Probing the dependence of the properties of cellulose acetates and their films on the degree of biopolymer substitution: Use of solvatochromic indicators and thermal analysis

Cellulose

Volumn 17, Issue 5, 2010, Pages 937-951

  Fidale, Ludmila C ^a   Ißbrücker, Constance ^b   Silva, Priscilla L ^a   Lucheti, Camila M ^a   Heinze, Thomas ^b   El Seoud, Omar A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Cellulose acetates, acidity, basicity, dipolarity of; Cellulose acetates, films of; Cellulose acetates, thermal properties of; Cellulose esters, solvatochromic parameters of; Solvatochromic indicators

Indexed keywords

CELLULOSE ACETATES; CELLULOSE ACETATES, ACIDITY, BASICITY, DIPOLARITY OF; CELLULOSE ESTERS, SOLVATOCHROMIC PARAMETERS OF; CELLULOSE TRIACETATE; DEGREE OF SUBSTITUTION; DSC AND TGA; ESTER GROUPS; ETHYL ACETATES; HYDROGEN BONDINGS; IR MEASUREMENTS; MODEL SYSTEM; N ,N-DIMETHYLANILINE; NITROANILINES; NON-LINEAR; PREFERENTIAL SOLVATION; PYRIDINIUM; SOLVATOCHROMIC; SOLVATOCHROMIC PARAMETERS; SOLVATOCHROMIC PROBES; THERMAL ANALYSIS; THERMAL PROPERTIES;

BINARY MIXTURES; CELLULOSE; DATA PROCESSING; ESTERIFICATION; ESTERS; ETHANOL; HYDROGEN BONDS; INFRARED IMAGING; THERMOANALYSIS; THERMODYNAMIC PROPERTIES;

CELLULOSE FILMS;

ACIDITY; CELLULOSE; CELLULOSE ACETATE; CELLULOSE ESTERS; DATA PROCESSING; ESTERIFICATION; HYDROGEN BONDS; THERMAL ANALYSIS; THERMAL PROPERTIES; THIN FILMS;

EID: 77956872053     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-010-9438-2     Document Type: Article

References (72)

1. Abraham MH, Grellier PL, Abboud J-L, Doherty RM, Taft RW (1988) Solvent effects in organic chemistry-recent developments. Can J Chem 66: 2673-2686.
2. Arici E, Greiner A, Hou H, Reuning A, Wendorff JH (2000) Optical properties of guest host systems based on cellulose derivatives. Macromol Chem Phys 201: 2083-2090.
3. Armarego WFL, Chai CLL (2009) Purification of laboratory chemicals. Elsevier, New York.
4. ASTM D1795-94 (2001) Standard test methods for intrinsics viscosity of cellulose.
5. ASTM D817-96 (2002) Standard test methods of testing cellulose acetate.
6. Bastos EL, Silva PL, El Seoud OA (2006) Thermosolvatochromism of betaine dyes revisited: theoretical calculations of the concentrations of alcohol-water hydrogen-bonded species and application to solvation in aqueous alcohols. J Phys Chem A 110: 10287-10295.
7. Braud HS, Araújo AM, Santos DB, Assunção RMN, Meireles CS, Cerqueira DA, Filho GR, Ribeiro CA, Messadeq Y, Ribeiro SJL (2008) Thermal behavior of cellulose acetate produced from homogeneous acetylation of bacterial cellulose. Thermocchim Acta 471: 61-69.
8. Braun S, Kalinowski HO, Berger S (2004) 200 and more basic NMR experiments. Wiley-VCH, Weinheim, p 128.
9. Carollo P (2004) Cellulose acetates: properties and applications. Wiley-VCH, Weinheim, p 335.
10. Diamantoglou M, Lemke H, Vienken J (1994) Cellulose esters as membrane materials for hemodialysis. Int J Artif Organs 17: 385-391.
11. Diamantoglou M, Platz J, Vienken J (1999) Cellulose carbamates and derivatives as hemocompatible membrane materials for hemodialysis. Artif Organs 23: 15-22.
12. El Seoud OA (2007) Solvation in pure and mixed solvents: some recent developments. Pure Appl Chem 79: 1135-1151.
13. El Seoud OA (2009) Understanding solvation. Pure Appl Chem 81: 697-707.
14. El Seoud OA, Heinze T (2005) Organic esters of cellulose: new perspectives for old polymers. Springer, Berlin, pp 103-149.
15. El Seoud OA, Siviero F (2006) Kinetics of the pH-independent hydrolyses of 4-nitrophenyl chloroformate and 4-nitrophenyl heptafluorobutyrate in water-acetonitrile mixtures: consequences of solvent composition and ester hydrophobicity. J Phys Org Chem 19: 793-802.
16. El Seoud OA, El Seoud MI, Farah JPS (1997) Kinetics of the pH-independent hydrolysis of bis(2, 4-dinitrophenyl) carbonate in acetonitrile-water mixtures: Effects of the structure of the solvent. J Org Chem 62: 5928-5933.
17. Fidale LC, Ruiz N, Heinze T, El Seoud OA (2008) Cellulose swelling by aprotic and protic solvents: what are the similarities and differences? Macromol Chem Phys 209: 1240-1254.
18. Fischer K, Spange S (2000) Empirical surface polarity parameters for native polysaccharides. Macromol Chem Phys 201: 1922-1929.
19. Fischer K, Spange S, Fischer S, Bellmann C, Adams J (2002) Probing the surface polarity of native celluloses using genuine solvatochromic dyes. Cellulose 9: 31-40.
20. Fischer K, Prause S, Spange S, Cichos F, Borczkyskowski C (2003a) Surface polarity of cellulose derivates observed by coumarin 151 and 153 as solvatochromic and fluorochromic probes. J Polym Sci B 41: 1210-1218.
21. Fischer K, Heinze T, Spange S (2003b) Probing the polarity of various cellulose derivatives with genuine solvatochromic indicators. Macromol Chem Phys 204: 1315-1322.
22. Glasser WG (1995) Novel cellulose derivatives. III. Thermal analysis of mixed esters with butyric and hexanoic acid. J Polym Sci Part B: Polym Phys 33: 2045-2054.
23. Greiner H, Hou A, Reuning A, Thomas JH, Wendorff S, Zimmermann Y (2003) Synthesis and opto-electronic properties of cholesteric cellulose esters. Cellulose 10: 37-52.
24. Heinze T, Schaller J (2000) New water soluble cellulose esters synthesized by an effective acylation procedure. Macromol Chem Phys 201: 1214-1218.
25. Heinze T, Rahn K, Berghmans H (1996) Thermal studies on homogeneously synthesized cellulose p-toluenesulfonates. J Appl Polym Sci 60: 1891-1900.
26. Israelachvili J (1991) Intermolecular and surface forces. Academic Press, San Diego.
27. Jandura P, Riedl B, Kokta V (2000) Thermal degradation behavior of cellulose fibers partially esterified with some long chain organic acids. Polym Degrad Stab 70: 387-394.
28. Kamide K, Saito M (1985) Thermal analysis of cellulose acetate solids with total degrees of substitution of 0. 49, 1. 75, 2. 46, and 2. 92. Polym J 17: 919-928.
29. Kamide K, Okajima K, Saito M (1981) Nuclear magnetic resonance study of thermodynamic interaction between cellulose acetate and solvent. Polym J 13: 115-125.
30. Kamide K, Saito M, Miyazaki Y (1993) Molecular weight determination [in polymer characterization]. Polym Charact, 115-144.
31. Kamlet MJ, Abboud JLM, Taft RW (1981) An examination of linear solvatation energy relationships. Prog Phys Org Chem 13: 485.
32. T(33), a solvatochromic polarity and micellar probe for neutral aqueous solutions. Chem Phys Lipids 50: 51-56.
33. Kesting RE, Ditter JF, Jackson KF, Murray AS (1979) DRY-RO membranes from cellulose acetate carbamates. J Appl Polym Sci 24: 1439-1450.
34. Khristenko IV, Kholin YV, Mchedlov-Petrossyan NO, Reichardt C, Zaitsev VN (2006) Probing of chemically modified silica surfaces by solvatochromic pyridinium N-phenolate betaine indicators. Colloid J 68: 511-517.
35. Kosaka PM, Kawano Y, El Seoud OA, Petri DFS (2007) Catalytic activity of lipase immobilized onto ultrathin films of cellulose esters. Langmuir 23: 12167-12173.
36. Kowsaka K, Okajima K, Kamide K (1988) Determination of the distribution of the substituent group in cellulose acetate by full assignment of all carbonyl carbon peaks of carbon-13 (proton-decoupled) NMR spectra. Polymer J 20: 827-836.
37. Lagalante AF, Spadi M, Bruno TJ (2000) Kamlet-Taft solvatochromic parameters of eight alkanolamines. J Chem Eng Data 45: 382-385.
38. Laurence C, Nicolet P, Dalati MT, Abboud J-LM, Notario R (1994) The empirical treatment of solvent-solute interactions: 15 years of pi*. J Phys Chem 98: 5807-5816.
39. Macquarrie DJ, Tavener SJ, Gray GW, Heath PA, Rafelt JS, Saulzet SI, Hardy JJE, Clark JH, Sutra P, Brunel D, Renzo F, Fajula F (1999) The use of Reichardt's dye as an indicator of surface polarity. New J Chem 23: 725-731.
40. Martins CT, Lima MS, El Seoud OA (2005) A novel, convenient, quinoline-based merocyanine dye: probing solvation in pure and mixed solvents and in the interfacial region of an anionic micelle. J Phys Org Chem 18: 1072-1785.
41. Matsuguchi M, Sadaoka Y, Mizuguchi H, Umeda K, Sakai Y (1997) Solvatochromic study of water sorption in polymer films. J Appl Polym Sci 63: 1681-1691.
42. Matsuguchi M, Umeda S, Sadaoka Y, Sakai Y (1998) Characterization of polymers for a capacitive-type humidity sensor based on water sorption behavior. Sens Actuators B 49: 179-185.
43. Matsuura T, Sourirajan S (1972) Physicochemical criteria for reverse osmosis separation of aldehydes, ketones, ethers, esters, and amines in aqueous solutions using porous cellulose acetate membranes. J Appl Polym Sci 16: 1663-1686.
44. Nada AMA, Hassan ML (2000) Thermal behavior of cellulose and some cellulose derivatives. Polym Degrad Stab 67: 111-115.
45. Necula AM, Olaru N, Olaru L, Homocianu M, Ioan S (2010) Influence of the substitution degrees on the optical properties of cellulose acetates. J Appl Polym Sci 115: 1751-1757.
46. Osterby BR, McKelvey RD (1996) Convergent synthesis of betaine-30, a solvatochromic dye: An advanced undergraduate project and demonstration. J Chem Educ 73: 260.
47. Patel KS, Patel KC, Patel RD (1970) Pyrolysis of cellulose and its derivatives. Makromol Chem 132: 7-22.
48. Paul SA, Piasta D, Spange S, Pothan LA, Thoma S, Bellmann C (2008) Solvatochromic and electrokinetic studies of banana fibrils prepared from steam-exploded banana fiber. Biomacromolecules 9: 1802-1810.
49. Pothan LA, Zimmermann Y, Thomas S, Spange S (2000) Determination of polarity parameters of chemically modified cellulose fibers by means of the solvatochromic technique. J Polym Sci B 38: 2546-2553.
50. Puleo AC, Paul DR, Kelley SS (1989) The effect of degree of acetylation on gas sorption and transport behavior in cellulose acetate. J Membrane Sci 47: 301-332.
51. Regiani AM, Frollini E, Marson GA, Arantes GM, El Seoud OA (1999) Some aspects of acylation of cellulose under homogeneous solution conditions. J Polym Sci A 37: 1357-1363.
52. Reichardt C (2003) Solvents and solvent effects in organic chemistry, 3rd edn. Wiley-VCH, Weinheim, pp 2, 329, 389.
53. Reichardt C (2004) Pyridinium N-phenolate betaine dyes as empirical indicators of solvent polarity: some new findings. Pure Appl Chem 76: 1903-1919.
54. Reichardt C (2008) Pyridinium-N-phenolate betaine dyes as empirical indicators of solvent polarity: Some new findings. Pure Appl Chem 80: 1415-1432.
55. Rustemeyer P (2004) Cellulose acetates: properties and applications. Wiley-VCH, Weinheim, p 267.
56. Sato BM, Oliveira CG, Martins CT, El Seoud OA (2010) Thermo-solvatochromism in binary mixtures of water and ionic liquids: on the relative importance of solvophobic interactions. Phys Chem Chem Phys 12: 1764-1771.
57. Schwenker RF, Beck LR (1960) The differential thermal analysis of textile and other high polymeric materials. Text Res J 30: 624-626.
58. Scott RPW (2000) The thermodynamic properties of methanol-water association and its effect on solute retention in liquid chromatography. Analyst 125: 1543-1547.
59. Sealey JE, Samaranayake G, Todd JG, Glasser WG (1996) Novel cellulose derivatives. IV. Preparation and thermal analysis of waxy esters of cellulose. J Polym Sci Part B: Polym Phys 34: 1613-1620.
60. Spange S, Heinze T, Klemm D (1992) On the polarity and donor-acceptor-properties of polysaccharides. Polym Bull 28: 697-702.
61. Spange S, Vilsmeier E, Zimmermann Y (2000) Probing the surface polarity of various silicas and other moderately strong solid acids by means of different genuine solvatochromic dyes. J Phys Chem B 104: 6417-6428.
62. Spange S, Fischer K, Prause S, Heinze T (2003) Empirical polarity parameters of celluloses and related materials. Cellulose 10: 201-212.
63. Spange S, Prause S, Vilsmeier E, Thiel WR (2005) Probing surface basicity of solid acids with an aminobenzodifurandione dye as the solvatochromic probe. J Phys Chem B 109: 7280-7289.
64. Stana-Kleinschek K, Strnad S, Ribitsch V (1999) Surface characterization and adsorption abilities of cellulose fibers. Polym Eng Sci 39: 1412-1424.
65. Suppan P, Ghoneim N (1997) Solvatochromism. The Royal Society of Chemistry, Cambridge, p 21.
66. Tada EB, Novaki LP, El Seoud OA (2000) Solvatochromism in pure and binary solvent mixtures: effects of the molecular structure of the zwitterionic probe. J Phys Org Chem 13: 679-687.
67. Takahashi A, Kawaharada T, Kato T (1979) Melting temperature of thermally reversible gel. V. heat of fusion of cellulose triacetate and the melting of dellulose diacetate-benzyl alcohol gel. Polym J 11: 671-675.
68. Toufik J, Carreno M, Josefowicz M, Labarre D (1995) Activation of the complement system by polysaccharidic surfaces bearing carboxymethyl, carboxymethylbenzyl-amide and carboxymethylbenzylamide sulphonate groups. Biomaterials 16: 993-1002.
69. Walther D (1974) Polarity of organic solvents and film-forming polymers by solvatochromism of 1, 2-diimine complexes of molybdenum (0). J Prakt Chem 316: 604-614.
70. Zimmermann Y, Anders S, Hofmann K, Spange S (2002) Influence of chemical solvent properties on the external and internal surface polarity of silica particles in slurry. Langmuir 18: 9578-9586.
71. Zollinger H (1991) Color Chemistry. Wiley-VCH, Weinheim, p 389.
72. Zugenmaier P (2004) Characteristics of cellulose acetates-4. 1 Characterization and physical properties of cellulose acetates. Macromol Symp 208: 81-166.