Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis of Cresol-Based Benzoxazines
2.2. Characteristics of Products
2.2.1. Fourier Transform Infrared Spectroscopy
2.2.2. Nuclear Magnetic Resonance
2.2.3. Differential Scanning Calorimetry
2.2.4. Thermogravimetric Analysis
2.2.5. Headspace Coupled with Gas Chromatography Analysis
2.3. Composite Preparation for Abrasion Tests
2.4. Abrasion Tests
3. Results and Discussion
3.1. Fourier Transform Infrared Spectroscopy
3.2. Nuclear Magnetic Resonance
3.3. Differential Scanning Calorimetry
3.4. Thermogravimetric Analysis
3.5. Abrasion Tests
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Benzoxazine | Substrates | ||
---|---|---|---|
Cresol | Amine | Aldehyde | |
oC-A | o-Cresol | Aniline | Formaldehyde |
mC-A | m-Cresol | ||
pC-A | p-Cresol | ||
oC-pT | o-Cresol | p-Toluidine | |
mC-pT | m-Cresol | ||
pC-pT | p-Cresol |
Wavenumber (cm−1) | Vibrations | |||||
---|---|---|---|---|---|---|
oC-A | mC-A | pC-A | oC-pT | mC-pT | pC-pT | |
690 | 690 | 690 | 657 | 763 | 663 | bending C–Har. |
757 | 752 | 752 | 754 | 736 | ||
943 | 950 | 945 | 939 | 946 | 941 | –O–C–N– |
1217 | 1247 | 1228 | 1242 | 1253 | 1220 | stretching C–O–C |
1480 | 1498 | 1496 | 1467 | 1512 | 1498 | stretching C=Car. |
1608 | 1589 | 1585 | 1602 | 1585 | 1612 | |
2893 | 2893 | 2900 | 2914 | 2904 | 2912 | stretching C–Halif. |
3040 | 3062 | 3004 | 3070 | 3014 | 3014 | stretching C–Har. |
Chemical Shift (ppm) | Hydrogen Atoms Corresponding to Individual Chemical Shifts | |||||
---|---|---|---|---|---|---|
oC-A | mC-A | pC-A | oC-pT | mC-pT | pC-pT | |
2.33 | 2.35 | 2.32 | 2.26; 2.34 | 2.30; (x2) | 2.29; 2.31 | isolated -CH3 groups |
4.69 | 4.66 | 4.64 | 4.64 | 4.59 | 4.59 | methylene bridge from oxazine ring Ar-CH2-N- |
5.46 | 5.41 | 5.38 | 5.41 | 5.35 | 5.34 | methylene bridge from oxazine ring -O-CH2-N- |
6.87–7.37 | 6.74–7.36 | 6.78–7.26 | 6.85–7.15 | 6.60–7.11 | 6.74–7.12 | signals from protons of aromatic rings |
Chemical Shift (ppm) | Carbon Atoms Corresponding to Individual Chemical Shifts | |||||
---|---|---|---|---|---|---|
oC-A | mC-A | pC-A | oC-pT | mC-pT | pC-pT | |
15.7 | 21.2 | 20.6 | 15.7; 20.6 | 20.5; 21.1 | 20.6; 20.7 | (s) isolated -CH3 groups from cresol and p-toluidine molecule |
50.4 | 50.2 | 50.5 | 50.7 | 50.4 | 50.7 | (s) methylene bridge from oxazine ring Ar-CH2-N- |
79.4 | 79.4 | 79.5 | 80.0 | 79.9 | 80.1 | (s) methylene bridge from oxazine ring -O-CH2-N- |
118.2–152.6 | 117.3–154.2 | 116.7–152.2 | 118.6–152.7 | 117.2–154.1 | 116.7–152.2 | (m) signals from protons of aromatic rings |
Analyzed Benzoxazine | Characteristic Heat Effect | |||||
---|---|---|---|---|---|---|
oC-A | mC-A | pC-A | oC-pT | mC-pT | pC-pT | |
240 | 209 | 210 | 235 | 238 | 202 | Onset temperature (°C) |
256 | 222 | 229 | 256 | 247 | 224 | Maximum peak temperature (°C) |
155.1 | 287.8 | 221.6 | 143.2 | 272.4 | 216.7 | Polymerization enthalpy (J/g) |
TGA Characteristic Temperatures of Benzoxazines | Specific Stages of TGA Analysis | |||||
---|---|---|---|---|---|---|
oC-A | mC-A | pC-A | oC-pT | mC-pT | pC-pT | |
166.1 | 156.0 | 168.6 | 147.8 | 189.4 | 145.4 | 5% mass loss (°C) |
192.3 | 194.5 | 195.1 | 187.7 | 208.8 | 180.7 | 10% mass loss (°C) |
243.7 | 378.7 | 372.2 | 240.1 | 380.4 | 342.5 | 50% mass loss (°C) |
10.5 | 21.2 | 16.6 | 8.4 | 18.8 | 10.9 | Char yield (900 °C) (%) |
oC-A | mC-A | pC-A | oC-pT | mC-pT | pC-pT | Resole (180 °C) | |
---|---|---|---|---|---|---|---|
Total VOC (mass %) | 4.0 ± 0.3 | 6.9 ± 0.4 | 4.1 ± 0.4 | 3.9 ± 0.2 | 2.9 ± 0.5 | 3.9 ± 0.3 | 12.7 ± 0.6 |
Sample | V (g/min) | V (mm/min) | MRR (g/min) | |||
---|---|---|---|---|---|---|
Value | ± | Value | ± | Value | ± | |
oC-A | 6.14 | 1.77 | 15.42 | 4.24 | 0.11 | 0.03 |
mC-A | 2.26 | 0.73 | 5.72 | 3.38 | 0.17 | 0.02 |
pC-A | 5.06 | 0.83 | 13.56 | 2.38 | 0.14 | 0.01 |
oC-pT | unable to test because of too brittle sample | |||||
mC-pT | unable to test because of too brittle sample | |||||
pC-pT | unable to test because of too brittle sample | |||||
Reference sample | 0.71 | 0.02 | 4.86 | 0.77 | 0.22 | 0.04 |
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Jamrozik, A.; Barczewski, M.; Framski, G.; Baranowski, D.; Jakubowska, P.; Klapiszewski, Ł.; Jesionowski, T.; Voelkel, A.; Strzemiecka, B. Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites. Materials 2020, 13, 2995. https://doi.org/10.3390/ma13132995
Jamrozik A, Barczewski M, Framski G, Baranowski D, Jakubowska P, Klapiszewski Ł, Jesionowski T, Voelkel A, Strzemiecka B. Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites. Materials. 2020; 13(13):2995. https://doi.org/10.3390/ma13132995
Chicago/Turabian StyleJamrozik, Artur, Mateusz Barczewski, Grzegorz Framski, Daniel Baranowski, Paulina Jakubowska, Łukasz Klapiszewski, Teofil Jesionowski, Adam Voelkel, and Beata Strzemiecka. 2020. "Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites" Materials 13, no. 13: 2995. https://doi.org/10.3390/ma13132995