Synthesis of soluble poly(amide-ether-imide-urea)s bearing amino acid moieties in the main chain under green media (ionic liquid)

Amino Acids

Volumn 40, Issue 2, 2011, Pages 487-492

  Mallakpour, Shadpour ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Chiral diamine; Green chemistry; Imidazolium ionic liquid; L Leucine; Optically active polymers; Polyurea

Indexed keywords

DIMETHYL SULFOXIDE; IONIC LIQUID; N,N DIMETHYLACETAMIDE; N,N DIMETHYLFORMAMIDE; POLY(AMIDE ETHER IMIDE UREA)DERIVATIVE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; INTERMETHOD COMPARISON; MOLECULAR WEIGHT; POLYMERIZATION; PRIORITY JOURNAL; SOLUBILITY; SOLVENT EFFECT; STRUCTURE ANALYSIS; THERMOGRAVIMETRY; THERMOSTABILITY; X RAY DIFFRACTION;

AMIDES; DIAMINES; ETHER, ETHYL; IMIDES; IONIC LIQUIDS; LEUCINE; POLYMERIZATION; POLYMERS; SOLUBILITY; UREA;

EID: 78751571313     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0660-x     Document Type: Article

References (35)

1. E Andrzejewska M Podgorska-Golubska I Stepniak M Andrzejewski 2009 Photoinitiated polymerization in ionic liquids: kinetics and viscosity effects Polymer 50 2040 2047 1:CAS:528:DC%2BD1MXksValtLo%3D 10.1016/j.polymer.2009.02. 034
2. Z Du T Qiu Q Zhou X Wang D Liu 2001 Synthesis and characterization of a novel kind of thermotropic liquid crystalline poly(urea-ester)s based on bis(4′-hydroxyphenyl)-tolyene-2, 4-diurea J Appl Polym Sci 82 577 583 1:CAS:528:DC%2BD3MXmtFamur4%3D 10.1002/app.1885 (Pubitemid 32827145)
3. F Gasparrini D Misiti R Rompietti C Villani 2005 New hybrid polymeric liquid chromatography chiral stationary phase prepared by surface-initiated polymerization J Chromatogr A 1064 25 38 1:CAS:528:DC%2BD2MXkslyguw%3D%3D 10.1016/j.chroma.2004.11.089 15729817 (Pubitemid 40126578)
4. K Hong S Park 2000 Preparation of polyurea microcapsules containing ovalbumin Mater Chem Phys 64 20 24 1:CAS:528:DC%2BD3cXht1KjurY%3D 10.1016/S0254-0584(99)00241-2 (Pubitemid 30556652)
5. SH Huang ZW Bai SR Li ZQ Pan 2007 Synthesis of polymer-type chiral stationary phases and their enantioseparation evaluation by high-performance liquid chromatography Chirality 19 129 140 1:CAS:528:DC%2BD2sXpsVyiug%3D%3D 10.1002/chir.20324 17117402 (Pubitemid 46122657)
6. Y Ikeuchi M Nakagawa M Yoshikawa H Yoshida S Sakurai 2009 Chiral polyamides consisting of N-α-benzoyl-l-glutamic acid as a diacid component J Polym Sci Part A Polym Chem 47 2530 2538 1:CAS:528:DC%2BD1MXltVyqtLo%3D 10.1002/pola.23335
7. SK Jewrajka E Yilgor I Yilgor JP Kennedy 2009 Polyisobutylene-based segmented polyureas. I. Synthesis of hydrolytically and oxidatively stable polyureas J Polym Sci Part A Polym Chem 47 38 48 1:CAS:528: DC%2BD1MXis1Ciug%3D%3D 10.1002/pola.23118
8. G Johnston-Hall JR Harjani PJ Scammells MJ Monteiro 2009 RAFT-mediated polymerization of styrene in readily biodegradable ionic liquids Macromolecules 42 1604 1609 1:CAS:528:DC%2BD1MXhs1Slt7w%3D 10.1021/ma802795j
9. P Kubisa 2009 Ionic liquids as solvents for polymerization processes-progress and challenges Prog Polym Sci 34 1333 1347 1:CAS:528:DC%2BD1MXhtlCntrnJ 10.1016/j.progpolymsci.2009.09.001
10. K Kurita M Masuda S Aibe K Kurakami S Ishii SI Nishimura 1994 Synthetic carbohydrate polymers containing trehalose residues in the main chain: preparation and characteristic properties Macromolecules 27 7544 7549 1:CAS:528:DyaK2cXntVWmsr8%3D 10.1021/ma00104a007
11. KP Lee SH Choi SY Kim TH Kim JJ Ryoo K Ohta JY Jin T Takeuchi C Fujimoto 2003 Comparison of monomeric and polymeric chiral stationary phases J Chromatogr A 987 111 118 1:CAS:528:DC%2BD3sXptl2jtw%3D%3D 10.1016/S0021-9673(02)01462-0 12613803 (Pubitemid 36140086)
12. SV Ley C Ramarao AL Lee N Ostergaard SC Smith IM Shirley 2003 Microencapsulation of osmium tetroxide in polyurea Org Lett 5 185 187 1:CAS:528:DC%2BD38XpslOms7Y%3D 10.1021/ol020225+ 12529136 (Pubitemid 37141216)
13. X Li D Chen 2008 Synthesis and characterization of aromatic/aliphatic co-polyureas J Appl Polym Sci 109 897 902 1:CAS:528:DC%2BD1cXmvFWhu7o%3D 10.1002/app.24913
14. J Lindholm T Forstedt 2005 Investigation of the adsorption behaviour of a chiral model compound on a tartardiamide-based network-polymeric chiral stationary phase J Chromatogr A 1095 50 59 1:CAS:528:DC%2BD2MXht1Srur%2FP 10.1016/j.chroma.2005.07.122 16275282 (Pubitemid 41566493)
15. Long TE, Hunt MO (1998) Solvent-free polymerization and processes: recent trend in the minimization of conventional organic solvents. ACS Symposium. doi: 10.1021/bk-0713.ch001
16. 13C-NMR spectroscopy: effect of polymerization procedures J Polym Sci Part A Polym Chem 34 2157 2161 1:CAS:528:DyaK28Xks1akur8%3D 10.1002/(SICI)1099-0518(199608)34:11<2157::AID- POLA8>3.0.CO;2-W
17. Mallakpour S, Khani M (2010) Construction of chiral polyesters from polycondensation of multifunctional monomer containing both flexible amino acid and rigid pendant groups with aromatic diols. Amino Acids. doi: 10.1007/s00726-010-0539-x
18. S Mallakpour M Kolahdoozan 2008 Microwave-accelerated preparation of aromatic polyamides containing phthalimide and S-valine pendant groups in ionic liquids Iran Polym J 17 531 539 1:CAS:528:DC%2BD1cXhtV2ltrvI
19. S Mallakpour Z Rafiee 2008 Application of microwave-assisted reactions in step-growth polymerization: a review Iran Polym J 17 907 935 1:CAS:528:DC%2BD1MXit1Cnsb4%3D
20. S Mallakpour Z Rafiee 2009 Microwave-induced synthesis of new optically active and soluble polyamides containing pendent 4-(2- phthalimidiylpropanoylamino)-benzoylamino-groups Amino Acids 37 665 672 1:CAS:528:DC%2BD1MXhtFyqt7nK 10.1007/s00726-008-0186-7 18836680
21. S Mallakpour H Seyedjamali 2008 Synthesis and characterization of novel organosoluble and optically active aromatic polyesters containing l-methionine and phthalimide pendent groups Amino Acids 34 531 538 1:CAS:528: DC%2BD1cXlsVOgsLw%3D 10.1007/s00726-007-0005-6 18060345
22. Mallakpour S, Seyedjamali (2010) Design and synthesis of novel organosoluble chiral poly(amide-ether-imide-urea) containing l-leucine moieties in the main chain. Colloid Polym Sci. doi: 10.1007/s00396-010-2202-1
23. S Mallakpour MH Shamoahammadi 2004 Microwave-promoted rapid synthesis of new optically active poly(amide imide)s derived from N,N′-(pyromellitoyl)- bis-l-isoleucine diacid chloride and aromatic diamines J Appl Polym Sci 92 951 959 1:CAS:528:DC%2BD2cXitVWls7Y%3D 10.1002/app.13720 (Pubitemid 38395245)
24. S Mallakpour A Zadehnazari 2010 Microwave irradiation as a versatile tool for increasing reaction rates and yields in synthesis of optically active polyamides containing flexible l-leucine amino acid Amino Acids 38 1369 1376 1:CAS:528:DC%2BC3cXlt1Omur4%3D 10.1007/s00726-009-0347-3 19756941
25. H Ni AD Skaja MD Soucek 2000 Acid-catalyzed moisture-curing polyurea/polysiloxane ceramer coatings Prog Org Coat 40 175 184 1:CAS:528:DC%2BD3cXoslSktLY%3D 10.1016/S0300-9440(00)00116-8 (Pubitemid 32071028)
26. CM Roland R Casalini 2007 Effect of hydrostatic pressure on the viscoelastic response of polyurea Polymer 48 5747 5752 1:CAS:528: DC%2BD2sXhtVSkurfI 10.1016/j.polymer.2007.07.017 (Pubitemid 47379367)
27. CM Roland JN Twigg Y Vu PH Mott 2007 High strain rate mechanical behavior of polyurea Polymer 48 574 578 1:CAS:528:DC%2BD2sXlsFGhtg%3D%3D 10.1016/j.polymer.2006.11.051 (Pubitemid 46038351)
28. H Sakai K Tanaka H Fukushima K Tsuchiya K Sakai T Kondo M Abe 2008 Preparation of polyurea capsules using electrocapillary emulsification Colloids Surf B Biointerfaces 66 287 290 1:CAS:528:DC%2BD1cXhtVyktL7K 10.1016/j.colsurfb.2008.07.009 18768303
29. SS Sarva S Deschanel MC Bouce W Chen 2007 Stress-strain behavior of a polyurea and a polyurethane from low to high strain rates Polymer 48 2208 2213 1:CAS:528:DC%2BD2sXjvVahtL8%3D 10.1016/j.polymer.2007.02.058 (Pubitemid 46483572)
30. V Sendijarevic A Sendijarevic I Sendijarevic RE Bailey D Pemberton K Reimann 2004 Hydrolytic stability of toluene diisocyanate and polymeric Methylenediphenyl diisocyanate based polyureas under environmental conditions Environ Sci Technol 38 1066 1072 1:CAS:528:DC%2BD2cXksFCnug%3D%3D 10.1021/es035072f 14998020
31. B Tamami H Yeganeh GA Koohmareh 2005 Synthesis and characterization of polyureas derived from 4-aryl-2, 6-bis(4-aminophenyl) pyridines and diisocyanates Iran Polym J 14 785 792 1:CAS:528:DC%2BD2MXht1GhurrN
32. XT Tao T Watanabe DC Zou S Shimoda H Sato S Miyata 1995 Polyurea with large positive birefringence for second harmonic generation Macromolecules 28 2637 2643 1:CAS:528:DyaK2MXks1GrtL0%3D 10.1021/ma00112a007
33. Y Yang Z Zhi X Yang L Lu X Wang 1998 Synthesis and characterization of novel polyurea-imides Eur Polym J 34 1893 1897 10.1016/S0014-3057(98)00037-8
34. ZD Zhai YP Shi T Wang 2005 Development and validation of HPLC methods for enantioseparation of mirtazapine enantiomers at analytical and semipreparative scale using polysaccharide chiral stationary phases Anal Chim Acta 550 123 129 1:CAS:528:DC%2BD2MXhtVSqs7vJ 10.1016/j.aca.2005.06.044 (Pubitemid 41317685)
35. Q Zhong X Han L He TE Beesey WS Trahanovsky DW Armstrong 2005 Chromatographic evaluation of poly (trans-1, 2-cyclohexanediyl-bis acrylamide) as a chiral stationary phase for HPLC J Chromatogr A 1066 55 70 1:CAS:528:DC%2BD2MXhslWltrY%3D 10.1016/j.chroma.2004.12.088 15794555 (Pubitemid 40283550)