Photoinitiators and curable compositions
A photoinitiator and photoinitiation technology, applied in the fields of compounds of group 5/15 elements of the periodic table, organic chemistry, chemical instruments and methods, etc., can solve problems such as migration and movement
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Embodiment 1
[0266] THIOXANTHON-1 is a polymerizable thioxanthone with the following structure and is a 50% by weight solution in VEEA. THIOXANTHON-1 was prepared according to Example 1 of EP 2684876 A (AGFA):
[0267] .
[0268] GENOPOL AB1 is a polymeric 4-dimethylaminobenzoic acid derivative supplied by Rahn.
[0269] VEEA is 2-(vinylethoxy)ethyl acrylate available from NIPPON SHOKUBAI, Japan.
[0270] INHIB is a mixture of polymerization inhibitors with a composition according to Table 2:
[0271] Table 2
[0272]
[0273] Cupferron TM AL is aluminum N-nitrosophenylhydroxylamine from WAKO CHEMICALS LTD.
[0274] The PET100 substrate is a 100 μm thick transparent polyethylene terephthalate substrate available from AGFA-GEVAERT.
[0275] Measurement methods
[0276] 1. Molecular weight
[0277] Molecular weights of compounds were determined using TLC-MS according to the following procedure. TLC was performed as given in the synthetic examples. Using an Agilent 1100 HPLC p...
Embodiment 2
[0290] This example illustrates the reduced extractability of RAFT functionalized acylphosphine oxide INI-RAFT-1. Comparisons were made with the commercial photoinitiator TPO-L and the comparative RAFT functionalized photoinitiator COMP-RAFT-1.
[0291] Synthesis of COMP-RAFT-1 (step 2)
[0292]
[0293] Dissolve 3g (7.6mmol) (4-bromomethyl-2,6-dimethyl-benzoyl)-phenyl-phosphinic acid ethyl ester in 30ml ethanol, and add to 2.74g (12.2mmol) di In a solution of ethyl dithiocarbamate sodium salt and 0.113 g (0.75 mmol) sodium iodide in 40 ml ethanol. The reaction mixture was heated to 78°C for 4 hours. The mixture was cooled to room temperature. The solvent was removed under reduced pressure, and using preparative column chromatography on a Prochrom TM Purification of crude COMP-RAFT-1 on LC80 column using Kromasil TM C18 100 Å 10 µm as silica and methanol / 0.2M ammonium acetate as eluent. 0.98 gCOMP-RAFT-1 was isolated (in Reveleris provided by GRACE TM TLC analysis...
Embodiment 3
[0309] This example illustrates the synthesis of photoinitiators according to the invention.
[0310] Synthesis of INI-RAFT-2
[0311]
[0312] Step 1: Irgacure TM Acylation of 2959
[0313] 9g (40mmol) Irgacure TM 2959 was dissolved in 150ml ethyl acetate at 40°C. 4.45 g (44 mmol) triethylamine were added. A solution of 9.20 g (40 mmol) 2-bromo-2-methyl-propionyl bromide in 25 ml ethyl acetate was added dropwise and the reaction was continued at room temperature for 16 hours. A further 2.23 g (22 mmol) of triethylamine were added, followed by 4.6 g (20 mmol) of 2-bromo-2-methyl-propionyl bromide in 10 ml of ethyl acetate. The reaction was allowed to continue for another 1 hour at room temperature. Precipitated salts were removed by filtration. The ethyl acetate fraction was washed twice with a mixture of 50 ml water and 50 ml brine, washed over MgSO 4 Dry and evaporate under reduced pressure. The acylation product is in GraceResolve provided by GRACE TM Purific...
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