Thermo- and pH-sensitivity of poly(N-vinylcaprolactam-co-maleic acid) in aqueous solution

Polymer Bulletin

Volumn 71, Issue 11, 2014, Pages 2863-2880

  Popescu, Irina ^a   Prisacaru, Anca Irina ^a   Suflet, Dana Mihaela ^a   Fundueanu, Gheorghe ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

Dicarboxylic polyelectrolyte; Hydrogen bonds; Maleic acid copolymers; Phase behavior; Stimuli sensitive polymers

Indexed keywords

CONTROLLED DRUG DELIVERY; HYDROGEN BONDS; LIGHT SCATTERING; MACROMOLECULES; PH SENSORS; PHASE BEHAVIOR; PHASE SEPARATION; POLYELECTROLYTES;

CLOUD POINT MEASUREMENTS; HYDROGEN BONDING INTERACTIONS; LOWER CRITICAL SOLUTION TEMPERATURE; MALEIC ACID COPOLYMERS; PH-SENSITIVE COPOLYMERS; POLYMER CONCENTRATIONS; STIMULI-SENSITIVE POLYMERS; VISCOMETRIC MEASUREMENTS;

SOLUTION MINING;

EID: 84919934524     PISSN: 01700839     EISSN: 14362449     Source Type: Journal    
DOI: 10.1007/s00289-014-1227-x     Document Type: Article

References (43)

1. Bawa P, Pillay V, Choonara YE, du Toit LC (2009) Stimuli-responsive polymers and their applications in drug delivery. Biomed Mater 4:022001–022015. doi:10.1088/1748-6041/4/2/02200
2. Buengera D, Topuza F, Groll J (2012) Hydrogels in sensing applications. Prog Polym Sci 37:1678–1719. doi:10.1016/j.progpolymsci.2012.09.001
3. Lau ACW, Wu C (1999) Thermally sensitive and biocompatible poly(N-vinylcaprolactam): synthesis and characterization of high molar mass linear chains. Macromolecules 32:581–584. doi:10.1021/ma980850n
4. Laukkanen A, Valtola L, Winnik FM, Tenhu H (2004) Formation of colloidally stable phase separated poly(N-vinylcaprolactam) in water: a study by dynamic light scattering, microcalorimetry, and pressure perturbation calorimetry. Macromolecules 37:2268–2274. doi:10.1021/ma035124l
5. Maeda Y, Nakamura T, Ikeda I (2002) Hydration and phase behavior of poly(N-vinylcaprolactam) and poly(N-vinylpyrrolidone) in water. Macromolecules 35:217–222. doi:10.1021/ma011034
6. Dubovik AS, Machaeva EE, Grinberg VY, Khokhlov AR (2005) Energetics of cooperative transitions of N-vinylcaprolactam polymers in aqueous solutions. Macromol Chem Phys 206:915–928. doi:10.1002/macp.200400554
7. Li W, Wu P (2014) On the thermodinamic phase behavior of poly(N-vinylcaprolactam) solution in the presence of different ionic liquids. Polym Chem 5:761–770. doi:10.1039/C3PY01104F
8. Shtanko NI, Lequieu W, Goethlas EJ, du Prez FE (2003) pH- and thermo-responsive properties of poly(N-vinylcaprolactam-co-acrylic acid) copolymers. Polym Int 52:1605–1610. doi:10.1002/pi.1347
9. Makhaeva EE, Tenhu H, Khokhlov AR (2002) Behavior of poly(N-vinylcaprolactam-co-methacrylic acid) macromolecules in aqueous solution: interplay between coulombic and hydrophobic interaction. Macromolecules 35:1870–1876. doi:10.1021/ma0105789
10. Okhapkin IM, Nasimova IR, Makhaeva EE, Khokhlov AR (2003) Effect of complexation of monomer units on pH- and temperature-sensitive properties of poly(N-vinylcaprolactam-co-methacrylic acid). Macromolecules 36:8130–8138. doi:10.1021/ma035114k
11. Cao Y, He W (2011) Functionalized biocompatible poly(N-vinyl-2-caprolactam) with pH-dependent lower critical solution temperature behaviors. Macromol Chem Phys 212:2503–2510. doi:10.1002/macp.201100414
12. Tang S, Cao Y, Goddard SC, He W (2014) Synthesis of 3-(tert-butoxycarbonylmethyl)-N-vinyl-2-caprolactam and homologous copolymerization toward biocompatible carboxylated poly(N-vinyl-2-caprolactam) responsive to pH and temperature. J Polym Sci Part A: Polym Chem 52:112–120. doi:10.1002/pola.26977
13. Maeda Y, Yamamoto H, Ikeda I (2001) Effects of ionization of incorporated imidazole groups on the phase transitions of poly(N-isopropylacrylamide), poly(N, N-diethylacrylamide), and poly(N-vinylcaprolactam) in water. Langmuir 17:6855–6859. doi:10.1021/la0106438
14. Shatalov GV, Verezhnikov VN, Plaksitskaya TV, Kuznetzov VA, Poyarkova TN, Yan’shina AV (2006) Synthesis of N, N-dimethylaminoethyl methacrylate copolymers with N-vinyl caprolactam and their complexing and flocculating behavior. Polym Sci Ser A 48:563–568. doi:10.1134/S0965545X06060022
15. Liang X, Kozlovskaya V, Chen Y, Zavgorodna O, Kharlampieva E (2012) Thermosensitive multilayer hydrogels of poly(N-vinylcaprolactam) as nanothin films and shaped capsules. Chem Mater 24:3707–3719. doi:10.1021/cm301657q
16. Pich A, Tessier A, Boyo V, Lu Y, Adler H-JP (2006) Synthesis and characterization of poly(vinylcaprolactam)-based microgels exhibiting temperature and pH-sensitive properties. Macromolecules 39:7701–7707. doi:10.1021/ma060985q
17. Schachschal S, Balaceanu A, Melian C, Demco DE, Eckert T, Richtering W, Pich A (2010) Polyampholyte microgels with anionic core and cationic shell. Macromolecules 43:4331–7339. doi:10.1021/ma100184h
18. Imaz A, Forcada J (2011) Synthesis strategies to incorporate acrylic acid into N-vinylcaprolactam-based microgels. J Polym Sci Part A: Polym Chem 49:3218–3227. doi:10.102/pola.24758
19. Rao KM, Mallikarjuna B, Rao KSVK, Siraj S, Rao KC, Subha MCS (2013) Novel thermo/pH sensitive nanogels composed from poly(N-vinylcaprolactam) for controlled release of an anticancer drug. Colloids Surf, B 102:891–897. doi:10.1016/j.colsurfb.2012.09.009
20. Ilavský M, Mamytbekov G, Bouchal K, Hanyková L (1999) Phase transition in swollen gels 27. Effect of negative charge concentration on swelling and mechanical behaviour of poly(N-vinylcaprolactam) gels. Polym Bull 43:109–116
21. Sauvage E, Amos DA, Antalek B, Schroeder KM, Tan JS, Plucktaveesah N (2004) Amphiphilic maleic acid-containing alternating copolymers—1. Dissociation behavior and compositions. J Polym Sci Pol Phys 42:3571–3583. doi:10.1002/polb.20202
22. Popescu I, Suflet DM, Pelin IM, Popa MI (2012) Influence of the comonomer on the dissociation of some alternating maleic acid copolymers. J Macromol Sci Part B-Phys 51:1–15. doi:10.1080/00222348.2011.609784
23. Kesim H, Rzaev ZMO, Dinçer S, Pisşkin E (2003) Functional bioengineering copolymers. II. Synthesis and characterization of amphiphilic poly(N-isopropyl acrylamide-co-maleic anhydride) and its macrobranched derivatives. Polymer 44:2897–2909. doi:10.1016/S0032-3861(03)00177-0
24. Weiss-Malik RA, Solis FJ, Vernon BL (2004) Independent control of lower critical solution temperature and swelling behavior with pH for poly(N-isopropylacrylamide-co-maleic acid. J Appl Polym Sci 94:2110–2116. doi:10.1002/app.21000
25. Popescu I, Suflet DM, Pelin IM, Chitanu GC (2011) Biomedical applications of maleic anhydride copolymers. Rev Roum Chim 56:173–188
26. Azori M (1988) Polymeric prodrugs systems based on poly(N-vinylpyrrolidone-alt-maleic anhydride). In: Migliaresi C, Nicolais L, Guisti P, Chiellini E (eds) Poymers in medicine III: proceedings of the Third International Conference on Polymers in Medicine, Porto Cervo, Italy, June 9–13, 1987. Elsevier Science Publishers B. V., Amsterdam, pp 189–199
27. Can HK, Doğan AL, Rzaev ZMO, Uner AH, Güner A (2006) Synthesis, characterization, and antitumor activity of poly(maleic anhydride-co-vinyl acetate-co-acrylic acid). J Appl Polym Sci 100:3425–3432. doi:10.1002/app.21834
28. Karakus G, Zengin HB, Polat ZA, Yenidunya AF, Aydin S (2013) Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation. Polym Bull 70:1591–1612. doi:10.1007/s00289-012-0860-5
29. Boghina C (1977) Copolymerization of N-vinyl-ε-caprolactam with maleic anhydride. Makromol Chem 178:1039–1047
30. Güven G, Rzaev ZMO (2008) Complex-radical copolymerization of N-vinyl pyrrolidone with isostructural analogs of maleic anhydride. Polym Bull 60:741–752. doi:10.1007/s00289-008-0909-7
31. Liu T, Chen J, Sugihara S, Maeda Y (2012) Study on hydration of poly(N-vinylcaprolactam) microgels by near-IR and mid-IR spectroscopy. Colloid Polym Sci 290:763–767. doi:10.1007/s00396-012-2621-2
32. Sun S, Wu P (2011) Infrared spectroscopic insight into hydration behavior of poly(N-vinylcaprolactam) in water. J Phys Chem B 115:11609–11618. doi:10.1021/jp2071056
33. Mȕller M, Kessler B, Richter S (2005) Preparatio of monomodal polyelectrolyte complex nanoparticles of PDADMAC/poly(maleic acid-alt-α-methylstyrene) by consecutive centrifugation. Langmuir 21:7044–7051. doi:10.1021/la050716d
34. Tripto E, Quinn JF, Caruso F (2005) Assembly of multilayer films from polyelectrolytes containing weak and strong acid moieties. Langmuir 21:8785–8792. doi:10.1021/la051197h
35. Spěváček J, Dybal J, Starovoytova L, Zhigunov A, Sedláková Z (2012) Temperature-induced phase separation and hydration in poly(N-vinylcaprolactam) aqueous solutions: a study by NMR and IR spectroscopy, SAXS, and quantum-chemical calculations. Soft Matter 8:6110–6119
36. Lozinsky VI, Simenel IA, Kulakova VK et al (2003) Synthesys and studies of N-vinylcaprolactam/N-vinylimidazole copolymers that exhibit the “proteinlike” behavior in aqueous media. Macromolecules 36:7308–7323. doi:10.1021/ma034456n
37. Balaceanu A, Demco DE, Moler M, Pich A (2011) Microgel heterogeneous morphology reflected in temperature-induced volume transition and 1H high-resolution transverse relaxation NMR. The case of poly(N-vinylcaprolactam)microgel. Macromolecules 44:2161–2169. doi:10.1021/ma200103y
38. Meeussen F, Nies E, Berghmans H, Verbrugghe S, Goethals E, du Prez F (2000) Phase behavior of poly(N-vinyl caprolactam) in water. Polymer 41:8597–8602. doi:10.1016/S0032-3861(00)00255-X
39. Delben F, Paoletti S, Prasso RD, Benegas JC (2006) Potentiometric titration of maleic acid copolymers in dilute aqueous solution: experimental results and theoretical interpretation. Macromol Chem Phys 207:2299–2310. doi:10.1002/macp.200600479
40. Reinhardt S, Steinert V, Werner K (1996) Investigations on the dissociation behavior of hydrolyzed alternating copolymers of maleic anhydride and propene-II. Viscometric behavior. Eur Polym J 32:939–942. doi:10.1016/0014-3057(96)00029-8
41. Kawaguchi S, Kitano T, Ito K (1991) Infrared and ultraviolet spectroscopic studies on intramolecular hydrogen bonding in an alternating copolymer of isobutylene and maleic acid. Macromolecules 24:3036–6030. doi:10.1021/ma00022a020
42. Hirose Y, Onodera M, Kawaguchi S, Ito K (1995) Monte Carlo simulation studies of conformational properties of polyelectrolytes with maleic acid units. Polym J 27:519–528
43. Yin X, Hoffman AS, Stayton P (2006) Poly(N-isopropylacrylamide-co-propylacrylic acid) copolymers that respond sharply to temperature and pH. Biomacromolecules 7:1381–1385. doi:10.1021/bm0507812