Preparation method of high-whiteness thermosensitive color developing agent containing sulfonylurea structure

A technology containing sulfonylurea and high whiteness, which is applied in the field of preparation of heat-sensitive developer, which can solve the problem that the purity of color developer and whiteness affect the quality of thermal paper, the preparation process is cumbersome and complicated, and the heat-sensitive paper is dark. problems, to achieve the effect of preventing poor color, improving the purity of filter cake, and preventing oxidation and discoloration

Pending Publication Date: 2022-03-01

HEBEI JIANXIN CHEM IND CO LTD

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AI-Extracted Technical Summary

Problems solved by technology

[0004] Since the production process of thermal paper is to directly compound and coat the color developer, color coupler, stabilizer and other functional components on the surface of the paper base, the entire use process does not involve the color developer purification or similar purification process, so the obvious The purity and whiteness of the colorant will directly affect the quality of thermal paper; at the same time, in industrial production, since most of the sulfonylurea color developers are synthesized in a highly polar solvent, the residual solvent will cause the color d...

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Method used

[0024] The sulfonylurea group is an excellent hydrogen bond assembly unit, which is easy to carry out intermolecular assembly through intermolecular hydrogen bonding, thereby forming forms such as gels. When the intermediate product N-p-toluenesulfonyl-N'-(3-hydroxyphenyl) urea system reacts with PTSC, at first adjust the pH=10-11 of the intermediate product system, destroying due to the phenylsulfonylurea group There is the formation of molecular self-assembly that causes the system to form a gel-like state, so that the intermediate product precipitated due to non-solubility is dissolved;...

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Abstract

A preparation method of a high-whiteness thermosensitive color developing agent containing a sulfonylurea structure comprises the following steps: dissolving MAP in an organic solvent, slowly dropwise adding PTSI into the organic solvent, and carrying out heat preservation to a reaction endpoint to obtain an intermediate product N-p-toluenesulfonyl-N '-(3-hydroxyphenyl) urea system; adding alkali liquor into the obtained intermediate product system for dissolving, then slowly dropwise adding an organic solution of PTSC, simultaneously dropwise adding the alkali liquor to control the pH value of the system, and carrying out heat preservation reaction to the end point to obtain a product N-p-toluenesulfonyl-N '-(3-p-toluenesulfonyloxyphenyl) urea system; adding an alcohol solvent into the prepared N-p-toluenesulfonyl-N-(3-p-toluenesulfonyloxy phenyl) urea system, neutralizing with acid, and filtering to obtain a filter cake; and carrying out post-treatment and vacuum drying on the filter cake to obtain a final product. According to the preparation method disclosed by the invention, the sulfonylurea color developing agent with high yield, high purity, whiter color and less solvent residue can be obtained, and the process operation is more suitable for industrial production.

Application Domain

Organic compound preparationSulfonic acid amide preparation

Technology Topic

SolventPhenyl group +10

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Examples

Experimental program(6)

Example Embodiment

[0030] Example 1

[0031] One-step reaction: access N in the reactor 1 2 After the air was transferred, 500 L DMAC was added, stirred and stirred, adding 272.75 kg (2.50 kmol) amino phenol (MAP), dissolved at 40 ° C, slowly added 517.65 kg (2.63 kmol) of toluenesulfonyl isocyanate (PTSI), The dropwise addition of 2.5 h, 40 ° C for insulation, and the insulation is 2 hours to reach the end point.

[0032] Two-step reaction: Configuration of toluenesulfonyl chloride (PTSC): 524.42 kg (2.75 kmol) PTSC was dissolved in 525 L DMAC.

[0033] Transfer the material in the reactor 1 to N 2 In the reaction kettle 2 of the atmosphere, 10% NaOH solution 1196 kg (2.99 kmol) is pumped in the reaction kettle 2, the system pH = 10-11, and the DMAC solution of toluenesulfonyl chloride (PTSC) is slowly added drop. % NaOH is dissolved 300kg (2.25 kmol) to ensure that the system pH = 10-11, the temperature is between 40-60 ° C, the dropwise time is 1.0 h, and the insulation 1H reaches the end point of the reaction.

[0034] Socket: Transfer the reactor 2 system to N 2 In the anatum of the atmosphere, 3075 l of methanol was pumped in the kettle, and 35% hydrochloric acid was added dropwise to the system pH = 3-5, and the pH was stabilized, the system was pumped into the two-in-1 pressure filtration, cake.

[0035] Post-treatment: The filter cake first replaced the mother liquor with 1025 L of methanol, then washed to neutral with water, and finally replaced the filter cake removable water with 1025L methanol again.

[0036] Vacuum drying: Transfer the filter cake to a double cone dryer, dried at 40 ° C for 2 h; slowly warmed to 70 ° C, thermal temperature for 1 h; continued to heat up to 100 ° C, heat insulation for 1 h, fell to room temperature.

[0037] Product total yield: 94.5%, HPLC content: 99.52%, color: bright white.

Example Embodiment

[0038] Example 2

[0039] One-step reaction: access N in the reactor 1 2After the air was returned, 750 L DMAC was added, stirred, and 272.75 kg (2.50 kmol) amino phenol (Map) was added, and 542.3 kg (2.75 kmol) of toluenesulfonyl isocyanate (PTSI) was slowly added dropwise. Take the dropwise time of 3.5 h, 30 ° C for insulation, and the insulation was 1.5 hours arrived at the end.

[0040] Two-step reaction: Configuration of toluenesulfonyl chloride (PTSC): 572.10 kg (3.00 kmol) PTSC was dissolved in 720l DMAC.

[0041] Transfer the material in the reactor 1 to N 2 In the atmosphere of the reaction kettle 2, a 20% NaOH solution was pumped in the reaction kettle 2, the system pH = 10-11, and the DMAC solution of toluenesulfonyl chloride (PTSC) was slowly added drop. % NaOH is 513.31kg (2.57kmol) to ensure that the system pH = 10-11, between 40-60 ° C, the dropwise time is 1.5 h, and the insulation 1H reaches the end point of the reaction.

[0042] Socket: Transfer the reactor 2 system to N 2 In the anatum of the atmosphere, 2940 L of methanol was pumped in the kettle, and 40% dilute sulfate was added dropwise to the system pH = 3-5, and the pH was stable, the system was pumped into a two-in-1 pressure filtration, cake.

[0043] Post-processing: The filter cake first was first placed with 1470 L of methanol, and then washed to neutral with water, and finally wash the filter cake residual water with 1470L methanol again.

[0044] Vacuum drying: Transfer the filter cake to a double cone dryer, 25 ° C is dried in vacuo; slowly warmed to 80 ° C, thermal temperature for 1 h; continued to heat up 100 ° C, heat insulation for 1 h, and fell to room temperature.

[0045] Product total yield: 93.8%, HPLC content: 99.55%, color: bright white.

Example Embodiment

[0046] Example 3

[0047] One-step reaction: access N in the reactor 1 2 After the air was replaced, 1000 L DMAC was added, stirred, and 272.75 kg (2.50 kmol) amino phenol (MAP) was added, and 566.95 kg (2.88 kmol) of toluenesulfonyl isocyanate (PTSI) was slowly added dropwise. The dropped time was 4.0 h, and the insulation was carried out at 30 ° C, and the temperature was 1 h to the end point.

[0048] Two-step reaction: Configuration of toluenesulfonyl chloride (PTSC): 619.78 kg (3.25 kmol) PTSC was dissolved in 900l DMAC.

[0049] Transfer the material in the reactor 1 to N 2 In the reaction kettle 2, 15% Na is pumped in the reactor 2. 2 CO 3 The solution is 1060 kg (1.5 kmol), the system pH = 10-11, slowly added DMAC solution of toluenesulfonyl chloride (PTSC) while dripping 40% NaOH 280kg (2.80 kmol) to ensure the system pH = 10-11, temperature It was between 40-60 ° C, the dropwise time was 1.5 h, and the insulation 1 h reached the end of the reaction.

[0050] Socket: Transfer the reactor 2 system to N 2 In the anatum of the atmosphere, 4000 l ethanol was pumped in the kettle, and 30% hydrochloric acid was added dropwise to the system pH = 3-5, and the pH was stable, the system was pumped into the two-in-1 percent.

[0051] Post-treatment: The filter cake first replaced the mother liquor with 1900 L of ethanol, then washed with water to neutral, and finally replaced the filter cake residual water with 1900L ethanol again.

[0052] Vacuum drying: Transfer the filter cake to a double cone dryer, dried in vacuo at 50 ° C for 2 h; slowly warmed to 80 ° C, thermal temperature for 1 h; continued to warm to 100 ° C, heat insulation for 1 h, fell to room temperature.

[0053] Product total yield: 93.4%, HPLC content: 99.65%, color: bright white.

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the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine

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Classification and recommendation of technical efficacy words

Guaranteed yield
Prevent oxidation and discoloration

Preparation method of high-whiteness thermosensitive color developing agent containing sulfonylurea structure

AI-Extracted Technical Summary

Problems solved by technology

Method used

Abstract

Image

Examples

Example Embodiment

Example Embodiment

Example Embodiment

PUM

Description & Claims & Application Information

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