شیمى کاربردى روز

شیمى کاربردى روز

سنتز و شناسایی رزین‌های اپوکسی سیکلوآلیفاتیک دو و سه عاملی با معرفی روش اپوکسی‌دار کردن کاربردی

نوع مقاله : مقاله علمی پژوهشی

نویسندگان
1 گروه مهندسی پلیمر، پژوهشکده مهندسی کامپوزیت، مجتمع دانشگاهی مواد و فناوری های ساخت، دانشگاه صنعتی مالک اشتر، تهران، ایران
2 دانشکده شیمی، دانشگاه صنعتی شریف، تهران، ایران
چکیده
رزین‌های اپوکسی سیکلوآلیفاتیک، به‌دلیل وجود حلقه‌های شش‌کربنی با شکل فضایی منعطف در ساختار اصلی، قابلیت کاربرد در ساخت قطعات کامپوزیتی با کارایی بالا را داشته و مورد توجه صنایع کامپوزیت قرار گرفته‌اند. پژوهشگران با به روش‌های مختلفی موفق به سنتز این رزین شده‌ و به خواص شیمیایی، فیزیکی، مکانیکی، حرارتی و الکتریکی مقبولی رسیده‌اند ولی همواره با مشکلاتی در روش سنتز، فرایند تولید و مواد اولیه مواجه بوده‌اند و این امر کاربرد رزین‌های فوق را محدود نموده است. این پژوهش با هدف اصلاح روش‌های سنتز و استفاده از مونومرهای تجاری، سعی دارد گامی در جهت کاربردی‌کردن رزین‌های سیکلوآلیفاتیک بردارد. به‌این‌منظور، سنتز و شناسایی رزین اپوکسی سیکلوآلیفاتیک سه‌عاملی دی‌گلیسیدیل-5،4-اپوکسی-سیکلوهگزان-2،1-دی‌کربوکسیلات با استفاده از ماده اولیه‌ی تتراهیدروفتالیک‌انیدرید از چهار روش متفاوت انجام و مسیر بهینه ارائه شد. برای سنتز رزین اپوکسی سیکلوآلیفاتیک، از فرایندهای مختلفی مانند اپوکسی‌دارکردن کربوکسیلیک‌اسید با اپی‌کلروهیدرین، آلیل‌دارکردن کربوکسیلیک‌اسید با آلیل‌برماید، اپوکسی‌دار کردن مستقیم باند دوگانه شاخه‌ها و باند دوگانه سیکلوآلکن با ترکیب‌های متا-کلروپربنزوئیک‌اسید (m-CPBA) و تری‌کلروایزوسیانوریک‌اسید (TCCA) استفاده شد. اپوکسی‌دارکردن آلکن‌ها دارای چالش‌هایی مانند خلوص پایین، زمان واکنش طولانی، هزینه بالا و جداسازی دشوار است، به‌همین‌دلیل در این مقاله روش مناسب و کاربردی برای اپوکسی‌دارکردن آلکن‌ها با استفاده از TCCA ارائه شد. در این پژوهش دو رزین اپوکسی دو و سه‌عاملی سنتزشده و مراحل سنتز آنها با آنالیزهای FT-IR، 1H-NMR، 13C-NMR و وزن‌اکی‌والان گروه‌های اپوکسی (EEW) مورد بررسی و تایید قرار گرفت. وزن اکی‌والان رزین‌های سنتزشده دو و سه‌عاملی به‌ترتیب 152 و 108 (g/eq) بدست آمد و فرایند پخت آنها با استفاده از آنالیز DSC ارزیابی و تائید شد.
کلیدواژه‌ها
موضوعات

عنوان مقاله English

Synthesis and Characterization of Bi- and Tri-Functional Cycloaliphatic Epoxy Resins by Introducing the Applied Epoxidation Method

نویسندگان English

Mahsa Ghasri 1
Mehrzad Mortezaei 1
Hassan Fattahi 1
Maryam Tavakolizadeh 2
1 Department of Polymer Engineering, Faculty of Materials and Manufacturing Technologies, Malek-Ashtar University of Technology, Tehran, Iran
2 Department of Chemistry, Sharif University of Technology, Tehran, Iran
چکیده English

Cycloaliphatic epoxy resins, due to the presence of saturated six-carbon rings with a flexible space shape in the main structure, have the ability to be used in the manufacture of high-performance composite parts and have received the attention of composite industries. Researchers have succeeded in synthesizing this resin in various ways and have achieved acceptable chemical, physical, mechanical, thermal and electrical properties, but they have always faced problems in the synthesis method, production process and raw materials, and this limits the use of the above resins. With the aim of improving the synthesis methods and using commercial monomers, this research tries to take a step towards the application of cycloaliphatic epoxy resins. For this purpose, the synthesis and characterize tri-functional cycloaliphatic epoxy resin of diglycidyl-4,5-epoxy-cyclohexane-1,2-dicarboxylate (ECDAD) using raw material of tetrahydrophthalic anhydride was performed by four different methods and the optimal route was presented. For the synthesis of cycloaliphatic epoxy resin, the processes of epoxidation of carboxylic acid with epichlorohydrin, allylation of carboxylic acid with allyl bromide, direct epoxidation of double bond of branches and double bond of cycloalkene with compounds of 3-chloroperoxybenzoic acid (m-CPBA) and trichloroisocyanuric acid (TCCA) were used and different methods were compared. Generally, the epoxidation of alkenes has challenges such as low purity, long reaction time, high cost, and difficult separation, therefore, in this article, a suitable and practical method for the epoxidation of alkenes using TCCA was presented. In this research, two epoxy resins (bi-functional and tri-functional) were synthesized and their synthesis steps were investigated and confirmed by FT-IR, 1H-NMR, 13C-NMR analysis and the measurement of the epoxy equivalent weight (EEW). The EEW of the synthesized resins of bi- and tri-functional was 152 and 108 (g/eq), respectively, and their curing process was evaluated and confirmed using DSC analysis.

کلیدواژه‌ها English

Epoxy Resin
Cycloaliphatic
Synthesis
Bi- and Tri-Functional Epoxy
Epichlorohydrin
TCCA
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