Photoinitiators for UV CuringKey Products Selection Guide 2003
Ciba Specialty Chemicals
Coating Effects Value beyond chemistry
Typical physical Chemical class Chemical identity Appearance Freezing point (FP, °C) Specific UV/VIS
properties Melting point (MP, °C) gravity Absorption peaks
Photoinitiators Boiling point (BP, °C) (water = 1) (nm) in methanol
IRGACURE 184 �-Hydroxyketone 1-Hydroxy-cyclohexyl- white to off-white MP 45–49 °C 1.1–1.2 246, 280, 333
phenyl-ketone crystalline powder
IRGACURE 500 �-Hydroxyketone IRGACURE 184 (50 wt%), clear, pale yellow FP<0 °C 1.1 250, 332
Benzophenone (50 wt%) liquid recrystallization below 18°C
DAROCUR 1173 �-Hydroxyketone 2-Hydroxy-2-methyl-1- clear, light liquid at room temp. 1.1 245, 280, 331
phenyl-1-propanone yellow liquid MP 4°C, BP 80–81°C
IRGACURE 2959 �-Hydroxyketone 2-Hydroxy-1-[4-(2-hydroxyethoxy) off-white powder MP 86–90 °C 1.3 276
phenyl]-2-methyl-1-propanone
DAROCUR MBF Phenylglyoxylate Methylbenzoylformate clear liquid liquid at room temp. 1.2 255, 325
MP 17 °C
BP 246–248 °C
IRGACURE 754 Phenylglyoxylate oxy-phenyl-acetic acid 2-[2 oxo-2 light yellow liquid at room temp. 1.2 255, 325
phenyl-acetoxy-ethoxy]-ethyl ester liquid MP < -22 °C
and oxy-phenyl-acetic 2-
[2-hydroxy-ethoxy]-ethyl ester
IRGACURE 651 Benzyldimethyl-ketal Alpha, alpha-dimethoxy- white to light MP 64–67 °C 1.2 250, 340
alpha-phenylacetophenone yellow powder
IRGACURE 369 �-Aminoketone 2-Benzyl-2-(dimethylamino)-1-[4- slightly yellow MP 110–114 °C 1.2 233, 324
(4-morpholinyl) phenyl]-1-butanone powder
IRGACURE 907 �-Aminoketone 2-Methyl-1-[4-(methylthio)phenyl] white to light MP 70–75 °C 1.2 230, 304
-2-(4-morpholinyl)-1-propanone beige powder
IRGACURE 1300 �-Aminoketone IRGACURE 369 (30 wt%) + light yellow MP 55–60 °C 1.2 251, 323
IRGACURE 651 (70 wt%) powder
DAROCUR TPO Mono Acyl Diphenyl (2,4,6-trimethylbenzoyl)- light yellow MP 88–92 °C 1.2 295, 368, 380, 393
Phosphine (MAPO) phosphine oxide powder
DAROCUR 4265 MAPO/ DAROCUR TPO (50 wt%) + light yellow liquid at room temp. 1.1 240, 272, 380
�-Hydroxyketone DAROCUR 1173 (50 wt%) viscous liquid
IRGACURE 819 Bis Acyl Phosphine Phosphine oxide, phenyl bis light yellow MP 127–133 °C 1.2 295, 370
(BAPO) (2,4,6-trimethyl benzoyl) powder
IRGACURE 819DW BAPO Dispersion IRGACURE 819 (45% active) light yellow liquid dispersion at 1.1 295, 370
dispersed in water liquid room temp.
IRGACURE 2022 BAPO/ IRGACURE 819 (20 wt%) + light yellow liquid at room temp. 1.1 246, 282, 370
�-Hydroxyketone DAROCUR 1173 (80 wt%) liquid
IRGACURE 2100 Phosphine oxide – light yellow liquid at room temp. 1.1 275, 370
viscous liquid
IRGACURE 784 Metallocene Bis (eta 5-2,4-cyclopentadien-1-yl) orange powder MP 160–170 °C > 1 398, 470
Bis [2,6-difluoro-3-(1H-pyrrol-1-yl)
phenyl]titanium
IRGACURE 250 Iodonium salt Iodonium, (4-methylphenyl) yellow to brownish 75% solution 1.5 242
[4-(2-methylpropyl) phenyl]-, liquid liquid at room temp.
hexafluorophosphate(1-) Storage below 30°C.
Photoinitiator Acetone n-Butyl IBOA IDA PEA HDDA TrPGDA TMPTA TMPEOTA DAROCUR
(Solubility, Weight %) Acetate 1173
IRGACURE 184 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 500 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
DAROCUR 1173 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 2959 19 3 5 5 5 10 20 5 5 35
DAROCUR MBF > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 754 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 651 > 50 > 50 40 30 > 50 40 25 > 50 45 > 50
IRGACURE 369 17 11 10 5 15 10 6 5 5 25
IRGACURE 907 > 50 35 35 25 45 35 22 25 20 > 50
IRGACURE 1300 > 50 45 > 50 35 > 50 > 50 35 25 25 > 50
DAROCUR TPO 47 25 15 7 34 22 16 14 13 > 50
DAROCUR 4265 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 819 14 6 5 5 15 5 5 5 > 5 30
IRGACURE 2022 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 2100 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50
IRGACURE 784 30 10 5 NA 15 10 5 5 NA 7
IBOA = isobornyl acrylate; IDA = isodecyl acrylate; PEA = 2-phenoxyethyl acrylate; HDDA = hexane diol diacrylate;TrPGDA = tripropyleneglycol diacrylate; TMPTA = trimethyolpropane triacrylate; TMPEOTA = trimethyolpropaneethoxytriacrylate.
Note: the solid photoinitiators were dissolved in liquid monomers (by weight ratio), heated in oven (50–60°C) and mixed. Samples were then kept at room temperature for 24 hours. If no recrystallization occurred, results were then recorded. Only 5% increments of photoinitiators were employed in the study. For example the solubility ofIRGACURE 907 in IBOA is 35% which means that its solubility is above 35% but below 40%.
IRG
AC
UR
E 18
4
IRG
AC
UR
E 50
0
DA
RO
CU
R 1
173
IRG
AC
UR
E 29
59
DA
RO
CU
R M
BF
IRG
AC
UR
E 75
4
IRG
AC
UR
E 20
22
IRG
AC
UR
E 21
00
IRG
AC
UR
E 78
4
300
250
200
150
100
50
0
Thermal Gravimetric Analysis (TGA in N2 at 10°C/min)
Tem
per
atur
e °C
15% wt loss
10% wt loss
5% wt loss
IRG
AC
UR
E 65
1
IRG
AC
UR
E 36
9
IRG
AC
UR
E 13
00
DA
RO
CU
R T
PO
DA
RO
CU
R 4
265
IRG
AC
UR
E 81
9
IRG
AC
UR
E 90
7
UPES Wood Top and
Intermediate Coat� ❍ ❍ � � � � �
Acrylated Wood Top
and Intermediate Coat� � � � ❍ ❍ ❍ � �
Wood Fillers ❍ ❍ � ❍ ❍ � ❍ �
Clear Top Coats on
Plastic and Metal� ❍ � ❍ ❍ ❍ ❍
Pigmented Top Coats
on Plastic and Metal� ❍ � � ❍ ❍ ❍ ❍ � � � � �
UV Powder Coatings � ❍ �
Dispersions for Facades � ❍ ❍
Adhesives � ❍ � ❍ ❍ ❍ ❍ � ❍ ❍ �
Glass Fiber Composites � ❍ ❍ � �
Gel Coats � ❍ ❍ � �
Etch Resists for PCB � � � ❍ �
Solder Masks ❍ � � ❍ �
Epoxy Resists ❍
Flexo Printing Plates � ❍ ❍
Laser Direct Imaging
Offset Printing Plates�
Offset Inks ❍ ❍ ❍ � � � ❍ ❍ � � �
Screen Inks � ❍ ❍ � � ❍ ❍ ❍ � � � �
Flexo Inks
Inkjet Inks❍ ❍ ❍ � � � ❍ ❍ � � � �
Over Print Varnishes � � � � � ❍ ❍ ❍
Cationic Polymerization �
Thick Sections
Polymerization❍ ❍ � � ❍
UV Stabilized
Clear Coatings� � ❍ ❍ ❍ ❍ ❍ � � � �
Water-based UV
Formulations� � ❍ � ❍ � ❍ ❍
Xi- and Xn-free
Applications� � � � � �
Low Volatility,
Low Odor� � � � � �
Surface cure, co-initiator
for pigment systems
� recommended application
❍ possible application
Through cure, pigmented systems
IRG
AC
UR
E 78
4
IRG
AC
UR
E 21
00
IRG
AC
UR
E 20
22
IRG
AC
UR
E 81
9 D
W
IRG
AC
UR
E 81
9
DA
RO
CU
R 4
265
DA
RO
CU
R T
PO
IRG
AC
UR
E 13
00
IRG
AC
UR
E 90
7
IRG
AC
UR
E 36
9
IRG
AC
UR
E 65
1
DA
RO
CU
R M
BF
IRG
AC
UR
E 29
59
DA
RO
CU
R 1
173
IRG
AC
UR
E 75
4
IRG
AC
UR
E 50
0
IRG
AC
UR
E 18
4
UV CuringApplications IR
GA
CU
RE
250
200 220 240 260 280 300 320 340
1.2
1.0
0.8
0.6
0.4
0.2
0.0
Key products, surface cure Absorption Spectra 0.001% (Acetonitrile) Wavelength (nm)A
bso
rban
ce
IRGACURE 184
DAROCUR 1173
IRGACURE 754
IRGACURE 2959
200 220 240 260 280 300 320 340 360 380
Key products, a-Amino Ketones Absorption Spectra 0.001% (Acetonitrile) Wavelength (nm)
Ab
sorb
ance
IRGACURE 1300
IRGACURE 907
IRGACURE 369
1.6
1.4
1.2
1.0
0.8
0.6
0.4
0.2
0.0
DAROCUR TPO
IRGACURE 2022
IRGACURE 2100
IRGACURE 819
300 320 340 360 380 400 420 440
3
0.5
1
2
2.5
1.5
0
Key products, through cure Absorption Spectra 0.1% (Acetonitrile) Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
DAROCUR 1173 % in Acetonitrile Wavelength (nm)A
bso
rban
ce
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 184 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 754 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 500 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 369 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 907 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 1300 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
200
3
2.5
2
1.5
1
0.5
0
220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 819 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
0.10 0.010 0.001
IRGACURE 784 % in 1-Methyl-2-pyrrolidone (NMP) Wavelength (nm)
Ab
sorb
ance
3.5
3
2.5
2
1.5
1
0.5
0
250 300 350 400 450 500 550 600
0.0
1.0
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500
IRGACURE 250 % in Acetonitrile Wavelength (nm)
Ab
sorb
ance
0.2
0.4
0.6
0.8
C
OOH
IRGACURE 184
PC
O O
DAROCUR TPO
C OH
O
OHO
CH3
CH3
IRGACURE 2959
C OH
O
CH3
CH3
DAROCUR 1173
C
O
DAROCUR BP
CC
O
O
OCH3
DAROCUR MBF
COH
O
C
O+
IRGACURE 500
C
O
O
O
CH3
H3C
IRGACURE 651
C
O
S
CH3
N O
CH3
CH3
IRGACURE 907
N C
O
NO
CH3
CH3
CH3
IRGACURE 369
N C
O
NOC
O
O
O+
CH3
CH3
CH3
CH3
H3C
IRGACURE 1300 F
TiF
N
F
F
N
IRGACURE 784
P
O O
C
O
C
IRGACURE 819 and IRGACURE 819 DW
C OH
O
+C P
O O CH3
CH3
DAROCUR 4265
Please note that Ciba® IRGACURETM and Ciba® DAROCURTM are registered trademarks of Ciba Specialty Chemicals Inc.
Chemical Structures
F
F F
FF P F
+
-
IRGACURE 250
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Edition 2003Copyright © 2003 Ciba Specialty Chemicals Inc. All rights reserved.All product names in capital letters are either registered or pending trademarks and property of Ciba Specialty Chemicals.
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g-48/2003 October, Printed in Switzerland
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