A kind of method of synthesizing fluoran class black thermal pressure-sensitive coupler

A technology of fluoranes and couplers, applied in the field of organic dyes, can solve problems such as waste acid generation, increased production risk, and environmental protection issues

Active Publication Date: 2017-03-29
上海瑞年精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the six-stage catalyst is used in the plan, and a large amount of waste acid is produced in the production process, which has serious environmental protection problems; and the use of concentrated sulfuric acid increases the risk of production

Method used

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  • A kind of method of synthesizing fluoran class black thermal pressure-sensitive coupler
  • A kind of method of synthesizing fluoran class black thermal pressure-sensitive coupler
  • A kind of method of synthesizing fluoran class black thermal pressure-sensitive coupler

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] In a 500ml reactor, add 200ml of toluene, add 37.5g (0.1mol) of benzophenone acid, 21.3g (0.1mol) of DPA, catalyst NKC-950g(H + > 0.24mol), heat and stir at 110°C for 10 hours, then cool to 80°C, filter, wash NKC-9 with a small amount of toluene and apply it, add 120ml of water to the filtrate, and then add 30% sodium hydroxide dropwise to adjust the pH of the water phase> After 10, heat and reflux for 2 to 4 hours, divide the water phase, cool the organic phase to below 20°C, filter, wash the filter cake with a small amount of methanol, and dry to obtain 45.7 g of the product with a yield of 85%. Test, the content of the compound of formula I in the product> 99.5%, melting point 207.5~208℃.

[0046] The qualitative and quantitative analysis data of the product are as follows: 1H NMR (400MHz, CDCl3): δ6.4-7.8(m,18H),4.0(s,1H),3.1(t,J=7.3Hz,2H),2.34(s , 3H), 2.12 (s, 3H), 1.15 (t, J = 7.3 Hz, 2H); MS (ESI): m / z = 539 (M + +H).

[0047] R in the benzophenone acid described in ...

Embodiment 2

[0049] In a 500ml reactor, add 200ml of toluene, add 37.5g (0.1mol) of benzophenone acid, 21.3g (0.1mol) of DPA, perfluorosulfonic acid resin Nafion-H60g(H + > 0.12mol), heated and stirred at 110°C for 8 hours, then cooled to 80°C, filtered, Nafion-H was washed with a small amount of toluene and applied, the filtrate was added with 100ml of water, and then 30% sodium hydroxide was added dropwise to adjust the pH of the water phase> After 10, heat and reflux for 2 to 4 hours, divide the water phase, cool the organic phase to below 20°C, filter, wash the filter cake with a small amount of methanol, and dry to obtain 47.2 g of the product, with a yield of 90%. Test, the content of the compound of formula I in the product> 99.5%, melting point 208.1-208.6°C.

[0050] The qualitative and quantitative analysis data of the product are as follows: 1H NMR (400MHz, CDCl3): δ6.4-7.8(m,19H),4.0(s,1H),3.1(t,J=7.3Hz,2H), 2.12(s ,3H),1.15(t,J=7.3Hz,2H); MS(ESI): m / z=525(M + +H).

[0051] R in the...

Embodiment 3

[0053] In a 500ml reactor, add 200ml of xylene, add 37.5g (0.1mol) of benzophenone acid, 21.3g (0.1mol) of DPA, NKC-950g(H + > 0.12mol), heat and stir at 115°C for 9 hours, then cool to 80°C, filter, wash NKC-9 with a small amount of toluene and apply, add 120ml of water to the filtrate, and then add 30% sodium hydroxide dropwise to adjust the pH of the water phase> After 10, heat and reflux for 2 to 4 hours, divide the water phase, cool the organic phase to below 20°C, filter, wash the filter cake with a small amount of methanol, and dry to obtain 48.5 g of product, with a yield of 90%, tested by HPLC After that, the content of the compound of formula I in the product> 99.5%, melting point 207.5~208℃. R in the benzophenone acid described in this example 1 Represents ethyl, R 2 Represents p-methylphenyl.

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Abstract

The invention provides a method for synthesizing fluorane type black thermal-pressure sensitive color formers. The method, which takes benzophenone acid and 4-methoxy-2-methyl diphenyl amine as raw materials, comprises the following steps: adding benzophenone acid, 4-methoxy-2-methyl diphenyl amine and a catalyst into an organic solvent for reaction, and filtering the reaction liquid to obtain filtrate after the reaction is ended; adding water into the filtrate and regulating the pH of the filtrate to be greater than 10, and then heating and refluxing to remove a water phase and to obtain an organic phase; cooling and crystallizing the organic phase, and filtering to obtain the fluorane type color formers. The color formers prepared by the method comprise aryls which replace the alkyls in a conventional black color former, so that a conjugated system in the color former molecules is further increased, and the photon absorbing intensity of the color formers is increased. An efficient and recoverable a solid-acid catalyst is adopted, so that consumption of acid and alkalis in the preparation process is reduced, the discharge amount of waste acid and waste water is greatly reduced, the production cost is saved, and the color formers are more environmentally friendly.

Description

Technical field [0001] The invention belongs to the field of organic dyes, and specifically relates to a method for synthesizing a fluoran-based black heat pressure-sensitive coupler. Background technique [0002] Thermo-pressure-sensitive couplers are organic dyes with special properties. They are usually colorless. They react with the developer to develop colors after being heated or pressed. They mainly include crystal violet and benzofurans. The main structure and substituted functional groups show different colors. At present, it is mainly used in the production of carbonless copy paper. Black is currently the most important variety in heat and pressure sensitive couplers. [0003] The domestic patent application No. 200610145067X discloses a method for preparing 3-dibutylamino-6-methyl-7-anilinofluorane. In fact, 2-methyl-4-methoxy-diphenylamine DPA is used as Raw material, dissolve BBA in 90-102% sulfuric acid or fuming sulfuric acid. After all of it is dissolved, react w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00
Inventor 罗纲张良张少刚李新范雪东
Owner 上海瑞年精细化工有限公司
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