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

Document Type : Research Paper

Authors

Department of Polymer Science, Faculty of Polyurethane and Advanced materials, Iran Polymer and Petrochemical Institute, P.O. Box 14975-112,Tehran, Iran

Abstract

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.

Keywords

References

  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.

 

Iranian Journal of Polymer Science and Technology
Volume 32, Issue 4 - Serial Number 162
November and December 2019
Pages 327-337

Files

Share

How to cite

Statistics