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Photoinitiators and curable compositions

一种光引发剂、光引发的技术，应用在周期表第5/15族元素的化合物、有机化学、化学仪器和方法等方向，能够解决迁移和移动等问题

Active Publication Date: 2022-01-11
AGFA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for packaging applications, unreacted RAFT reagents can cause problems with migration and set off

Method used

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  • Photoinitiators and curable compositions
  • Photoinitiators and curable compositions
  • Photoinitiators and curable compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0267] 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):

[0268] .

[0269] GENOPOL AB1 is a polymeric 4-dimethylaminobenzoic acid derivative supplied by Rahn.

[0270] VEEA is 2-(vinylethoxy)ethyl acrylate available from NIPPON SHOKUBAI, Japan.

[0271] INHIB is a mixture of polymerization inhibitors with a composition according to Table 2:

[0272] Table 2

[0273]

[0274] Cupferron TM AL is aluminum N-nitrosophenylhydroxylamine from WAKO CHEMICALS LTD.

[0275] The PET100 substrate is a 100 μm thick transparent polyethylene terephthalate substrate available from AGFA-GEVAERT.

[0276] Measurement methods

[0277] 1. Molecular weight

[0278] 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

[0291] 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.

[0292] Synthesis of COMP-RAFT-1 (step 2)

[0293]

[0294] 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

[0310] This example illustrates the synthesis of photoinitiators according to the invention.

[0311] Synthesis of INI-RAFT-2

[0312]

[0313] Step 1: Irgacure TM Acylation of 2959

[0314] 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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Abstract

Certain RAFT functionalized photoinitiators and their use in radiation curable compositions, inks and inkjet inks are disclosed. The specific RAFT-functionalized photoinitiators can be advantageously used to reduce migratables and undesirable odors.

Description

technical field [0001] The present invention relates to RAFT functionalized photoinitiators and their use in UV curable compositions, such as UV curable inks, especially UV curable inkjet inks. Background technique [0002] Flexographic printing systems are increasingly being replaced by industrial inkjet printing systems for packaging applications due to their flexibility of use, such as variable data printing, which when incorporated into production lines allows even last-minute packaging appearance changes . Radiation curable inkjet inks are particularly preferred because high quality images can be printed on non-absorbent ink receivers such as plastic packaging materials. [0003] For food and pharmaceutical packaging, so-called "low-migration" UV-curable inkjet inks have been designed where the amount of migratory compounds after UV curing is minimized. Such low migration inkjet inks are exemplified in EP 2053101 A (AGFA), EP 2671722 A (AGFA) and WO 2016 / 007593 A (SUN...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09D11/101C08F2/46C08F4/32C09D11/30
CPCC08F2/50C08F4/34C09D11/101C09D11/30C08F2438/03C08F220/40B41M5/0023C07C329/06C07F9/3258C08F293/005C09D11/38
Inventor J.洛库菲尔
Owner AGFA NV
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