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Photoinitiator for UV (ultraviolet)-LED curing

A UV-LED and photoinitiator technology, which is applied in the field of UV-LED curing photoinitiator and its preparation, can solve the problems of limited selection of curing substrates, many synthesis steps, and poor product stability. The effect of strong intramolecular electron transfer performance, good electron delocalization, and excellent photoelectric properties

Inactive Publication Date: 2014-06-04
CHANGSHANG NEWSUN CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 1. The use of UV mercury lamps is large. A light curing equipment uses UV mercury lamps as little as 1-2, and as many as 6-8.
[0005] 2. The power of the UV mercury lamp is very large, ranging from 3KW to 20KW, and the power consumption is huge
[0006] 3. The traditional UV mercury lamp generates a lot of heat, which has great limitations in the selection of curing substrates.
[0007] 4. The traditional UV mercury lamp starts slowly and takes a long time to warm up. It is only suitable for continuous work, which causes waste to normal production and has poor flexibility.
[0008] 5. Extensive use of mercury lamps will inevitably cause mercury pollution
[0019] The research and development of carbazole-based photoinitiators mostly focus on carbazole oxime esters, such as U.S. Patents US2004 / 0170924A1, US2006 / 0241259A1, US2008 / 0096115A1, US2010 / 0136491A1, US2010 / 0086881A1 published a variety of single or multifunctional carb Azolyl oxime ester photoinitiators and carbazolyl oxime ester photoinitiators have high initiating activity, but their synthesis steps are many, and the product stability is not good
[0020] Chinese patent CN102250115A reports a carbazole ring-derived aromatic ketone compound, which constructs a di- or multi-functional photoinitiator by introducing different active groups on the carbazole aromatic ring, but the absorption of these compounds in the long-wave region is still very limited And some structured photolysis will inevitably produce odor, yellowing and other phenomena

Method used

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  • Photoinitiator for UV (ultraviolet)-LED curing
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  • Photoinitiator for UV (ultraviolet)-LED curing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1: Preparation of formula (III) compound PI6301

[0075] Step 1: Carbazole N-ethylation

[0076] Add 20g of carbazole, 30ml of benzene, 60ml of 30% sodium hydroxide solution, and 1g of tetrabutylammonium bromide into a 250ml three-necked flask, and control the temperature at 50°C for 3 hours, then slowly add 14.3g of bromoethane dropwise, and reflux for 5 hours . TLC followed the reaction process. After the reaction was completed, 70ml of benzene and 50ml of water were added, stirred and allowed to stand for stratification. The organic phase was washed twice with 50ml of water, and recrystallized with ethyl acetate after solvent removal to obtain 20.5g of N-ethylcarbazole. , yield 87.9%.

[0077] The second step: carboxylation

[0078] (a) With reference to the literature Inorganic Chemistry Communications 9(2006) 351–354, AlCl 3 (40g, 0.3mol) and acetyl chloride (35ml, 0.5mol) were dissolved in 25ml of dichloromethane, at normal temperature, the dichloro...

Embodiment 2

[0086] Embodiment 2: the preparation of formula (IV) compound PI6302

[0087] Referring to Example 1, the first, second and third steps were used to prepare 3,6-diacetyl chloride-9-ethylcarbazole;

[0088] The fourth step: the preparation of diethyl phenyl phosphite

[0089] Under stirring, 179g (1.0mol) of phenylphosphine dichloride was slowly added dropwise to 266.6g (2.2mol) of N,N-dimethylaniline and 276g (0.6mol) of ethanol in an ice bath kept at 20-30 The mixture was stirred at room temperature for 3h after the addition. Filter off the solid salt, wash with ether several times, combine the filtrate and washing liquid, evaporate the solvent under normal pressure, and then distill under reduced pressure to collect 158.5 g of b.p.109°C / 1.59kpa fraction, with a yield of 80%.

[0090] Step 5: Arbuzov reaction

[0091] Place 31 g of the obtained 3,6-diacetyl chloride-9-ethylcarbazole in a 250 ml three-necked flask, slowly add 38 g of phenyl diethyl phosphite dropwise under ...

Embodiment 3

[0093] Embodiment 3: Preparation of formula (XIII) compound PI6401

[0094] The first step: the preparation of 1,6-biscarbazolidine

[0095] Add 20g of carbazole, 30ml of benzene, 60ml of 30% sodium hydroxide solution, and 1g of tetrabutylammonium bromide into a 250ml three-necked flask, and slowly add 16.5g of 1,6-dibromohexane dropwise after controlling the temperature at 50°C for 3 hours. , Reflux reaction for 5h. TLC followed the reaction process. After the reaction was completed, 70ml of benzene and 50ml of water were added, stirred and allowed to stand for stratification, and the organic phase was washed twice with 50ml of water. After removing the solvent, it was recrystallized with ethyl acetate to obtain 1,6-biscarbazole hexyl Alkane 18g, yield 71%.

[0096] The second step: carboxylation of 1,6-biscarbazole hexane

[0097] (a) With reference to the literature Inorganic Chemistry Communications 9(2006) 351–354, AlCl 3 (40g, 0.3mol) and acetyl chloride (33.6ml, 0.4...

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Abstract

The invention discloses a structure of a photoinitiator applicable to UV (ultraviolet)-LED curing and a method for preparing the photoinitiator. The carbazolyl acyl phosphine oxide type photoinitiator is fine in electron delocalizability, has high intramolecular electron transfer performance and excellent photoelectric performance, has high absorbability in a long-wave region (365nm-395nm), is adaptable to high-power UV-LED ultraviolet curing, overcomes the shortcomings of high curing energy consumption and heavy pollution of traditional mercury lamps, and gets rid of the defects of proneness to yellow and high mobility of micromolecular photoinitiator due to the macromolecular structure.

Description

technical field [0001] The invention relates to a photoinitiator and a preparation method thereof, in particular to a photoinitiator for UV-LED curing and a preparation method thereof. Background technique [0002] Photocuring refers to the curing process of monomer, oligomer or polymer matrix under light induction. Photoinitiator is a kind of active intermediate (free base or cation). Photoinitiator is a key component of photocurable products, and it plays a decisive role in the photocuring rate of photocurable products. [0003] At present, the photocuring technology is mainly ultraviolet curing, and the light source is mainly a high-pressure mercury lamp. The 365nm, 313nm, 302nm, and 254nm spectral lines in the emission spectrum are very useful. Many photoinitiators have large absorption at the above wavelengths, although UV mercury Lamps provide an effective source of UV light, but have some notable drawbacks in their radiation process: [0004] 1. The use of UV mercu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86G03F7/004
Inventor 叶正培鲁祥勇
Owner CHANGSHANG NEWSUN CHEM IND
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