Ciba Specialty Chemicals

Photoinitiators for UV Curing

Coating Effects

Value beyond chemistry

Typical physical properties Photoinitiators IRGACURE 184

Chemical class

Chemical identity

Appearance

Freezing point (FP, C) Melting point (MP, C) Boiling point (BP, C)

Specific gravity (water = 1) 1.11.2

UV/VIS Absorption peaks (nm) in methanol 246, 280, 333

-Hydroxyketone

1-Hydroxy-cyclohexylphenyl-ketone

white to off-white crystalline powder clear, pale yellow liquid clear, light yellow liquid off-white powder

MP 4549 C

IRGACURE 500

-Hydroxyketone

IRGACURE 184 (50 wt%), Benzophenone (50 wt%)

FP<0 C recrystallization below 18 C liquid at room temp. MP 4C, BP 8081C MP 8690 C

1.1

250, 332

DAROCUR 1173

-Hydroxyketone

2-Hydroxy-2-methyl-1phenyl-1-propanone

1.1

245, 280, 331

IRGACURE 2959

-Hydroxyketone

2-Hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-propanone

1.3

276

DAROCUR MBF

Phenylglyoxylate

Methylbenzoylformate

clear liquid

liquid at room temp. MP 17 C BP 246248 C

1.2

255, 325

IRGACURE 754

Phenylglyoxylate

oxy-phenyl-acetic acid 2-[2 oxo-2 phenyl-acetoxy-ethoxy]-ethyl ester and oxy-phenyl-acetic 2[2-hydroxy-ethoxy]-ethyl ester

light yellow liquid

liquid at room temp. MP < -22 C

1.2

255, 325

IRGACURE 651

Benzyldimethyl-ketal

Alpha, alpha-dimethoxyalpha-phenylacetophenone

white to light yellow powder slightly yellow powder white to light beige powder light yellow powder light yellow powder light yellow viscous liquid light yellow powder light yellow liquid light yellow liquid light yellow viscous liquid

MP 6467 C

1.2

250, 340

IRGACURE 369

-Aminoketone

2-Benzyl-2-(dimethylamino)-1-[4(4-morpholinyl) phenyl]-1-butanone

MP 110114 C

1.2

233, 324

IRGACURE 907

-Aminoketone

2-Methyl-1-[4-(methylthio)phenyl] -2-(4-morpholinyl)-1-propanone

MP 7075 C

1.2

230, 304

IRGACURE 1300

-Aminoketone

IRGACURE 369 (30 wt%) + IRGACURE 651 (70 wt%)

MP 5560 C

1.2

251, 323

DAROCUR TPO

Mono Acyl Phosphine (MAPO)

Diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide DAROCUR TPO (50 wt%) + DAROCUR 1173 (50 wt%) Phosphine oxide, phenyl bis (2,4,6-trimethyl benzoyl) IRGACURE 819 (45% active) dispersed in water

MP 8892 C

1.2

295, 368, 380, 393

DAROCUR 4265

MAPO/ -Hydroxyketone

liquid at room temp.

1.1

240, 272, 380

IRGACURE 819

Bis Acyl Phosphine (BAPO)

MP 127133 C

1.2

295, 370

IRGACURE 819DW

BAPO Dispersion

liquid dispersion at room temp. liquid at room temp.

1.1

295, 370

IRGACURE 2022

BAPO/ -Hydroxyketone

IRGACURE 819 (20 wt%) + DAROCUR 1173 (80 wt%)

1.1

246, 282, 370

IRGACURE 2100

Phosphine oxide

liquid at room temp.

1.1

275, 370

IRGACURE 784

Metallocene

Bis (eta 5-2,4-cyclopentadien-1-yl) Bis [2,6-difluoro-3-(1H-pyrrol-1-yl) phenyl]titanium

orange powder

MP 160170 C

>1

398, 470

IRGACURE 250

Iodonium salt

Iodonium, (4-methylphenyl) [4-(2-methylpropyl) phenyl]-, hexafluorophosphate(1-)

yellow to brownish liquid

75% solution liquid at room temp. Storage below 30C.

1.5

242

Photoinitiator (Solubility, Weight %)

Acetone

n-Butyl Acetate

IBOA

IDA

PEA

HDDA

TrPGDA

TMPTA

TMPEOTA DAROCUR 1173

IRGACURE 184 IRGACURE 500 DAROCUR 1173 IRGACURE 2959 DAROCUR MBF IRGACURE 754 IRGACURE 651 IRGACURE 369 IRGACURE 907 IRGACURE 1300 DAROCUR TPO DAROCUR 4265 IRGACURE 819 IRGACURE 2022 IRGACURE 2100 IRGACURE 784

> 50 > 50 > 50 19 > 50 > 50 > 50 17 > 50 > 50 47 > 50 14 > 50 > 50 30

> 50 > 50 > 50 3 > 50 > 50 > 50 11 35 45 25 > 50 6 > 50 > 50 10

> 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 > 50 5 5 5

> 50 > 50 > 50 10 > 50 > 50 40 10 35 > 50 22 > 50 5 > 50 > 50 10

> 50 > 50 > 50 20 > 50 > 50 25 6 22 35 16 > 50 5 > 50 > 50 5

> 50 > 50 > 50 5 > 50 > 50 > 50 5 25 25 14 > 50 5 > 50 > 50 5

> 50 > 50 > 50 5 > 50 > 50 45 5 20 25 13 > 50 >5 > 50 > 50 NA

> 50 > 50

35 > 50 > 50 > 50 25 > 50 > 50 > 50 > 50 30 > 50 > 50 7

> 50 > 50 > 50 > 50 > 50 > 50 40 10 35 > 50 15 30 > 50 5 25 15 45

35 > 50 7 34

> 50 > 50 > 50 5 5 15

> 50 > 50 > 50 > 50 > 50 > 50 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 60C) 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 10C/min)

250

Temperature C

200

150

100
5% wt loss

50
10% wt loss

0 DAROCUR MBF DAROCUR TPO DAROCUR 1173 DAROCUR 4265 IRGACURE 184 IRGACURE 500 IRGACURE 754 IRGACURE 651 IRGACURE 369 IRGACURE 907 IRGACURE 819 IRGACURE 2959 IRGACURE 1300 IRGACURE 2022 IRGACURE 2100 IRGACURE 784

15% wt loss

IRGACURE 819 DW

IRGACURE 2022

IRGACURE 2959

IRGACURE 1300

DAROCUR 1173

DAROCUR 4265

DAROCUR MBF

DAROCUR TPO

IRGACURE 500

IRGACURE 754

IRGACURE 907

IRGACURE 819

IRGACURE 2100

IRGACURE 184

IRGACURE 651

IRGACURE 369

IRGACURE 784

UV Curing Applications

Surface cure, co-initiator for pigment systems 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

Through cure, pigmented systems

recommended application possible application

IRGACURE 250

Key products, surface cure Absorption Spectra 0.001% (Acetonitrile)

Wavelength (nm)

1.0

Absorbance

0.8

0.6
IRGACURE 2959

0.4
DAROCUR 1173

0.2
IRGACURE 184

0.0 200 220 240 260 280 300 320 340

IRGACURE 754

Key products, a-Amino Ketones Absorption Spectra 0.001% (Acetonitrile)

Wavelength (nm)

Absorbance

1.0 0.8 0.6 0.4 0.2 0.0 200 220 240 260 280 300 320 340 360 380
IRGACURE 369 IRGACURE 907 IRGACURE 1300

Key products, through cure Absorption Spectra 0.1% (Acetonitrile)

Wavelength (nm)

2.5

Absorbance

1.5
IRGACURE 819

1
IRGACURE 2022

0.5
DAROCUR TPO

0 300 320 340 360 380 400 420 440

IRGACURE 2100

DAROCUR 1173 % in Acetonitrile

Wavelength (nm)
3 2.5

IRGACURE 184 % in Acetonitrile

Wavelength (nm)

Absorbance

Absorbance
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

1.5

1.5

0.5 0

0.5 0 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

IRGACURE 754 % in Acetonitrile

Wavelength (nm)
3 2.5

IRGACURE 500 % in Acetonitrile

Wavelength (nm)

Absorbance

Absorbance
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

1.5

1.5

0.5 0

0.5 0 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

IRGACURE 369 % in Acetonitrile

Wavelength (nm)
3 2.5

IRGACURE 907 % in Acetonitrile

Wavelength (nm)

Absorbance

Absorbance
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

1.5

1.5

0.5 0

0.5 0 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

IRGACURE 1300 % in Acetonitrile

Wavelength (nm)
3 2.5

IRGACURE 819 % in Acetonitrile

Wavelength (nm)

Absorbance

Absorbance
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

1.5

1.5

0.5 0

0.5 0 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

IRGACURE 250 % in Acetonitrile

Wavelength (nm)
3.5 3 2.5

IRGACURE 784 % in 1-Methyl-2-pyrrolidone (NMP)

Wavelength (nm)

Absorbance

0.6

Absorbance
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500

2 1.5 1

0.4

0.2 0.5 0.0 0 250 300 350 400 450 500 550 600

0.10

0.010

0.001

Chemical Structures
IRGACURE 184
O C OH HO O

IRGACURE 2959
O CH3 C CH3 OH

DAROCUR TPO
O C O P

DAROCUR 1173
O CH3 C CH3 OH

DAROCUR BP O
C

DAROCUR MBF O
C C O O CH3

IRGACURE 500 O OH C

O C

IRGACURE 651 CH3 O

IRGACURE 369
O O N C CH3 CH3 N CH3

IRGACURE 907
O CH3 S H 3C C N CH3 O

H3C

IRGACURE 784 IRGACURE 1300

H3C

IRGACURE 819 and IRGACURE 819 DW

DAROCUR 4265
O C O P O CH3

IRGACURE 250
+

C CH3

OH F

F P F
-

F F

Please note that Ciba IRGACURETM and Ciba DAROCURTM are registered trademarks of Ciba Specialty Chemicals Inc.

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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 Buyers 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). Buyers sole remedy and Sellers sole liability for any claims shall be Buyers 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

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Value beyond chemistry