Synthesis and thermal behavior of novel poly(thiourea-amide)s derived from 1-(4-aminobenzoyl)-3-(3-aminophenyl) thiourea

High Performance Polymers

Volumn 23, Issue 6, 2011, Pages 424-433

  Kausar, Ayesha ^a,b   Zulfiqar, Sonia ^a,b   Ishaq, Muhammad ^a   Ahmad, Zahoor ^c   Sarwar, Muhammad Ilyas ^a  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^c KUWAIT UNIVERSITY   (Kuwait)

Author keywords

condensation; flame retardant; organosolubility; phenylthiourea; Poly(thiourea amide)s

Indexed keywords

ADIPOYL CHLORIDE; AMIDE SOLVENTS; AROMATIC POLYAMIDES; CRYSTALLINITIES; DIACID CHLORIDES; DIFUNCTIONAL; FTIR; INHERENT VISCOSITY; LIMITING OXYGEN INDEX; N ,N-DIMETHYLACETAMIDE; N-METHYLPYRROLIDONE; NMR TECHNIQUES; ORGANOSOLUBILITY; PHENYLTHIOUREA; POLY(THIOUREA-AMIDE)S; QUANTITATIVE YIELDS; STRUCTURAL ELUCIDATION; THERMAL BEHAVIORS; THERMAL STUDY; X-RAY DIFFRACTION STUDIES;

AROMATIC COMPOUNDS; AROMATIZATION; CHLORINE COMPOUNDS; CONDENSATION; DIMETHYL SULFOXIDE; DIMETHYLFORMAMIDE; GEL PERMEATION CHROMATOGRAPHY; GLASS TRANSITION; MONOMERS; POLYAMIDES; SIZE EXCLUSION CHROMATOGRAPHY; THERMOGRAVIMETRIC ANALYSIS; UREA; VISCOSITY; X RAY DIFFRACTION;

THIOUREAS;

EID: 80054059259     PISSN: 09540083     EISSN: 13616412     Source Type: Journal    
DOI: 10.1177/0954008311412405     Document Type: Article

References (44)

1. Liaw D-J, Chang F-C, Leung M-K, Chou M-Y, Muellen K. High thermal stability and rigid rod of novel organosoluble polyimides and polyamides based on bulky and noncoplanar naphthalene-biphenyldiamine. Macromolecules. 2005 ; 38 (9). 4024-4029 (Pubitemid 40672532)
2. Mikroyannidis JA. Aromatic polyamides and polyimides with benzoxazole or benzothiazole pendent groups prepared from 5-(2-Benzoxazole)- or 5-(2-Benzothiazole)-1,3-phenylenediamine. Macromolecules. 1995 ; 28 (15). 5177-5183
3. Ogata N. Novel synthetic methods of condensation polymers and their applications as new composite and optoelectronic materials. Pure Appl Chem. 1991 ; 63 (7). 951-960
4. Akutsu F, Inoki M, Sawano M, Kasashima Y, Naruchi K, Miura M. Synthesis and characterization of soluble aromatic polyamides derived from diamines with the 4,5-imidazolediyl structure. Polym J. 1998 ; 30 (10). 849-852 (Pubitemid 128606509)
5. Hsiao SH, Huang PC. Preparation and characterization of aromatic polyamides based on ether-sulfone-dicarboxylic acids. J Polym Sci Part A: Polym Chem. 1997 ; 35 (12). 2421-2429
6. Fomine S, Fomina L, Sanchez C, Ortiz A, Ogawa T. Polymers from coumarines. synthesis and characterization of polyamides derived from 6-{[3-(chloroformyl)phenyl]ethynyl}coumarin-3-carboxylic acid chloride. Polym J. 1997 ; 29 (1). 49-57 (Pubitemid 127610243)
7. Diakoumakos CD, Mikroyannidis JA. Modified polyisophthalamides bearing furamido pendant groups. Eur Polym J. 1995 ; 31 (8). 761-767
8. Liaw DJ, Liaw BY. Synthesis and characterization of new soluble polyamides containing ether and pendant cyclododecylidene groups. Polym Adv Technol. 1998 ; 9 (10-11). 740-745
9. Mohamed NA, Al-Dossary AOH. Structure-property relationships for novel wholly aromatic polyamide-hydrazides containing various proportions of para-phenylene and meta-phenylene units II. Thermal stability and degradation behaviour. Polym Degrad Stab. 2 03 ; 79 (1). 61-75 (Pubitemid 35353915)
10. Buhlmann P, Nishizawa S, Xiao KP, Umezawa Y. Strong hydrogen bond- mediated complexation of H2PO4- by neutral bis-thiourea hosts. Tetrahedron. 1997 ; 53 (5). 1647-1654 (Pubitemid 27055977)
11. Hari A, Miller BL. Rapid and efficient synthesis of 2-Amino-4H- benzothiazines. Org Lett. 2000 ; 2 (23). 3667-3670
12. Herr RJ, Kuhler JL, Meckler H, Opalka CJ. A convenient method for the preparation of primary and symmetrical N,N?-disubstituted thioureas. Synthesis. 2000 ; 2000 (11). 1569-1574
13. Kumamoto K, Misawa Y, Tokita S, Kubo Y, Kotsuki H. High-pressure-promoted condensation of isothiocyanates with aminopyridines: efficient synthesis of pyridine-thiourea conjugates as building blocks for hydrogen-bonding receptors. Tetrahed Lett. 2002 ; 43 (6). 1035-1038 (Pubitemid 34119248)
14. D'Cruz JD, Venkatachalam TK, Uckun FM. Novel thiourea compounds as dual-function microbicides. Biol Reprod. 2000 ; 63 (1). 196-205 (Pubitemid 30429403)
15. Wang C, Chen S, Zhao S. Inhibition effect of AC-treated mixed self-assembled film of phenylthiourea and 1-dodecanethiol on copper corrosion. J Electrochem Soc. 2004 ; 151 (1). B11 - B15
16. Shams El Din AM, El Hosary AA, Saleh RM, Abd El Kader JM. Pecularities in the behaviour of thiourea as corrosion inhibitor. Mater Corros. 1997 ; 28 (1). 26-31
17. Dehri I, Ozcan M. The effect of temperature on the corrosion of mild steel in acidic media in the presence of some sulphur-containing organic compounds. Mater Chem Phys. 2006 ; 98 (2). 316-323 (Pubitemid 44255663)
18. Sabaa MW, Mohamed RR, Yassin AA. Organic thermal stabilizers for rigid poly(vinyl chloride) VIII. Phenylurea and phenylthiourea derivatives. Polym Degrad Stab. 2003 ; 81 (1). 37-45
19. Yoganarasimhan SR, Sood RK. Semiconductivity of thiourea. Philosoph Mag. 1970 ; 22 (179). 1075-1080
20. Reetz MT, Kuhling KM, Deege A, Hinrichs H, Belder D. Super-high- throughput screening of enantioselective catalysts by using capillary array electrophoresis. Angew Chem Int Ed. 2000 ; 39 (21). 3891
21. Satchell DPN, Satchell RS The chemistry of sulfur-containing functional groups. Patai S Rappoport Z, ed. New York: Wiley ; 1993: 599.
22. Avalos M, Babiano R, Cintas P, Chavero MM, Higes FJ, Jimenez JL, et al. Reactions of 2-Amino-2-thiazolines with isocyanates and isothiocyanates. Chemical and computational studies on the regioselectivity, Adduct Rearrangement, and Mechanistic Pathways. J Org Chem. 2000 ; 65 (26). 8882-8892 (Pubitemid 32015142)
23. Kausar A, Zulfiqar S, Ahmed Z, Sarwar MI. Novel thermally stable poly(thiourea-amide-imide)s bearing C=S moieties and pyridine units in the backbone: Synthesis and properties. Polym Degrad Stab. 2010 ; 95 (12). 2611-2618
24. Kausar A, Zulfiqar S, Ahmed Z, Sarwar MI. Novel processable and heat resistant poly(phenylthiourea azomethine imide)s: Synthesis and characterization. Polym Degrad Stab. 2010 ; 95 (9). 1826-1833
25. Tobe Y, Sasaki S, Hirose K, Naemura K. Novel self-assembly of m-xylylene type dithioureas. Tetrahed Lett. 1997 ; 38 (27). 4791-4794 (Pubitemid 27277964)
26. Gunnlaugsson T Kruger PE, Jensen P, Tierney J, Ali HDP, Hussey GM. Colorimetric 'naked eye' sensing of anions in aqueous solution. J Org Chem. 2005 ; 70 (26). 10875-10878 (Pubitemid 43041101)
27. Yen YP, Ho KW. Development of colorimetric receptors for selective discrimination between isomeric dicarboxylate anions. Tetrahed Lett. 2006 ; 47 (41). 7357-7361
28. Ritter JA, Bipler JP.. Removal of mercury from waste water: Large scale performance of an ion exchange process. Water Sci Technol. 1992 ; 25 (3). 165-172
29. Zuo G, Muhammed M. Thiourea-based coordinating polymers: synthesis and bind ng to noble metals. React Polym. 1995 ; 24 (3). 165-181
30. Linton BR, Carr AJ, Orner BP, Hamilton AD. A versatile one-pot synthesis of 1,3-substituted guanidines from carbamoyl isothiocyanates. J Org Chem. 2000 ; 65 (5). 1566-1568 (Pubitemid 30145995)
31. Kumamoto K, Misawa Y, Tokita S, Kubob Y, Kotsukia H. High-pressure- promoted condensation of isothiocyanates with aminopyridines: efficient synthesis of pyridine-thiourea conjugates as building blocks for hydrogen-bonding receptors. Tetrahed Lett. 2002 ; 43 (6). 1035-1038 (Pubitemid 34119248)
32. Akito Y, Atsushi K, Takao S. Convenient reduction of nitrobenzenes to anilines using electrochemically generated nickel. J Org Chem. 1999 ; 64 (7). 2301-2303
33. Bae JW, Jin CY, Lee SH, Yoon COM, Yoon CM. A one-pot synthesis of N-alkylaminobenzenes from nitro aromatics: reduction followed by reductive amination using B10H14. Chem Commun. 2000 ; 19 (19). 1857-1858
34. Abiraj K, Gowda S, Gowda DC. Magnesium/hydrazinium monoformate: a new hydrogenation system for the selective reduction of nitro compounds. Synth React Inorg Met-Org Chem. 2002 ; 32 (8). 1409-1417
35. Jubert C, Knochel P. Preparation of new classes of aliphatic, allylic, and benzylic zinc and copper reagents by the insertion of zinc dust into organic halides, phosphates, and sulfonates. J Org Chem. 1992 ; 57 (20). 5425-5431
36. Srinivasa GR, Narendra Babu SN, Lakshmi C, Gowda DC. Conventional and microwave assisted hydrogenolysis using zinc and ammonium formate. Syn Comm. 2004 ; 34 (10). 1831-1837 (Pubitemid 38738392)
37. Kwolek SL, Morgan PW. Preparation of polyamides, polyurethanes, polysulfonamides and polyesters by low temperature solution polycondensation. J Polym Sci Part A: Polym Chem. 2003 ; 2 (6). 2693-2703
38. Mehdipour-Ataei S, Sarrafi Y, Hatami M, Akbarian-Feizi L. Poly sulfone ether amide amide)s as a new generation of soluble, thermally stable polymers. Eur Polym J. 2005 ; 41 (3). 491-499 (Pubitemid 40114556)
39. San-Jose N, Gomez-Valdemoro A, Garcia FC, Calderon V, Garcia JM. Novel aliphatic-aromatic poly(amide urea)s: Synthesis, characterization and application to the elimination of environmentally toxic heavy metal ion. React Funct Polym. 2008 ; 68 (9). 1337-1345
40. Mehdipour-Ataei S, Bahri-Laleh N. Preparation and characterization of thermally stable poly(amide-urea)s functionalized with anthraquinone chromophore. Polym Adv Technol. 2008 ; 19 (4). 291-298 (Pubitemid 351523527)
41. Mohanty AK, Das D, Panigrahi AK, Misra M. Synthesis and characterization of a novel polyamide: polycondensation of 2,5 diaminothiazole with terephthalic acid. Eur Polym J. 1998 ; 34 (12). 1889-1892 (Pubitemid 128416724)
42. Liu YL, Hsiue GH, Chiu YS, Jeng RJ, Perng LH. Phosphorus-containing epoxy for flame retardant. I. Synthesis, thermal, and flame-retardant properties. J Appl Polym Sci. 1996 ; 61 (4). 613-621
43. Bhuvana S, Madhumathi M, Sarojadevi M. Synthesis and characterization of processable heat resistant poly(amide-imides) for high temperature applications. Polym Bull. 2006 ; 57 (1). 61-72
44. Liu J, Gao Y, Wang F, Wu M. Preparation and characteristics of nonflammable polyimide materials. J Appl Polym Sci. 2000 ; 75 (3). 384-389