Photopolymerization Initiators

Photopolymerization initiators are used in many fields to generate photocurable composites. These composites are polymerized by irradiation with UV light and electron beam which leads to altered physical properties of the composites such as solubility, viscosity and adhesiveness. In particular, the phenomenon in which a liquid changes into a solid is most useful and is applied to surface-treating techniques in fields including paints, printing inks, dental materials, lithography, photoresist, etc. A growing number of intensive studies have been made for the development of improved properties for novel photopolymerization initiators.

Photopolymerization initiators can be divided roughly into three groups with the generated active species, as shown in the upper figure. The conventional photopolymerization initiators generate free radicals upon light irradiation, and the resulting radical starts the polymerization process. Typical initiators are represented by benzoin derivatives. Photo-acid generators which produce cations (acid) by light irradiation, were put to practical use in the late 1990s. Photo-base generators, which produce anions (base) by light irradiation, are of current interest in research.
Photopolymerization initiators are divided roughly into three groups as shown above. For a photopolymerization initiator to be an excellent initiator the following properties must be considered;
(1) High quantum yields in the generation of radicals, cations and anions
(2) Overlap in absorption wavelength of the photopolymerization initiators and emission wavelength of
the light source
(3) High thermal stability and high stability in darkness
(4) Highly soluble in monomers and oligomers
In addition to those just developed, we have a wide assortment of initiators, such as benzoin derivatives which are already in use.

C0014 C0014 H0617 H0617 B1225 B1225
D1640 D1640 D1702 D1702 D2375 D2375
D2963 D2963 M1245 M1245 B0103 B0103
C1150 C1150 C0292 C0292 E0063 E0063
H0991 H0991 P0211 P0211 I0678 I0678
P1410 P1410 P1377 P1377 M1209 M1209
F0362 F0362 B0139 B0139 B1275 B1275
B0481 B0481 D1621 D1621 B1267 B1267
B1164 B1164 C0136 C0136 C1485 C1485
I0591 I0591 F0021 F0021 A0061 A0061
B0050 B0050 B0221 B0221 B0079 B0079
B0222 B0222 B1019 B1019 B1015 B1015
B0942 B0942 B0869 B0869 B0083 B0083
B2380 B2380 B2381 B2381 D1801 D1801
D3358 D3358 D2248 D2248 D2238 D2238
D2253 D2253 B1231 B1231 M0792 M0792
N0528 N0528 A1028 A1028 T0157 T0157
T2041 T2041 T2042 T2042 T1188 T1188
T1608 T1608
C0014 (+/-)-Camphorquinone
H0617 1-Hydroxycyclohexyl Phenyl Ketone
B1225 2,2'-Bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole [Photopolymerization Initiator]
D1640 2,2-Diethoxyacetophenone
D1702 2,2-Dimethoxy-2-phenylacetophenone
D2375 2,4-Diethylthioxanthen-9-one
D2963 2-(3,4-Dimethoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine
M1245 2-(4-Methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine
B0103 2-Benzoylbenzoic Acid
C1150 2-Chlorobenzophenone
C0292 2-Chlorothioxanthone
E0063 2-Ethylanthraquinone
H0991 2-Hydroxy-2-methylpropiophenone
P0211 2-Isonitrosopropiophenone
I0678 2-Isopropylthioxanthone
P1410 2-Phenyl-2-(p-toluenesulfonyloxy)acetophenone
P1377 2-Pyridyl Tribromomethyl Sulfone
M1209 2-[2-(5-Methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine
F0362 2-[2-(Furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine
B0139 4,4'-Bis(diethylamino)benzophenone
B1275 4,4'-Bis(diethylamino)benzophenone
B0481 4,4'-Bis(dimethylamino)benzophenone
D1621 4,4'-Dichlorobenzophenone
B1267 4-Benzoyl 4'-Methyldiphenyl Sulfide
B1164 4-Benzoylbenzoic Acid
C0136 4-Chlorobenzophenone
C1485 4-Chlorobenzophenone
I0591 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate
F0021 9-Fluorenone
A0061 Acetophenone
B0050 Benzil
B0221 Benzil Zone Refined (number of passes:22)
B0079 Benzoin
B0222 Benzoin Zone Refined (number of passes:50)
B1019 Benzoin Ethyl Ether
B1015 Benzoin Isobutyl Ether
B0942 Benzoin Isopropyl Ether
B0869 Benzoin Methyl Ether
B0083 Benzophenone
B2380 Bis(4-tert-butylphenyl)iodonium Hexafluorophosphate
B2381 Bis(4-tert-butylphenyl)iodonium Trifluoromethanesulfonate
D1801 Dibenzosuberone
D3358 Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide
D2248 Diphenyliodonium Hexafluoroarsenate
D2238 Diphenyliodonium Hexafluorophosphate
D2253 Diphenyliodonium Trifluoromethanesulfonate
B1231 Methyl 2-Benzoylbenzoate
M0792 N-Methyl-9-acridone
N0528 Nifedipine
A1028 p-Anisil
T0157 Tetramethylthiuram Monosulfide
T2041 Tri-p-tolylsulfonium Hexafluorophosphate
T2042 Tri-p-tolylsulfonium Trifluoromethanesulfonate
T1188 Tribromomethyl Phenyl Sulfone
T1608 Triphenylsulfonium Tetrafluoroborate

Literature

M. Kakuoka, Kagaku Kogyo (Chem. Ind.), 2001, 497.
idem, ibid., 1999, 592.
T. Yamaoka, Nippon Setchaku Kyokaishi, 1989, 25, 144.


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