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Azonaphthalene dicarboximide compound and composition, preparation and application thereof

A technology of azonaphthalimide and compound, which is applied in the field of disperse dyes, can solve the problems of only grade 4 fastness to washing and rubbing fastness, staining with other colors, etc., and achieve good color fixing rate and good Effect of dyeing property and excellent light fastness

Inactive Publication Date: 2012-02-15
HANGZHOU FLARIANT SPECIALTY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dyes currently available on the market such as C.I. Disperse Orange 30 and C.I. Disperse Red 167 have only Grade 4 fastness to washing and rubbing fastness, which will cause white or light-colored parts to be stained with other colors during the washing process, so it is urgent need to improve

Method used

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  • Azonaphthalene dicarboximide compound and composition, preparation and application thereof
  • Azonaphthalene dicarboximide compound and composition, preparation and application thereof
  • Azonaphthalene dicarboximide compound and composition, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Chlorination reaction

[0045] Dissolve 20g of 1,8-naphthalene dicarboxylic anhydride (industrial product content is 99%, 0.1mol, molar weight 23.26g) in 200g sodium hypochlorite solution (available chlorine content is 10%), heat and reflux for 4 hours, cool, and use carbonic acid Sodium hydrogen was used to adjust the pH to 7.5±0.5, and the water was distilled off under reduced pressure, washed with 3×20 mL of water and dried to obtain 22.3 g of 4-chloro-1,8-naphthalene dicarboxylic anhydride (purity: 95.8%, 0.0918 mol), mol The yield was 91.8% (calculated as 1,8-naphthalene dicarboxylic anhydride, the same below).

[0046] (2) Imination reaction

[0047] 22.3g (purity is 95.8%, 0.0918mol) of 4-chloro-1,8-naphthalic anhydride prepared in step (1) and 9.5g methylamine aqueous solution (40% by mass, methylamine 0.122mol) are dissolved in In 220g of DMF (dimethylformamide), heat and reflux for 5 hours, cool, and remove the solvent DMF by distillation under reduced p...

Embodiment 2

[0054] (1) Chlorination reaction

[0055] The sodium hypochlorite charging capacity is changed into 240g, other conditions and operation are with embodiment 1, obtain 4-chloro-1,8-naphthalic anhydride 22.5g (purity is 96.2%, 0.093mol), molar yield 93.0% (with 1 , 8- naphthalene dicarboxylic anhydride).

[0056] (2) Imination reaction

[0057] The charging capacity of 40% methylamine is changed into 9.33g (methylamine 0.12mol), the charging capacity of DMF is changed into 170g, other conditions are the same as embodiment 1, obtain 4-chloro-1,8-naphthalimide 21.2g (content 96.1%, 0.0829mol), molar yield 89.1% (based on 4-chloro-1,8-naphthalene dicarboxylic anhydride).

[0058] (3) Hydrolysis reaction

[0059] The charging capacity of sodium hydroxide is changed into 4.2g (content 95%, 0.1mol), the charging capacity of methyl alcohol is changed into 128g, other conditions are the same as embodiment 1, obtain 4-hydroxyl-1,8-naphthalene dicarboxylic acid Amine 17.4g (purity 96....

Embodiment 3

[0063] (1) Chlorination reaction

[0064] The sodium hypochlorite charging capacity is changed into 220g, other conditions are the same as embodiment 1, obtain 4-chloro-1,8-naphthalene dicarboxylic anhydride 22.4g (purity is 96.0%, 0.0924mol), molar yield 92.4% (with 1, 8-naphthalic anhydride).

[0065] (2) Imination reaction

[0066] The charging capacity of methylamine is changed into 10.1g (0.13mol), the charging capacity of DMF is changed into 260g, other conditions are the same as embodiment 1, obtain 4-chloro-1,8-naphthalimide 22.1g (purity is 96.5%, 0.0868mol), and the molar yield is 93.9% (based on 4-chloro-1,8-naphthalene dicarboxylic anhydride).

[0067] (3) Hydrolysis reaction

[0068] The charging capacity of sodium hydroxide is changed into 4.7g (0.112mol), the charging capacity of methyl alcohol is changed into 214g, and other conditions are the same as embodiment 1, obtain 4-hydroxyl-1,8-naphthalimide 18.3g ( The purity is 96.9%, 0.0837mol), and the molar yi...

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Abstract

The invention discloses an azonaphthalene dicarboximide compound shown as a formula (I). In the formula (1), R1 is C1-C5 aliphatic hydrocarbon, aromatic hydrocarbon, substituted aromatic hydrocarbon or C3-C5 oxygen-containing aliphatic hydrocarbon; the substituted group of the substituted aromatic hydrocarbon is p-methoxy; R2, R3 and R4 are independently hydrogen, C1-C2 alkane, C1-C2 alcoxyl hydrocarbon, halogen or nitryl; the composition of the azonaphthalene dicarboximide compound consists of the following raw materials in part by mass: 20 to 60 parts of azonaphthalene dicarboximide compound, and 40 to 80 parts of auxiliary agent; and the auxiliary agent is an anionic surfactant. The azonaphthalene dicarboximide compound has the properties of excellent color fastness to sunlight, washing fastness and the like; and the composition has good dyeing property, color fixation and good lifting power.

Description

(1) Technical field [0001] The invention relates to a disperse dye, in particular to an azonaphthalimide compound and its composition, preparation and application. (2) Background technology [0002] With the rapid development of polyester fiber and the improvement of people's requirements for textiles, higher requirements are put forward for the dyeing performance and environmental protection performance of disperse dyes. The market needs disperse dyes with higher lifting power and better fastness properties in all aspects. The dyes currently available on the market such as C.I. Disperse Orange 30 and C.I. Disperse Red 167 have only Grade 4 fastness to washing and rubbing fastness, which will cause white or light-colored parts to be stained with other colors during the washing process, so it is urgent needs improvement. (3) Contents of the invention [0003] The object of the present invention is to provide a disperse dye compound and its composition with excellent washi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09B29/42C09B67/38
Inventor 李百春贾建洪刘武松
Owner HANGZHOU FLARIANT SPECIALTY
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