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Monoazo compound as well as product and application thereof

A monoazo compound technology, applied in the field of disperse dyes, can solve the problems of poor dry heat sublimation fastness, poor comprehensive performance, poor compatibility, etc., and achieve good dry heat sublimation fastness, bright color, Good dyebath stability

Inactive Publication Date: 2014-12-24
浙江昱泰染化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the fine denier, ultra-fine denier processing of polyester fibers, and the rapid development of functional blended fabrics, it is found that these dyes have poor wash resistance and dry heat sublimation fastness in the application of the above materials, and are different from other dyes. compatibility is not good
Chinese patent CN102127316 discloses that a class of N atom substituents is -CH 2 CH 2 NHCOR (where R is methyl, ethyl and phenyl) pyridone-type disperse dyes, the research found that its overall performance is still not good, especially the dyeing depth is very poor, only a small amount can be used for color matching

Method used

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  • Monoazo compound as well as product and application thereof
  • Monoazo compound as well as product and application thereof
  • Monoazo compound as well as product and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 15g of ice water and 5.8g of diamine compound represented by formula (II-1) into the reaction flask,

[0041]

[0042] Add 7.1g CNCH dropwise with stirring 2 COOCH 2 CH 3 , Keep the temperature ≤5℃ and react for 4 hours to obtain the compound of formula (Ⅲ-1),

[0043]

[0044] Add 13g of benzoyl chloride dropwise to the reaction flask, adjust the PH=5 with 12g of 30% liquid caustic soda, and control the temperature ≤10℃ to react for 8 hours to obtain the compound of formula (IV-1).

[0045]

[0046] Then, 4g of 30% liquid caustic soda was added dropwise to adjust the system PH≈9.5. Add 7.8g methyl acetoacetate and 6.0g 70% ethylamine aqueous solution, heat to 75℃ and keep the reaction for 12 hours, pour all the reaction liquid into about 200ml cold water, adjust the pH of the system with sulfuric acid <2, naturally cool down, filter, and wash twice with water to obtain 16.2g of the pyridone compound represented by formula (Ⅴ-1),

[0047]

[0048] Add 10.0ml water, 15.2g 30...

Embodiment 2

[0056] Substituting 10.9 g of methanesulfonyl chloride for 13 g of benzoyl chloride in Example 1, 9.4 g of the pyridone compound represented by formula (Ⅴ-2) was prepared.

[0057]

[0058] Substituting the p-nitroaniline represented by the equivalent formula (VI-2) for the o-nitroaniline in Example 1 to obtain the p-nitroaniline diazonium salt,

[0059]

[0060] According to the coupling method in Example 1, the pyridone compound represented by formula (Ⅴ-2) was mixed with an equivalent amount of p-nitroaniline diazonium salt solution to obtain the mono-coupled compound represented by formula (Ⅰ-6) Nitrogen compound 14.1g,

[0061]

[0062] Test data:

[0063] CompoundⅠ-6: Anal.Calcd.for[C 19 H 21 N 5 O 6 S]: C, 51.00; H, 4.73; N, 15.65%. Found: C, 50.91; H, 4.94; N, 15.31%. Main FT-IR absorptions(KBr pellets, cm -1 ): 3420(w), 2224(m), 1687(m), 1640(s), 1591(vs), 1442(s), 1335(m), 837(s).Negative ESI-MS: m / z =447.17,[MH] - .λ max / ε(l·mol -1 ·Cm -1 )=436.5 / 46003 and 310 / 5288.

Embodiment 3

[0065] Substituting 8 g of acetic anhydride for 13 g of benzoyl chloride in Example 1, 11.6 g of the pyridone type heterocyclic compound represented by formula (Ⅴ-3) was prepared.

[0066]

[0067] Substituting 8.4 g of o-nitrop-anisidine represented by formula (VI-1) for the o-nitroaniline in Example 1 to obtain o-nitrop-anisidine diazonium salt,

[0068]

[0069] According to the coupling method in Example 1, the pyridone compound represented by formula (V-3) was mixed with an equivalent amount of o-nitro-p-anisidine diazonium salt solution to obtain the formula (I-8) 19.5g of the monoazo compound shown,

[0070]

[0071] Test data:

[0072] CompoundⅠ-8: Anal.Calcd.for[C 20 H 22 N 6 O 6 ]: C, 54.29; H, 5.01; N, 19.00%. Found: C, 54.06; H, 4.97; N, 18.87%. Main FT-IR absorptions(KBr pellets, cm -1 ): 3450(w), 2225(w), 1683(m), 1620(s), 1504(s), 1465(vs), 1406(m), 1269(m), 1184(m). 1 H NMR(500MHz, CDCl 3 )δ: 15.91(d,1H,NH), 8.07(m,1H,benzene), 7.79(d,1H,benzene), 7.38(m,1H,benzene), 4...

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Abstract

The invention discloses a monoazo compound as well as a product and application thereof, belonging to the technical field of disperse dyes. The monoazo compound is shown in a formula (I). The monoazo compound has the significant application in dyeing and printing on a synthetic fiber material as a disperse dye, especially has good comprehensive performance when being applied to a polyester ammonia elastic fabric, and particularly has excellent properties such as color fastness to washing, color fastness to water, dry heating sublimation resistant fastness, sun-proof fastness, deep dyeing performance and the like.

Description

Technical field: [0001] The invention relates to a monoazo compound, product and application, and belongs to the technical field of disperse dyes. Background technique: [0002] Disperse dyes with pyridone intermediates as coupling components are important varieties in yellow, orange and other color systems, and they often have the characteristics of bright color, high molar extinction coefficient, and good washing fastness. A large number of varieties of this type of structure have been registered in the Color Index, such as C.I. Disperse Yellow 119, 211, 241, etc. However, with the fine denier and ultra-fine denier processing of polyester fibers, as well as the rapid development of functional blended fabrics, it has been found that these dyes have poor fastness to water washing and dry heat sublimation in the application of the above materials. The compatibility is not good. Chinese patent CN102127316 discloses a type of N atom substituent is -CH 2 CH 2 NHCOR (where R is meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B29/42C09B67/22C09B67/38C09B67/36D06P1/18D06P3/54D06P3/85
Inventor 陈旭袁小红
Owner 浙江昱泰染化科技有限公司