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Uracil Schiff-base and preparation method and use thereof

A technology of uracil-Schiff base and semi-uracil, applied in the field of uracil-Schiff base and its preparation, can solve the problems of poor stabilization effect, opaque PVC products, poor PVC compatibility, etc., and achieves strong stability and high transparency , the effect of no three wastes

Active Publication Date: 2019-05-07
衢州建华南杭药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1,3-Dimethyl-6-aminouracil is the most widely used organic heat stabilizer for PVC. Because the melting point is 295°C, which is much higher than the processing temperature of PVC products, it has poor compatibility with PVC and poor stabilizing effect. , PVC products are opaque

Method used

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  • Uracil Schiff-base and preparation method and use thereof
  • Uracil Schiff-base and preparation method and use thereof
  • Uracil Schiff-base and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 1000 ml three-necked flask equipped with a stirring device, add 700 ml of water, add sulfuric acid to adjust pH: 3-4, add 5.60 g of 1,3-dimethyl-6-aminouracil, keep pH: 3-4 , until the uracil is completely dissolved, drop 3.11 g of isovaleraldehyde, a yellow precipitate is formed in the stirring reaction, filter, wash the filter cake three times, and dry to obtain the uracil Schiff base, whose structural formula is shown in formula (III). Yield: 95.1%, light yellow solid, melting range: 165-178℃, close to PVC melt flow temperature, purity: 95.5%, moisture: 3.5%, other impurities: ≤1.0%; 1H NMR (DMSO)δ : 0.83-0.88 (6H, 6Hz, 2CH3), 1.3 (1H, 1.3Hz, 1CH), 1.8-2.1 (2H, 1CH2,) 3.2 (6H, 1H, 2CH3), 4.2 (1H, 1.5 Hz, 1CH), ; IR(KBr): 3383, 3198, 2955, 1698, 1670, 1610 , 1496 , 1376 , 1050 , 788, 500 cm -1 .

[0023]

[0024] Formula (III).

Embodiment 2

[0026] In a 1000 ml three-necked flask equipped with a stirring device, add 700 ml of water, add acetic acid to adjust pH: 3-4, add 5.60 g of 1,3-dimethyl-6-aminouracil, keep pH: 3-4 , until the uracil is completely dissolved, add 0.1g phase transfer catalyst, raise the temperature to 80°C, add 7.66g C14 aldehyde (myristal) dropwise, a yellow precipitate is formed in the stirring reaction, filter, wash the filter cake 3 times, and dry to obtain urea Pyrimidine Schiff base, whose structural formula is shown in formula (IV). Yield: 96.2%, light yellow solid, melting range: 141-156℃, good compatibility with PVC, purity: 94.8%, moisture: 3.7%, other impurities: ≤1.5%; 1H NMR (DMSO)δ: 0.83 -0.88 (6H, 6Hz, 2CH3), 1.3 (1H, 1.3 Hz, 1CH), 1.8-2.2 (24H, 12CH2), 3.2 (6H, 1H, 2CH3), 4.2 (1H, 1.5 Hz, 1CH), ; IR ( KBr): 3383, 3250, 3198, 2955, 1698, 1670, 1610 , 1496 , 1376 , 1050 , 788, 500 cm -1 . )

[0027]

[0028] Formula (IV)

Embodiment 3

[0030] The compound of formula III in Example 1 and the compound of formula IV in Example 2, 1,3-dimethyl-6-semiuracil (DMAU), were respectively used as PVC heat stabilizers for double-roll test. The formula for the double-roll test is shown in Table 1:

[0031] Table 1: Uracil Schiff base PVC heat stabilizer double-roll test formula table

[0032]

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Abstract

The present invention relates to a uracil Schiff-base and a preparation method and use thereof, and belongs to the technical field of chemical products. The uracil Schiff-base is expressed by a structural formula (I) as shown in the description. In the formula (I), R is selected from C4-C13 aliphatic radicals, aryl radicals and terpenic radicals that are all derived from an aldehyde raw material.The uracil Schiff-base and the preparation method and use thereof have the advantage that the synthesis process of the uracil Schiff-base is simple without three wastes and with no pollution, thus facilitating promotion and application thereof; due to the introduction of a long carbon chain into the molecular structure, the compound is allowed to have a reduced melting point, so that the compoundis present in a molten state at a processing temperature of PVC (polyvinyl chloride), thereby improving the compatibility of the compound in a PVC melt and facilitating the elimination of free radicals on the molten-state chain of the PVC; and therefore, better stability can be provided and higher transparency of a product can be achieved.

Description

technical field [0001] The invention belongs to the technical field of chemical products, in particular to a uracil Schiff base and a preparation method and application thereof. Background technique [0002] my country's polyvinyl chloride (PVC) output and consumption are the largest countries in the world, and the output and products have accounted for more than 50% of the world's. There are many styles of PVC products, and there is a diverse demand for heat stabilizers for PVC processing. [0003] At present, the common metal-containing heat stabilizers in the domestic market include lead salts, rare earths, calcium zinc, and organic tin. Except for calcium and zinc, they all belong to heavy metal pollution. Lead salt stabilizers have been gradually banned in my country. Butyltin has been banned in the EU. [0004] Metal-free organic heat stabilizers mainly include epoxy compounds, phosphites, polyols, β-diketones, nitrogen-containing species such as uracil, etc. Since the...

Claims

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Application Information

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IPC IPC(8): C07D239/545C08K5/29C08L27/06
Inventor 戚鹏鹏毛江洪唐吉元
Owner 衢州建华南杭药业有限公司
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