5,7,2325] The better anticancer activities of these analogs might rely on other mechanisms rather than detoxification, but this remained unclear The isoxazole and pyrazole curcuminoids (O5-O7, P5-P7) displayed poor/inactive anticancer activities toward KB cancer cell line, indicating that fluorine (-F) group in phenyl ring gave a negative effect on the inhibitory activities Although the special effects of fluorine atom on the biological activities were reported, the mechanism has been difficult to divine [26] IV CONCLUSION Structure-activity relationship analysis suggested that i) the isoxazole/pyrazole phenolic motif (O1, P1) is responsible for better anticancer activity against KB cancer cell line, whereas the fluoro substituent in phenyl ring gives a negative effect on the inhibitory activity ii) The scaffold of meta-OCH3 isoxazole curcuminoid (O4) demonstrated close cytotoxicity against KB In general, we pointed out a similar trend to the previous reports and confirmed that curcumin-based isoxazole and pyrazole analogs exerted stronger anticancer effects than curcumin In addition, we demonstrated for the first time the anticancer activity of curcuminoids bearing both fluorinesubstituted aromatic group and isoxazole/pyrazole ring ACKNOWLEDGMENT We gladly acknowledge the use of the Ho Chi Minh City University of Technology and Education facilities to complete our work REFERENCES [1] Y X Xu, K R Pindolia, N Janakiraman, R A Chapman, and S C Gautam, “Curcumin inhibits IL1 alpha and TNF-alpha induction of AP-1 and NF-kB DNA-binding activity in bone marrow stromal cells”, Hematopathol Mol Hematol., vol 11, pp 49–62, 1997 489 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) [21] S Awasthi et al., “Curcumin–glutathione interactions and the role of human glutathione S-transferase P1-1”, Chem Biol Interact., vol 128, pp 19–38, Aug 2000 [22] A T Dinkova-Kostova and P Talalay, “Relation of structure of curcumin analogs to their potencies as inducers of Phase detoxification enzymes”, Carcinogenesis, vol 20, pp 911–914, May 1999 [23] S Mishra, S Patel, and C G Halpani, “Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application”, Chem Biodivers., vol 16, 47 pages, Feb 2019 [24] M Ahmed, M A Qadir, A Hameed, M Imran, and M Muddassar, “Screening of curcumin-derived isoxazole, pyrazoles, and pyrimidines for their anti-inflammatory, antinociceptive, and cyclooxygenase-2 inhibition”, Chem Biol Drug Des., vol 91, pp 338–343, Jan 2018 [25] R Sribalan et al., “Synthesis of a Water-Soluble Pyrazole Curcumin Derivative: In Vitro and In Vivo AGE Inhibitory Activity and Its Mechanism”, ChemistrySelect, vol 2, pp 1122–1128, Jan 2017 [26] C Isanbor and D O’Hagan, “Fluorine in medicinal chemistry: A review of anti-cancer agents”, J Fluor Chem., vol 127, pp 303–319, Mar 2006 490 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) Modeling of Flow Mixed with Polymers in Open Channel Flow: Application on the Blumenau River in Brazil Walid Bouchenafa SNF SA Rue Adrienne Bolland, 42163, Andrézieux, France wbouchenafa@snf.com Airton Hoenicke AXCHEM Brasil Indústria Química R Frederico Jensen, 200 Itoupavazinha, Blumenau - SC, 89066-300, Brazil airton@axchem-brasil.com.br Huyen Xuan Dang-Vu Ho Chi Minh City University of Technology (HCMUT) Vietnam National University Ho Chi Minh City Ho Chi Minh City, Vietnam xhuyen@hcmut.edu.vn Abstract: Extreme weather with heavy and prolonged rain along with rapid melting snow is one of the main causes of river flooding Many techniques have been developed for flood control and while structural methods like sea walls, dikes, and barriers are expensive and long processing, drag reducing polymer is a less expensive and easy-to-deploy nonstructural technique In this study, as a part of the BLUMPOL project (BLUMENAU POLYMER), a case study on the modeling of a watercourse containing a flow without and with drag reducing polymers is presented The objective is to improve knowledge of the drag reduction effect on open channel flows The modeling results show that the addition of polymers in the flows leads to a marked drag reduction resulting in decreasing the water depth up to 18% of its initial depth Keywords: flood risk management, open channel flow, drag reduction, polymer, Mike Hydro rivers I INTRODUCTION Floods are the most common natural disasters often resulting in considerable economic losses and human and social tragedies [1] Extreme events in India and the Philippines in 2018, Vietnam in 2021, and Brazil in 2022 show how devastating the effects of floods can be Additionally, some megacities such as Bangkok, Mumbai, Jakarta, Rio De Janeiro, Shanghai, Hochiminh City, Dhaka, London, Paris, and Rotterdam are extremely vulnerable to riverine flooding due to increased risk from urbanization and the effects of climate change [2] An effective river flood risk protection system can significantly improve public safety and reduce social damages and economic losses related to floods Therefore, flood risk management is still a huge challenge for government and local authorities [3], especially when the adaptation of populations bordering rivers in the face of the risk of flooding is in perpetual evolution The preferred strategy for flood control is currently the protection technique [4] The method of reducing drag by Copyright © authors This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License Bruna Luiza Cunico AXCHEM Brasil Indústria Química R Frederico Jensen, 200 Itoupavazinha, Blumenau - SC, 89066-300, Brazil bruna@axchem-brasil.com.br Trong Dang-Vu SNF HC One chemical Plant Road, Riceboro, GA 31323, USA Tvu2@snf.com adding polymers can be considered an effective new technique to reinforce the measures already deployed in the river flood risk management protection strategy since it reduces the flow up to 18% of its initial height [5] and therefore avoids the overflow of rivers in case of flooding [6] The approach presented in this article aims to minimize the impacts of river flooding in urban areas The present work is based on the results of research works describing the phenomenon of drag reduction by the addition of polymers in a free surface flow on a watercourse under highly controlled hydraulic conditions [7] During this work, it was found that the addition of polymers, for free surface flows, with a low quantity of 20 PPM (particles per million), leads to a significant reduction in drag Indeed, the interactions between the polymer and the turbulent structures of the flow tend to increase the thickness of the boundary layer and modify the velocity profile near the wall by the establishment of an elastic sub-layer between the viscous layer and the logarithmic zone of the boundary layer [8], which subsequently causes a decrease in the water depth Following this interpretation, the authors hypothesized that similar phenomena also occur on the Blumenau River located in Brazil and prone to flooding To this, first, a hydraulic simulation model faithfully describing the flow dynamics of the Blumenau River is developed in this study The quasi-two-dimensional hydrodynamic software Mike Hydro River (MHR) is used to simulate the flows in our case study Two models are developed and then compared with each other, the first reference model is dedicated to a flow without polymers and validated using data from measurements of water heights and discharge The second model is devoted to the same Blumenau River considering the presence of a quantity of 20 ppm of polymers in the flow Mignot et al [8] measured the variation in water depth by injecting different concentrations of polymers flows in channels at the laboratory scale Their work showed that from 20 ppm of PAM the backwater curves become asymptomatic with a stable decrease in water depth 491 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) of 20% whatever the concentration above 20 ppm of polymers make it possible to characterize the topography of a studied system, such as, for example, satellite images that can be obtained from national or international organizations involved in the collection and storage of satellite images such as the National Aeronautics and Space Administration NASA and the Indian Institute of Remote Sensing IIRS Some of this data is freely available In addition, the most common technique for updating bathymetric data is called laser remote sensing or LIDAR (Light Detection And Ranging), it is a useful technique for simultaneously measuring topography and bathymetry [9] The mapping of the study area can be reproduced using a digital terrain model (DTM) which provides precise morphological and topographical data The bathymetry of our study area is prepared from a digital terrain model and provided as input data for the model II APPLICATION CASES The hydraulic modeling is carried out on a river called Itajai, which crosses the city of Blumenau located in the southeastern part of Brazil at an altitude of 21 m A length of 91 km was selected from the Indaial department to the estuary at Fazenda to better evaluate the drag reduction processes by the addition of polymers The water depth during the 2016 flood varies along the river from 8.5 to 10 meters The width of the river varies between 250 to 330 meters, the slope is low in the order of S0 ∼10-4 The bed of the Itajai River contains pebbles, gravel, and alluvial materials The flow regime of Itajai is fluvial, the discharge during the 2016 flood was 2368 m3/s The site selected for the study is a meandering watercourse, crossed by twelve bridges Note that areas with little or no data face particular challenges Remote sensing and the use of the Geographic Information System (GIS) technique are particularly useful solutions These techniques can also be used in areas where physical accessibility is an issue Although satellite imagery, aerial photography, and LIDAR technology can generate realtime data, the cost of data acquisition is always a concern: the purchase of expensive data and technologies such as LIDAR should be compared to the benefits of getting more accurate modeling results Figure Itajai River in Blumenau a) in 2019 and b) during the flood in 2016 Figure Bathymetry of the Seine river in Paris using the LIDAR technique (www.norbit.com) The flow resistance coefficient is estimated from the medium surface condition It depends on the type of soil and characterizes the linear head losses Generally, it is interpreted by the Manning coefficient K intervening in the Manning-Strickler formula which gives the expression of the average velocity for a flow in a uniform regime [10]: Figure Location of the study site and definition of measurement points The choice of the river for the modeling is justified by the possibility of carrying out in-situ trials within the framework of the BLUEPOL project to better assess the phenomenon of drag reduction by the injection of polymers at the scale of a real watercourse 𝑣⃗ = 𝐾𝑅ℎ3 𝑆02 III STATE OF THE ART ON DATA REQUIRED FOR MODELING Where 𝑅ℎ [m] is the hydraulic radius, 𝑆0 is the energy slope, equal to that of the channel bottom, 𝐾 = where K Three input databases are required to launch the modeling regardless of the hydraulic model selected: 1) a map of the study area to locate the watercourse and define its crosssections as well as the slopes and its considered length, 2) a flow resistance coefficient defining the structure of the riverbed and its lateral banks, and finally 3) initial and boundary conditions characterizing the flow The data entry method and its qualities define the final modeling results [m1/2s-1] and η [m1/2s-1] are the Strickler and Manning coefficients respectively η The initial conditions are described by hydraulic data such as the discharges at any point of the river for the start of the simulation In our case study, the hydraulic data on the discharge as well as the measurements of the water depth along Itajai are used as input data for the modeling The downstream boundary condition is a known relationship between discharge and water depth A DTM model is used to define the river morphology and its cross-sections Itajai flow is simulated during the September 2016 flood period The measurement data is used to validate the modeling results and correct the flow model without polymers The cross-sections determine the relationship between water depth and surface They are typically obtained based on topographic surveys orthogonal to the bed of the watercourse Indeed, the topography is another important aspect for the evaluation of flow propagation within a stretch of a finite-length river Traditionally, topographic and bathymetric data are obtained from land surveying and bathymetric surveys are usually collected from local organizations Nevertheless, currently, several technologies 492 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) IV FLOW HYDRODYNAMIC WITHOUT AND WITH POLYMERS laboratory conditions, that adding polymers to a large-scale watercourse reduces water depth As the polymer arrived at a cross section, water depth decreased quite linearly with time and eventually reached a lower plateau of maximum drag reduction with a constant reduced water depth MODELING The hydrodynamic processes of river flows could be represented by different simplified approaches [9], and the choice of a modeling approach must be consistent with the study context There are several main hydrodynamic modeling software for open channel flows, such as HEC-RAS, LISFLOOD-FR, TELEMAC, and MIKE HYDO In the context of modeling flows mixed with polymers, the representation of the flow dynamics remains quite crucial to better assess the effectiveness of the drag reduction technique The Mike Hydro River (MHR) hydrodynamic model is considered best suited for modeling this type of flow This model makes it possible to explicitly describe and represent the flow dynamics using the Barré de Saint Venant equations describing the movement of open channel flows in shallow water [11] The model calculates the water depth and flows velocity at any point along the river The principle of the MHR model is discussed in [12] and [13] Figure Simulated water depth over 30 km and the difference between water depth on the cross-section before and after the polymer injection The model of flow mixed with a concentration of 20 ppm of polymers shows a significant reduction in the Itajai flow resistance coefficient Figure shows the water depth for a flow with polymers over a first distance of 30 km from the injection point and the cross-section shows the difference in water depth when injecting the polymers Two hydraulic phenomena are observed in the modeled system: a decrease in water depth along the watercourse up to 18% of its initial depth and in return, an increase in flow capacity up to 30% The relative water depth reduction decreased almost linearly with distance from the injection point and vanished at about 25 km downstream, at which the water depth was hardly affected by the polymer addition Indeed, the phenomenon of drag reduction caused by the injection of polymers into a watercourse can reduce the local water depth while increasing the flow velocity and contributing subsequently to protection more effectively against the effects of flooding in the vulnerable area [7] This phenomenon makes it possible to improve river flood risk management strategies Figure Visualization of Itajai flows modeled by Mike Hydro River In their studies [8], the authors showed the impact of the polymer on the change in Strickler's coefficient In the modeling of flows mixed with polymers, the approach used to introduce the polymers into the model consists in varying the Manning coefficient for each profile across the modeled section [14] V RESULTS The modeled water depth of the Itajai river with polymer injection is shown in the Fig Figure Water depth at Itajai before and after polymer injections VI CONCLUSION The addition of polymers strongly decreases the drag force that the walls apply on the flow, leading to highly increased mean velocities and highly decreased water depths [7] The results in the laboratory showed that the flow resistance coefficient decreases to 50% when injecting 20 ppm of polymers The Manning coefficient has been modified in our model to introduce the polymers effect This drag reduction method has already proven to be effective for reducing the water depth in real water course [7] Figure Modeled water depth with 20 ppm polymer In this work, the Mike Urban Hydro was used to model Itajai flows A comparison of the model results before polymer injection, with the measurement data, showed a remarkable capacity of the modeling system set up allowing to reproduce effectively the flow dynamics of Itajai The measurement data made it possible to better correct the developed model Fig confirms previous experiments in As part of the BLUM POL project which aims to carry out a real trials in the Blumenau river A modeling study was carried out to show the simulations results The model 493 2022 6th International Conference on Green Technology and Sustainable Development (GTSD) [5] W Bouchenafa, A Lefevre, and B Quillien, “Augmenter le coefficient de Strickler par la technique de réduction de la trnée dans les écoulements surface libre”, International Journal of Innovation and Applied Studies, ISSN 2028-9324 vol 24, No Aug 2018, pp 1-8 [6] R Pich, “Method for limiting freshet levels and controlling floods “, Patent# WO 2014199037 A1., 2014 [7] W.Bouchenafa, B Dewals, A Lefevre, E.Mignot, “Water Soluble Polymers as a Means to Increase Flow Capacity: Field Experiment of Drag Reduction by Polymer Additives in an Irrigation Canal” Journal of Hydraulic Engineering vol 147, No (August 2021) https://ascelibrary.org/doi/abs/10.1061/%28ASCE%29HY.19 43-7900.0001904 [8] E Mignot, N Rivière, A Lefevre and B Quillien “Smoother Than Smooth: Increasing the Flow Conveyance of an OpenChannel Flow by Using Drag Reduction Methods” J Hydraul Eng., 2019, 145(4): 04019011, p [9] W.J Lillycrop, L.E., Parson and J.L Irish, “Development and operation of the SHOALS airborne LIDAR hydrographic survey system”, Proceedings of SPIE 2694 CIS Selected Papers: Laser Remote Sensing of Natural Waters: From Theory to Practice, St Petersburg, November 01, 1996.26 (1996): 26 37 [10] M Soutter, A Mermoud, A Musy “ Infénierie des eaux et du sol Processus et aménagements”, Presses polytechniques et universitaires romandes 2007, p 294 [11] B J Dewals, S Detrembleur, P Archambeau, S Erpicum, J Ernst, M Pirotton “Caractérisation micro-échelle du risque d’inondation: modélisation hydraulique détaillée et quantification des impacts socio-économiques”, La Houille Blanche, N°2n 2011, pp 28-34 [12] Mike Powered by DHI “MIKE 1D DHI Simulation Engine for 1D river and urban modelling, Référence Manual”, p 334, [13] S Patro, C Chatterjee, S Mohanty, R Singh, N S Raghuwanshi, “Flood Inundation Modeling using MIKE FLOOD and Remote Sensing Data” J Indian Soc Remote Sens March 2009 37:107–118 [14] W Bouchenafa, A Lefevre, “Modélisation des écoulements mélangés avec des polymères dans une rivière pour la gestion des risques d’inondation t” International Journal of Innovation and Applied Studies ISSN 2028-9324 vol 28 No Dec 2019, pp 10-17 [15] L Timbre, P Willems, J Berlamont, “Validation of a quasi-2D hydrodynamic river flood model using historical and ERSSAR derived flood maps”, XXXI IAHR CONGRESS, September 11~16, 2005, Seoul, Korea, pp 137-147 developed was calibrated on the results obtained for another river and it requires a final validation step during our next trial in Blumenau river Numerical modeling of river flows can be used to assess the impact of river flood risk Modeling can also be used to test the effectiveness of different flood risk solutions in more detail [15] Any type of modeling can be a powerful tool to help decision-makers understand flood risk In our case study, the hydraulic modeling showed interest in the drag reduction method to avoid the overflow of the banks in a major flood event However, model results need to be validated against measured data A measurement campaign on Itajai is in preparation to better assess the effectiveness of the drag reduction technique by adding polymers and thus validate the numerical model ACKNOWLEDGMENT This project will mobilize more than ten people during the next measurement campaigns The modeling work was done in partnership with the company AXCHEM Brazil The authors thank AXCHEM represented by Armin, for the data needed for the Blumenau river REFERENCES [1] G Merkuryeva, M Kornevs, “Water Flow Forecasting and River Simulation for Flood Risk Analysis”, Information Technology and Management Science, doi: 10.2478/itms2013-0006, pp 42-46, 2013 [2] Z W Kundzewicz, D L T Hegger, P Matczak, and P P J Driessen, “Water Flow Forecasting and River Simulation for Flood Risk Analysis”, National Academy of Sciences, vol 115, No 49, 12321-12325, December 2018 [3] Peter P J Driessen, Dries L T Hegger, Zbigniew W Kundzewicz, Helena F M W van Rijswick, Ann Crabbé, Corinne Larrue, Piotr Matczak, Maria Pettersson, Sally Priest, Cathy Suykens, Gerrit Thomas Raadgever and Mark Wiering “Governance Strategies for Improving Flood Resilience in the Face of Climate Change”, Water MDPI, vol 10, No 1595, 2018 [4] P Driessen, D Hegger, M H N Bakker, H Rijswick and Z Kundzewicz,, “Toward more resilient flood risk governance”, Ecology and Society, 21(4): 53, 2016 494 Proceedings of 2022 International Conference on Green Technology and Sustainable Development (GTSD) July 29-30, 2022 - Nha Trang City, Vietnam th HCMUTE-Vietnam, NTU-Vietnam, LHU-Vietnam, HCMC DOST-Vietnam, RMUTL-Thailand, NPU-Taiwan, KSU-Taiwan VIETNAM NATIONAL UNIVERSITY – HO CHI MINH CITY PRESS E-mail: vnuhp@vnuhcm.edu.vn Website: www.vnuhcmpress.edu.vn Headquarters: Representative office: Room 501, VNU-HCM Headquarter, Linh Block K, University of Social Sciences and Trung Ward, Thu Duc District, HCMC Humanities, 10-12 Dinh Tien Hoang Street, Ben Nghe Ward, District 1, HCMC Phone: 028 62726361 Phone: 028 62726390 Publication Director Dr DO VAN BIEN Editor SIN KE DUYEN Proofreader NHU NGOC Book Cover Designer CHAU NGOC THIN, HCMUTE Associate Partner of Organising Manuscript and Responsible for Copyright HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY AND EDUCATION (HCMUTE) 1st Edition Quantity: 200 copies, Size: 19 x 27 cm Registration Number of Publication Plan: 1942023/CXBIPH/1-02/ĐHQGTPHCM Publication Decision Number 25/QĐ-NXB by VNU-HCM Press issued on on March 15, 2023 Printed at: Hung Phu Printing & Packaging Co., Ltd Address: 162A/1, KP1A, An Phu ward, Thuan An city, Binh Duong province Legal deposit in 2022 ISBN: 978-604-73-9622-1 Copyright of works has been protected by Publication Law and Vietnam Intellectual Property Law All forms of publication, copying and distribution of content are strictly prohibited without the consent of the author and the Publisher PROTECT COPYRIGHT TOGETHER FOR GOOD BOOK Proceedingsof20226thInternationalConference onGreenTechnologyandSustainableDevelopment (GTSD) Co-organized by: In cooperation with: Sponsored by: Ho Chi Minh City University of Technology and Education (HCMUTE) Add: 01 Vo Van Ngan Str., Linh Chieu Ward, Thu Duc City, Ho Chi Minh City, Vietnam Website: www.hcmute.edu.vn Email: oia@hcmute.edu.vn - khcn@hcmute.edu.vn