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Structural Relaxation of Acetaminophen Glass

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Purpose

The aim is to determine the structural stability of acetaminophen glass with time and temperature change, and to examine the merits of adapting the structural relaxation models of the glassy state for pharmaceuticals.

Methods

Differential scanning calorimetry technique has been used to study the acetaminophen glass after keeping the samples for various periods at fixed temperatures and after keeping at various temperatures for fixed periods.

Results

A general formalism for thermodynamic changes during storage in a temperature fluctuating environment is given and the kinetics of the enthalpy and entropy decrease determined. At a fixed temperature, the decrease occurs according to a non-exponential kinetics. For the same storage time, but at different temperatures, the enthalpy and entropy decrease rises to a maximum value at a certain temperature and then declines. The peak appears at the temperature at which the internally equilibrated state of the sample is reached for a fixed storage time. The change in the normalized heat capacity during the heating of acetaminophen has been analysed in terms of a non-exponential, non-linear enthalpy relaxation model.

Conclusion

A single set of parameters that fit the data for unannealed acetaminophen glass does not fit the calorimetric data for annealed glass. Since acetaminophen molecules form intermolecular hydrogen-bonds in the crystal state and likely to form such bonds more easily in the disordered state, effect of such bonds on structural relaxation is likely to be significant.

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References

  1. B. C. Hancock G. Zografi (1997) ArticleTitleCharacteristics and significance of the amorphous state in pharmaceutical systems J. Pharm. Sci. 86 1–12 Occurrence Handle9002452 Occurrence Handle1:CAS:528:DyaK28XntlOqt7k%3D Occurrence Handle10.1021/js9601896

    Article  PubMed  CAS  Google Scholar 

  2. A. T. M. Serajuddin (1999) ArticleTitleSolid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs J. Pharm. Sci. 88 1058–1066 Occurrence Handle10514356 Occurrence Handle1:CAS:528:DyaK1MXltl2jtbk%3D Occurrence Handle10.1021/js980403l

    Article  PubMed  CAS  Google Scholar 

  3. C. Leuner J. Dressman (2000) ArticleTitleImproving drug solubility for oral delivery using solid dispersions Eur. J. Pharm. Biopharm. 50 47–60 Occurrence Handle10840192 Occurrence Handle1:CAS:528:DC%2BD3cXjslyju7c%3D Occurrence Handle10.1016/S0939-6411(00)00076-X

    Article  PubMed  CAS  Google Scholar 

  4. L. Yu (2001) ArticleTitleAmorphous pharmaceutical solids: preparation, characterization and stabilization Adv. Drug Del. Rev. 48 27–42 Occurrence Handle1:CAS:528:DC%2BD3MXivFejsrg%3D Occurrence Handle10.1016/S0169-409X(01)00098-9

    Article  CAS  Google Scholar 

  5. A. M. Kaushal P. Gupta A. K. Bansal (2004) ArticleTitleAmorphous drug delivery systems: molecular aspects, design and performance Crit. Rev. Ther. Drug Carr. Syst. 21 133–193 Occurrence Handle1:CAS:528:DC%2BD2cXlvFWksL0%3D Occurrence Handle10.1615/CritRevTherDrugCarrierSyst.v21.i3.10

    Article  CAS  Google Scholar 

  6. A. Paul (1982) Chemistry of Glasses Chapman and Hall New York

    Google Scholar 

  7. S. R. Elliott (1984) Physics of Amorphous Materials Longmans London

    Google Scholar 

  8. G. W. Scherer (1986) Relaxation in Glass and Composites Wiley New York

    Google Scholar 

  9. I. Gutzow J. Schmelzer (1995) The vitreous state: Thermodynamics, Structure, Rheology and Crystallization Springer Berlin Heidelberg New York

    Google Scholar 

  10. S. V. Nemilov (1995) Thermodynamics and Kinetic Aspects of the Vitreous State CRC Boca Raton, FL

    Google Scholar 

  11. J. Perez (2001) Materiaux Non Cristallins et Science du Desordre Presses Polytechniques et Universitaires Romandes Lausanne

    Google Scholar 

  12. A. J. Kovacs (1963) ArticleTitleTransition vitreuse dans les polymères amorphes. Etude phénoménologique Fortschr. Hochpolym-Forsch. 3 394–507

    Google Scholar 

  13. A. J. Kovacs J. J. Aklonis J. M. Hutchinson (1977) Isobaric volume and enthalpy recovery of glasses (I). A critical survey of recent phenomenological approaches P. H. Gaskell (Eds) Structure of Non-crystalline Materials Taylor & Francis London 153–163

    Google Scholar 

  14. A. J. Kovacs J. J. Aklonis J. M. Hutchinson A. R. Ramos (1979) ArticleTitleIsobaric volume and enthalpy recovery of glasses (II). A transparent multiparameter theory J. Polym. Sci. Polym. Phys. 17 1097–1162 Occurrence Handle1:CAS:528:DyaE1MXksFOks7c%3D Occurrence Handle10.1002/pol.1979.180170701

    Article  CAS  Google Scholar 

  15. I. M. Hodge (1994) ArticleTitleEnthalpy relaxation and recovery in amorphous materials J. Non-Cryst. Solids 169 211–266 Occurrence Handle1:CAS:528:DyaK2cXjtlantrY%3D Occurrence Handle10.1016/0022-3093(94)90321-2

    Article  CAS  Google Scholar 

  16. J. M. O'Reilly (1980) Enthalpy relaxation of poly(vinyl chloride) A. G. Walton (Eds) Structure and Properties of Amorphous Polymers Elsevier Amsterdam 165–171

    Google Scholar 

  17. K. Adachi K. Kotaka (1982) ArticleTitleVolume and enthalpy relaxation in polystyrene Polym. J. 14 959–970 Occurrence Handle1:CAS:528:DyaL3sXlsVygsA%3D%3D Occurrence Handle10.1295/polymj.14.959

    Article  CAS  Google Scholar 

  18. G. B. McKenna (1989) Glass formation and glassy behaviour Comprehensive Polymer Science Pergamon Oxford 311

    Google Scholar 

  19. J. Perez (1992) Physique et mecanique des polymeres amorphes Lavoisier, Tec & Doc Paris

    Google Scholar 

  20. J. M. O'Reilly. Review of structure and mobility in amorphous polymers. In Critical Reviews in Solid State and Materials Science. CRC, Boca Raton, FL. 13:227–259 (1987)

  21. R. O. Davies G. O. Jones (1953) ArticleTitleThermodynamic and kinetic properties of glasses Adv. Phys. 2 370–410 Occurrence Handle10.1080/00018735300101252

    Article  Google Scholar 

  22. G. Adam J. H. Gibbs (1965) ArticleTitleThe temperature dependence of cooperative relaxation properties in glass-forming liquids J. Chem. Phys. 43 139–146 Occurrence Handle1:CAS:528:DyaF2MXkt1Oqsbc%3D Occurrence Handle10.1063/1.1696442

    Article  CAS  Google Scholar 

  23. M. H. Cohen D. Turnbull (1959) ArticleTitleMolecular transport in liquids and glasses J. Chem. Phys. 31 1164–1169 Occurrence Handle1:CAS:528:DyaF3cXjslWmtg%3D%3D Occurrence Handle10.1063/1.1730566

    Article  CAS  Google Scholar 

  24. T. Hikima M. Hanaya M. Oguni (1999) ArticleTitleMicroscopic observation of a peculiar crystallization in the glass transition region and β-process as potentially controlling the growth rate in triphenylethylene J. Mol. Struct. 479 245–250 Occurrence Handle1:CAS:528:DyaK1MXit1Wiu7c%3D Occurrence Handle10.1016/S0022-2860(98)00875-8

    Article  CAS  Google Scholar 

  25. F. Paladi M. Oguni (2003) ArticleTitleGeneration and extinction of crystal nuclei in an extremely non-equilibrium glassy state of salol J. Phys. Condens. Matter 15 3909–3917 Occurrence Handle1:CAS:528:DC%2BD3sXlsV2rtbY%3D Occurrence Handle10.1088/0953-8984/15/23/306

    Article  CAS  Google Scholar 

  26. F. Paladi M. Oguni (2002) ArticleTitleAnomalous generation and extinction of crystal nuclei in nonequilibrium supercooled liquid o-benzylphenol Phys. Rev. B 65 144202 Occurrence Handle10.1103/PhysRevB.65.144202 Occurrence Handle1:CAS:528:DC%2BD38XivVWrtbk%3D

    Article  CAS  Google Scholar 

  27. L. Boesch A. Napolitano P. B. Macedo (1970) ArticleTitleSpectrum of volume relaxation times in B 2 O 3 J. Am. Ceram. Soc. 53 148–153 Occurrence Handle1:CAS:528:DyaE3cXhtVegsr4%3D

    CAS  Google Scholar 

  28. C. T. Moynihan P. B. Macedo C. J. Montrose P. K. Gupta M. A. Debolt J. F. Dill B. E. Dom P. W. Drake A. J. Easteal P. B. Eltermann R. A. Moeller H. Sasabe J. A. Wilder (1976) ArticleTitleStructural relaxation in vitreous materials Ann. N. Y. Acad. Sci. 279 15–36 Occurrence Handle1:CAS:528:DyaE2sXjsVGjtQ%3D%3D

    CAS  Google Scholar 

  29. K. Hofer J. Perez G. P. Johari (1991) ArticleTitleDetecting enthalpy ‘cross-over’ in vitrified solids by differential scanning calorimetry Philos. Mag. Lett. 64 37–43 Occurrence Handle1:CAS:528:DyaK3MXlsVeqtbo%3D

    CAS  Google Scholar 

  30. A. L. Greer F. Spaepen (1981) ArticleTitleCreep, diffusion and structural relaxation in metallic glasses Ann. N. Y. Acad. Sci. 371 218–237 Occurrence Handle1:CAS:528:DyaL38XhvVGnurY%3D

    CAS  Google Scholar 

  31. T. Egami (1981) ArticleTitleStructural relaxation in metallic glasses Ann. N. Y. Acad. Sci. 371 238–251 Occurrence Handle1:CAS:528:DyaL38XovFylsg%3D%3D

    CAS  Google Scholar 

  32. A. Fransson G. Backstrom (1987) ArticleTitleIsothermal enthalpy relaxation of glycerol Int. J. Thermophys. 8 352–362 Occurrence Handle10.1007/BF00503947

    Article  Google Scholar 

  33. H. Fujimori Y. Adachi M. Oguni (1992) ArticleTitleTemperature jump method for characterization of structural fluctuations and irreversible relaxation process in liquids and glasses Phys. Rev. B. 46 14501–14504 Occurrence Handle1:CAS:528:DyaK3sXks1alsw%3D%3D Occurrence Handle10.1103/PhysRevB.46.14501

    Article  CAS  Google Scholar 

  34. K. Takeda O. Yamamuro H. Suga (1991) ArticleTitleThermodynamic study of 1-butene. Exothermic and endothermic enthalpy relaxations near the glass transition J. Phys. Chem. Solids 52 607–615 Occurrence Handle1:CAS:528:DyaK3MXhslamu7c%3D Occurrence Handle10.1016/0022-3697(91)90155-S

    Article  CAS  Google Scholar 

  35. J. P. Johari A. Hallbrucker E. Mayer (1987) ArticleTitleThe glass–liquid transition of hyperquenched water Nature 330 552–553 Occurrence Handle1:CAS:528:DyaL1cXhtF2htb8%3D Occurrence Handle10.1038/330552a0

    Article  CAS  Google Scholar 

  36. A. Hallbrucker G. P. Johari E. Mayer (1989) ArticleTitleGlass transition in pressure-amorphized hexagonal ice: a comparison with amorphous forms made from the vapor and liquid J. Phys. Chem. 93 7751–7752 Occurrence Handle1:CAS:528:DyaL1MXmtF2rsb8%3D Occurrence Handle10.1021/j100360a003

    Article  CAS  Google Scholar 

  37. G. P. Johari (2003) ArticleTitleWater's T g endotherm, sub-T g peak of glasses and T g of water J. Chem. Phys. 119 2935–2937 Occurrence Handle1:CAS:528:DC%2BD3sXlsFKgtbg%3D Occurrence Handle10.1063/1.1586256

    Article  CAS  Google Scholar 

  38. S. Ram G. P. Johari (1990) ArticleTitleGlass–liquid transition in hyperquenched metal alloys Philos. Mag. B. 61 299–310 Occurrence Handle1:CAS:528:DyaK3cXitVejtLs%3D

    CAS  Google Scholar 

  39. I. M. Hodge A. R. Berens (1982) ArticleTitleEffects of annealing and prior history on enthalpy relaxation in glassy polymers 2. Mathematical modeling Macromolecules 15 762–770 Occurrence Handle1:CAS:528:DyaL38XktVOjtro%3D Occurrence Handle10.1021/ma00231a016

    Article  CAS  Google Scholar 

  40. H. S. Chen T. T. Wang (1981) ArticleTitleSub-T g structural relaxation in glassy polymers J. Appl. Phys. 52 5898–5902 Occurrence Handle1:CAS:528:DyaL3MXmt1SltLg%3D Occurrence Handle10.1063/1.329827

    Article  CAS  Google Scholar 

  41. R.-J. Roe J. J. Curro (1983) ArticleTitleSmall angle X-ray scattering study of density fluctuation in polystyrene annealed below the glass transition temperature Macromolecules 16 428–434 Occurrence Handle1:CAS:528:DyaL3sXhtVyjur8%3D Occurrence Handle10.1021/ma00237a018

    Article  CAS  Google Scholar 

  42. G. Sartor E. Mayer J. P. Johari (1994) ArticleTitleThermal history and enthalpy relaxation of an interpenetrating network polymer with exceptionally broad relaxation time distribution J. Polym. Sci. Polym. Phys. 32 683–689 Occurrence Handle1:CAS:528:DyaK2cXhvFeisLs%3D Occurrence Handle10.1002/polb.1994.090320410

    Article  CAS  Google Scholar 

  43. J. M. G. Cowie R. Ferguson (1986) ArticleTitleThe ageing of poly(vinyl methyl ether) as determined from enthalpy relaxation measurements Polym. Commun. 27 258–260 Occurrence Handle1:CAS:528:DyaL28XlsFeru7s%3D

    CAS  Google Scholar 

  44. W. Pascheto M. G. Parthun A. Hallbrucker G. P. Johari (1994) ArticleTitleCalorimetric studies of structural relaxation in AgI-AgPO3 glasses J. Non-Cryst. Solids 171 182–190 Occurrence Handle1:CAS:528:DyaK2cXltFGms74%3D Occurrence Handle10.1016/0022-3093(94)90354-9

    Article  CAS  Google Scholar 

  45. M. Hanaya M. Nakayama M. Oguni (1994) ArticleTitleRemarkable non-exponentiality of the enthalpy relaxation in fast ion conducting glass (AgI)0.5(AgPO 3 )0.5 far from equilibrium J. Non-Cryst. Solids 172 608–614 Occurrence Handle10.1016/0022-3093(94)90496-0

    Article  Google Scholar 

  46. H. S. Chen (1981) ArticleTitleOn mechanism of structural relaxation in a Pd48Ni32P20 glass J. Non-Cryst. Solids 46 289–305 Occurrence Handle1:CAS:528:DyaL38XhvVOlu7g%3D Occurrence Handle10.1016/0022-3093(81)90007-7

    Article  CAS  Google Scholar 

  47. G. Sartor E. Mayer G. P. Johari (1994) ArticleTitleCalorimetric studies of the kinetic unfreezing of molecular motions in hydrated lysozyme, hemoglobin, and myoglobin Biophys. J. 66 249–258 Occurrence Handle8130342 Occurrence Handle1:CAS:528:DyaK2cXkslKnt7k%3D Occurrence Handle10.1016/S0006-3495(94)80774-X

    Article  PubMed  CAS  Google Scholar 

  48. S. Rüdisser A. Hallbrucker E. Mayer (1996) ArticleTitleProbing DNA's dynamics and conformational substrates by enthalpy relaxation and its recovery J. Phys. Chem. 100 458–461 Occurrence Handle10.1021/jp952533d

    Article  Google Scholar 

  49. S. Rüdisser A. Hallbrucker E. Mayer G. P. Johari (1997) ArticleTitleEnthalpy, entropy, and structural relaxation behaviors of A- and B-DNA in their vitrified states and the effect of water on the dynamics of B-DNA J. Phys. Chem. 101 266–277

    Google Scholar 

  50. G. Sartor G. P. Johari (1996) ArticleTitleStructure relaxation of a vitrified high-protein food, beef, and the phase transformations of its water content J. Phys. Chem. 100 10450–10463 Occurrence Handle1:CAS:528:DyaK28XjtFWmtLs%3D Occurrence Handle10.1021/jp960150p

    Article  CAS  Google Scholar 

  51. G. P. Johari G. Sartor (1996) ArticleTitleVitrification and structural relaxation of a water-swollen protein, wheat gluten and thermodynamic of its water-protein ↔ ice equilibrium J. Chem. Soc. Faraday Trans. 92 4521–4531 Occurrence Handle1:CAS:528:DyaK28XnsV2isr8%3D Occurrence Handle10.1039/ft9969204521

    Article  CAS  Google Scholar 

  52. G. Sartor K. Hofer G. P. Johari (1996) ArticleTitleStructural relaxation and H-bonding in isomeric octanols and their LiCl solutions by calorimetry J. Phys. Chem. 100 6801–6807 Occurrence Handle1:CAS:528:DyaK28XhvV2itbk%3D Occurrence Handle10.1021/jp953352e

    Article  CAS  Google Scholar 

  53. G. P. Johari G. Sartor (1997) ArticleTitleHydrogen-bond equilibrium and the enthalpy and entropy relaxations in a non-polar state of vitrified 2-methyl-3-heptanol J. Phys. Chem. B 101 8331–8340 Occurrence Handle1:CAS:528:DyaK2sXmtFClt74%3D Occurrence Handle10.1021/jp970764+

    Article  CAS  Google Scholar 

  54. P. D. Martino G. F. Palmieri S. Martelli (2000) ArticleTitleMolecular mobility of the paracetamol amorphous form Chem. Pharm. Bull. 48 1105–1108 Occurrence Handle10959571

    PubMed  Google Scholar 

  55. M. Sacchetti (2001) ArticleTitleThermodynamic analysis of DSC data for acetaminophen polymorphs J. Therm. Anal. Calorim. 63 345–350 Occurrence Handle1:CAS:528:DC%2BD3MXisFWju7o%3D Occurrence Handle10.1023/A:1010180123331

    Article  CAS  Google Scholar 

  56. E. V. Boldyreva V. A. Drebushchak I. E. Paukov Y. A. Kovalevskaya T. N. Drebushchak (2004) ArticleTitleDSC and adiabatic calorimetry study of the polymorphs of paracetamol, an old problem revisited J. Therm. Anal. Calorim. 77 607–623 Occurrence Handle1:CAS:528:DC%2BD2cXmvFSmtLc%3D Occurrence Handle10.1023/B:JTAN.0000038998.47606.27

    Article  CAS  Google Scholar 

  57. D. Zhou G. G. Z. Zhang D. Law D. J. W. Grant E. A. Schmitt (2002) ArticleTitlePhysical stability of amorphous pharmaceuticals: importance of configurational thermodynamic quantities and molecular mobility J. Pharm. Sci. 91 1863–1872 Occurrence Handle12115813 Occurrence Handle1:CAS:528:DC%2BD38XlvV2ksL4%3D Occurrence Handle10.1002/jps.10169

    Article  PubMed  CAS  Google Scholar 

  58. R. R. Lagasse (1982) ArticleTitleImproved calorimetric procedure for monitoring the approach to thermodynamic equilibrium in glassy polymers J. Polym. Sci. Polym. Phys. 20 279–295 Occurrence Handle1:CAS:528:DyaL38Xht1els7c%3D Occurrence Handle10.1002/pol.1982.180200210

    Article  CAS  Google Scholar 

  59. J. P. Joule. Observations on the alteration of the freezing-point in thermometers. In Scientific papers of James Prescott Joule, The Physical Society of London, Taylor and Francis, 1:558–559 (1884).

  60. S. Nemilov and G. P. Johari, A mechanism for spontaneous relaxation of glass at room temperature. Philos. Mag. 83:3117–3132 (2003); 84:845 (2004).

    Google Scholar 

  61. A. J. Kovacs R. A. Stratton J. D. Ferry (1963) ArticleTitleDynamic mechanical properties of polyvinyl acetate in shear in the glass transition temperature range J. Phys. Chem. 67 152–161 Occurrence Handle1:CAS:528:DyaF3sXkslaqtQ%3D%3D

    CAS  Google Scholar 

  62. D. J. Plazek G. C. Berry (1986) Physical aging of polymer glasses R. Uhlmann N. J. Kreidl (Eds) Glass Science & Technology Academic New York 363–399

    Google Scholar 

  63. A. Q. Tool (1946) ArticleTitleRelation between inelastic deformability and thermal expansion of glass in its annealing range J. Am. Ceram. Soc. 29 240–253 Occurrence Handle1:CAS:528:DyaH28XjsFShsw%3D%3D

    CAS  Google Scholar 

  64. O. S. Narayanaswamy (1971) ArticleTitleA model of structural relaxation in glasses J. Am. Ceram. Soc. 54 491–498 Occurrence Handle1:CAS:528:DyaE3MXltlant70%3D

    CAS  Google Scholar 

  65. G. W. Scherer (1971) ArticleTitleUse of the Adam–Gibbs equation in the analysis of structural relaxation J. Am. Ceram. Soc. 67 504–511 Occurrence Handle10.1111/j.1151-2916.1984.tb19643.x

    Article  Google Scholar 

  66. I. M. Hodge (1987) ArticleTitleEffects of annealing and prior history on enthalpy relaxation in glassy polymers. 6. Adam–Gibbs formulation of nonlinearity Macromolecules 20 2897–2908 Occurrence Handle1:CAS:528:DyaL2sXmtFygurg%3D Occurrence Handle10.1021/ma00177a044

    Article  CAS  Google Scholar 

  67. F. L. Cumbrera A. Munoz (1992) ArticleTitleA phenomenological model for the enthalpy relaxation of glasses: part 2. Effects of a continuous distribution of relaxation times Thermochim. Acta 196 137–153 Occurrence Handle10.1016/0040-6031(92)85014-M

    Article  Google Scholar 

  68. J. Perez (1988) ArticleTitleDefect diffusion model for volume and enthalpy recovery in amorphous polymers Polymer 29 483–489 Occurrence Handle1:CAS:528:DyaL1cXhsFWgtL4%3D Occurrence Handle10.1016/0032-3861(88)90367-9

    Article  CAS  Google Scholar 

  69. T. S. Chow (1984) ArticleTitleKinetics of free volume and physical aging in polymer glasses Macromolecules 17 2336–2340 Occurrence Handle1:CAS:528:DyaL2cXmtFWqtrg%3D Occurrence Handle10.1021/ma00141a024

    Article  CAS  Google Scholar 

  70. T. S. Chow (1992) ArticleTitleGlassy state relaxation and deformation in polymers Adv. Polym. Sci. 103 149–190 Occurrence Handle1:CAS:528:DyaK38Xlslagsbc%3D Occurrence Handle10.1007/BFb0020905

    Article  CAS  Google Scholar 

  71. T. S. Chow (1992) ArticleTitleFractal dynamic theory of glasses and physical aging: linear and cross-linked polymer Macromolecules 25 440–444 Occurrence Handle1:CAS:528:DyaK38XitFymsw%3D%3D Occurrence Handle10.1021/ma00027a068

    Article  CAS  Google Scholar 

  72. S. M. Rekhson (1986) ArticleTitleMemory effects in glass transition J. Non-Cryst. Solids 84 68–85 Occurrence Handle1:CAS:528:DyaL28XlsFyqtLY%3D Occurrence Handle10.1016/0022-3093(86)90763-5

    Article  CAS  Google Scholar 

  73. V. G. Rotiashvilli A. R. Nekhoda V. I. Irzhak B. A. Rosenberg (1984) ArticleTitleThe volume structural relaxation theory for amorphous polymer J. Polym. Sci. Polym. Phys. 22 1041–1059 Occurrence Handle10.1002/pol.1984.180220609

    Article  Google Scholar 

  74. J.-Y. Cavaille S. Etienne J. Perez L. Monnerie G. P. Johari (1986) ArticleTitleDynamic shear measurements of physical ageing and the memory effect in a polymer glass Polymer 27 686–692 Occurrence Handle1:CAS:528:DyaL28XksVeksb8%3D Occurrence Handle10.1016/0032-3861(86)90125-4

    Article  CAS  Google Scholar 

  75. E. Muzeau J.-Y. Cavaille R. Vassoille J. Perez G. P. Johari (1992) ArticleTitleEffects of sub-T g annealings on the anelastic relaxation in poly(methyl methacrylate) Macromolecules 25 5108–5110 Occurrence Handle1:CAS:528:DyaK38XltlWqs78%3D Occurrence Handle10.1021/ma00045a043

    Article  CAS  Google Scholar 

  76. G. P. Johari (1976) ArticleTitleGlass transitions and secondary relaxations in molecular liquids and crystals Ann. N. Y. Acad. Sci. 279 117–140 Occurrence Handle1:CAS:528:DyaE2sXpvFWksQ%3D%3D

    CAS  Google Scholar 

  77. G. P. Johari (1982) ArticleTitleEffects on annealing on the secondary relaxations in glass J. Chem. Phys. 77 4619–4626 Occurrence Handle1:CAS:528:DyaL3sXkvFGn Occurrence Handle10.1063/1.444414

    Article  CAS  Google Scholar 

  78. K. Pathmanathan G. P. Johari J.-P. Faivre L. Monnerie (1986) ArticleTitleDielectric study of secondary relaxations and the ‘memory effect’ in two compatible polystyrene blends J. Polym. Sci. Polym. Phys. 24 1587–1595 Occurrence Handle1:CAS:528:DyaL28XkvFygt78%3D Occurrence Handle10.1002/polb.1986.090240715

    Article  CAS  Google Scholar 

  79. A. Winter-Klein (1937) ArticleTitleLes causes et les effets de la trempe du verre Rev. Opt. 16 361–385 Occurrence Handle1:CAS:528:DyaA1cXjsVSlug%3D%3D

    CAS  Google Scholar 

  80. G. P. Johari J. Perez (1994) ArticleTitleThe internal energy of an equilibrium glass at 0 K J. Mol. Phys. 83 235–244 Occurrence Handle1:CAS:528:DyaK2cXntVyrurc%3D Occurrence Handle10.1080/00268979400101221

    Article  CAS  Google Scholar 

  81. W. Kauzmann (1948) ArticleTitleThe nature of the glassy state and the behaviour of liquids at low temperatures Chem. Rev. 43 219–256 Occurrence Handle1:CAS:528:DyaH1MXktVCh Occurrence Handle10.1021/cr60135a002

    Article  CAS  Google Scholar 

  82. G. P. Johari (2000) ArticleTitleAn equilibrium supercooled liquid's entropy and enthalpy in the Kauzmann and the third law extrapolations, and a proposed experimental resolution J. Chem. Phys. 113 751–761 Occurrence Handle1:CAS:528:DC%2BD3cXksV2hs7c%3D Occurrence Handle10.1063/1.481850

    Article  CAS  Google Scholar 

  83. G. P. Johari (2001) ArticleTitleThe configurational entropy theory and the heat capacity decrease of orientationally disordered crystals on cooling to 0 K Philos. Mag. B 81 1935–1950 Occurrence Handle1:CAS:528:DC%2BD38XhvVWqsQ%3D%3D Occurrence Handle10.1080/13642810110063239

    Article  CAS  Google Scholar 

  84. F. E. Simon (1930) ArticleTitleFünfundzwanzig Jahr Nernstchen Wärmesatz Ergeb. Exakten Naturwiss. 9 244–260

    Google Scholar 

  85. G. P. Johari (1980) ArticleTitleOn the excess entropy of disordered solids Philos. Mag. 41 41–47 Occurrence Handle1:CAS:528:DyaL3cXitVCnsLo%3D

    CAS  Google Scholar 

  86. F. H. Stillinger (1988) ArticleTitleSupercooled liquids, glass transitions and the Kauzmann paradox J. Chem. Phys. 88 7818–7825 Occurrence Handle1:CAS:528:DyaL1cXkvF2hsrY%3D Occurrence Handle10.1063/1.454295

    Article  CAS  Google Scholar 

  87. H.-P. Wittman (1991) ArticleTitleOn the validity of the Gibbs–diMarzio theory of the glass transition of lattice polymers J. Chem. Phys. 95 8449–8458 Occurrence Handle10.1063/1.461274

    Article  Google Scholar 

  88. M. Pyda B. Wunderlich (2000) ArticleTitleAnalysis of the residual entropy of the amorphous polyethylene at zero Kelvin J. Polym. Sci. Polym. Phys. 40 1245–1253 Occurrence Handle10.1002/polb.10160 Occurrence Handle1:CAS:528:DC%2BD38XktlWjsrs%3D

    Article  CAS  Google Scholar 

  89. D. Huang S. L. Simon G. B. McKenna (2003) ArticleTitleEquilibrium heat capacity of glass forming poly(a-methyl styrene) far below the Kauzmann temperature: The case of missing glass transition J. Chem. Phys. 119 3590–3593 Occurrence Handle1:CAS:528:DC%2BD3sXlvFCqsLw%3D Occurrence Handle10.1063/1.1599271

    Article  CAS  Google Scholar 

  90. R. W. Douglas (1966) ArticleTitleGlasses and time Brit. J. Appl. Phys. 17 435–448 Occurrence Handle1:CAS:528:DyaF28XptFyiuw%3D%3D Occurrence Handle10.1088/0508-3443/17/4/301

    Article  CAS  Google Scholar 

  91. J. M. O'Reilly I. M. Hodge (1991) ArticleTitleEffects of heating rate on enthalpy recovery in polystyrene J. Non-Cryst. Solids 131 451–456 Occurrence Handle10.1016/0022-3093(91)90338-7

    Article  Google Scholar 

  92. S.-L. Wang S.-Y. Lin Y.-S. Wei (2002) ArticleTitleTransformation of metastable forms of acetaminophen studied by thermal Fourier transform infrared (FT-IR) microspectroscopy Chem. Pharm. Bull. 50 153–156 Occurrence Handle11848200 Occurrence Handle1:CAS:528:DC%2BD38Xks12ktLc%3D Occurrence Handle10.1248/cpb.50.153

    Article  PubMed  CAS  Google Scholar 

  93. E. V. Boldyreva T. P. Shakhtshneider M. A. Vasichenko H. Ahsbahs H. Uchtmann (2000) ArticleTitleAnisotropic crystal structure distortion of the monoclinic polymorph of acetaminophen at high hydrostatic pressures Acta Crystallogr. B 56 299–309 Occurrence Handle10794283 Occurrence Handle10.1107/S0108768199013634

    Article  PubMed  Google Scholar 

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Acknowledgments

This research was partly supported by a grant from Pfizer, Inc. and partly by the Discovery Grant from Natural Sciences and Engineering Research Council of Canada.

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Correspondence to G. P. Johari.

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Gunawan, L., Johari, G.P. & Shanker, R.M. Structural Relaxation of Acetaminophen Glass. Pharm Res 23, 967–979 (2006). https://doi.org/10.1007/s11095-006-9898-0

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  • DOI: https://doi.org/10.1007/s11095-006-9898-0

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