Photoinitiators for UV Curing

Ciba Specialty Chemicals
Photoinitiators for UV Curing
Key Products Selection Guide 2003
Coating Effects
Value beyond chemistry
Typical physical
Freezing point (FP, °C)
Specific
properties
Melting point (MP, °C)
gravity
Absorption peaks
Photoinitiators
Boiling point (BP, °C)
(water = 1)
(nm) in methanol
MP 45–49 °C
1.1–1.2
246, 280, 333
1.1
250, 332
1.1
245, 280, 331
IRGACURE 184
IRGACURE 500
DAROCUR 1173
IRGACURE 2959
Chemical class
-Hydroxyketone
-Hydroxyketone
-Hydroxyketone
-Hydroxyketone
Chemical identity
Appearance
1-Hydroxy-cyclohexyl-
white to off-white
phenyl-ketone
crystalline powder
IRGACURE 184 (50 wt%),
clear, pale yellow
FP<0 °C
Benzophenone (50 wt%)
liquid
recrystallization below 18 °C
UV/VIS
2-Hydroxy-2-methyl-1-
clear, light
liquid at room temp.
phenyl-1-propanone
yellow liquid
MP 4°C, BP 80–81°C
2-Hydroxy-1-[4-(2-hydroxyethoxy)
off-white powder
MP 86–90 °C
1.3
276
liquid at room temp.
1.2
255, 325
1.2
255, 325
phenyl]-2-methyl-1-propanone
DAROCUR MBF
Phenylglyoxylate
Methylbenzoylformate
clear liquid
MP 17 °C
BP 246–248 °C
IRGACURE 754
Phenylglyoxylate
oxy-phenyl-acetic acid 2-[2 oxo-2
light yellow
liquid at room temp.
phenyl-acetoxy-ethoxy]-ethyl ester
liquid
MP < -22 °C
Alpha, alpha-dimethoxy-
white to light
MP 64–67 °C
1.2
250, 340
alpha-phenylacetophenone
yellow powder
MP 110–114 °C
1.2
233, 324
MP 70–75 °C
1.2
230, 304
MP 55–60 °C
1.2
251, 323
MP 88–92 °C
1.2
295, 368, 380, 393
liquid at room temp.
1.1
240, 272, 380
MP 127–133 °C
1.2
295, 370
1.1
295, 370
and oxy-phenyl-acetic 2[2-hydroxy-ethoxy]-ethyl ester
IRGACURE 651
IRGACURE 369
IRGACURE 907
IRGACURE 1300
DAROCUR TPO
DAROCUR 4265
IRGACURE 819
IRGACURE 819DW
IRGACURE 2022
IRGACURE 2100
Benzyldimethyl-ketal
-Aminoketone
-Aminoketone
-Aminoketone
2-Benzyl-2-(dimethylamino)-1-[4-
slightly yellow
(4-morpholinyl) phenyl]-1-butanone
powder
2-Methyl-1-[4-(methylthio)phenyl]
white to light
-2-(4-morpholinyl)-1-propanone
beige powder
IRGACURE 369 (30 wt%) +
light yellow
IRGACURE 651 (70 wt%)
powder
Mono Acyl
Diphenyl (2,4,6-trimethylbenzoyl)-
light yellow
Phosphine (MAPO)
phosphine oxide
powder
MAPO/
DAROCUR TPO (50 wt%) +
light yellow
-Hydroxyketone
DAROCUR 1173 (50 wt%)
viscous liquid
Bis Acyl Phosphine
Phosphine oxide, phenyl bis
light yellow
(BAPO)
(2,4,6-trimethyl benzoyl)
powder
BAPO Dispersion
IRGACURE 819 (45% active)
light yellow
liquid dispersion at
dispersed in water
liquid
room temp.
liquid at room temp.
1.1
246, 282, 370
liquid at room temp.
1.1
275, 370
orange powder
MP 160–170 °C
>1
398, 470
Iodonium, (4-methylphenyl)
yellow to brownish
75% solution
1.5
242
[4-(2-methylpropyl) phenyl]-,
liquid
liquid at room temp.
BAPO/
IRGACURE 819 (20 wt%) +
light yellow
-Hydroxyketone
DAROCUR 1173 (80 wt%)
liquid
Phosphine oxide
–
light yellow
viscous liquid
IRGACURE 784
Metallocene
Bis (eta 5-2,4-cyclopentadien-1-yl)
Bis [2,6-difluoro-3-(1H-pyrrol-1-yl)
phenyl]titanium
IRGACURE 250
Iodonium salt
hexafluorophosphate(1-)
Storage below 30°C.
Photoinitiator
Acetone
n-Butyl
(Solubility, Weight %)
IBOA
IDA
PEA
HDDA
TrPGDA
TMPTA
TMPEOTA DAROCUR
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
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
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
47
25
15
34
22
16
14
13
> 50
> 50
> 50
> 50 > 50 > 50
> 50
> 50
> 50
> 50
> 50
14
6
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
30
10
10
5
5
NA
7
DAROCUR TPO
DAROCUR 4265
IRGACURE 819
IRGACURE 784
5
5
5
5
30 > 50
7
5
NA
15
IBOA = isobornyl acrylate; IDA = isodecyl acrylate; PEA = 2-phenoxyethyl acrylate; HDDA = hexane diol diacrylate;
TrPGDA = tripropyleneglycol diacrylate; TMPTA = trimethyolpropane triacrylate; TMPEOTA = trimethyolpropane
ethoxytriacrylate.
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 of
IRGACURE 907 in IBOA is 35% which means that its solubility is above 35% but below 40%.
Thermal Gravimetric Analysis (TGA in N2 at 10°C/min)
300
200
150
100
5% wt loss
50
10% wt loss
15% wt loss
IRGACURE 784
IRGACURE 2100
IRGACURE 2022
IRGACURE 819
DAROCUR 4265
DAROCUR TPO
IRGACURE 1300
IRGACURE 907
IRGACURE 369
IRGACURE 651
IRGACURE 754
DAROCUR MBF
IRGACURE 2959
DAROCUR 1173
IRGACURE 500
0
IRGACURE 184
Temperature °C
250
Surface cure, co-initiator
Intermediate Coat
Acrylated Wood Top
and Intermediate Coat
Wood Fillers
Clear Top Coats on
Plastic and Metal
Pigmented Top Coats
on Plastic and Metal
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Dispersions for Facades
IRGACURE 250
IRGACURE 784
IRGACURE 2100
IRGACURE 2022
IRGACURE 819 DW
IRGACURE 819
DAROCUR 4265
DAROCUR TPO
●
❍
❍
UV Powder Coatings
IRGACURE 1300
Through cure, pigmented systems
for pigment systems
UPES Wood Top and
IRGACURE 907
IRGACURE 369
IRGACURE 651
DAROCUR MBF
IRGACURE 2959
DAROCUR 1173
IRGACURE 754
IRGACURE 500
IRGACURE 184
UV Curing
Applications
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Adhesives
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Glass Fiber Composites
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Gel Coats
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Etch Resists for PCB
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Solder Masks
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Epoxy Resists
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Flexo Printing Plates
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Laser Direct Imaging
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Offset Printing Plates
Offset Inks
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Screen Inks
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Flexo Inks
Inkjet Inks
Over Print Varnishes
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Cationic Polymerization
Thick Sections
Polymerization
UV Stabilized
Clear Coatings
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Water-based UV
●
Formulations
Xi- and Xn-free
Applications
Low Volatility,
Low Odor
● recommended application
❍ possible application
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Key products, surface cure Absorption Spectra 0.001% (Acetonitrile)
Wavelength (nm)
1.2
Absorbance
1.0
0.8
0.6
IRGACURE 2959
0.4
DAROCUR 1173
0.2
IRGACURE 184
IRGACURE 754
0.0
200
220
240
260
280
300
320
Key products, a-Amino Ketones Absorption Spectra 0.001% (Acetonitrile)
340
Wavelength (nm)
1.6
1.4
Absorbance
1.2
1.0
0.8
0.6
0.4
IRGACURE 369
0.2
IRGACURE 907
IRGACURE 1300
0.0
200
220
240
260
280
300
320
340
360
Key products, through cure Absorption Spectra 0.1% (Acetonitrile)
380
Wavelength (nm)
3
Absorbance
2.5
2
1.5
IRGACURE 819
1
IRGACURE 2022
0.5
DAROCUR TPO
IRGACURE 2100
0
300
320
340
360
380
400
420
440
IRGACURE 184 % in Acetonitrile
Wavelength (nm)
3
2.5
2.5
Absorbance
Absorbance
DAROCUR 1173 % in Acetonitrile
3
2
1.5
1
0.5
240
260
280
300
320
340
360
380
400
420
IRGACURE 754 % in Acetonitrile
440
460
1
200 220
480 500
3
2.5
2.5
2
1.5
1
240
260
280
300
320
340
360
380
400
420
IRGACURE 500 % in Acetonitrile
Wavelength (nm)
3
Absorbance
Absorbance
1.5
0
200 220
0.5
440
460
480 500
Wavelength (nm)
2
1.5
1
0.5
0
0
200 220
240
260
280
300
320
340
360
380
400
420
IRGACURE 369 % in Acetonitrile
440
460
200 220
480 500
3
2.5
2.5
2
1.5
1
240
260
280
300
320
340
360
380
400
420
IRGACURE 907 % in Acetonitrile
Wavelength (nm)
3
Absorbance
Absorbance
2
0.5
0
0.5
440
460
480 500
Wavelength (nm)
2
1.5
1
0.5
0
0
200 220
240
260
280
300
320
340
360
380
400
420
IRGACURE 1300 % in Acetonitrile
440
460
200 220
480 500
3
2.5
2.5
2
1.5
1
240
260
280
300
320
340
360
380
400
420
IRGACURE 819 % in Acetonitrile
Wavelength (nm)
3
Absorbance
Absorbance
Wavelength (nm)
0.5
440
460
480 500
Wavelength (nm)
2
1.5
1
0.5
0
0
200 220
240
260
280
300
320
340
360
380
400
420
IRGACURE 250 % in Acetonitrile
440
460
200 220
480 500
240
260
280
300
320
340
360
380
400
420
IRGACURE 784 % in 1-Methyl-2-pyrrolidone (NMP)
Wavelength (nm)
1.0
440
460
480 500
Wavelength (nm)
3.5
3
0.8
Absorbance
Absorbance
2.5
0.6
0.4
2
1.5
1
0.2
0.5
0.0
0
200
220
240
260
280
300
320
340
360
380
400
420
440
460
480 500
250
300
350
400
450
0.10
500
0.010
550
600
0.001
Chemical Structures
IRGACURE 184
O
C
DAROCUR TPO
IRGACURE 2959
O CH3
OH
O
HO
C
OH
O
O
C
P
CH3
DAROCUR 1173
C
C
OH
C
CH3
C
O
CH3
C
IRGACURE 907
IRGACURE 369
O
O
N
O CH3
CH3
O
CH3
C
S
N
C
H 3C
CH3
H 3C
O
O
IRGACURE 651
CH3
O
C
IRGACURE 500
O
+
OH
C
DAROCUR MBF
O
DAROCUR BP
O
O CH3
N
O
CH3
O
IRGACURE 784
IRGACURE 1300
O
N
O
CH3
C
N
CH3
CH3
+
O
CH3
C
O
H3C
IRGACURE 819 and IRGACURE 819 DW
O O
O
C
C
P
F
N
F
Ti
F
O
F
N
IRGACURE 250
DAROCUR 4265
+
O
O
C
P
O CH3
+
C
OH
CH3
F
F
F
P
F
-
F
F
Please note that Ciba® IRGACURETM and Ciba® DAROCURTM are registered trademarks of Ciba Specialty Chemicals Inc.
Head office
Ciba Specialty Chemicals Inc.
PO Box
CH-4002 Basel
Switzerland
www.cibasc.com
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Edition 2003
Copyright © 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.
IMPORTANT: The following supersedes Buyer’s documents. SELLER MAKES NO REPRESENTATION
OR WARRANTY, EXPRESS OR IMPLIED, INCLUDING OF MERCHANTABILITY OR FITNESS FOR A
PARTICULAR PURPOSE. No statements herein are to be construed as inducements to infringe any
relevant patent. Under no circumstances shall Seller be liable for incidental, consequential or indirect damages for alleged negligence, breach of warranty, strict liability, tort or contract arising
in connection with the product(s). Buyer’s sole remedy and Seller’s sole liability for any claims
shall be Buyer’s purchase price. Data and results are based on controlled or lab work and must be
confirmed by Buyer by testing for its intended conditions of use. The product(s) has (have) not
been tested for, and is (are) therefore not recommended for, uses for which prolonged contact
with mucous membranes, abraded skin, or blood is intended; or for uses for which implantation
within the human body is intended.
Please note that products may differ from country to country. If you have any queries, kindly
contact your local Ciba Specialty Chemicals representative.
Further information at website: http://www.cibasc.com/coatingeffects
g-48/2003 October, Printed in Switzerland
Ciba Specialty Chemicals is a member of: Ecological and Toxicological Association
of Dyes and Organic Pigments Manufacturers)
Value beyond chemistry