TWI381023B - Novel bis-reactive dye with n, n-dialkylamino bridge group - Google Patents

Description

Novel double reactive dyes with N,N-dialkylamino bridging groups

The invention relates to a novel reactive dye of N , N -dialkylamino ( N , N -dialkylamino) as a bridging group, in particular to a dip dyeing and cold application of a hydroxyl group-containing and polyamine fiber. New reactive dyes for dyeing, continuous dyeing, printing and digital printing.

The azo dye is a dye precursor composed of a diazo component and an even component, and is widely used because of its wide color gamut and high molecular absorption coefficient, and is used as a reactive dye for dark dyeing such as orange, red, navy, and black. Pigment precursor. Among the azo dyes, the sulphato-ethyl-sulphone (hereinafter referred to as SES) developed by Hoechst in Germany in 1957 is the most famous, and its structure is as follows. Formula (A), and such a dye can dye the fabric to a very dark color.

Fiber reactive dyes have been used in the dyeing and finishing industry for many years. Nowadays, the development of reactive dyes is facing the economic appeal of higher fixation and higher dyeing. In order to go beyond the high dyeing and economical characteristics of C.I. Reactive Black 5, many teams have been involved in development research over the years, as published in Hoyerst, Hoyer, et al., in US Patent No. 4,244,258. Sulfonyl is a bridged tetrazozo structure in which the dye can be as shown in formula (B).

In the U.S. Patent No. 5,629,410, the tetrazozo structure of an aminocarbonyl or aminosulfonyl bridge is disclosed in the U.S. Patent No. 5,629,410, the disclosure of which is incorporated herein by reference. (C) is shown.

However, the new compounds developed by the above research team are still unable to meet the market requirements in terms of dyeing depth, hue shift, leveling and washing fastness, so there is an urgent need for improvement.

Through a multi-study experiment, it was found that a new compound containing an N , N -dialkylamino bridging group (shown in the following formula (D)) and a N , N -dialkylamino bridging group were applied to the reactive dye. The novel structure of yellow, orange, red, navy, black and other synthetic structures can express high color, high fixation, stable fiber and dye bonding, and excellent fastness characteristics.

Accordingly, the present invention provides a novel reactive dye structure having a novel N , N -dialkylamine group as a bridging group, and the cellulose dye fiber dyed by the reactive dye can exhibit good fixation rate and excellent dyeing depth. And has excellent washing fastness and wet fastness characteristics.

The structural formula of the novel reactive dye having the N , N -dialkylamino bridging group of the present invention is as shown in the following formula (I): Wherein E ₁ and E ₂ are each independently selected from a substituted or unsubstituted benzene group structure, a substituted or unsubstituted naphthalene group structure, and a substituted or unsubstituted group. a group consisting of monoazo group structures; R is hydrogen, C _1-4 alkyl, C _1-4 alkylcarbonyl, phenyl, nitroso, or substituted a C _1-4 alkyl group substituted, wherein the substituent is selected from the group consisting of a halogen, a hydroxy group, a carboxyl group, or a sulfo group; (R ₁ ) _{0 -3} and (R ₂ ) _0-3 are 0 to 3 identical or different substituents, and each independently selected from hydrogen, halogen, hydroxy, carboxyl, sulfonic acid, nitro, cyano a group consisting of C _1-4 alkyl, C _1-4 alkoxy, ureido, and amido; R ₃ and R ₄ are each independently hydrogen or C _{1- 4} alkyl; R ₅ and R ₆ are each independently hydrogen, C _1-4 alkyl or benzene ring; G and G' are each independently selected from hydrogen, a group consisting of a substituted or unsubstituted C _1-4 alkyl group; (R ₇ ) _0-3 is 0 to 3 identical or different substituents, each independently selected from hydrogen, Halogen, hydroxy, carboxy, sulfonate, nitro, cyano, C _1-4 alkyl, C _1-4 alkoxy, ureido or amine; B and B' are each independently selected from linear, -SO _a group consisting of ₂ - and -CONH-(CH ₂ ) _k -SO ₂ -; k is an integer of 1, 2, 3, 4, 5 or 6; Q is -SO ₂ -U, -CONH-(CH ₂ ) _d- SO ₂ -U, -O-(CH ₂ ) _r -CONH-(CH ₂ ) _d -SO ₂ -U, β -thiosulfatoethylsulfonyl, -R'- SO ₂ -U or -R'-U';R' is C _1-4 alkyl or phenyl; d and r are each independently an integer of 2, 3 or 4; U is -CH ₂ CH ₂ W or -CH =CH ₂ ;W is -Cl, -OSO ₃ H, -OPO ₃ H, quaternary ammonium, pyridine, carboxypyridinium, methylpyridinium, carbonamine Carbonamidopyridinium, or R ₈ and R ₉ are each independently hydrogen or C _1-4 alkyl; U 'is the α, β - propan acyl halide (α, β-halopropionyl), α- propyl acyl halide (α-haloacryloyl), β - Β-halopropionyl, or α-haloacryloyl; X is a halogen; and m and n are each independently an integer of 2, 3 or 4.

In the reactive dye of the formula (I) of the present invention, wherein E ₁ and E ₂ may each independently be a substituted or unsubstituted phenyl group structure, preferably a structure of the following formula ( ^* represents a coupling position):

Wherein ^* is a coupling position, and R ₁₀ is hydrogen, a C _1-4 alkyl group, a C _2-4 alkanoic acid group, or a C _1-4 alkyl group substituted with a substituent, and the substituent is a hydroxyl group or a cyanide group. A base, a carboxyl group, a sulfonic acid group, a methoxycarbonyl group, an ethoxycarbonyl group, or an acetoxy group.

In the reactive dye of the formula (I) of the present invention, wherein E ₁ and E ₂ may each independently be a substituted or unsubstituted naphthyl group structure, preferably a structure of the following formula ( ^* represents a coupling position):

In the reactive dye of the formula (I) of the present invention, wherein E ₁ and E ₂ may each independently be a substituted or unsubstituted monoazo group structure, preferably a structure of the following formula ( ^* indicates a coupling position) :

For the convenience of description, the compounds are all expressed in the form of free acid in the specification, but the dyes in the present invention are often in the form of water-soluble salts when they are manufactured or used, and suitable salts may be alkali metals or alkaline earth metals. An ammonium salt or an organic amine salt, preferably a sodium salt, a potassium salt, a lithium salt, an ammonium salt or a triethanolamine salt.

The dye of the present invention can be prepared by a known method, and the reaction sequence of the preparation thereof is not strictly limited, and the chromophore can be prepared first, and then the desired dye can be synthesized; or in the preparation process of the dye, Only synthesize chromophores.

The dyes of the present invention are suitable for use in the dyeing or printing of fibrous materials, especially cellulosic fibrous materials, and fibrous materials comprising cellulosic fibers. The fibrous material is not particularly limited and may be natural or regenerated cellulose fibers such as cotton, hemp, linen, hemp, ramie, mucilage, or fibrous materials containing cellulose fibers. The dyes of the invention are also suitable for dyeing and printing of fiber blended fabrics containing hydroxyl fibers.

The dyes of the present invention can be fixed to the fibers in a variety of ways, particularly in the form of aqueous dye solutions and printing pastes. Dyeing and printing are carried out by means of dip dyeing, continuous dyeing, cold press dyeing, printing and printing, and digital printing.

The dyeing or printing of the present invention can be carried out according to a conventionally known and conventional method, wherein the exhaust dyeing method is a well-known inorganic neutrality. Salts such as anhydrous sodium sulfate and sodium chloride and well-known acid binders such as sodium carbonate and sodium hydroxide are used singly or in combination. The amount of inorganic neutral salts and bases is not critical, and inorganic neutral salts and bases can be added to the dye bath once or in portions by conventional methods. Further, a dyeing agent (e.g., a leveling agent, a retarding agent, etc.) may be added according to a conventional method, and the dyeing temperature is usually from 40 ° C to 90 ° C, preferably from 50 ° C to 70 ° C.

Cold press dyeing is a substance to be dyed, which is padded with well-known inorganic neutral salts (such as anhydrous sodium sulfate and sodium chloride) and well-known acid binders (such as sodium carbonate, sodium hydroxide), and then at room temperature. Next, the resulting material was dyed in a roll form.

The continuous dyeing method is to mix a well-known acid binder (such as sodium carbonate or sodium hydrogencarbonate) with a padding liquid, and the material to be dyed is padded by a usual method, and then the resultant material is dried or steam-fixed. The two-bath padding method is to dye the material to be dyed with a dye, and then to treat with a well-known inorganic neutral salt (such as sodium sulfate or sodium citrate), and it is preferred to dry or steam the treated material according to a usual method. Steam solid color.

A fabric printing method, for example, a single-phase printing method, which prints a printing paste containing a well-known acid binder (such as sodium hydrogencarbonate) on a substance to be printed, and fixes it by drying or steaming; the two-phase printing method includes Printing a substance to be printed, immersing the obtained substance in a solution containing an inorganic neutral salt (such as sodium chloride) and a well-known acid binder (such as sodium hydroxide or sodium carbonate) at a high temperature (90 ° C or higher). color. The method according to the invention is not limited to the dyeing or printing method of the preceding list.

For the sake of further explanation, the following examples will be more specifically described. The following examples are illustrative of the invention and the scope of the invention is not limited thereby. Wherein the compound is expressed in the form of a free acid, but the actual form may be a metal salt, more preferably an alkali metal salt, especially a sodium salt, unless otherwise stated, the parts or percentages used in the examples are In weight, the temperature is in °C Celsius.

Example 1

Take 14.05 parts of p-aminostyrene hydrazine dissolved in 50 parts of water, the temperature is controlled at 0~5 ° C, add 45% NaOH aqueous solution, stir for a while and then add 2 parts of 40% methylamine (methylamine), at room temperature After reacting for 4 hours, it was separated by filtration and dried to give a product structure of the formula (1).

Example 2

Take 16 parts of o-aminoanilinyl vinyl hydrazine (OAVS) dissolved in 60 parts of water, the temperature is controlled at 0~5 ° C, add 45% NaOH aqueous solution, stir for a while and then add 2 parts of 40% methylamine, The reaction was carried out for 4 hours at room temperature to give a product structure of the formula (2).

Example 3

Take 28.1 parts of p-aminostyrene hydrazine dissolved in 100 parts of water, the temperature is controlled at 0~5 ° C, add 45% NaOH aqueous solution, stir for a while and then add 3 parts of ethanolamine (ethanolamine), react at room temperature, reaction After completion, filtration and drying are carried out to obtain a product structure such as formula (3).

Example 4

Take 14.05 parts of p-aminostyrene oxime dissolved in 50 parts of water, the temperature is controlled at 0~5 ° C, add 45% NaOH aqueous solution, stir for a while and then add 4 parts of 40% methylamine, react at room temperature for 4 hours. Thereafter, an aqueous solution of 16 parts of anthranilyl vinyl hydrazine which is vinylated at a low temperature is further added, and the temperature is controlled at room temperature and stirred for a while to obtain a product structure such as the formula (4).

Example 5

(a) First, 9.4 parts of 1,3-phenyl-p-phenylenediamine-4-sulfonic acid (M4 acid) was dissolved, and then 9.5 parts of trimeric were added dropwise. In the cyanuric chloride ice dispersion, the temperature was controlled at 0 to 5 ° C, and the reaction was carried out for 1 hour. After filtration, the filtrate was taken. Adjust the pH to neutral and add 3.59 parts of sodium nitrite to dissolve in water. The solution and 19 parts of 32% aqueous hydrochloric acid were controlled to diazotize at 0 to 5 ° C, and the reaction was completed for about 2 hours.

(b) After dissolving 16 parts of 1-naphthol-8-amino-3,6-disulfonic acid (H acid) with a liquid base , adding dropwise to the aqueous solution obtained in the above (a), adding a portion of 14 parts of β-sulfatoethylsulfone aniline (PASE) after a certain period of time, and adjusting pH=3 with a 15% aqueous sodium carbonate solution. 5, the reaction is 2 hours standby.

(c) 30 parts of water is added to 2 parts of the compound of the formula (1) and 3 parts of a 32% aqueous solution of hydrochloric acid, and the mixture is stirred and dispersed. Then, 0.76 parts of an aqueous solution of sodium nitrite is added dropwise, and the diazotization is controlled at 0 to 5 ° C. The reaction is completed in about 1 hour.

(d) adding the aqueous solution obtained in (b) to the solution (c) for coupling reaction, adjusting the pH to 5 to 7 with a 15% aqueous solution of sodium carbonate, and after taking the reaction for 4 hours, it is taken out by general salting out to obtain a blue product. The structure is as follows:

Example 6

(a) After dissolving 9.4 parts of M4 acid, it was added dropwise to 9.5 parts of cyanuric acid ice dispersion, the temperature was controlled at 0 to 5 ° C, and the reaction was carried out for 1 hour. After filtration, the filtrate was taken. The pH was adjusted to neutrality, and 3.59 parts of an aqueous solution of sodium nitrite and 19 parts of a 32% aqueous solution of hydrochloric acid were added to control diazotization at 0 to 5 ° C, and the reaction was completed in about 2 hours.

(b) After diluting 16 parts of H acid with a liquid base, it is added dropwise to the aqueous solution obtained in the above (a), and after reacting for a while, 14 parts of p-aminostyrene oxime (PASE) is added to 15% sodium carbonate aqueous solution. Adjust pH=3~5 and react for 2 hours.

(c) taking 30 parts of water, adding 14 parts of the compound of the formula (2) and 8 parts of a 32% aqueous solution of hydrochloric acid, stirring and dispersing, and then adding 0.7 part of an aqueous solution of sodium nitrite dropwise to control diazotization at 5 to 10 ° C. The reaction is completed in about 1 hour.

(d) adding the aqueous solution obtained in (b) to the solution (c) for coupling reaction, adjusting the pH to 5 to 7 with a 15% aqueous solution of sodium carbonate, and after taking the reaction for 4 hours, it is taken out by general salting out to obtain a blue product. The structure is as follows:

Example 7

(a) First, 1.73 parts of m-aminobenzenesulfonic acid (M acid) was dissolved in 15% aqueous sodium carbonate solution, and 1.86 parts of cyanuric acid cyanide ice dispersion was added dropwise, and pH was adjusted with 15% sodium carbonate aqueous solution. 3.5~4, the temperature is controlled at 5~10 °C, and the reaction is carried out for 2 hours. After filtration, the filtrate is taken for use.

(b) After dissolving 3.19 parts of H acid with a liquid base, adding the solution to the aqueous solution obtained in the above (a), adjusting the pH of the reaction solution to 3 to 4 with sodium hydrogencarbonate powder, and controlling the temperature at 15 to 20 ° C After 4 hours of reaction, an aqueous solution was obtained.

(c) 20 parts of water was added to 2.14 parts of the compound of the formula (3) and 2.5 parts of a 32% aqueous solution of hydrochloric acid, and the mixture was stirred and dispersed, and then 0.76 parts of an aqueous solution of sodium nitrite was quickly added thereto to control diazotization at 0 to 5 ° C. The reaction is completed in about 1.5 hours, added to the aqueous solution obtained in the above (b), and the pH of the reaction is adjusted to 6-7 with sodium hydrogencarbonate powder. After 3 hours of reaction, it is taken out by general salting out to obtain a red product having the following structure:

Example 8

(a) First, 3.19 parts of H acid is dissolved in liquid alkali, and added dropwise to 1.86 parts of cyanuric acid ice dispersion, the pH value is adjusted with sodium bicarbonate powder, the temperature is controlled at 8~10 ° C, and the reaction is carried out for 2 hours. After filtration, the filtrate was taken for use.

(b) taking 20 parts of water, adding 2.14 parts of the compound of the formula (3) and 2.5 parts of a 32% aqueous solution of hydrochloric acid, stirring and dispersing, and then rapidly adding 0.76 parts of an aqueous solution of sodium nitrite to control diazotization at 0 to 5 ° C. The reaction was completed in about 1.5 hours. The filtrate obtained in the above (a) was added, and the pH of the reaction was slowly adjusted to 5 to 7 with sodium hydrogencarbonate powder. After 3 hours of reaction, a red product was obtained.

(c) After dissolving 1.41 parts of m-aminostyrene oxime (MASE) with a 15% aqueous sodium carbonate solution, it is quickly added to the aqueous solution obtained in the above (b), and the pH of the reaction solution is adjusted at 35 to 40 ° C with sodium hydrogencarbonate powder. The value was adjusted to be between 5 and 7. After 4 hours of reaction, a red product was obtained, and the structure was as follows:

Example 9

(a) First, 2.6 parts of N-(5-amino-2-sulfonic acid phenyl) -β -alanine (CEM4) acid was dissolved in a 15% aqueous solution of sodium carbonate, and 1.86 parts of cyanuric acid was added dropwise. In the dispersion, the temperature is controlled at 5 to 10 ° C, and the reaction is carried out for 2 hours to obtain an aqueous solution for use.

(b) After dissolving 2.81 parts of p-aminostyrene oxime with a liquid base, it is quickly added to the aqueous solution obtained in the above (a), and the pH is adjusted to 3 to 5 with sodium hydrogencarbonate powder, and the temperature is controlled at 30 to 35. Between ° C, an aqueous solution was obtained after the reaction overnight.

(c) 20 parts of water was added to 2.14 parts of the compound of the formula (3) and 2.5 parts of a 32% aqueous solution of hydrochloric acid, and the mixture was stirred and dispersed, and then 0.76 parts of an aqueous solution of sodium nitrite was quickly added thereto to control diazotization at 0 to 5 ° C. The reaction is completed in about 1.5 hours, and added to the aqueous solution obtained in the above (b), and the pH of the reaction solution is adjusted to 5-7 with sodium hydrogencarbonate powder. After 4 hours of reaction, a yellow product is obtained, and the structure is as follows:

Example 10

(a) First, 2.39 parts of 2-amino-5-naphthol-7-sulfonic acid (J acid) was dissolved in a liquid base, and 1.9 parts of a solution was added dropwise. In the cyanuric acid ice dispersion, the pH was adjusted to 1~3 with a 15% sodium carbonate aqueous solution, the temperature was controlled at 5 to 10 ° C, and the reaction was carried out for 1.5 hours. After filtration, the filtrate was taken for use.

(b) After dissolving 2.8 parts of p-aminostyrene oxime (PASE) with a liquid base, it is quickly added to the aqueous solution obtained in the above (a), and the pH is adjusted to 3 to 5 with a 15% aqueous sodium carbonate solution, and the temperature is controlled. Between 30 and 35 ° C, an aqueous solution was obtained after the reaction overnight.

(c) taking 30 parts of water, adding 2 parts of the compound of the formula (2) and 3 parts of a 32% aqueous solution of hydrochloric acid, stirring and dispersing, and then adding 0.7 part of an aqueous solution of sodium nitrite dropwise, and controlling diazotization at 5 to 10 ° C, The reaction is completed in about 1 hour.

(d) adding the aqueous solution obtained in (b) to the solution (c) for coupling reaction, adjusting the pH to 5 to 7 with a 15% aqueous solution of sodium carbonate, and after taking the reaction for 4 hours, taking out by general salting out, a yellow product can be obtained. as follows:

Example 11~44

Referring to the synthesis of Examples 5 to 10, the reactive dyes of the formula (11) to the formula (44) in which N , N -dialkylamine is used as a bridging group can be obtained.

Table 1

Example 45

(a) firstly dissolve 3.19 parts of H acid with liquid alkali, add 1.86 parts of cyanuric acid cyanide ice dispersion, adjust pH to 1~3 with sodium bicarbonate powder, and control the temperature at 8~10 °C. The reaction was carried out for 2 hours, and the filtrate was taken for use after filtration.

(b) After dissolving 2.8 parts of PASE with liquid alkali, it is quickly added to the aqueous solution obtained in the above (a), and the pH is adjusted to 3 to 5 with a 15% sodium carbonate aqueous solution, and the temperature is controlled between 30 and 35 ° C. After the reaction overnight, an aqueous solution was obtained.

(c) taking 20 parts of water, adding 2.14 parts of the compound of the formula (4) and 2.5 parts of a 32% aqueous solution of hydrochloric acid, stirring and dispersing, and then rapidly adding 0.76 parts of an aqueous solution of sodium nitrite to control diazotization at 0 to 5 ° C. The reaction was completed in about 1.5 hours, and the filtrate obtained in the above (b) was added, and the pH of the reaction was slowly adjusted to 5 to 7 with sodium hydrogencarbonate powder, and a red dye was obtained after 3 hours of reaction.

Example 46

(a) firstly dissolve 3.19 parts of H acid with liquid alkali, add 1.86 parts of melamine chloride ice dispersion, adjust pH to 1~3 with sodium bicarbonate powder, and control the temperature at 8~10 °C. The reaction was carried out for 2 hours, and the filtrate was taken for use after filtration.

(b) After dissolving 2.8 parts of p-aminostyrene oxime with a liquid base, it is quickly added to the aqueous solution obtained in the above (a), and the pH is adjusted to 3 to 5 with a 15% sodium carbonate aqueous solution, and the temperature is controlled at 30~. Between 35 ° C, an aqueous solution was obtained after the reaction overnight.

(c) First, 2.39 parts of J acid is dissolved in liquid alkali, and 1.9 parts of melamine chloride ice dispersion is added dropwise, pH is adjusted to 1~3 with 15% sodium carbonate aqueous solution, and the temperature is controlled at 5~10 °C. The reaction was carried out for 1.5 hours. After filtration, the filtrate was taken for use.

(d) After dissolving 2.8 parts of p-aminostyrene oxime with a liquid base, it is quickly added to the aqueous solution obtained in the above (a), and the pH is adjusted to 3 to 5 with a 15% aqueous sodium carbonate solution, and the temperature is controlled at 30~ Between 35 ° C, an aqueous solution was obtained after the reaction overnight.

(e) taking 20 parts of water, adding 2.14 parts of the compound of the formula (4) and 2.5 parts of a 32% aqueous solution of hydrochloric acid, stirring and dispersing, and then rapidly adding 0.76 parts of an aqueous solution of sodium nitrite to control diazotization at 0 to 5 ° C. The reaction was completed in about 1.5 hours, and the solutions obtained in the above (b) and (d) were added, and the pH of the reaction was slowly adjusted to 5 to 7 with sodium hydrogencarbonate powder, and a dark blue dye was obtained after 3 hours of reaction.

Test example 1

3 parts of the dye prepared in Example 5 was dissolved in 100 ml of water to prepare 30 parts/boost dye solution; 25 ml of alkaline agent (using caustic soda 15 ml/liter and Glauber's salt 30 parts/liter) was added to the pressure. The mixture was uniformly stirred, and the resulting mixture was poured into a Roller dye press, and then the cotton fabric was subjected to roller dyeing and then rolled into a shaft shape. This form of cotton fabric was stored at room temperature for 4 hours. Then, the obtained blue dye is first washed with cold water, then washed with boiling hot water for 10 minutes, then soaped with boiling non-ionic detergent for 10 minutes, and finally washed again with cold water. After drying, blue dye can be obtained. Excellent dyeing and coloring.

Test example 2

3 parts of the dye prepared in Example 10 was dissolved in 100 ml of water to prepare 30 parts/boost dye solution; 25 ml of alkaline agent (using caustic soda 15 ml/liter and Glauber's salt 30 parts/liter) was added to the pressure. The mixture was uniformly stirred, and the resulting mixture was poured into a Roller dye press, and then the cotton fabric was subjected to roller dyeing and then rolled into a shaft shape. This form of cotton fabric was stored at room temperature for 4 hours. Then, the obtained yellow dye is first washed with cold water and then washed with boiling hot water for 10 minutes. The bell is then soaped for 10 minutes with a boiling non-ionic detergent, and finally washed once with cold water. After drying, the yellow dye has excellent dyeing and coloring rate.

Test Example 3

Take 100 parts of urea, 10 parts of m-nitrobenzenesulfonate sodium salt, 20 parts of baking soda, 55 parts of sodium alginate, and 815 parts of warm water in total, 1000 parts.

Three parts of the dye prepared in Example 7 were sprinkled on the above 100 parts of the auxiliary paste, and stirred rapidly. A 100 mesh 45 degree twill printing screen is overlaid on a suitable size of mercerized cotton twill, and the color paste is placed on the screen and scraped.

The scraped cloth was placed in an oven at 65 ° C for 5 minutes to dry; the dried cloth was placed in a steamer and steamed at a constant pressure saturated steam of 102 to 105 ° C for 10 minutes.

Then, the obtained red dye is first washed with cold water, then washed with boiling hot water for 10 minutes, then soaped with boiling non-ionic detergent for 10 minutes, and finally washed again with cold water. After drying, the red dye is excellent. Dyeing and coloring rate.

In summary, the present invention can achieve the object of the invention by the disclosed technical idea, which has novelty, advancement and industrial applicability, and is consistent with the invention patent element. However, those disclosed above are preferred embodiments, and those that are modified or modified in part and derived from the technical idea of the present invention are easily inferred by those skilled in the art, and do not depart from the scope of the patent.

The above-mentioned embodiments are merely examples for convenience of description, and the scope of the claims is intended to be limited to the above embodiments.

Claims (18)

a reactive dye having an N , N -dialkylamino bridging group of the following formula (I), Wherein E ₁ and E ₂ are each independently selected from the group consisting of a substituted or unsubstituted phenyl group structure, a substituted or unsubstituted naphthyl group structure, and a substituted or unsubstituted monoazo group structure. a group; R is hydrogen, C _1-4 alkyl, C _1-4 alkylcarbonyl, phenyl, nitroso, or substituted C _1-4 alkyl, wherein the substituent is selected from halogen a group consisting of a hydroxyl group, a carboxyl group, or a sulfonic acid group; in (R ₁ ) _a and (R ₂ ) _b , each of a and b has 0 to 3 identical or different substituents, and each R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, hydroxy, carboxy, sulfonic acid, nitro, cyano, C _1-4 alkyl, C _1-4 alkoxy, ureido and amine. a group; R ₃ and R ₄ are each independently hydrogen or C _1-4 alkyl; R ₅ and R ₆ are each independently hydrogen, C _1-4 alkyl or benzene ring; G and G' are each independently selected from hydrogen , a group consisting of a substituted or unsubstituted C _1-4 alkyl group; in (R ₇ ) _c , the c system contains 0 to 3 identical or different substituents, and each R _{The 7} series are each independently selected from the group consisting of hydrogen, halogen, hydroxy, carboxyl, sulfonate, nitro, cyano, C _1-4 alkyl, C _1-4 alkoxy, ureido or amine; B and B' are each Independently selected from the group consisting of linear, -SO ₂ - and -CONH-(CH ₂ ) _k -SO ₂ -; k is an integer of 1, 2, 3, 4, 5 or 6; Q is -SO ₂ -U, -CONH-(CH ₂ ) _d -SO ₂ -U, -O-(CH ₂ ) _r -CONH-(CH ₂ ) _d -SO ₂ -U, β -thiosulfate sulfonate (β -thiosulfatoethylsulfonyl), -R'-SO ₂ -U or -R'-U'; d contains 0 to 2 identical or different substituents; R' is C _1-4 alkyl or phenyl; r is each independently an integer of 2, 3 or 4; U is -CH ₂ CH ₂ W or -CH=CH ₂ ; W is -Cl, -OSO ₃ H, -OPO ₃ H, quaternary ammonium salt, pyridine, carboxyl group Pyridyl, methylpyridyl, caraminopyridyl, or ; R ₈ and R ₉ are each independently hydrogen or C _1-4 alkyl; U 'is the α, β - propan acyl halide, α - propan acyl halide, β - propan-halo acyl, halo, or Bing Xixi α- Base; X is a halogen; and m and n are each independently an integer of 2, 3 or 4. A reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein R is hydrogen, C _1-4 alkyl, C _1-4 alkylcarbonyl, phenyl, sub A nitro group, or a C _1-4 alkyl group substituted with a hydroxy group or a sulfonic acid group. The reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein in (R ₁ ) _a and (R ₂ ) _b , each of a and b contains 0 to Three identical or different substituents, and each of R ₁ and R ₂ is independently selected from the group consisting of hydrogen, sulfonate, C _1-4 alkyl and C _1-4 alkoxy. A reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein G and G' are each independently selected from the group consisting of hydrogen, And the group consisting of Q. The reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein (R ₇ ) _c , c contains 0 to 3 identical or different substituents, And each R ₇ system is independently selected from the group consisting of hydrogen, sulfonic acid groups, C _1-4 alkyl groups, and C _1-4 alkoxy groups. A reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein B and B' are each independently -SO ₂ - or -CONH-(CH ₂ ) _k -SO ₂ -. A reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein Q is selected from the group consisting of -SO ₂ -U, -CONH-(CH ₂ ) _d -SO ₂ -U a group consisting of -R'-SO ₂ -U and -R'-U'. The reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein E ₁ and E ₂ are each independently substituted or unsubstituted phenyl group structure is as follows structure: Wherein ^* is a coupling position, and R ₁₀ is hydrogen, a C _1-4 alkyl group, a C _2-4 alkanoic acid group, or a C _1-4 alkyl group substituted with a substituent, and the substituent is a hydroxyl group or a cyanide group. Base, carboxyl group, sulfonic acid group, methoxymethyl phenyl phenyl group, ethoxylated phenyl phenyl group, or ethoxylated oxygen. The reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein each of E ₁ and E ₂ is a substituted or unsubstituted naphthyl group structure. structure: Where ^* is the coupling position and the e is 0 to 1. A reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein each of E ₁ and E _{2 is} independently substituted or unsubstituted monoazo group structure is as follows Structure: Where ^* is the coupling position. A reactive dye having an N , N -dialkylamino bridging group as described in claim 1 wherein X is chlorine. The reactive dye having an N , N -dialkylamino bridging group as described in claim 1, wherein the compound of the formula (I) is a compound of the following formula (II): A reactive dye having an N , N -dialkylamino bridging group according to claim 12, wherein the formula (II) is a structure of the following formula (5): A reactive dye having an N , N -dialkylamino bridging group according to claim 12, wherein the formula (II) is a structure of the following formula (6): A reactive dye having an N , N -dialkylamino bridging group according to claim 12, wherein the formula (II) is a structure of the following formula (7): A reactive dye having an N , N -dialkylamino bridging group according to claim 12, wherein the formula (II) is a structure of the following formula (8): A reactive dye having an N , N -dialkylamino bridging group according to claim 12, wherein the formula (II) is a structure of the following formula (9): A reactive dye having an N , N -dialkylamino bridging group according to claim 12, wherein the formula (II) is a structure of the following formula (10):