Phosphorus-Containing Silsesquioxane Derivatives as Additive or Reactive Components of Epoxy Resins
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Analytical Techniques
2.2.1. Nuclear Magnetic Resonance Spectroscopy (NMR)
2.2.2. Infrared Spectroscopy (FT-IR)
2.2.3. Thermogravimetric Analysis (TGA)
2.2.4. Scanning Electron Microscope and Energy-Dispersive X-ray Spectroscopy (SEM, EDS)
2.2.5. Differential Scanning Calorimetry (DSC)
2.2.6. Cone Calorimetry
2.2.7. Nanomechanical Analysis
2.2.8. Static Water Contact Angle (WCA)
2.3. Synthetic Procedures
2.3.1. Synthesis of Octakis[(3-glycidoxypropyl)dimethylsiloxy]octasilsesquioxane (8GS)
2.3.2. Synthesis of 10-Hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPA)
2.3.3. Synthesis of Phosphorus-Containing Silsesquioxanes (4P4GS and 8PS)
2.3.4. Epoxy Resin Samples Preparation
3. Results and Discussion
3.1. Silsesquioxanes Synthesis and Characterization
3.2. Scanning Electron Microscopy and Energy-Dispersive X-Ray Spectroscopy Measurements
3.3. Surface Properties
3.4. Mechanical Properties
3.5. TGA and DSC Measurements
3.6. Flammability
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample | E 652 (g) | IDA (g) | Modifier | Modifier Mass (g) |
---|---|---|---|---|
Ref. | 40 | 20 | - | - |
1%-8GS | 20.166 | 8GS | 0.4 | |
5%-8GS | 20.828 | 8GS | 2 | |
10%-8GS | 21.656 | 8GS | 4 | |
1%-4P4GS | 20.056 | 4P4GS | 0.4 | |
5%-4P4GS | 20.28 | 4P4GS | 2 | |
10%-4P4GS | 20.56 | 4P4GS | 4 | |
1%-8PS | 20 | 8PS | 0.4 | |
5%-8PS | 20 | 8PS | 2 | |
10%-8PS | 20 | 8PS | 4 |
Sample | Calculated Element Weight (%) | Measured Element Weight (%) | Error (%) | |||
---|---|---|---|---|---|---|
Si | P | Si | P | Si | P | |
Ref | - | - | - | - | - | - |
1%-8GS | 0.15 | - | 0.19 | 0.01 | 7.05 | 55.63 |
5%-8GS | 0.74 | - | 0.91 | 0.01 | 3.59 | 56.14 |
10%-8GS | 1.42 | - | 1.69 | 0.01 | 3.13 | 55.94 |
1%-4P4GS | 0.1 | 0.03 | 0.07 | 0.02 | 18.71 | 54.88 |
5%-4P4GS | 0.51 | 0.14 | 0.4 | 0.1 | 4.86 | 12.84 |
10%-4P4GS | 0.97 | 0.27 | 0.88 | 0.25 | 3.48 | 6.61 |
1%-8PS | 0.08 | 0.04 | 0.12 | 0.07 | 11.79 | 19.81 |
5%-8PS | 0.38 | 0.21 | 0.3 | 0.17 | 5.21 | 8.55 |
10%-8PS | 0.74 | 0.41 | 0.73 | 0.41 | 3.68 | 4.99 |
Sample | WCA (°) |
---|---|
Ref | 77.1 ± 3.4 |
1%-8GS | 81 ± 4.69 |
5%-8GS | 81.7 ± 1.93 |
10%-8GS | 80.2 ± 3.9 |
1%-4P4GS | 82.7 ± 2.55 |
5%-4P4GS | 81 ± 0.97 |
10%-4P4GS | 81.3 ± 1.75 |
1%-8PS | 82.5 ± 0.8 |
5%-8PS | 79.7 ± 1.04 |
10%-8PS | 50.1 ± 3.31 |
Sample | Modulus (500–1500 nm) | Hardness (500–1500 nm) | ||
---|---|---|---|---|
Mean (MPa) | Std. Dev. (%) | Mean (MPa) | Std. Dev. (%) | |
Ref. | 3064 | 1.6 | 127 | 1.7 |
1%-8GS | 3555 | 1.6 | 163 | 1.7 |
5%-8GS | 3149 | 1.4 | 136 | 1.7 |
10%-8GS | 3149 | 0.9 | 137 | 1.2 |
1%-4P4GS | 3071 | 1.2 | 129 | 1.4 |
5%-4P4GS | 3112 | 0.8 | 130 | 2.8 |
10%-4P4GS | 3086 | 1 | 132 | 1.1 |
1%-8PS | 3127 | 0.6 | 137 | 1.1 |
5%-8PS | 3210 | 1.8 | 139 | 2.1 |
10%-8PS | 3230 | 0.7 | 145 | 0.9 |
Sample | Mass Loss Temperature (°C) | Char Yield @ 800 °C (%) | ||||||
---|---|---|---|---|---|---|---|---|
T1% | T5% | T10% | T20% | T40% | T60% | T80% | ||
Ref. | 104.2 | 155.4 | 201.3 | 325.7 | 350.8 | 368.8 | 401.6 | 6.6 |
1%-8GS | 96.7 | 146.8 | 190.3 | 325.4 | 352 | 369.7 | 404.4 | 7.6 |
5%-8GS | 100.1 | 143.8 | 189 | 329.1 | 356.3 | 377.7 | 424.9 | 10.9 |
10%-8GS | 111 | 153.3 | 199.6 | 320 | 355.1 | 386.6 | 469.2 | 14.1 |
1%-4P4GS | 104 | 151.7 | 196 | 326.3 | 351.7 | 368.8 | 401.5 | 6.9 |
5%-4P4GS | 105.6 | 152.4 | 198.2 | 318.5 | 344.6 | 364 | 400 | 8 |
10%-4P4GS | 101.3 | 149.3 | 194.9 | 315.1 | 342.2 | 363.4 | 412.1 | 10.2 |
1%-8PS | 110.7 | 161.4 | 208.9 | 321.8 | 347.6 | 366.9 | 400.2 | 7.2 |
5%-8PS | 104.1 | 152.3 | 197.6 | 317.8 | 343.2 | 361.9 | 392.6 | 7.8 |
10%-8PS | 106.6 | 154.9 | 202.9 | 309.2 | 334.7 | 353.9 | 392.2 | 8.7 |
Sample | Step I | Step II | ||||||
---|---|---|---|---|---|---|---|---|
Range (°C) | Change (%) | Tmax (°C) | Rate (%K−1) | Range (°C) | Change (%) | Tmax (°C) | Rate (%K−1) | |
Ref. | 41–270 | 14.1 | 176 | 0.11 | 270–600 | 78.7 | 353.8 | 1.14 |
1%-8GS | 52–260 | 13.6 | 161.3 | 0.12 | 260–600 | 77.7 | 362.8 | 1.15 |
5%-8GS | 44–255 | 12.7 | 150.5 | 0.12 | 255–600 | 75.9 | 361.8 | 0.99 |
10%-8GS | 40–255 | 13.8 | 161.3 | 0.12 | 255–600 | 71.1 | 345.7 | 0.72 |
1%-4P4GS | 46–263 | 13.5 | 167.8 | 0.12 | 263–600 | 79 | 356.7 | 1.26 |
5%-4P4GS | 41–260 | 13.9 | 167.7 | 0.11 | 260–600 | 77.5 | 354.5 | 1 |
10%-4P4GS | 40–250 | 12.8 | 161.3 | 0.12 | 250–650 | 76.6 | 349.8 | 1 |
1%-8PS | 50–270 | 14.2 | 180.5 | 0.11 | 270–600 | 78.1 | 359.8 | 1.1 |
5%-8PS | 45–255 | 13.2 | 167.2 | 0.12 | 255–600 | 78.4 | 350.8 | 1.1 |
10%-8PS | −250 | 13.7 | 170.2 | 0.11 | 250–600 | 77.3 | 346.2 | 1.1 |
Sample | Mass Loss Temperature (°C) | Residue @ 800 °C (%) | ||||||
---|---|---|---|---|---|---|---|---|
T1% | T5% | T10% | T20% | T40% | T60% | T80% | ||
Ref | 113.5 | 171.3 | 222.8 | 318.7 | 343.3 | 363.5 | 490 | 0.96 |
1%-8GS | 104.7 | 153.1 | 197.8 | 312.8 | 346.4 | 374.4 | 457 | 0.44 |
5%-8GS | 94.7 | 143.2 | 184.3 | 305.8 | 350.7 | 387.1 | 543.9 | 0.59 |
10%-8GS | 104.3 | 148.6 | 191.6 | 309.8 | 355.8 | 400 | 561.9 | 2 |
1%-4P4GS | 106.1 | 157 | 202.4 | 312.3 | 345 | 369.7 | 431.3 | 0 |
5%-4P4GS | 105.2 | 154.4 | 198.3 | 308.1 | 340.4 | 364.4 | 497.8 | 0.8 |
10%-4P4GS | 98.8 | 147.5 | 190.3 | 301.3 | 339.6 | 368.7 | 542 | 1.48 |
1%-8PS | 109.4 | 158 | 202.7 | 312.3 | 343.9 | 371 | 436.2 | 0.23 |
5%-8PS | 99 | 147.4 | 190.2 | 300.7 | 337.8 | 359.7 | 501.2 | 0 |
10%-8PS | 102.2 | 149.9 | 197.2 | 297.6 | 333.5 | 361.3 | 537.7 | 2.73 |
Sample | Step I | Step II | Step III | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
Range (°C) | Change (%) | Tmax (°C) | Rate (%K−1) | Range (°C) | Change (%) | Tmax (°C) | Rate (%K−1) | Range (°C) | Change (%) | Tmax (°C) | Rate (%K−1) | |
Ref. | 55–260 | 13.4 | 196.8 | 0.1 | 260–470 | 65.6 | 333.5 | 1.14 | 470–680 | 20.1 | 569.5 | 0.2 |
1%-8GS | 45–257 | 14 | 169.3 | 0.12 | 257–503 | 68.6 | 341.5 | 0.9 | 503–738 | 17 | 587.5 | 0.14 |
5%-8GS | 30–246 | 14.1 | 158 | 0.13 | 246–489 | 61.7 | 350.5 | 0.67 | 489–733 | 23.5 | 593.8 | 0.18 |
10%-8GS | 30–247 | 13.7 | 159.3 | 0.12 | 247–498 | 61 | 343 | 0.66 | 498–746 | 23.3 | 606.3 | 0.17 |
1%-4P4GS | 42–257 | 14 | 177 | 0.11 | 257–514 | 72.4 | 348.2 | 0.97 | 514–714 | 13.6 | 600.2 | 0.13 |
5%-4P4GS | 41–251 | 14 | 172.8 | 0.12 | 251–483 | 65.3 | 336.8 | 1 | 483–734 | 19.9 | 580.3 | 0.16 |
10%-4P4GS | 47–240 | 13.6 | 162 | 0.12 | 240–483 | 62.9 | 335.7 | 0.8 | 483–754 | 21.9 | 604.5 | 0.16 |
1%-8PS | 30–255 | 13.9 | 175.3 | 0.12 | 255–413 | 71.4 | 335.3 | 0.9 | 513–733 | 14.5 | 612.3 | 0.13 |
5%-8PS | 52–243 | 13.9 | 164.7 | 0.12 | 243–479 | 65.1 | 344.7 | 0.96 | 479–743 | 21 | 589.7 | 0.16 |
10%-8PS | 57–233 | 12.6 | 160.2 | 0.11 | 233–480 | 64 | 335.3 | 0.92 | 480–736 | 20.4 | 591.7 | 0.15 |
Sample | Tg (°C) |
---|---|
Ref. | 43.93 |
1%-8GS | 44.44 |
10%-8GS | 42.24 |
1%-4P4GS | 45.91 |
10%-4P4GS | 41.47 |
1%-8PS | 43.57 |
10%-8PS | 39.88 |
Sample | TTI (s) | TTF (s) | pHRR (kWm−2) | MARHE (kWm−2) | FIGRA (kWm−2s−1) | THR (MJm−2) | SEA (m2kg−1) | TSR (m2m−2) |
---|---|---|---|---|---|---|---|---|
Ref. | 63 | 393 | 854.5 | 405.9 | 3.9 | 139.4 | 842.2 | 4733.4 |
1%-8GS | 65 | 380 | 932 | 399.2 | 4.1 | 138.2 | 796.7 | 4435 |
5%-8GS | 56 | 485 | 678.2 | 372.5 | 2.9 | 143.1 | 832.4 | 4844 |
10%-8GS | 58 | 455 | 566 | 348.8 | 2.1 | 144.6 | 932.7 | 5538.4 |
1%-4P4GS | 51 | 470 | 861.3 | 412.7 | 4.1 | 141.1 | 822.1 | 4527.6 |
5%-4P4GS | 60 | 402 | 845.3 | 436.7 | 4.3 | 143.7 | 755.1 | 4480.1 |
10%-4P4GS | 67 | 528 | 658.5 | 349.8 | 2.8 | 143.3 | 833.4 | 4970.4 |
1%-8PS | 60 | 425 | 931.1 | 413.1 | 4.5 | 137.9 | 790.8 | 4309.9 |
5%-8PS | 57 | 526 | 869.2 | 430.8 | 4.3 | 153.2 | 830.4 | 4574.1 |
10%-8PS | 60 | 438 | 776.6 | 399.7 | 3.8 | 134.9 | 835.6 | 4529.4 |
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Szołyga, M.; Dutkiewicz, M.; Nowicki, M.; Sałasińska, K.; Celiński, M.; Marciniec, B. Phosphorus-Containing Silsesquioxane Derivatives as Additive or Reactive Components of Epoxy Resins. Materials 2020, 13, 5373. https://doi.org/10.3390/ma13235373
Szołyga M, Dutkiewicz M, Nowicki M, Sałasińska K, Celiński M, Marciniec B. Phosphorus-Containing Silsesquioxane Derivatives as Additive or Reactive Components of Epoxy Resins. Materials. 2020; 13(23):5373. https://doi.org/10.3390/ma13235373
Chicago/Turabian StyleSzołyga, Mariusz, Michał Dutkiewicz, Marek Nowicki, Kamila Sałasińska, Maciej Celiński, and Bogdan Marciniec. 2020. "Phosphorus-Containing Silsesquioxane Derivatives as Additive or Reactive Components of Epoxy Resins" Materials 13, no. 23: 5373. https://doi.org/10.3390/ma13235373