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Photoinitiators: Classification
A photoinitiator is a compound especially added to a formulation to convert absorbed light energy, UV or visible light, into chemical energy in the form of initiating species, viz., free radicals or cations. Based on the mechanism by which initiating radicals are formed, photoinitiators are generally divided into two classes:
Type II photoinitiators undergo a bimolecular reaction where the excited state of the photoinitiator interacts with a second molecule (a coinitiator) to generate free radicals.
Type I photoinitiators undergo a unimolecular bond cleavage upon irradiation to yield free radicals.
UV photoinitiators of both Type I and Type II are available. However, visible light photoinitiators belong almost exclusively to the Type II class of photoinitiators. Table I summarizes the various classes of available Type I and Type II photoinitiators and their common applications.
X X1
X X X3 X X4 X3
X X X X X X X X
(1) In combination with benzophenone. (2) Only systems of high reactivity. (3) Partially in combination with thioxanthones. (4) Thin layers only.
additional substituted acetophenones and benzophenones that are potential photoinitiators are available from Aldrich; search our product database at www.sigma-aldrich.com. Spectra were recorded on a Perkin Elmer UV/Vis Lambda 2 spectrophotometer using Perkin Elmer Computerized Spectroscopy Software 4.01. Concentrations are expressed as % weight of solute in volume of solvent. The solvent used was A.C.S. spectrophotometric grade methyl alcohol. For comparison purposes, the emission spectrum of a medium pressure mercury lamp, the most widely used energy source, is shown as the last figure.
Commonly Used Radical and Cationic Photoinitiators whose UV Absorption Spectra are Displayed in this Section. (Click on the photoinitiator name coded red to view the UV spectrum. Click on the product number coded blue to link to the product document sheet on the Sigma-Aldrich Web site.)
Cat. No. Photoinitiator A1,070-1 A8,840-9 A9,000-4 12,324-2 11,931-8 B515-1 39,939-6 17,200-6 19,578-2 B870-3 B930-0 40,562-0 26,246-3 B1,260-1 40,564-7 16,032-6 14,783-4 12,489-3 C7,240-4 40,807-7 D3,173-7 22,710-2 D11,050-7 Acetophenone, 99% Anisoin, 95% Anthraquinone, 97% Anthraquinone-2-sulfonic acid, sodium salt monohydrate, 97% (Benzene) tricarbonylchromium, 98% Benzil, 98% Benzoin, sublimed, 99.5+% Benzoin ethyl ether, 99% Benzoin isobutyl ether, tech., 90% Benzoin methyl ether, 96% Benzophenone, 99% Benzophenone/1-Hydroxycyclohexyl phenyl ketone, 50/50 blend 3,3',4,4'-Benzophenonetetracarboxylic dianhydride, sublimed, 98% 4-Benzoylbiphenyl, 99% 2-Benzyl-2-(dimethylamino)-4'morpholinobutyrophenone, 97% 4,4'-Bis(diethylamino)benzophenone, 99+% 4,4'-Bis(dimethylamino)benzophenone, 98% Camphorquinone, 98% 2-Chlorothioxanthen-9-one, 98% (Cumene)cyclopentadienyliron(II) hexafluorophosphate, 98% Dibenzosuberenone, 97% 2,2-Diethoxyacetophenone, 95% 4,4'-Dihydroxybenzophenone, 99%
Cat. No. 19,611-8 14,934-9 14,670-6 D14,966-7 D14,967-5 40,566-3 27,571-9 E1,220-6 F40-8 32,810-3 27,856-4 22,043-4 H2,020-2 40,561-2 40,565-5 15,753-8 19,805-6 M3,050-7 40563-9 15,650-7 29,074-2 T3,400-2 40,722-4 40,721-6
Photoinitiator 2,2-Dimethoxy-2-phenylacetophenone, 99% 4-(Dimethylamino)benzophenone, 98% 4,4'-Dimethylbenzil, 97% 2,5-Dimethylbenzophenone, tech., 95% 3,4-Dimethylbenzophenone, 99% Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide/ 2-Hydroxy-2-methylpropiophenone, 50/50 blend 4'-Ethoxyacetophenone, 98% 2-Ethylanthraquinone, 97+% Ferrocene, 98% 3'-Hydroxyacetophenone, 99+% 4'-Hydroxyacetophenone, 99% 3-Hydroxybenzophenone, 99% 4-Hydroxybenzophenone, 98% 1-Hydroxycyclohexyl phenyl ketone, 99% 2-Hydroxy-2-methylpropiophenone, 97% 2-Methylbenzophenone, 98% 3-Methylbenzophenone, 99% Methybenzoylformate, 98% 2-Methyl-4'-(methylthio)-2-morpholinopropiophenone, 98% Phenanthrenequinone, 99+% 4'-Phenoxyacetophenone, 98% Thioxanthen-9-one, 98% Triarylsulfonium hexafluoroantimonate salts, mixed, 50% in propylene carbonate Triarylsulfonium hexafluorophosphate salts, mixed, 50% in propylene carbonate
O C CH 3
CH O 3 O CH C OH OCH 3
0.0224 % 0.0011 %
0.0040 % 0.0014 %
O S ONa O H O 2
0.0010% 0.0004 %
0.0033 % 0.0006 %
Benzil, 98%
O O
.8
C C
OC
Cr CO
CO
.8
.6
0.0023 %
Absorbance
.6
Absorbance
0.0029 % 0.0011 %
0.0012 %
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
O
.8
O
.8
CH OH
CH C OCH CH 2 3
.6
0.0056 % 0.0017 %
Absorbance
.6
0.0027 % 0.0019 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
O
.8
O CH C
.8
CH C O CH CHCH 2 3 CH 3
OCH
.6
0.0110 %
Absorbance
.6
0.0043 % 0.0020 %
0.0069 %
.4
Absorbance
.4 .2 0 220
.2
0 220
240
260
280
300
380
400
420
440
240
260
280
300
380
400
420
440
B930-0
Benzophenone, 99%
O
.8
O
.8
O C OH
.6
0.0030 % 0.0012 %
Absorbance
.6
0.0150 % 0.0015 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
O
.8
O O C O O
O C
O O
.6
0.0030 %
Absorbance
0.0031 % 0.0004 %
0.0010 %
.4
.2
0 220
240
260
280
300
380
400
420
440
CH C
2 N(CH ) 32
.8
.8
CH CH 2 3
.6
0.0035 % 0.0020 %
Absorbance
.6
0.0020 % 0.0008 %
Absorbance
.4
.4
.2
.2
CH CH 3 2 CH CH N 3 2 O C CH CH 2 3 NCH CH 2 3
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
10
CH
.8
.8
CH 3
3 R
R = CH R= H
R = H R = CH 3
or
.6
Absorbance
0.0031% 0.0008 %
Absorbance
.6
0.0271 % 0.0071 %
.4
.4
.2
.2
CH
3 N 3
O C N
CH CH
3 3
CH
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
O Cl
Fe
S
.8
.8
CH 3 CH CH 3
PF
.6
0.0024 % 0.0007 %
Absorbance
.6
0.0055 % 0.0027 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
11
O C
.8
OCH CH 2 3 CH OCH CH 2 3
.8
.6
0.0016 % 0.0005 %
Absorbance
.6
0.0100 % 0.0014 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
O HO C OH
O OCH3 C C OCH 3
.8
.8
.6
0.0036 % 0.0009 %
Absorbance
.6
0.0020 % 0.0011 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
12
O O
.8
CH
.8
C C
CH 3
.6
0.0043 %
.6
0.0030 %
Absorbance
Absorbance
0.0009 %
0.0010 %
.4
.4
.2
CH 3 N CH 3 O C
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
CH
.8
CH
3 O C CH 3
.8
3 3
CH
.6
.6
0.0296 %
Absorbance
0.0039 %
Absorbance
0.0015 %
0.0013 %
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
13
27,571-9
4'-Ethoxyacetophenone, 98%
CH 3
C CH 3
P
.8
O C CH 3
O OH
.6
OCH CH 2 3
CH 3
CH 3
0.0223 %
Absorbance
.6
0.0044 % 0.0009 %
0.0019 %
.4
Absorbance
.4 .2 0 220
.2
0 220
240
260
280
300
380
400
420
440
240
260
280
300
380
400
420
440
F40-8
Ferrocene, 98%
O CH CH 2 3
.8
.8
Fe
.6
0.0018 % 0.0005 %
Absorbance
.6
0.0065 % 0.0028 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
14
3'-Hydroxyacetophenone, 99+%
27,856-4
4'-Hydroxyacetophenone, 99%
O C CH 3
O C CH 3
.8
.8
OH
OH
.6
0.0026 %
Absorbance
.6
0.0048 % 0.0009 %
Absorbance
0.0007 %
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
22,043-4
1
3-Hydroxybenzophenone, 99%
H2,020-2
4-Hydroxybenzophenone, 98%
O C HO
.8 .8
O HO C
0.0030 %
.6
.6
0.0051 % 0.0013 %
Absorbance
0.0011 %
Absorbance
.4 .2 0 220
.4
.2
0 220
240
260
280
300
380
400
420
440
240
260
280
300
380
400
420
440
15
2-Hydroxy-2-methylpropiophenone, 97%
O C OH
.8
O C
.8
OH C CH CH 3 3
.6
0.0047 %
Absorbance
.6
0.0053 % 0.0008 %
Absorbance
0.0019 %
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
15,753-8 H2,020-2
19,805-6
3-Methylbenzophenone, 99%
O
O C
C CH 3
.8
CH
.8
.6
0.0122 % 0.0013 %
Absorbance
.6
0.0071 % 0.0012 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
16
O O C
.8
.8
O CH S 3 C
CH C CH
3 N 3
OCH 3
.6 .6
0.0625 % 0.0025%
Absorbance
0.0052 % 0.0014 %
Absorbance
.4
.4
.2 .2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
15,650-7
1
Phenanthrenequinone, 99+%
29,074-2
4'-Phenoxyacetophenone, 98%
O
O O
.8
C CH 3
.8
.6
0.0049 % 0.0028 %
Absorbance
.6
0.0032 % 0.0008 %
Absorbance
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
17
Thioxanthen-9-one, 98%
40,722-4
S
.8
.8
SbF 6
.6
0.0016 %
Absorbance
.6
0.0108 % 0.0048 %
Absorbance
0.0005 %
.4
.4
.2
.2
0 220
240
260
280
300
380
400
420
440
0 220
240
260
280
300
380
400
420
440
40,721-6
.8
PF
.6
0.0223 % 0.0039 %
Absorbance
.4 .2 0 220
240
260
280
300
380
400
420
440
18
19