سنتز، شناسایی و خواص پلی‌آمیدهای آروماتیک نوین جاذب UV

نوع مقاله: پژوهشی


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


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.


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
  1. Cassidy P.E., Thermally Stable Polymers, Synthesis and Properties, Marcel Dekker, NewYork, 2-7, 1980.
  2. Frazer A.H., High Temperature Resistant Polymers, Interscience, New York, 1804-1805, 1968.
  3. Yousefi A. and Salarian M., Effect of Polyamide 6 on Crystalline Structure of Polymer in PVDF-Nanoclay Nanocomposite, Iran. J. Polym. Sci. Technol. (Persian), 25, 41-51, 2012.
  4. Mutar M.A., A Study of Synthesis and Characterization of New Aromatic Poly(amide-imide)s, Ibn AL-Haitham J. Pure. Appl. Sci., 28, 73-87, 2017.
  5. Khademinejad S., Mehdipour-Ataei S., Ziaee F., and Abbasi F., Poly(ether ether sulfone amide)s as a New Category of Processable Heat-resistant Polymers, Des. Monomers Polym., 19, 553-559, 2016.
  6. Zhang J., Hai Y., Zuo Y., Jiang Q., Shi C., and Li W., Novel Diamine-modified Composite Nanofiltration Membranes with Chlorine Resistance Using Monomers of 1,2,4,5-Benzene tetracarbonyl Chloride and m-Phenylenediamine, J. Mater. Chem. A, 3, 8816-8824, 2015.
  7. Mehdipour-Ataei S., Babanzadeh S., and Abouzari-Lotf  E., Nicotinic-based Poly(amide-ether-imide)s: A New Category of Soluble, Heat-resistant, and Flame-retardant Polyimides, Des. Monomers Polym.,18, 451-459, 2015.
  8. Ebadi H. and Mehdipour-Ataei S., Heat-resistant, Pyridine-based Polyamides Containing Ether and Ester Units with Improved Solubility, Chinese J. Polym. Sci., 28, 29-37, 2010.
  9. Mehdipour-Ataei S. and Babanzadeh S., Synthesis, Characterization and Properties of Novel Polyamides Containing Ferrocene Unit and Flexible Spacers, Appl. Organ. Chem., 21, 360-367, 2007.
  10. Mehdipour-Ataei S., Malekimoghaddam R., and Nami M., Novel Pyridine-based Ether Ester Diamine and Resulting Thermally Stable Poly(ether ester amide)s, Eur. Polym. J., 40, 2523-2529, 2004.
  11. Ghaemy M., Nasab S.M.A., and Alizadeh R., Synthesis and Characterization of New Soluble Polyamides from an Unsymmetrical Diamine Bearing a Bulky Triaryl Pyridine Pendent Group, J. Appl. Polym. Sci.,116, 3725-3731, 2010.
  12. Ali M.A. and Kaneko T., Polyamide Syntheses, Encyclopedia of Polymeric Nanomaterials, Springer, 1750-1762, 2015.
  13. Nazari S. and Shabanian M., Novel Heterocyclic Semi-aromatic Polyamides: Synthesis and Characterization, Des. Monomers Polym.,17, 33-39, 2014.
  14. Mehdipour-Ataei S. and Gharehkhani E., Preparation of Novel Pyridine-based Poly(ether amide)s via Three Different Routes and Investigation of Their Properties, High Perform. Polym., 25, 778-789, 2013.
  15. Abbasi A. and Mehdipour-Ataei S., A New Category of Thermally Stable Poly(ether amide ether imide)s with Increased Solubility, Polym. Adv. Technol., 24, 881-887, 2013.
  16. Zhang G., Zhao T.P., Wang Y.L., Liu S.L., Long S.R., and Yang J., Synthesis and Characterization of Novel Polyamide Containing Ferrocene and Thio-Ether Units, J. Macromol. Sci., Part A: Pure Appl. Chem.,47, 291-301, 2010.
  17. More A.S., Pasale S.K., and Wadgaonkar P.P., Synthesis and Characterization of Polyamides Containing Pendant Pentadecyl Chains, Eur. Polym. J., 46, 557-567, 2010.
  18. Dixit B.C., Dixit R.B., and Desai D.J., Synthesis and Characterization of Novel Ion-exchange Resin Based on Polyimide Containing 8-hydroxyquinoline as a Pendent Groups, J. Polym. Res., 17, 481-488, 2010.
  19. Mehdipour-Ataei S., Bahri-Laleh N., Rabei A., and Saidi S., Structure-property Relationships of Soluble Poly(ester-urea)s Containing Naphthyl Groups, High Perform. Polym.,19, 283-295, 2007.
  20. Chen Y., Ke H., Zeng D., Zhang Y., Sun Y., and Cheng H., Superior Polymer Backbone with Poly(arylene ether) over Polyamide for Single Ion Conducting Polymer Electrolytes, J. Membr. Sci., 525, 349-358, 2017.
  21. Pérez-Francisco J., Herrera-Kao W., González-Díaz M., and Aguilar-Vega M., Santiago-García J., Assessment of Random Aromatic co-Polyamides Containing two Different Bulky Pendant Groups, J. Appl. Polym. Sci., 135, 45884-45898, 2018.
  22. Plaza-Lozano D., Comesaña-Gándara B., and Viuda M., New Aromatic Polyamides and Polyimides Having an Adamantane Bulky Group, Mater. Today Commun., 5, 23-31, 2015.
  23. Mehdipour-Ataei S. and Amirshaghaghi A., Preparation and Properties of New Thermally Stable Poly(ether imide amide)s, Polym. Int., 53, 1185-1190, 2004.
  24. Iwashita K., Suzuki R., Katoh H., Ohta Y., and Yokozawa T., Novel Photoresist Using Photodeprotectable N-Alkoxybenzyl Aromatic Polyamide, J. Photopolym. Sci. Technol., 31, 467-472, 2018.
  25. Mehdipour-Ataei S. and Ehsani S., Nicotinamide-based Poly(ether amide)s: A Novel Type of Soluble Thermally Stable Polyamides, Polym. Adv. Technol., 26, 1512-1518, 2015.
  26. Hsiao S.H., Peng  S.C., Kung Y.R., Leu C.M., and Lee T.M., Synthesis and Electro-optical Properties of Aromatic Polyamides and Polyimides Bearing Pendent 3,6-dimethoxycarbazole Units, Eur. Polym. J., 73, 50-64, 2015.
  27. Liou G.S. and Chang C.W., Highly Stable Anodic Electrochromic Aromatic Polyamides   Containing N,N,N’,N’-Tetraphenyl-p-Phenylenediamine Moieties: Synthesis, Electrochemical, and Electrochromic Properties, Macromolecules, 41, 1667-1674, 2008.
  28. Ghaemy M. and Khajeh S., Syntheisi and Characterization of Polyamides Derived from (4-(4-(2,6-diphenylpyridine-4el)phenoxy)phenyl)-3,5-diaminobezamide, Chinese J. Polym. Sci., 30, 82-92, 2012.
  29. Hsiao S.H. and Liao Y.C., Synthesis and Properties of Novel Organosoluble and Light-colored Poly(ester-amide)s and Poly(ester-imide)s with Triptycene Moiety, J. Polym. Res., 25, 52-65, 2018.
  30. Grabiec E., Kurcok M., and Ewa S.B, Poly(amide imides) and Poly(ether imides) Containing 1,3,4-Oxadiazole or Pyridine Rings: Characterizations and Optical Properties, J. Phys. Chem. A, 113, 1481-1488, 2009.
  31. Amininasab S.M., Esmaili S., Taghavi M., and Shami Z., Synthesis and Characterization of New Fluorinated Photoactive Polyamides Based on Xanthenes Pendant: Evaluation of Antibacterial and Heavy Metal Ions Removal Behavior, Int. J. Polym. Anal. Charact., 21, 686-696, 2016.
  32. Kung Y.C. and Hsiao S.H., Fluorescent and Electrochromic Polyamides with Pyrenylamine Chromophore, J. Mater. Chem., 20, 5481-5492, 2010.
  33. Hsiao S.H., Liao W.K., and Liou G.S., Synthesis and Electrochromism of Highly Organosoluble Polyamides and Polyimides with Bulky Trityl-Substituted Triphenylamine Units, Polymers, 9, 511-528, 2017.