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Bulk coloured high polymer organic material containing pyrimido-pteridine or its mixture

A high molecular weight, organic material technology, applied in the direction of organic dyes, organic chemistry, dyeing methods, etc., can solve the problem of not being particularly excellent

Inactive Publication Date: 2005-02-02
CIBA SPECIALTY CHEM HLDG INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mixtures of known pyrimidopteridine compounds with high molecular weight organic materials generally have good lightfastness, but this is still not particularly excellent for many applications, especially when used as automotive paint

Method used

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  • Bulk coloured high polymer organic material containing pyrimido-pteridine or its mixture
  • Bulk coloured high polymer organic material containing pyrimido-pteridine or its mixture
  • Bulk coloured high polymer organic material containing pyrimido-pteridine or its mixture

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 : 198.8 g of commercially available 90% 2,4,5,6-tetraaminopyrimidine sulfate was slurried in 1 l of deionized water, then the suspension was adjusted to pH 7.9 by adding 30% aqueous sodium hydroxide solution ( measured with a pH glass electrode). At the beginning of the oxidation step, the pH was maintained at 7.9 and, if necessary, 30% aqueous sodium hydroxide was added. The reaction mixture was first stirred at room temperature for 15 minutes and then heated to 55°C over 30 minutes. Moderate airflow was then blown through the subsurface tube into the then almost clear orange solution, raising the temperature to 85°C over a further 30 minutes. The gradually thickening orange suspension was then stirred at 85° C. for 20 hours while blowing in air. After 3 hours, 150 ml of water were added and the pH control was stopped (total consumption of 30% sodium hydroxide solution: 197 ml). The fine orange precipitate was isolated hot by filtration through a hard fil...

Embodiment 2

[0071] Example 2 : The filtrate containing 10 l of still warm glacial acetic acid mentioned in Example 1 was left overnight at room temperature. The resulting fine precipitate was isolated by filtration through a hard filter paper, and the orange-red residue was stirred in 600 ml of water. This suspension, having a pH value of 4.37, was adjusted to pH 7 with 30% sodium hydroxide solution, then heated to 90° C. and adjusted to pH 7 again by further addition of sodium hydroxide solution. The suspension was stirred for one hour at 90°C, then filtered hot through a hard filter paper and the filter cake was washed with 1200 ml of water. While still moist, the orange-red filter cake was slurried in 600 ml dimethylacetamide and heated to boiling point, first distilling off the solvent / water mixture until the temperature of the suspension reached 140°C. At 140° C., the suspension was recrystallized for 17 hours, the reaction product was cooled to 90° C., filtered through a hard fil...

Embodiment 3

[0075] Example 3: 24.66 g of commercially available 97% 6-hydroxy-2,4,5,-triaminopyrimidine sulfate was slurried in 450 ml of deionized water, and the suspension was adjusted to pH by adding 30% aqueous sodium hydroxide The value is 7.5 (measured with a pH glass electrode). The mixture was heated to 80° C. within 30 minutes and the pH was adjusted continuously to 7.5 by addition of sodium hydroxide solution. A moderate air stream was then blown through the subsurface tube into the tan suspension, maintaining the temperature at 80°C throughout. After 22 hours, the gas flow was stopped and the orange suspension was cooled to 60°C and filtered through a hard filter paper. After washing with 150 ml of water, the still damp filter cake was mixed with 300 ml of glacial acetic acid (laboratory mixer) and the suspension was then placed in a Soxhlet tube and extracted with a further 1200 ml of boiling glacial acetic acid for 2 hours. The orange residue was collected by suction from...

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Abstract

A process for mass colouring high molecular weight organic material by using a pyrimidopteridine of formula (I) and / or (II) or a mixture thereof, wherein A, B, C and D are each independently of one another -NH2, -OH, hydrogen, C1-C4-alkyl; phenyl, biphenyl or naphthyl which are unsubstituted or substituted by halogen, -OH, -NH2, C1-C4alkyl or C1-C4alkoxy; -NHR1, -N(R1)2 or formula (1), wherein R1 is C1-C4alkyl; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl or C1-C4alkoxy, or -COXR2, X is a direct bond, -O- or -NH-, and R2 is C1-C4alkyl; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl or C1-C4alkoxy, with the proviso that at least two of the radicals A, B, C and D are -NH2 or -OH.

Description

technical field [0001] The present invention relates to a mass colored high molecular weight organic material comprising pyrimidopteridine or a mixture thereof. technical background [0002] Pyrimidopteridines are known compounds. in the yearbook 545 209 (1940), H. Wieland et al. mention hydroxyl-substituted pyrimidopteridines as reaction products of butterfly wing pigments. JACS, 77 , 2243-2248 (1955), a work devoted to the synthesis of amino- and hydroxyl-substituted pyrimidopteridines, describing these products as yellow substances lacking solubility. JP-A 93-202046, JP-A 93-202053, JP-A 94-41135 and JP-A 95-278456 disclose, as fluorescent pigments, pyrimidopteridines substituted on at least two nitrogen atoms of the ring system . DE-A 4415656 discloses pyrimidopterinium salts as pigments. Mixtures of known pyrimidopteridine compounds with high molecular weight organic materials generally have good lightfastness properties, but this is still not particularly excelle...

Claims

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Application Information

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IPC IPC(8): C07D475/02C07D487/14C08K5/00C08K5/34C08L101/00C09B17/00C09B57/00D06P1/00
CPCC09B17/00C08K5/0041C09B57/00C07D487/14C07D475/02D06P1/00
Inventor T·埃岑伯格M·许金
Owner CIBA SPECIALTY CHEM HLDG INC
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