FTIR, Weight, and Surface Morphology of Poly(vinyl chloride) Doped with Tin Complexes Containing Aromatic and Heterocyclic Moieties
Abstract
:1. Introduction
2. Materials and Methods
2.1. General
2.2. Synthesis of Complex 1
2.3. Synthesis of Complexes 2 and 3
2.4. Preparation of PVC Films
2.5. Irradiation of PVC Films
2.6. Measurement of PVC Functional Group Indices
2.7. Measurement of PVC Weight Loss
3. Results and Discussion
3.1. Synthesis of Trimethoprim–tin Complexes 1–3
3.2. Investigation of PVC Photodegradation through FTIR Spectrophotometry
3.3. Investigation of PVC Photodegradation through Weight Loss
3.4. Investigation of PVC Photodegradation through Surface Morphology
3.5. PVC Photostabilization Mechanisms
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Complex | Color | M.P. (°C) | Yield (%) | Elemental Analyses (%) Calculated (Found) | |||
---|---|---|---|---|---|---|---|
C | H | N | Sn | ||||
1 | White | 267–269 | 75 | 60.12 (60.25) | 5.05 (5.10) | 8.76 (8.78) | 18.57 (18.48) |
2 | Off white | 217–218 | 79 | 56.42 (56.36) | 5.21 (5.25) | 13.16 (13.23) | 13.94 (14.01) |
3 | White | 245–246 | 82 | 53.28 (53.27) | 6.46 (6.39) | 13.81 (13.89) | 14.63 (14.76) |
Complex | FTIR, Wave Number (ν, cm−1) | ||||
---|---|---|---|---|---|
NH2 | NH | C=N | Sn–C | Sn–N | |
1 | 3406 | 3176 | 1680 | 605 | 497 |
2 | 3408 | 3180 | 1680 | 607 | 586 |
3 | 3406 | 3163 | 1682 | 605 | 516 |
Complex | 1H NMR (DMSO-d6: δ, ppm, J in Hz) | 13C NMR (DMSO-d6: δ, ppm) |
---|---|---|
1 | 3.16 (s, exch., 1H, NH), 3.61 (s, 2H, CH2), 3.64 (s, 3H, OMe), 3.76 (s, 6H, 2 OMe), 6.64 (s, 2H, 3,4,5-(OMe)3C6H2), 7.47–7.53 (m, 17H, 3 Ph and NH2), 7.95 (s, 1H, pyrimidinyl) | 32.7 (CH2), 56.4 (OMe), 60.4 (OMe), 106.7 (C2/C6 of 3,4,5-(OMe)3C6H2), 109.2 (C5 of pyrimidinyl), 128.5 (C3/C5 of Ph), 128.2 (C4 of Ph), 133.7 (C1 of 3,4,5-(OMe)3C6H2), 136.6 (C4 of 3,4,5-(OMe)3C6H2), 137.0 (C2/C6 of Ph), 137.5 (C1 of Ph), 141.0 (C3/C5 of 3,4,5-(OMe)3C6H2), 153.3 (C4 of pyrimidinyl), 161.1 (C2 of pyrimidinyl), 164.3 (C1 of pyrimidinyl) |
2 | 3.46 (s, exch., 2H, 2 NH), 3.56 (s, 4H, 2 CH2), 3.64 (s, 6H, 2 OMe), 3.74 (s, 12H, 4 OMe), 6.28 (s, exch., 4H, 2 NH2), 6.59 (s, 4H, 3,4,5-(OMe)3C6H2), 7.26–7.36 (10H, 2 Ph), 7.96 (s, 2H, pyrimidinyl) | 33.2 (CH2), 56.3 (OMe), 60.4 (OMe), 106.4 (C2/C6 of 3,4,5-(OMe)3C6H2), 107.2 (C5 of pyrimidinyl), 127.4 (C3/C5 of Ph), 127.6 (C4 of Ph), 133.1 (C1 of 3,4,5-(OMe)3C6H2), 135.3 (C4 of 3,4,5-(OMe)3C6H2), 135.5 (C2/C6 of Ph), 136.3 (C1 of Ph), 151.5 (C3/C5 of 3,4,5-(OMe)3C6H2), 153.2 (C4 of pyrimidinyl), 160.4 (C2 of pyrimidinyl), 163.2 (C1 of pyrimidinyl) |
3 | 0.89 (t, J = 7.6 Hz, 6H, 2 Me), 1.30 (sextet, J = 7.6 Hz, 4H, 2 MeCH2), 1.49 (quintet, J = 7.6 Hz, 4H, 2 MeCH2CH2), 1.69 (t, J = 7.6 Hz, 4H, 2 MeCH2CH2CH2), 3.30 (s, exch., 2H, 2 NH), 3.54 (s, 4H, 2 CH2), 3.63 (s, 6H, 2 OMe), 3.74 (s, 12H, 4 OMe), 6.11 (s, exch., 4H, 2 NH2), 6.58 (s, 4H, 3,4,5-(OMe)3C6H2), 7.51 (s, 2H, pyrimidinyl) | 14.2 (Me), 16.5 (SnCH2), 26.1 (SnCH2CH2), 28.1 (MeCH2), 33.3 (CH2), 56.3 (OMe), 60.4 (OMe), 106.4 C2/C6 of 3,4,5-(OMe)3C6H2), 107.0 (C5 of pyrimidinyl), 135.8 (C1 of 3,4,5-(OMe)3C6H2), 136.3 (C4 of 3,4,5-(OMe)3C6H2), 150.0 (C3/C5 of 3,4,5-(OMe)3C6H2), 153.2 (C4 of pyrimidinyl), 161.2 (C2 of pyrimidinyl), 163.1 (C1 of pyrimidinyl) |
PVC Additive | Rq Reduction (Fold) | Reference |
---|---|---|
Trimethoprim–tin complexes | 11.3 | [current work] |
Naproxen–tin complexes | 5.2 | [50] |
2-(4-Isobutylphenyl)propanoate-nickel complexes | 6.3 | [51] |
Carvedilol–tin complexes | 6.4 | [36] |
Furosemide–tin complexes | 6.6 | [52] |
Valsartan–tin complexes | 7.4 | [53] |
Telmisartan–tin complexes | 9.4 | [54] |
Ciprofloxacin–tin complexes | 16.6 | [55] |
4-(Benzylideneamino)benzenesulfonamide–tin complexes | 18.4 | [56] |
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Yaseen, A.A.; Yousif, E.; Al-Tikrity, E.T.B.; El-Hiti, G.A.; Kariuki, B.M.; Ahmed, D.S.; Bufaroosha, M. FTIR, Weight, and Surface Morphology of Poly(vinyl chloride) Doped with Tin Complexes Containing Aromatic and Heterocyclic Moieties. Polymers 2021, 13, 3264. https://doi.org/10.3390/polym13193264
Yaseen AA, Yousif E, Al-Tikrity ETB, El-Hiti GA, Kariuki BM, Ahmed DS, Bufaroosha M. FTIR, Weight, and Surface Morphology of Poly(vinyl chloride) Doped with Tin Complexes Containing Aromatic and Heterocyclic Moieties. Polymers. 2021; 13(19):3264. https://doi.org/10.3390/polym13193264
Chicago/Turabian StyleYaseen, Anaheed A., Emad Yousif, Emaad T. B. Al-Tikrity, Gamal A. El-Hiti, Benson M. Kariuki, Dina S. Ahmed, and Muna Bufaroosha. 2021. "FTIR, Weight, and Surface Morphology of Poly(vinyl chloride) Doped with Tin Complexes Containing Aromatic and Heterocyclic Moieties" Polymers 13, no. 19: 3264. https://doi.org/10.3390/polym13193264