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Method for synthesizing polymeric azo dyes

A polymer, azo-based technology, applied in the coupling reaction of azo dyes, azo dyes, organic dyes, etc., can solve problems such as difficulty and expensive impurities

Inactive Publication Date: 2002-10-30
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in applications where even relatively low levels of impurities would be problematic, phase transfer catalysts are not an option since it is too expensive and difficult, if not impossible, to separate said impurities from the desired end product. Program

Method used

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  • Method for synthesizing polymeric azo dyes

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Experimental program
Comparison scheme
Effect test

Embodiment 3

[0077] With stirring, to a 5 L, cooling jacketed, round bottom flask was added sequentially: 4-Nitroaniline (2.5 moles, 345 g), water (2.0 L), and hydrochloric acid (37%, 0.5 L) . The mixture was cooled to 0-10 °C and pre-cooled IBN (15 °C, 2.6 moles, 268 g) was added to the flask. At this point the diazotization reaction will occur immediately. After the IBN addition was complete, the reaction mixture was stirred for an additional hour. The diazonium salt formed is then ready for the sequential azo coupling reaction.

[0078] Into a 20 L glass reactor, add PHS-MMA (55-45 molar ratio, 2.5 moles, 300 g), THF (2.5 L), methanol (3.0 L), and tetramethylammonium hydroxide (TMAH, 25 %, 2.5 liters), and the mixed solution was cooled to 0-10°C. The azo coupling reaction was performed by pumping the diazonium salt solution and the PHS solution simultaneously through a 1 / 4 inch by 60 inch in-line static mixer (from Cole-Parmer Instrument Co.). Two gear pumps (70 and 80 in Figure 1)...

Embodiment 4

[0080] To a 5 L, cooled jacketed, round bottom flask were added sequentially with stirring: aminoacetanilide (AAA, 2.5 moles, 375.0 g), water (1.5 L), and hydrochloric acid (37%, 0.5 L) . The suspension was cooled to 0-5 °C. Pre-cooled IBN (15°C, 2.55 moles, 262.6 grams) was added to the flask. When the AAA reacts, the newly formed diazonium salt dissolves in water, giving a brown solution.

[0081]In a 20-liter reactor at 5°C, PHS-MMA (55-45 molar ratio, 2.3 moles, 506 g) was dissolved in THF (4.9 liters), water (1.3 liters), methanol (2.5 liters), and in a mixture of TMAH (25%, 1.9 L). The diazonium salt solution and the PHS solution were pumped at a flow ratio of 1:4.2 between the diazonium salt solution and the PHAS-MMA solution through a 1 / 4 inch x 60 inch in-line static mixer connected to a centrifugal pump. Monitoring is performed using flow gravimetric analysis. The contact time of the reactants was about 2 seconds. It took approximately 50 minutes to pump all th...

Embodiment 5

[0083] 2-(Methacryloyloxy)ethylacetoacetate (MEAA, 2.5 moles, 535.0 grams) and THF (4.0 L) were added to a 10 L round bottom flask. The solution was degassed by bubbling nitrogen gas through the solution for 1 hour. Then, a solution of methyl methacrylate (MMA, 2.5 mol, 250.0 g) and 2,2'-azobisisobutyronitrile (AIBN, 41.0 g) in THF was injected into the first solution. The mixture was further degassed with nitrogen for 30 minutes. The nitrogen vent needle was then removed and the mixture was stirred overnight at 65°C in a sealed container. The solution was then precipitated into 25 liters of 2-propanol. The polymer product (MEAA-MMA, 50-50 molar ratio) was collected as a yellow solid in 96% yield. GPC showed that the weight average molecular weight Mw of the polymer was 32800.

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Abstract

A method of coupling a diazonium salt with an organic polymer comprising, on order, the steps of: providing a polymer in one liquid phase; providing a diazonium salt in a separate liquid phase; contacting the separate phases, and thereby reacting the polymer and the diazonium salt.

Description

field of invention [0001] The invention relates to a method for synthesizing polymeric azo dyes from diazonium salts and polymers. The resulting polymeric azo dye compounds are useful in the production of antireflective coating compositions for use in conjunction with photoresist materials in microelectronic devices. Background of the invention [0002] It has been found that many chemical preparation methods which provide acceptable results on a small or laboratory scale prove to be impractical or uneconomical when attempting to employ said methods for large-scale production. This is the case when a product is prepared by the rapid reaction of two or more compounds contained in two or more separate phases. This rapid reaction requires rapid interfacial mixing (macroscopically and microscopically) so that the reactants contained in one phase are brought into rapid and intimate contact with the reactants contained in the other phase. This will allow for an efficient and sub...

Claims

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Application Information

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IPC IPC(8): G03F7/11C08F8/30C09B41/00C09B69/10G03F7/021G03F7/09
CPCC09B69/106G03F7/021G03F7/091
Inventor 单会丁术季E·B·冈萨雷斯D·N·坎纳
Owner MERCK PATENT GMBH
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