Supporting Information. Novel thermoplastic cellulose esters containing bulky moieties and soft segments
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1 Supporting Information Novel thermoplastic cellulose esters containing bulky moieties and soft segments Zhangyan Chen 1, 2, Jinming Zhang 1, *, Peng Xiao 1, Weiguo Tian 1, Jun Zhang 1, 2, * 1 CAS Key Laboratory of Engineering Plastics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing, , China. 2 University of Chinese Academy of Sciences, Beijing , China Supporting information content Number of pages: 17 Number of figures: 28 Number of tables: 14 S1
2 Figure S1. Synthetic routine of cellulose acetate in the ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl). DS Ac = 7I 3I Figure S2. 1 H-NMR spectrum and equation of the degree of substitution (DS) of cellulose acetate (I is the peak integral of protons). Table S1. DS of cellulose acetate synthesized by the homogeneous esterification of cellulose with chloride in AmimCl. T/ C t/h DS Ac 3.0: : S2
3 Figure S3. Synthetic routine of cellulose acetate butyrate in AmimCl. DS Bt = 7I H10 3I DS Ac = 21I H (7-9) - 28I H10 9I H10 H (7-9) Figure S4. 1 H-NMR spectrum and DS equation of cellulose acetate butyrate. Table S2. DS of cellulose acetate butyrate synthesized by the homogeneous esterification of cellulose with n-butyryl chloride and chloride in AmimCl under different reaction conditions. n-butyryl DS Bt DS Ac DS Total 1.5: : : : : : : : S3
4 Figure S5. Synthetic routine of cellulose benzoate acetate in AmimCl. DS B = 7I H (8-10) 5I H ( 1-6) DS Ac = 7I 3I H (8-10) Figure S6. 1 H-NMR spectrum and DS equation of cellulose benzoate acetate. Table S3. DS of cellulose benzoate acetate synthesized by the homogeneous esterification of cellulose with benzoyl chloride and chloride in AmimCl under different reaction conditions. benzoyl DS B DS Ac DS Total 1.0: : : : : : : : S4
5 Figure S7. Synthetic routine of cellulose β-naphthoate acetate in AmimCl. DS β- Np = I H (8-14) I DS Ac = 7I 3I H (8-14) Figure S8. 1 H-NMR spectrum and DS equation of cellulose β-naphthoate acetate. Table S4. DS of cellulose β-naphthoate acetate synthesized by the homogeneous esterification of cellulose with β-naphthyl chloride and chloride in AmimCl under different reaction conditions. β-naphthyl DS β-np DS Ac DS Total 2.0: : : : : : : : S5
6 Figure S9. Synthetic routine of cellulose α-naphthoate acetate in AmimCl. DS α- Np = I H (8-14) I DS Ac = 7I 3I H (8-14) Figure S10. 1 H-NMR spectrum and DS equation of cellulose α-naphthoate acetate. Table S5. DS of cellulose α-naphthoate acetate synthesized by the homogeneous esterification of cellulose with α-naphthyl chloride and chloride in AmimCl under different reaction conditions. α-naphthyl DS α-np DS Ac DS Total 2.0: : : : : : : : S6
7 Figure S11. Synthetic routine of cellulose adamantate acetate in AmimCl. H (7-10) Figure S12. 1 H-NMR spectrum of cellulose adamantate acetate. 2,3 9,13,16 11,14,17 10,12,15 DS Ac = 3I 18 I 7 + I 18 DS Ad = 3I 7 I 7 + I Figure S C-NMR spectrum and DS equation of cellulose adamantate acetate. S7
8 Table S6. DS of cellulose adamantate acetate synthesized by the homogeneous esterification of cellulose with adamantyl chloride and chloride in AmimCl under different reaction conditions. adamantyl DS Ad DS Ac DS Total 4.0: : : : : : : : S8
9 Figure S14. Synthetic routine of cellulose 4-tert-butylbenzoate acetate in AmimCl. DS tbp = 7I H (8-9) 4I DS Ac = 28I H (7, 10)-63I H (8-9) 12I H (7, 10) H (8-9) Figure S15. 1 H-NMR spectrum and DS equation of cellulose 4-tert-butylbenzoate acetate in AmimCl. Table S7. DS of cellulose 4-tert-butylbenzoate acetate synthesized by the homogeneous esterification of cellulose with 4-tert-butylbenzoyl chloride and chloride in AmimCl under different reaction conditions. 4-tert-butylbenzoyl DS t-bp DS Ac DS Total 4.0: : : : : : : : S9
10 Figure S16. Synthetic routine of cellulose 4-butylbenzoate acetate. DS Bp = 7I H (8-9) 4I H13 DS Ac = 7I H (7, 11-12)-7I H (8-9) 3I H (7, 11, 12) H (8, 9) H10 Figure S17. 1 H-NMR spectrum and DS equation of cellulose 4-butylbenzoate acetate in AmimCl. Table S8. DS of cellulose 4-butylbenzoate acetate synthesized by the homogeneous esterification of cellulose with 4-butylbenzoyl chloride and chloride in AmimCl under different reaction conditions. 4-butylbenzoyl DS Bp DS Ac DS Total 4.0: : : : : : : : S10
11 Figure S18. Synthetic routine of cellulose phenylacetate acetate in AmimCl. 7I H (9-11) DS Pa = 5I H (1-6, 8) -2I H (9-11) 35I DS Ac = 15I H (1-6, 8) -6I H (9-11) H (9-11) H (1-6, 8) Figure S19. 1 H-NMR spectrum and DS equation of cellulose phenylacetate acetate in AmimCl. Table S9. DS of cellulose phenylacetate acetate synthesized by the homogeneous esterification of cellulose with phenyl chloride and chloride in AmimCl under different reaction conditions. phenyl DS Pa DS Ac DS Total 1.5: : : : : : : : S11
12 Figure S20. Synthetic routine of cellulose phenylpropionate acetate in AmimCl. DS Pp = 7I H (10-12) 5I DS Ac = 7I 3I H (10-12) H (8-9) Figure S21. 1 H-NMR spectrum and DS equation of cellulose phenylpropionate acetate. Table S10. DS of cellulose phenylpropionate acetate synthesized by the homogeneous esterification of cellulose with phenylpropionyl chloride and chloride in AmimCl under different reaction conditions. phenylpropionyl DS Pp DS Ac DS Total 1.5: : : : : : : : S12
13 Figure S22. Synthetic routine of cellulose cinnamate acetate in AmimCl. DS Cm = I H (8-12) I DS Ac = 7I 3I H (10-12) H (8-9) Figure S23. 1 H-NMR spectrum and DS equation of cellulose cinnamate acetate. Table S11. DS of cellulose cinnamate acetate synthesized by the homogeneous esterification of cellulose with cinnamoyl chloride and chloride in AmimCl under different reaction conditions. cinnamoyl DS Cm DS Ac DS Total 2.0: : : : : : : : S13
14 Figure S24. Synthetic routine of cellulose phenoxyacetate acetate in AmimCl. 7I H (9-11) 35I DS Poa = DS 5I H (1-6, 8) -2I Ac = H (9-11) 15I H (1-6, 8) -6I H (9-11) H (9-11) H (1-6, 8) Figure S25. 1 H-NMR spectrum and DS equation of cellulose phenoxyacetate acetate. Table S12. DS of cellulose phenoxyacetate acetate synthesized by the homogeneous esterification of cellulose with phenoxy chloride and chloride in AmimCl under different reaction conditions. phenoxy DS Poa DS Ac DS Total 2.0: : : : : : : : S14
15 Figure S26. Synthetic routine of cellulose phenoxyformate acetate in AmimCl. DS Pcm = 7I H (8-10) 5I H ( 1-6) DS Ac = 7I 3I H (8-10) Figure S27. 1 H-NMR spectrum and DS equation of cellulose phenoxyformate acetate. Table S13. DS of cellulose phenoxyformate acetate synthesized by the homogeneous esterification of cellulose with phenyl chloroformate and chloride in AmimCl under different reaction conditions. phenyl chloroformate /AGU DS Pcm DS Ac DS Total 2.0: : : : : : : : S15
16 Weight(%) Weight(%) Weight(%) Weight(%) 100 CB-1.76-Ac-1.23 N 2 Air 100 Cα-Np-2.02-Ac-0.88 N 2 Air Temperature( C) Temperature( C) 100 CPoa-1.98-Ac-1.02 N 2 Air 100 CPp-2.25-Ac-0.75 N 2 Air Temperature( C) Temperature( C) Figure S28. TGA curves of CB-1.76-Ac-1.23, Cα-Np-2.02-Ac-0.88, CPoa-1.98-Ac-1.02, and CPp-2.25-Ac-0.75 under N 2 and air atmosphere Table S14. Thermal degradation properties of the synthesized cellulose esters under N 2 atmosphere and air atmosphere. T onset, the onset decomposition temperature; T max, the maximum decomposition temperature. Samples N 2 atmosphere Air atmosphere T onset / C T max / C T onset / C T max / C CA CB-1.76-Ac CtBp-1.96-Ac Cα-Np-2.02-Ac Cβ-Np-2.00-Ac CAd-2.14-Ac CPa-2.05-Ac CPp-2.25-Ac S16
17 CCm-1.96-Ac CPoa-1.98-Ac CPcm-2.07-Ac CBt-2.04-Ac CBp-2.05-Ac S17
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