Synthesis, Characterization, and Gas Permeation Properties

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t-Butylcarbamates of Cellulose Derivatives Macromolecules 1996, 29, 4360–4369. (f) Simril, V. L.; Hershberger, A. Mod. Plast. 1950, 27, 95–102. 14. (a) Sakaguchi, T.; Shiotsuki, M.; Masuda, T. Macromolecules 2004, 37, 4104–4108. (b) Merkel, T. C.; Bondar, V. I.; Nagai, K.; Freeman, B. D. J. Polym. Sci., Part B: Polym. Phys. 2000, 38, 273–296. (c) Toy, L. G.; Nagai, K.; Freeman, B. D.; Pinnau, I.; He, Z.; Masuda, T.; Teraguchi, M.; Yampolskii, Y. P. Macromolecules 2000, 33, 2516–2524. 15. (a) Kanaya, T.; Tsukushi, I.; Kaji, K.; Sakaguchi, T.; Kwak, G.; Masuda, T. Macromolecules 2002, 35, 5559–5564. (b) Kanaya, T.; Tsukushi, I.; Kaji, K.; Teraguchi, M.; Kwak, G.; Masuda, T. J. Phys. Soc., Suppl. A 2000, 70, 332–334. (c) Kanaya, T.; Teraguchi, M.; Masuda, T.; Kaji, K. Polymer 1999, 40, 7157–7161. 16. (a) Graham, T. J. Membr. Sci. 1995, 100, 27–31. (b) Graham, T. Philos. Mag. 1866, 32, 401–420. 134
Chapter 5 135 Chapter5 Synthesis and Properties of Amino Acid Esters of Hydroxypropyl Cellulose Abstract The amino acid esters of hydroxypropyl cellulose [R' = H (2a), CH3 (2b), CH2CH(CH3)2 (2c), CH2CONH2 (2d), CH2CH2CONH2 (2e), CH2CH2CH2CH2NHOCOC(CH3)3 (2f)] were synthesized in good yield by the reaction of t-butoxycarbonyl (t-Boc)-protected amino acids with hydroxy groups of hydroxypropyl cellulose (1; molar substitution (MS), 4.61). The amino acid functionalities displaying varied chemical nature, shape, and bulk were utilized and the bulk of the substituent on the α-carbon of amino acids was elucidated to be of vital significance for the observed degree of incorporation (DSEst). The 1 H NMR spectra and elemental analysis were employed to determine the degree of incorporation of amino acid moiety (DSEst) and almost complete substitution of the hydroxy protons was revealed for 2a, 2b, and 2f. The presence of the peaks characteristic of the carbonyl group in the FTIR spectra furnished further evidence for the successful esterification of hydroxypropyl cellulose. The starting as well as the resulting polymers (1 and 2a–f) were soluble in polar organic solvents; however, the esterification of 1 with bulky organic moieties resulted in an increased hydrophobicity as all of the amino acid-functionalized polymers (2a–f) were insoluble in water. The onset temperatures of weight loss of 2a–f were 175–230 °C, indicating fair thermal stability. The amino acid functionalization led to the enhanced polymer chain stiffness, and the glass transition temperatures of the derivatized polymers were 30–40 °C higher than that of 1 (Tg 3.9 °C; cf. Tg of 2a–f, 35.1–43.3 °C).
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Synthesis, Characterization, and Ga
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Table of Contents General Introduct
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General Introduction cellulose deri
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General Introduction biogenetically
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General Introduction chemistry offe
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General Introduction solution-diffu
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General Introduction A simplified t
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General Introduction been observed
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polymers. 41,46 General Introductio
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General Introduction Keeping in vie
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General Introduction the derivatize
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General Introduction strategy (G1-a
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General Introduction In conclusion,
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General Introduction 5. (a) Kobayas
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General Introduction 15. (a) Goetma
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General Introduction American Chemi
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General Introduction Macromolecules
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Silylation of Ethyl Cellulose Intro
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Silylation of Ethyl Cellulose milli
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Silylation of Ethyl Cellulose chlor
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Silylation of Ethyl Cellulose Resul
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Silylation of Ethyl Cellulose Solub
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Silylation of Ethyl Cellulose 1.034
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Silylation of Ethyl Cellulose poly(
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Silylation of Ethyl Cellulose the r
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Silylation of Ethyl Cellulose D.; Y
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Chapter 2 51 Chapter 2 Synthesis, C
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53 Chapter 2 are few and far betwee
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55 Chapter 2 constant volume/variab
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57 Chapter 2 Membrane Density. Memb
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59 Chapter 2 IR spectrum of 1 (Figu
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61 Chapter 2 1,3-bis(trifluoromethy
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63 Chapter 2 The increase in the po
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65 Chapter 2 other fluorinated poly
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67 Chapter 2 of the gas permeabilit
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69 Chapter 2 Gas Diffusivity and So
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71 Chapter 2 mobility of the perflu
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73 Chapter 2 1325-1329. (b) Hamza,
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Chapter 3 75 Chapter 3 Synthesis an
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77 Chapter 3 cost, and above all ap
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79 Chapter 3 molecular weights (Mn
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81 Chapter 3 1.99-2.07 (m, 2H, (CH3
Page 85 and 86: 83 Chapter 3 25 °C, ppm): 11.9, 13
Page 87 and 88: 85 Chapter 3 38.1, 44.7, 46.8, 47.9
Page 89 and 90: 87 Chapter 3 CH2CH2C(=O)O), 2.50-4.
Page 91 and 92: 89 Chapter 3 1091, 1053, 853, 806,
Page 93 and 94: 91 Chapter 3 dendrons (G1-a-ІІ-G1
Page 95 and 96: 93 Chapter 3 (DMAP) as a base, as s
Page 97 and 98: Figure 3. FTIR spectra of 1, 2c, an
Page 99 and 100: 97 Chapter 3 (partly soluble) and 3
Page 101 and 102: 99 Chapter 3 increased polarity of
Page 103 and 104: 101 Chapter 3 that of 1, and approx
Page 105 and 106: 103 Chapter 3 derivatization per th
Page 107 and 108: 105 Chapter 3 (2a-c) were in the or
Page 109 and 110: 107 Chapter 3 2709-2719. (b) Schenn
Page 111 and 112: 109 Chapter 3 17. van Krevelen, D.
Page 113 and 114: Chapter 4 111 Chapter 4 Synthesis,
Page 115 and 116: 113 Chapter 4 Since, no significant
Page 117 and 118: 115 Chapter 4 Materials. Ethyl cell
Page 119 and 120: DStotal = DSEt + DSCarb (for 1a and
Page 121 and 122: 119 Chapter 4 Figure 2. 1 H NMR spe
Page 123 and 124: 121 Chapter 4 ruling out the possib
Page 125 and 126: 123 Chapter 4 t-butyl moiety. A str
Page 127 and 128: 125 Chapter 4 reported to lead to t
Page 129 and 130: 127 Chapter 4 Table 4. Gas Permeabi
Page 131 and 132: 129 Chapter 4 augmentation in eithe
Page 133 and 134: 131 Chapter 4 indicate the signific
Page 135: 133 Chapter 4 M.-R. J. Appl. Polym.
Page 139 and 140: 137 Chapter5 acid- and peptide-cont
Page 141 and 142: 139 Chapter5 Specific rotations ([
Page 143 and 144: 141 Chapter5 1.66 (brs, 1.1H, NHCH(
Page 145 and 146: 143 Chapter5 as shown in Scheme 1,
Page 147 and 148: 145 Chapter5 in Table 1. The molecu
Page 149 and 150: 147 Chapter5 almost same pattern of
Page 151 and 152: Conclusions Table 3. Thermal Proper
Page 153 and 154: 151 Chapter5 W.; Jing, X. J. Polym.
Page 155 and 156: Chapter 5 Synthesis and Properties
Page 157 and 158: Acknowledgments While submitting th
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