سنتز، شناسایی و خواص پلی‌آمیدهای آروماتیک نوین جاذب UV

نوع مقاله: پژوهشی

نویسندگان

تهران، پژوهشگاه پلیمر و پتروشیمی ایران، پژوهشکده علوم پلیمر، گروه پلی‌یورتان و مواد پیشرفته، صندوق پستی112-14975

چکیده

فرضیه: پلی‌آمیدهای آروماتیک دسته مهمی از پلیمرهای کارآمد و مقاوم گرمایی به‌شمار می‌آیند. مهم‌ترین مسئله در به‌کارگیری این پلیمرها مشکل‌بودن فراورش است که از دمای ذوب و دمای انتقال شیشه‌ای زیاد و ماهیت حل‌نا‌پذیری آن‌ها در اغلب حلال‌های آلی بی‌پروتون ناشی می‌شود. مشکل اصلی پلیمرهای مقاوم گرمایی، حفظ پایداری گرمایی و هم‌زمان افزایش حل‌پذیری آن‌هاست که با طراحی و سنتز مونومرهای جدید می‌توان بر آن غلبه کرد.
روش‌ها: ابتدا، بیس(4-اکسی بنزوﺋیک اسید)-5،1-آنتراکینون (DA1) و بیس(3-اکسی بنزوﺋیک اسید)-5،1-آنتراکینون (DA2) به‌ترتیب از راه واکنش‌های جانشینی هسته‌دوست 4-هیدروکسی بنزوئیک اسید و 3-هیدروکسی بنزوئیک اسید با 5،1- دی‌کلروآنتراکینون سنتز شدند. در مرحله بعد، روش Yamazaki برای سنتز پلی‌آمیدهای نوین از واکنش پلیمرشدن ‌تراکمی دی‌اسیدهای به‌دست‌آمده با دی‌آمین‌های آروماتیک متفاوت از جمله اکسی دی‌آنیلین (ODA)، پارافنیلن دی‌آمین (PPDA)، 6،2-دی‌آمینوپیریدین (DAP)، 5،1-‌دی‌آمینونفتالین (DAN) و دی‌آمینودی‌فنیل متان (DADPM) در مجاورت تری‌فنیل‌فسفیت (TPP) و پیریدین به‌عنوان معرف فعال‌کننده و N-متیل-2-پیرولیدون به‌عنوان حلال به‌کار گرفته شد.
یافته‌ها: ساختار مونومرها و پلیمرهای تهیه‌شده با روش‌های مختلف طیف‌نمایی شناسایی شد. خواص فیزیکی و گرمایی پلیمرهای جدید نظیر پایداری و رفتار گرمایی، حل‌پذیری، گرانروی و جذب فرابنفش مطالعه و رابطه ساختار-خواص آن‌ها بررسی شد. پلیمرهای تهیه‌شده در محدوده 370-344 نانومتر جذب UV نشان دادند. واردکردن ترکیب حجیم و آروماتیک آنتراکینونی به زنجیر اصلی پلیمر موجب شد تا در مجموع پلیمرها از پایداری گرمایی زیاد و حل‌پذیری بهبودیافته‌ای در حلال‌های قطبی بی‌پروتون برخوردار باشند.

کلیدواژه‌ها


عنوان مقاله [English]

Synthesis, Characterization, and Properties of Novel Aromatic UV Absorber Polyamides

نویسندگان [English]

  • Samal Babanzadeh
  • Shahram Mehdipour–Ataei
Department of Polymer Science, Faculty of Polyurethane and Advanced materials, Iran Polymer and Petrochemical Institute, P.O. Box 14975-112,Tehran, Iran
چکیده [English]

Hypothesis: Aromatic polyamides are well known as a main group of high performance and heat-resistant polymers. One of the drawbacks to utilize these polymers is the difficulty in processing due to their insoluble nature in aprotic organic solvents in addition to their high melting point or glass transition temperature. One way of overcoming the main problem of heat-resistant polymers - i.e., enhancing solubility without too much scarifying of the thermal stability is designing new monomers.
Methods: Firstly, bis(4-oxybenzoic acid)-1,5-anthraquinone (DA1) and bis(3-oxybenzoic acid)-1,5-anthraquinone (DA2) were prepared through aromatic nucleophilic substitution reaction of 4-hydroxybenzoic acid and 3-hydroxybenzoic acid with 1,5-dichloro anthraquinone, respectively. In the next step, the Yamazaki method was applied for synthesis of novel polyamides by polycondensation reaction of the obtained new diacids with commercial aromatic diamines such as oxydianiline (ODA), p-phenylene diamine (PPDA), 2,6-diaminopyridine (DAP), and diaminodiphenyl methane (DADPM) in presence of triphenylphosphite and pyridine as the activating agents and N-methyl-2-pyrolidone (NMP) as a solvent.
Findings: The structures of prepared novel monomers and polymers were characterized using different spectroscopy methods. The thermal and physical properties of novel polymers such as thermal stability and behavior, solubility, viscosity and ultra violet absorption were studied and the structure-property relationship of these polymers was investigated. The prepared polymers showed defined UV-Vis absorption bands at the range of 344-370 nm. Inclusion of an aromatic and bulky anthraquinone unit to the main chain of polymers led to high thermal stability while their solubility was improved in polar aprotic solvents.

کلیدواژه‌ها [English]

  • aromatic polyamide
  • polycondensation
  • thermal stability
  • solubility
  • UV absorber
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