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

Head officeCiba Specialty Chemicals Inc.PO BoxCH-4002 BaselSwitzerlandwww.cibasc.com

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.

IMPORTANT: The following supersedes Buyer’s documents. SELLER MAKES NO REPRESENTATIONOR WARRANTY, EXPRESS OR IMPLIED, INCLUDING OF MERCHANTABILITY OR FITNESS FOR APARTICULAR PURPOSE. No statements herein are to be construed as inducements to infringe anyrelevant patent. Under no circumstances shall Seller be liable for incidental, consequential or in-direct damages for alleged negligence, breach of warranty, strict liability, tort or contract arisingin connection with the product(s). Buyer’s sole remedy and Seller’s sole liability for any claimsshall be Buyer’s purchase price. Data and results are based on controlled or lab work and must beconfirmed by Buyer by testing for its intended conditions of use. The product(s) has (have) notbeen tested for, and is (are) therefore not recommended for, uses for which prolonged contactwith mucous membranes, abraded skin, or blood is intended; or for uses for which implantationwithin the human body is intended.Please note that products may differ from country to country. If you have any queries, kindlycontact 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 Associationof Dyes and Organic Pigments Manufacturers) Value beyond chemistry

SCI

TSAL

P

SKNIDNAGNIGAMILAIRETAMCINORTCELE

SG

NITAO

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Industrial

Transportation

Powder

Wood

Architecture/DecorativeMineral Slurry

Microelectronics

Information Storage

Printed C

ircuit Board

sO

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er Co

ating

s Pho

to

Publ

icat

ion

Pack

agin

g

Displays

Autom

otive

Spec

ialty

Packaging

Electrical & Electro

nics

Construction & PipesHousehold & Molding

Fibers

Dig

ital

Imag

ing