Synthesis method of novel SBQ photosensitive monomer

A synthesis method and monomer technology, which are applied in the synthesis field of new SBQ photosensitive monomers, can solve the problems of large operation load of equipment, reduced reaction selectivity, and increased environmental protection pressure in waste acid water treatment volume, and achieve a simple production process and environmental protection. Friendly, overcoming harsh reaction conditions

Inactive Publication Date: 2016-06-22
DENBISHI FINE CHEM KUSN
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Problems solved by technology

Pan Xiangchun et al. (CN101216668A) used sulfuric acid to catalyze the preparation of SBQ monomer. During the synthesis process, the separation and emulsification of the feed liquid was relatively serious, and the strong acid corroded the equipment strongly, resulting in a large operating load of the equipment, and the amount of waste acid water treatment increased the pressure on environmental protection.
[0005] Synthesis of SBQ monomer Due to the complete symmetry of the two aldehyde groups of the raw material terephthalaldehyde, there are competing side reactions during the synthesis process, and more bis-quaternary ammonium pyridinium quaternary ammonium salts (diene by-products or doubles) are generated. reduced reaction selectivity

Method used

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  • Synthesis method of novel SBQ photosensitive monomer
  • Synthesis method of novel SBQ photosensitive monomer

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preparation example Construction

[0034] Synthetic method of the present invention specifically comprises the steps:

[0035] (1) Synthesis of intermediate 4-picoline (containing substituted picoline) quaternary ammonium salt:

[0036] Add methanol and 4-picoline into the reactor, add dimethyl sulfate dropwise under the condition of lower than 10°C, and keep the temperature under stirring for 5~8h after dropping, and the holding temperature is 20~50°C; The colorless transparent solution is the intermediate 4-picoline quaternary ammonium salt solution; wherein: the molar ratio of dimethyl sulfate and 4-picoline (containing substituted pyridine) is 1: (1 ~ 1.2); The amount added is 1 to 10 times the amount of 4-picoline.

[0037] (2) Product SBQ monomer synthesis:

[0038] Add methanol, terephthalaldehyde and a catalyst into the reactor, add dropwise or all at once the intermediate solution obtained in step (1) at the reflux temperature, and filter after reflux for 5 to 8 hours, freeze and crystallize the filt...

Embodiment 1

[0041] Embodiment 1 (adopting each described material proportion and temperature condition, reaction time)

[0042] 1) Synthesis of intermediate 4-picoline quaternary ammonium salt

[0043] Add 20 mL of methanol and 9.5 g of 4-picoline into the reaction flask, drop 13 g of dimethyl sulfate at a temperature lower than 10°C, and keep it at 20°C for 6 hours to obtain an intermediate solution for later use.

[0044] 2) Synthesis of SBQ

[0045] Add 20.7 grams of terephthalaldehyde, 1.0 grams of hexahydropyridine, and 30 mL of methanol into the reaction flask, and add the intermediate solution dropwise at reflux temperature. Wash 2 to 3 times to obtain 15 grams of SBQ crude product, the product in the filtrate can be further recovered, and the crude product yield is 63%.

[0046] 3) SBQ crude product purification

[0047] Add 15 grams of SBQ crude product and 25 grams of methanol to the reactor, stir in an oil bath at 80°C for 0.5h, filter, discard the filter cake impurities, ad...

Embodiment 2

[0052] 1) Synthesis of intermediate 4-picoline quaternary ammonium salt

[0053] Add 50 mL of methanol and 18 g of 4-picoline into the reaction flask, drop 25.3 g of dimethyl sulfate at a temperature lower than 10°C, and keep the temperature at 20°C for 5 hours to obtain an intermediate solution for later use.

[0054] 2) Synthesis of SBQ monomer

[0055] Add 70 grams of terephthalaldehyde, 3 grams of hexahydropyridine, and 100 mL of methanol into the reaction flask. At the reflux temperature, add the intermediate dropwise. After the dripping, continue to reflux for 6 hours, cool down to room temperature, filter, and wash twice with 500 mL of ethyl acetate. 40 grams of the crude product were obtained, and the yield of the crude product was 59%.

[0056] 3) SBQ monomer purification

[0057] Add 40 grams of crude SBQ and 72 grams of methanol to the reactor, reflux in an oil bath at 80°C for 0.5 h, filter, add 18 grams of water and 1.2 grams of acetic acid to the filtrate, diss...

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Abstract

The invention discloses a synthesis method of a novel SBQ photosensitive monomer. The synthesis method comprises the following steps: by using an organic alkali catalyst instead of the traditional weak acid/strong acid acidic catalytic system, synthesizing an intermediate pyridine quaternary ammonium salt, adding the intermediate pyridine quaternary ammonium salt into an organic alkali mixed solution composed of methanol, toluene or any other organic solvent and terephthalaldehyde dropwisely or at one time, reacting under reflux for 5-8 hours, filtering to obtain a yellow homogeneous solution, cooling to crystallize, and purifying to obtain the brilliant yellow SBQ photosensitive monomer product with the purity of higher than 99%.

Description

technical field [0001] The invention relates to the technical field of synthesis of photosensitive polymer compounds, in particular to a method for synthesizing a novel SBQ photosensitive monomer, which is mainly used in the processing and manufacturing fields of photocured products such as screen printing and photoresist. Background technique [0002] SBQ is a photosensitive agent for organic styryl pyridinium salt resin photosensitive glue (SBQ photosensitive glue). SBQ photosensitive adhesive has high sensitivity, which is 3~4 times higher than that of commonly used screen printing photosensitive materials, and the amount of SBQ photosensitive agent is very small, and only 1~5% mol of hydroxyl group can have satisfactory sensitivity. A sensitizing initiator needs to be added. SBQ photosensitive monomer, as a non-diazo one-component photosensitive adhesive, relies on the singlet photocycloaddition reaction to cross-link PVA, so it has strong stability when it is not expos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/48
CPCC07D213/48
Inventor 温涛陈颖赵锦程
Owner DENBISHI FINE CHEM KUSN
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