High fastness orange reactive dyes and process for their preparation

Abstract

The application discloses a high-fast orange reactive dye and a preparation method thereof, relates to the field of reactive dyes, and comprises a structure general formula as follows: formula 1: formula 2: or formula 3: wherein R1 is halogen; R2 is -H, -SO3M, -CH3, -COOM or -CHO; and M is Na, K or Li. The application has the effects of improving the fixing effect and dyeing performance of the reactive dye.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of reactive dyes, in particular to a high-fastness orange reactive dye and a preparation method thereof. BACKGROUND

[0002] Reactive dyes, also known as reactive dyes, contain active groups that can react with hydroxyl groups in cellulose and amino groups in protein fibers. During dyeing, covalent bonds are formed between the dye and the fiber to form "dye-fiber" compounds. Reactive dyes have the characteristics of bright color, good level dyeing, simple dyeing method, complete color spectrum, and low cost, and are mainly used for dyeing and printing of cotton, hemp, viscose, silk, and wool fibers and their blended fabrics.

[0003] At present, most of the reactive dyes use cyanuric chloride and para-ester or para-ester derivatives as active groups, but their fixation rate and various dyeing fastness are low. Therefore, it is particularly important to develop a reactive dye with good fixation effect and dyeing effect. SUMMARY

[0004] In order to improve the fixation effect and dyeing performance of reactive dyes, the present application provides a high-fastness orange reactive dye and a preparation method thereof.

[0005] In a first aspect, the present application provides a high-fastness orange reactive dye using the following technical solution:

[0006] A high-fastness orange reactive dye has the following general structure:

[0007] Formula 1:

[0008]

[0009] Formula 2: Or formula 3: Wherein, R1 is halogen; R2 is -H, -SO3M, -CH3, -COOM or -CHO; M is Na, K or Li.

[0010] Preferably, the general structure is:

[0011] Formula 1:

[0012]

[0013] Preferably, R1 is -Cl or -F.

[0014] Preferably, R1 is -Cl.

[0015] Preferably, R2 is SO3M; M is Na.

[0016] By adopting the technical scheme, the dye molecule structure contains multiple active groups, and a heterocyclic active group 6-amino-N-2 (β-ethyl sulfone group sulfate ethyl)-indolinone is introduced as a new active group to form complementation with the cyanuric chloride active group, so that the fixation rate reaches 85% or more, various dyeing performances such as washing fastness, rubbing fastness, sunlight fastness and chlorine fastness are high, the dissolving effect is good, and the high-fastness orange active dye shown in formula 1 has a fixation rate of 95% on cotton fabric when the dye concentration is 0.5% (o.w.f), and the washing fastness and dry rubbing fastness are both 5 levels, the sunlight fastness is 6 levels, and the dyeing performance is good.

[0017] In a second aspect, the application provides a preparation method of a high-fastness orange active dye, which adopts the following technical scheme:

[0018] A preparation method of a high-fastness orange active dye comprises the following steps:

[0019] a: uniformly mixing 6-amino-N-2 (β-ethyl sulfone group sulfate ethyl)-indolinone and water, adjusting pH to obtain a first dissolving product;

[0020] b: mixing cyanuric chloride beaten with an ice water mixture with the first dissolving product, adjusting pH to obtain a mono-condensation product, mixing the mono-condensation product with sodium 2,4-diamino benzene sulfonate, adjusting pH to obtain a di-condensation product.

[0021] c: reacting the di-condensation product, hydrochloric acid and sodium nitrite to obtain a diazonium salt;

[0022] d: mixing 3,5-diamino benzoic acid with water to obtain a second dissolving product, adjusting pH, and uniformly mixing the second dissolving product with the diazonium salt to obtain the high-fastness orange active dye.

[0023] Preferably, in the step a, the weight ratio of the 6-amino-N-2 (β-ethyl sulfone group sulfate ethyl)-indolinone to water is 1: (4-8).

[0024] Preferably, in the step a, the weight ratio of the 6-amino-N-2 (β-ethyl sulfone group sulfate ethyl)-indolinone to water is 1:6.

[0025] Preferably, in the step a, the pH is adjusted to 6.5-7.0.

[0026] Preferably, in the step b, when the cyanuric chloride beaten with the ice water mixture is mixed with the first dissolving product, the weight ratio of the cyanuric chloride to the ice water mixture is 1: (4-6).

[0027] Preferably, in step b, the weight ratio of the tricyanogen chloride to the ice water mixture is 1:5.

[0028] Preferably, in step b, the molar ratio of the tricyanogen chloride to the 6-amino-N-2(β-ethyl sulfone sulfate ethyl)-indolinone in the first dissolution product is (0.8-1.2):1.

[0029] Preferably, in step b, the molar ratio of the tricyanogen chloride to the 6-amino-N-2(β-ethyl sulfone sulfate ethyl)-indolinone in the first dissolution product is 1:1.

[0030] Preferably, in step b, the tricyanogen chloride pulped with the ice water mixture is mixed with the first dissolution product, the temperature is controlled at 5-10°C, the pH is adjusted to 3.0-4.0, and the reaction is maintained for 3.5-4.5h to obtain a monocondensate.

[0031] Preferably, in step b, the molar ratio of the sodium 2,4-diamino benzene sulfonate to the tricyanogen chloride is (0.8-1.1):1.

[0032] Preferably, in step b, the molar ratio of the sodium 2,4-diamino benzene sulfonate to the tricyanogen chloride is 1:1.

[0033] Preferably, in step b, the monocondensate is mixed with the sodium 2,4-diamino benzene sulfonate, the pH is adjusted to 3.5-4.5, the temperature is controlled at 25-35°C, and the reaction is maintained for 4.5-5.5h to obtain a di-condensate.

[0034] Preferably, in step b, the molar ratio of the tricyanogen chloride to the hydrochloric acid in step c is 1:(1.4-1.8), and the molar ratio of the tricyanogen chloride to the sodium nitrite in step c is 1:(0.9-1.2).

[0035] Preferably, in step b, the molar ratio of the tricyanogen chloride to the hydrochloric acid in step c is 1:1.5, and the molar ratio of the tricyanogen chloride to the sodium nitrite in step c is 1:1.

[0036] Preferably, in step c, the volume concentration of the hydrochloric acid is 29-36%.

[0037] Preferably, in step c, the volume concentration of the hydrochloric acid is 30%.

[0038] Preferably, in step c, the di-condensate is stirred uniformly after the addition of the hydrochloric acid, the temperature is lowered to 0°C, and the diazonium salt is obtained after the reaction by adding the sodium nitrite.

[0039] Preferably, the molar ratio of cyanuric chloride in the step b to 3, 5-diaminobenzoic acid in the step d is 3: (1-3).

[0040] Preferably, the molar ratio of cyanuric chloride in the step b to 3, 5-diaminobenzoic acid in the step d is 3:1.

[0041] Preferably, in the step d, 3, 5-diaminobenzoic acid is mixed with water, and the pH is adjusted to 6-7 to obtain a second dissolution product.

[0042] Preferably, in the step d, the weight ratio of 3, 5-diaminobenzoic acid to water is 1: (4-6).

[0043] Preferably, in the step d, the weight ratio of 3, 5-diaminobenzoic acid to water is 1:5.

[0044] Preferably, in the step d, the second dissolution product is uniformly mixed with the diazonium salt, the pH is adjusted to 6.5-7.0, the temperature is controlled to 5-10℃, and the reaction is carried out for 3.5-4.5h to obtain the high-fastness orange reactive dye.

[0045] By adopting the technical scheme, the heterocyclic active group 6-amino-N-2 (β-ethyl sulfone group sulfate ethyl)-indolinone is introduced as a new active group, and is formed into a double active group with cyanuric chloride, which are complementary to each other, the dyeing performance is improved, and the fixation rate reaches 95%; further, one dye molecule contains six active groups, the dyeing fastness is further improved, the washing fastness and dry rubbing fastness both reach level 5, and the light fastness reaches level 6, and the dyeing performance is good.

[0046] In a third aspect, the application provides an application of a high-fastness orange reactive dye in dyeing of cotton fibers and textiles thereof, which adopts the following technical scheme:

[0047] The concentration of the high-fastness orange reactive dye is 0.5-12% (o.w.f).

[0048] By adopting the technical scheme, when the concentration (o.w.f) of the high-fastness orange reactive dye is (0.5-12%), the fixation effect and dyeing performance in the cotton fibers and textiles thereof are both well improved, and the fixation rate is as high as 85% or more, and the fastnesses are excellent.

[0049] In summary, the application has at least one of the following beneficial technical effects:

[0050] 1. The introduction of the heterocyclic active group 6-amino-N-2(β-ethyl sulfone sulfate ethyl)-indolinone as a new active group improves the fixation effect, as well as various dyeing properties such as wash fastness, rubbing fastness, light fastness and chlorine fastness, and has good solubility.

[0051] 2. Using cyanuric chloride and 6-amino-N-2(β-ethyl sulfone sulfate ethyl)-indolinone double active group as active groups, the dyeing properties and fixation rate are improved.

[0052] 3. A dye molecule contains 6 active groups, which improves the dyeing fastness.

[0053] 4. The high-fastness orange reactive dye is applied to cotton fibers and textiles, and when the concentration (o.w.f) is (0.5-12%), the fixation effect and dyeing properties are both well improved, with a fixation rate of up to 86% or more and excellent fastness. BRIEF DESCRIPTION OF DRAWINGS

[0054] Figure 1 is the synthesis route diagram of the high-fastness orange reactive dye of formula 4 in the present application. DETAILED DESCRIPTION

[0055] The present application will be further described in conjunction with the following examples. The following examples are only used to illustrate the present application and should not be regarded as limiting the scope of the present application. In the following examples, the specific conditions are not specified, and the methods used are conventional methods known in the art unless otherwise specified. The consumables and reagents used are commercially available unless otherwise specified. Unless otherwise specified, the professional and scientific terms used herein have the same meaning as understood by those skilled in the art. In addition, any method or material similar or equivalent to that described can also be applied in the present application.

[0056] The raw materials used in the examples are commercially available.

[0057] Example 1

[0058] Example 1 discloses a high-fastness orange reactive dye, which is prepared by the following steps:

[0059] Step a, dissolution: 0.3 moles of 6-amino-N-2(β-ethyl sulfone sulfate ethyl)-indolinone are added to water and uniformly dispersed, the weight ratio of 6-amino-N-2(β-ethyl sulfone sulfate ethyl)-indolinone to water is 1:6, the pH of the system is adjusted to 6.5-7.0 with baking soda to obtain a first dissolution product, and the reaction formula is as follows:

[0060]

[0061] Step b, mono-reaction: 0.3 moles of cyanuric chloride is slurried with ice water mixture, the weight ratio of cyanuric chloride to ice water mixture is 1:5, the first dissolved product obtained in step a is added dropwise into the cyanuric chloride slurry, the temperature is controlled at 5-10°C, the system pH is adjusted to 3.0-4.0 with sodium bicarbonate, and the reaction is maintained for 4 hours to obtain a mono-reaction product, the reaction formula is as follows:

[0062]

[0063] Di-reaction: 0.3 moles of 2,4-diaminobenzenesulfonic acid sodium is added to the mono-reaction product, the system pH is adjusted to 3.5-4.5 with sodium bicarbonate, and then the temperature is raised to 25-35°C, and the reaction is maintained for 5 hours to obtain a di-reaction product, the reaction formula is as follows:

[0064]

[0065] Step c, diazo reaction: 0.45 moles of hydrochloric acid (volume concentration is 30%) is added to the di-reaction product obtained in step b and stirred uniformly, the temperature is lowered to 0°C, and then 0.3 moles of sodium nitrite is added to obtain a diazonium salt, the reaction formula is as follows:

[0066]

[0067] Step d, coupling reaction: 0.1 moles of 3,5-diaminobenzoic acid is added to water, the weight ratio of 3,5-diaminobenzoic acid to water is 1:5 to obtain a second dissolved product, the system pH is adjusted to 6-7 with sodium bicarbonate, and the diazonium salt obtained in step c is added, the reaction is carried out at a temperature of 5-10°C and a pH of 6.5-7.0 for 4 hours to obtain a high-fastness orange reactive dye-Formula 4, the reaction formula is as follows:

[0068]

[0069] The synthesis route of the high-fastness orange reactive dye-Formula 4 is shown in Figure 1 .

[0070] Example 2

[0071] Example 2 discloses a high-fastness orange reactive dye prepared by the following steps:

[0072] Step a, dissolution: 0.2 moles of 6-amino-N-2(β-ethylsulfonyl sulfate ethyl)-indolinone is slurried with water, the weight ratio of 6-amino-N-2(β-ethylsulfonyl sulfate ethyl)-indolinone to water is 1:6, the system pH is adjusted to 6.5-7.0 with sodium bicarbonate to obtain a first dissolved product, the reaction formula is as follows:

[0073]

[0074] Step b, mono-reaction: 0.2 moles of cyanuric chloride is slurried with ice water mixture, the weight ratio of cyanuric chloride to ice water mixture is 1:5, the first dissolved product obtained in step a is added dropwise into the cyanuric chloride slurry, the temperature is controlled at 5-10°C, the system pH is adjusted to 3.0-4.0 with sodium bicarbonate, and the reaction is maintained for 4 hours to obtain a mono-reaction product, the reaction formula is as follows:

[0075]

[0076] Di-reaction: 0.2 moles of 2,4-diaminobenzenesulfonic acid sodium is added into the mono-reaction product, the system pH is adjusted to 3.5-4.5 with sodium bicarbonate, and then the temperature is raised to 25-35°C, and the reaction is maintained for 5 hours to obtain a di-reaction product, the reaction formula is as follows:

[0077]

[0078] Step c, diazo reaction: 0.3 moles of hydrochloric acid (volume concentration is 30%) is added into the di-reaction product obtained in step b, and stirred uniformly, and then the temperature is lowered to 0°C, and then 0.2 moles of sodium nitrite is added to obtain a diazonium salt, the reaction formula is as follows:

[0079]

[0080] Step d, coupling reaction: 0.1 moles of 3,5-diaminobenzoic acid is added into water, the weight ratio of 3,5-diaminobenzoic acid to water is 1:5 to obtain a second dissolved product, the system pH is adjusted to 6-7 with sodium bicarbonate, and then the diazonium salt obtained in step c is added, and the reaction is maintained for 4 hours at a temperature of 5-10°C and under the condition of pH=6.5-7.0 to obtain a high-fastness orange reactive dye of formula 5, the reaction formula is as follows:

[0081]

[0082] Example 3

[0083] Example 3 discloses a high-fastness orange reactive dye, which is prepared by the following steps:

[0084] Step a, dissolution: 0.1 moles of 6-amino-N-2(β-ethylsulfonyl sulfate ethyl)-indolinone is added into water, the weight ratio of 6-amino-N-2(β-ethylsulfonyl sulfate ethyl)-indolinone to water is 1:6, the system pH is adjusted to 6.5-7.0 with sodium bicarbonate to obtain a first dissolved product, the reaction formula is as follows:

[0085]

[0086] Step b, mono-reaction: 0.1 mole of cyanuric chloride is slurried with ice water mixture, the weight ratio of cyanuric chloride to ice water mixture is 1:5, the first dissolved product obtained in step a is added dropwise into the cyanuric chloride slurry, the temperature is controlled at 5-10°C, the system pH is adjusted to 3.0-4.0 with sodium bicarbonate, and the reaction is maintained for 4 hours to obtain a mono-reaction product, the reaction formula is as follows:

[0087]

[0088] Di-reaction: 0.1 mole of 2,4-diaminobenzenesulfonic acid sodium is added to the mono-reaction product, the system pH is adjusted to 3.5-4.5 with sodium bicarbonate, and then the temperature is raised to 25-35°C, and the reaction is maintained for 5 hours to obtain a di-reaction product, the reaction formula is as follows:

[0089]

[0090] Step c, diazo reaction: 0.15 moles of hydrochloric acid (30% by volume) is added to the di-reaction product obtained in step b and stirred uniformly, the temperature is lowered to 0°C, and then 0.1 moles of sodium nitrite is added to obtain a diazonium salt, the reaction formula is as follows:

[0091]

[0092] Step d, coupling reaction: 0.1 moles of 3,5-diaminobenzoic acid is added to water, the weight ratio of 3,5-diaminobenzoic acid to water is 1:5 to obtain a second dissolved product, the system pH is adjusted to 6-7 with sodium bicarbonate, and the diazonium salt obtained in step c is added, the reaction is carried out at a temperature of 5-10°C and a pH of 6.5-7.0 for 4 hours to obtain a high-fastness orange reactive dye of formula 6, the reaction formula is as follows:

[0093]

[0094] Comparative Example 1

[0095] Comparative Example 1 selects a common reactive orange 107 on the market.

[0096] Experimental Test

[0097] Experiment 1: UV-visible absorption spectrum test

[0098] The high-fastness orange reactive dyes obtained in Examples 1-3 above and the reactive orange 107 of Comparative Example 1 are prepared into a solution at 1 g / 500 ml water. At room temperature, the UV-visible spectrophotometer is used to scan the UV absorption spectrum in the wavelength range of 200-800 nm, and the high-fastness orange reactive dyes of Examples 1-3 above and the reactive orange 107 of Comparative Example 1 are prepared into an aqueous solution with a concentration of 1 ml / 100 ml, and the visible absorption spectrum curve of each dye is determined. The molar extinction coefficient and the absorption peak value of the spectrum are shown in Table 1.

[0099] Table 1:

[0100] Data source Absorption peak values Molar extinction coefficient Example 1 480 523 Example 2 472 465 Example 3 453 425 Comparative Example 1 470 386

[0101] Referring to Table 1, the molar extinction coefficients of Examples 1-3 are higher than that of Comparative Example 1, which indicates that the dyeing depth of Examples 1-3 will be higher than that of Comparative Example 1 at the same concentration, and the molar extinction coefficient of Example 1 is greater than that of Examples 2 and 3, which indicates that the dyeing effect of high-fastness orange reactive dye-Formula 4 is better than that of high-fastness orange reactive dye-Formula 5 and high-fastness orange reactive dye-Formula 6.

[0102] Experiment 2: Dyeing experiment of dyes on cotton fabric

[0103] The high-fastness orange reactive dyes of Examples 1-3 and the reactive orange 107 of Comparative Example 1 were respectively dyed on cotton fabric with a fabric weight of 5 g, a sodium sulfate concentration of 20 g / L, a bath ratio of 1:20, a pH of 8.0 adjusted by soda ash, and a dye concentration of 4% (o.w.f) by using a 60°C temperature rising dyeing method, and the fabric samples were obtained after post-treatment.

[0104] (1) According to the national standards, the color fastnesses of the cotton fabric samples after dyeing were determined according to GB / T 3920 2008 for rubbing color fastness and GB / T 3921 2008 for washing color fastness, and the results are shown in Table 2.

[0105] Table 2: Color fastnesses of cotton fabric dyeing at a dye concentration of 4% (o.w.f)

[0106]

[0107] Referring to the data in Table 2, the fastnesses and solubility of the high-fastness orange reactive dyes of Examples 1-3 are better than those of the traditional reactive orange 107 dye of Comparative Example 1; further, the washing fastness and dry rubbing fastness of the high-fastness orange reactive dye of Example 1 on cotton fabric reach level 5, the wet rubbing fastness and chlorine fastness reach level 4, and the sunlight fastness reaches level 6, which indicates that the high-fastness orange reactive dye-Formula 4 obtained in Example 1 has good fastness performance and is better than the high-fastness orange reactive dye-Formula 5 obtained in Example 2 and the high-fastness orange reactive dye-Formula 6 obtained in Example 2; and the solubility of the high-fastness orange reactive dye-Formula 4 obtained in Example 1 is also better than that of the high-fastness orange reactive dye-Formula 5 obtained in Example 2 and the high-fastness orange reactive dye-Formula 6 obtained in Example 2.

[0108] (2) The fabric sample after dyeing of Example 1 was used as a standard sample, and the fabric samples after dyeing of Example 2, Example 3 and Comparative Example 1 were used as test samples, and the color was measured on a colorimeter, and the results are shown in Table 3.

[0109] Table 3:

[0110] Example Spectroscopy Intensity Total color difference Saturation Red-green difference Yellow-blue difference Example 2 94％ 90％ 1.152 -0.125 -0.428 0.542 Example 3 90％ 88％ 1.642 -0.025 -0.698 0.663 Comparative Example 1 87％ 80％ 2.854 -1.256 -1.045 -0.378

[0111] Referring to Table 3, the fabric sample dyed by the high-fast orange reactive dye provided in Example 1 is used as a standard sample, the spectrums of Examples 2-3 all reach more than 90%, the intensity reaches more than 88%, and the total color difference is less than 2, while the spectrum of Comparative Example 1 is less than 90%, the intensity is 80%, and the total color difference reaches 2.854. It is shown that the dyeing effect of the high-fast orange reactive dye-Formula 4, the high-fast orange reactive dye-Formula 5 and the high-fast orange reactive dye-Formula 6 is better than that of Reactive Orange 107, and the dyeing effect of the high-fast orange reactive dye-Formula 4 is better than that of the high-fast orange reactive dye-Formula 5 and the high-fast orange reactive dye-Formula 6.

[0112] Experiment 3: Dyeing experiment of dyes on cotton fabric

[0113] The high-fast orange reactive dyes in Examples 1-3 and the Reactive Orange 107 in Comparative Example 1 are respectively used for dyeing cotton fabric with the following conditions: cotton fabric: 5 g, sodium sulfate concentration: 20 g / L, bath ratio 1: 20, pure alkali to adjust pH = 8.0, dye concentration: 0.5-12% (o.w.f); dyeing is carried out by using 60°C temperature rising dyeing method, and then the fixation rate is determined. The fixation rate detection results are shown in Table 4.

[0114] Table 4: Fixation rate of dyes on cotton fabric

[0115]

[0116]

[0117] Referring to Table 4, when the concentration of the high-fast orange reactive dyes provided in Examples 1-3 on cotton fabric is (0.5-12)% (o.w.f), the fixation rate reaches more than 86%, while when the concentration of the Reactive Orange 107 in Comparative Example 1 on cotton fabric is (0.5-12)% (o.w.f), the highest fixation rate is only 82%. Especially, the high-fast orange reactive dye-Formula 4 prepared in Example 1 has a fixation rate increased by (13-17)% on cotton fabric when the concentration is (0.5-12)% (o.w.f) based on the traditional Reactive Orange 107, and the fixation effect is excellent.

[0118] The specific embodiments are only an explanation of the present application, which is not a limitation of the present application, and those skilled in the art can make modifications to the embodiments without creative contribution after reading the specification, but as long as it is within the scope of the claims of the present application, it is protected by the patent law.

Claims

1. A high fastness orange reactive dye, characterized by: A structure general formula as follows: formula 1 wherein R1is halogen; R2is SO3M; M is Na.

2. A high fastness orange reactive dye according to claim 1, characterized in that: The R1 is -Cl.

3. A process for the preparation of high fastness orange reactive dyes according to claim 1 or 2, characterized in that: Comprising the following steps: a: mixing 2-((2-(5-amino-3-oxoindolin-1-yl)ethyl)sulfonyl)ethyl hydrogen sulfate and water uniformly, adjusting pH to obtain a first dissolution product; b: mixing the tricyanogen cyanamide beaten with ice water mixture with the first dissolution product, adjusting pH to obtain a condensate, mixing the condensate with sodium 2,4-diaminobenzenesulfonate, adjusting pH to obtain a di-condensate; c: reacting the di-condensate, hydrochloric acid and sodium nitrite to obtain a diazonium salt; d: mixing 3,5-diaminobenzoic acid with water to obtain a second dissolution product, adjusting pH, mixing the second dissolution product with the diazonium salt uniformly to obtain the high-fastness orange reactive dye.

4. A process for the preparation of high fastness orange reactive dyes according to claim 3, characterized by: In the step a, the weight ratio of the 2-((2-(5-amino-3-oxoindolin-1-yl)ethyl)sulfonyl)ethyl hydrogen sulfate to water is 1:(4-8).

5. A process for the preparation of high fastness orange reactive dyes according to claim 3, characterized by: In the step b, the molar ratio of the tricyanogen cyanamide to the 2-((2-(5-amino-3-oxoindolin-1-yl)ethyl)sulfonyl)ethyl hydrogen sulfate in the first dissolution product is (0.8-1.2):

1.

6. A process for the preparation of high fastness orange reactive dyes according to claim 3, characterized by: In the step b, the molar ratio of the sodium 2,4-diaminobenzenesulfonate to the tricyanogen cyanamide is (0.8-1.1):

1.

7. A process for the preparation of high fastness orange reactive dyes according to claim 3, characterized by: In the step b, the molar ratio of the tricyanogen cyanamide to the hydrochloric acid in the step c is 1:(1.4-1.8), and the molar ratio of the tricyanogen cyanamide in the step b to the sodium nitrite in the step c is 1:(0.9-1.2).

8. A process for the preparation of high fastness orange reactive dyes according to claim 3, characterized by: In the step b, the molar ratio of the tricyanogen cyanamide to the 3,5-diaminobenzoic acid in the step d is 3:(1-3).

9. Use of a high fastness orange reactive dye according to claim 1 or 2 for dyeing cotton fibers and their textiles, characterized in that, The concentration of the high-fastness orange reactive dye is 0.5-12%(o.w.f).

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