High-Performance Photoinitiating Systems for LED-Induced Photopolymerization
Abstract
:1. Introduction
2. Dye-Based PISs
2.1. Carbazole-Based Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
C1 | λmax ~ 364 εmax ~ 11,750 ε405nm ~ 2600 | [59] |
C2 | λmax ~ 374 εmax ~ 11,180 ε405nm ~ 5200 | [59] |
C3 | λmax ~ 364 εmax ~ 14,000 ε405nm ~ 2450 | [59] |
C4 | λmax ~ 388 εmax ~ 6000 ε405nm ~ 5200 | [59] |
A1 | λmax ~ 330 εmax ~ 8800 ε405nm ~ 1350 | [60] |
A2 | λmax ~ 340 εmax ~ 40,000 ε405nm ~ 7800 | [60] |
A3 | λmax ~ 333 εmax ~ 33,000 ε405nm ~ 5700 | [60] |
A4 | λmax ~ 349 εmax ~ 18,000 ε405nm ~ 3300 | [60] |
A3–1 | λmax ~ 350 εmax ~ 49,000 | [61] |
A3–2 | λmax ~ 360 εmax ~ 53,000 | [61] |
A3–3 | λmax ~ 415 εmax ~ 29,000 | [61] |
A3–4 | λmax ~ 394 εmax ~ 29,000 | [61] |
2.2. Triphenylamine-Based Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
CDM2 | λmax ~ 467 εmax ~ 77,190 ε460nm ~ 75,490 ε520nm ~ 12,000 | [62] |
Dye3 | λmax ~ 352 εmax ~ 26,610 ε405nm ~ 4110 | [63] |
Dye4 | λmax ~ 357 εmax ~ 17,700 ε405nm ~ 4740 | [63] |
HABI1 | λmax ~ 383 εmax ~ 6600 | [64] |
HABI2 | λmax ~ 385 εmax ~ 12,100 | [64] |
HABI3 | λmax ~ 384 εmax ~ 14,800 | [64] |
PI-PAG | λmax ~ 381 εmax ~ 23,200 ε365nm ~ 19,200 ε405nm ~ 14,900 | [65] |
2.3. Naphthalimide-Based Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
NDP1 | λmax ~ 421 εmax ~ 620 ε405nm ~560 | [71] |
NDP2 | λmax ~ 417 εmax ~ 5600 ε405nm ~ 5100 | [71] |
NDP3 | λmax ~ 334 εmax ~ 13,100 | [71] |
NDP4 | λmax ~ 426 εmax ~ 9800 ε405nm ~ 8200 | [71] |
NDP5 | λmax ~ 340 εmax ~ 17,800 | [71] |
NDP6 | λmax ~ 431 εmax ~ 17,400 ε405nm ~ 12,100 | [71] |
NDP7 | λmax ~ 440 εmax ~ 11,300 ε405nm ~ 8800 | [71] |
NDA1 | λmax ~ 416 εmax ~ 4600 ε405nm ~ 4300 ε455nm ~ 1200 | [72] |
NDA2 | λmax ~ 431 εmax ~ 14,600 ε405nm ~ 10,300 | [72] |
NDA3 | λmax ~ 387 εmax ~ 18,000 ε405nm ~ 13,000 ε455nm ~ 1000 | [72] |
NDA4 | λmax ~ 439 εmax ~ 16,300 ε405nm ~ 9300 | [72] |
NAS1 | λmax ~ 389 ε405nm ~ 10,100 | [73] |
NAS2 | λmax ~ 385 ε405nm ~ 9300 | [73] |
NAS3 | λmax ~ 340 ε405nm ~ 6100 | [73] |
NAS4 | λmax ~ 387 ε405nm ~ 12,800 | [73] |
NAS5 | λmax ~ 391 ε405nm ~ 12,600 | [73] |
NAS6 | λmax ~ 395 ε405nm ~ 11,700 | [73] |
Naphth-Iod | λmax ~ 340 | [75] |
2.4. Coumarine-Based Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
CoumA | λmax ~ 421 εmax ~ 35,200 ε405nm ~ 30,600 | [77] |
CoumB | λmax ~ 405 εmax ~ 28,100 ε405nm ~ 28,100 | [77] |
7M-P | λmax ~ 350 εmax ~ 20,440 ε365nm ~ 16,660 ε405nm ~ 280 | [78] |
7M-CN-P | λmax ~ 352 εmax ~ 18,930 ε365nm ~ 16,800 ε405nm ~ 360 | [78] |
7M-NO2-P | λmax ~ 351 εmax ~ 19,100 ε365nm ~ 16,770 ε405nm ~ 460 | [78] |
7M-Me-P | λmax ~ 349 εmax ~ 22,700 ε365nm ~ 18,200 ε405nm ~ 240 | [78] |
7M-iPr-P | λmax ~ 350 εmax ~ 18,440 ε365nm ~ 14,960 ε405nm ~ 220 | [78] |
2.5. Chalcone-Based Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
Chalcone 1 | λmax ~ 425 εmax ~ 8930 ε405nm ~ 7450 | [85] |
Chalcone 2 | λmax ~ 369 εmax ~ 20,520 ε405nm ~ 4830 | [85] |
Chalcone 3 | λmax ~ 369 εmax ~ 17,740 ε405nm ~ 5960 | [85] |
Chalcone 4 | λmax ~ 408 εmax ~ 23,900 ε405nm ~ 23,580 | [85] |
Chalcone 5 | λmax ~ 370 εmax ~ 21,100 ε405nm ~ 7020 | [85] |
Chalcone 6 | λmax ~ 360 εmax ~ 24,900 ε405nm ~ 3530 | [85] |
Chalcone 7 | λmax ~ 405 εmax ~ 18,740 ε405nm ~ 18,740 | [85] |
Chalcone 8 | λmax ~ 430 εmax ~ 7990 ε405nm ~ 6760 | [85] |
Chalcone 9 | λmax ~ 428 εmax ~ 8540 ε405nm ~ 7200 | [85] |
Chalcone 10 | λmax ~ 430 εmax ~ 10,500 ε405nm ~ 9020 | [85] |
Bis-chalcone 1 | λmax ~ 370 εmax ~ 21,900 ε405nm ~ 12,740 | [86] |
Bis-chalcone 2 | λmax ~ 380 εmax ~ 28,200 ε405nm ~ 19,730 | [86] |
Bis-chalcone 3 | λmax ~ 332 εmax ~ 18,200 ε405nm ~ 4420 | [86] |
Bis-chalcone 4 | λmax ~ 369 εmax ~ 4980 ε405nm ~ 2550 | [86] |
Bis-chalcone 5 | λmax ~ 347 εmax ~ 23,100 ε405nm ~ 6800 | [86] |
Bis-chalcone 6 | λmax ~ 364 εmax ~ 22,700 ε405nm ~ 10,070 | [86] |
Bis-chalcone 7 | λmax ~ 430 εmax ~ 38,900 ε405nm ~ 26,420 | [86] |
Bis-chalcone8 | λmax ~ 330 εmax ~ 19,800 ε405nm ~ 2960 | [86] |
Bis-chalcone 9 | λmax ~ 370 εmax ~ 24,600 ε405nm ~ 13,670 | [86] |
Bis-chalcone 10 | λmax ~ 350 εmax ~ 49,300 ε405nm ~ 2220 | [86] |
3. Type Ⅱ Photoinitiators
3.1. Benzophenone Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
BP | λmax ~ 253 εmax ~ 22,000 ε363nm ~250 | [104,107] |
BPB | λmax ~ 290 εmax ~ 14,610 | [100] |
Py_BP | λmax ~ 348 εmax ~ 26,000 ε405nm ~1400 | [103] |
Py_BP5 | λmax ~ 395 εmax ~ 4400 | [104] |
BPND | λmax ~ 431 εmax ~ 15,700 ε405nm ~ 10,900 ε470nm ~ 5700 | [106] |
BP1 | λmax ~ 369 εmax ~ 22,300 | [107] |
BP2 | λmax ~ 341 εmax ~ 13,300 | [107] |
BP3 | λmax ~ 368 εmax ~ 20,200 | [107] |
BP4 | λmax ~ 369 εmax ~ 42,900 | [107] |
BP5 | λmax ~ 374 εmax ~ 27,800 | [107] |
A4 | λmax ~ 349 εmax ~ 18,000 | [108] |
A3–1 | λmax ~ 350 εmax ~ 49,000 | [108] |
A3–2 | λmax ~ 360 εmax ~ 53,000 | [108] |
BPN | λmax ~ 400 εmax ~ 43,700 ε405nm ~ 42,400 | [109] |
BPC | λmax ~ 342 εmax ~ 18,600 ε365nm ~ 6000 | [110] |
BPC1 | λmax ~ 334 εmax ~ 13,910 ε365nm ~ 3270 | [111] |
BPC2 | λmax ~ 325 εmax ~ 13,900 ε365nm ~ 2210 | [111] |
BPC3 | λmax ~ 334 εmax ~ 13,350 ε365nm ~ 3460 | [111] |
BPC4 | λmax ~ 325 εmax ~ 12,400 ε365nm ~ 2170 | [111] |
BT1 | λmax ~ 359 εmax ~ 21,000 ε405nm ~ 1800 | [112] |
BT2 | λmax ~ 373 εmax ~ 27,200 ε405nm ~ 5000 | [112] |
BT3 | λmax ~ 370 εmax ~ 41,600 ε405nm ~ 6100 | [112] |
BT4 | λmax ~ 377 εmax ~ 21,700 ε405nm ~ 6700 | [112] |
3.2. Thioxanthone Photoinitiators
Chemical Structures | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
TX | λmax ~ 380 εmax ~ 5300 | [131] |
ITX | λmax ~ 386 εmax ~ 6500 ε395nm ~ 3900 | [132] |
TX-C | λmax ~ 434 εmax ~ 2010 | [118,119] |
TX-A | λmax ~ 368 εmax ~ 14,000 | [120,121] |
TX-NPG | λmax ~ 392,583 ε392nm ~ 1670 ε583nm ~ 440 | [124] |
TX-MPM | λmax ~ 410 εmax ~ 4390 | [126] |
TX-1 | λmax ~ 438 εmax ~ 4400 | [127] |
TX-2 | λmax ~ 438 εmax ~ 4800 | [127] |
TX-3 | λmax ~ 444 εmax ~ 4100 | [127] |
TX-MPA | λmax ~ 407 εmax ~ 3610 | [128] |
TX-2DPA | λmax ~ 478 εmax ~ 3400 ε405nm ~ 2000 | [129] |
TX-2CBZ | λmax ~ 396 εmax ~ 7900 ε405nm ~ 5900 | [129] |
TX-2PTZ | λmax ~ 305,415 ε305nm ~ 2400 ε405nm ~ 2600 | [129] |
4. Type Ⅰ Photoinitiators
4.1. Oxime Ester Photoinitiators
Structure | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
O-3 | λmax ~ 436 εmax ~ 41,690 ε450nm ~ 37,450 | [136] |
O-3F | λmax ~ 436 εmax ~ 29,930 ε450nm ~ 26,630 | [136] |
O-3O | λmax ~ 436 εmax ~ 29,950 ε450nm ~ 26,620 | [136] |
O-4 | λmax ~ 433 εmax ~ 7680 ε450nm ~ 6790 | [136] |
DCCA | λmax ~ 436 εmax ~ 51,000 ε450nm ~ 45,000 | [138] |
OEC3–1 | λmax ~ 406 εmax ~ 51,000 ε450nm ~ 21,000 | [139] |
OEC3–2 | λmax ~ 405 εmax ~ 42,000 ε450nm ~ 17,000 | [139] |
OXE-B | λmax ~ 431 εmax ~ 33,000 ε405nm ~ 22,000 | [140] |
OXE-D | λmax ~ 431 εmax ~ 34,000 ε405nm ~ 22,500 | [140] |
OXE-E | λmax ~ 437 εmax ~ 28,500 ε405nm ~ 16,500 | [140] |
OXE-F | λmax ~ 437 εmax ~ 36,000 ε405nm ~ 21,000 | [140] |
OXE-G | λmax ~ 436 εmax ~ 31,500 ε405nm ~ 18,000 | [140] |
OXE-H | λmax ~ 435 εmax ~ 26,500 ε405nm ~ 17,000 | [140] |
OXE-I | λmax ~ 437 | [140] |
OXE-J | λmax ~ 441 εmax ~ 50,000 ε405nm ~ 25,000 | [140] |
OXE-K | λmax ~ 435 εmax ~ 31,000 ε405nm ~ 18,000 | [140] |
OXE1 | λmax ~ 350 εmax ~ 46,900 ε405nm ~ 1100 | [141] |
OXE2 | λmax ~ 357 εmax ~ 29,300 ε405nm ~ 4410 | [141] |
E-FBOXE-Me | λmax ~ 260 ε260nm ~ 17,980 ε395nm ~ 20 | [142] |
E-FBOXE-Ph | λmax ~ 262 ε260nm ~ 51,410 ε395nm ~ 50 | [142] |
OXE-EM | λmax ~ 374 εmax ~ 16,400 ε355nm ~ 12,500 | [143] |
OXE-IM | λmax ~ 374 εmax ~ 16,000 ε355nm ~ 12,800 | [143] |
OXE-EP | λmax ~ 374 εmax ~ 17,000 ε355nm ~ 13,200 | [143] |
OXE-IP | λmax ~ 374 εmax ~ 16,600 ε355nm ~ 13,000 | [143] |
OXE-M | λmax ~ 369 εmax ~ 13,000 ε405nm ~ 4100 | [147] |
OXE-P | λmax ~ 368 εmax ~ 13,800 ε405nm ~ 4100 | [147] |
OXE-V | λmax ~ 369 εmax ~ 12,400 ε405nm ~ 3900 | [147] |
D1 | λmax ~ 372 εmax ~ 13,000 ε405nm ~ 5200 | [148] |
D2 | λmax ~ 372 εmax ~ 14,000 ε405nm ~ 5400 | [148] |
4.2. Acylphosphine Oxide Photoinitiators
Structure | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
TPO | λmax ~ 380 εmax ~ 570 ε385nm ~ 510 ε420nm ~ 20 | [150] |
TPO-L | λmax ~ 383 ε395nm ~ 130 | [149] |
BAPO | λmax ~ 384 ε395nm ~ 660 | [149] |
ADPO-1 | λmax ~ 373 ε395nm ~ 300 | [149] |
ADPO-2 | λmax ~ 379 ε395nm ~ 390 | [149] |
ADPO-3 | λmax ~ 382 ε395nm ~ 1060 | [149] |
ADPO-4 | λmax ~ 386 ε395nm ~ 160 | [149] |
ADPO-5 | λmax ~ 405 ε395nm ~ 26,600 | [149] |
ADPO-6 | λmax ~ 405 | [149] |
ADPO-7 | λmax ~ 384 | [149] |
DEAPO | λmax ~ 386 εmax ~ 43,810 ε385nm ~ 43,800 ε420nm ~ 5950 | [150] |
ETPO | λmax ~ 366 εmax ~ 13,830 ε395nm ~ 4530 ε405nm ~ 2270 | [151] |
ALPO | λmax ~ 362 εmax ~ 12,200 ε395nm ~ 2890 ε405nm ~ 1300 | [151] |
4.3. Other Type I photoinitiators
Structure | Absorption Properties (λ/nm, εmax/M−1 cm−1) | Refs. |
---|---|---|
Ivocerin® | λmax ~ 408 εmax ~ 711 ε385nm ~ 505 | [157] |
tetrakis(2,4,6-trimethylbenzoyl)stannane | [152] | |
NPIE1 | λmax ~ 397 εmax ~ 16,000 ε405nm ~ 15,000 | [156] |
NPIE2 | λmax ~ 398 εmax ~ 15,200 ε405nm ~ 14,400 | [156] |
NPIE3 | λmax ~ 398 εmax ~ 15,600 ε405nm ~ 14,900 | [156] |
NPIE4 | λmax ~ 397 εmax ~ 14,100 ε405nm ~ 13,100 | [156] |
NPIE5 | λmax ~ 397 εmax ~ 15,300 ε405nm ~ 14,500 | [156] |
NPIE6 | λmax ~ 397 εmax ~ 14,700 ε405nm ~ 13,800 | [156] |
NPIE7 | λmax ~ 397 εmax ~ 13,500 ε405nm ~ 12,800 | [156] |
NPIE8 | λmax ~ 397 εmax ~ 12,900 ε405nm ~ 12,000 | [156] |
NPIE9 | λmax ~ 397 εmax ~ 14,900 ε405nm ~ 14,000 | [156] |
5. Conclusions and Perspectives
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Liu, S.; Borjigin, T.; Schmitt, M.; Morlet-Savary, F.; Xiao, P.; Lalevée, J. High-Performance Photoinitiating Systems for LED-Induced Photopolymerization. Polymers 2023, 15, 342. https://doi.org/10.3390/polym15020342
Liu S, Borjigin T, Schmitt M, Morlet-Savary F, Xiao P, Lalevée J. High-Performance Photoinitiating Systems for LED-Induced Photopolymerization. Polymers. 2023; 15(2):342. https://doi.org/10.3390/polym15020342
Chicago/Turabian StyleLiu, Shaohui, Timur Borjigin, Michael Schmitt, Fabrice Morlet-Savary, Pu Xiao, and Jacques Lalevée. 2023. "High-Performance Photoinitiating Systems for LED-Induced Photopolymerization" Polymers 15, no. 2: 342. https://doi.org/10.3390/polym15020342