Patent Application
20190031881
This application claims the benefits of the Taiwan Patent Application. Serial Number 106124887 filed on Jul. 25, 2017 and the Taiwan Patent Application Serial Number 107110024 filed on Mar. 23, 2018, the subject matter of which is incorporated herein by reference.
The present disclosure relates to a reactive black dye composition. More particularly, the present disclosure relates to a reactive black dye composition with high fixing rate.
Currently, the dye used for digital printing is formulated with traditional P-TYPE dyes. Although the traditional dyes can be used in novel applications, but the fixing rate on the fabrics is not good enough and usually is about 50% to 70%. Hence, even though the traditional dyes can be used in novel applications, the reaction rate is low, and large amount of dyed waste water is generated which cause an issue of treatment of dyed waste water.
In addition, the traditional dyes are almost have single reactive group, so the traditional dye has low reactivity to the fabrics, resulting in uneven coloration and low fixing rate. Thus, the aforesaid issue of large amount of dyed waste water is occurred. Furthermore, even though the HE type reactive dyes have two reactive groups, the dying strength thereof is not as good as the traditional P-Type dyes.
Therefore, it is desirable to provide a novel reactive dye with high reactivity. Thus, the problem that the traditional dye with single reactive group has low fixing rate can be improved, the generation of the dyed waste water can be reduced, and the purpose of the environmental protection can be achieved.
An object of the present disclosure is to provide a reactive black dye composition, which shows high fixing rate on dyed fibers.
The reactive black dye composition of the present disclosure comprises the following components:
wherein X1 is —OH or —NH2;
In the reactive black dye composition of the present disclosure, the reactive blue dye used as the main component are introduced with two monochlorotriazine (MCT) reactive groups, which can increase the dye uptake of the dyes on the fibers, and therefore the obtained reactive black dye composition can show high fixing rate. Compared to the conventional reactive black dye composition with one reactive group, the reactivity of the reactive black dye composition of the present disclosure can be greatly increased, and thus the fixing rate of the reactive black dye composition can be increased from 50˜70% to 85% or more. When the reactive black dye composition is used in digital printing or textile printing, the problem that the fixing rate of the reactive black dye composition is not high enough can be solved. Therefore, the dyes in the waste water can be reduced, and the purposes of environmental protection and energy saving can further be achieved.
In the present disclosure, X31 and X41 in the reactive blue dye can respectively be Cl, Br or I. In one embodiment, X31 and X41 are respectively Cl.
In the present disclosure, the reactive blue dye can be represented by the following formula (I-1):
wherein R11 is defined as above.
In one embodiment of the present disclosure, the reactive blue dye of the formulas (I) or (I-1) can be a compound represented by anyone of the following formulas (I-2) to (I-4):
In the present disclosure, the reactive red dye can be represented by the following formula (II):
wherein R12 is H, —C2H4SO3H, —C2H4OC2H4OH or
In one embodiment of the present disclosure, the red chromophore in the reactive red dye can be
wherein m is 1 or 2.
In the present disclosure, X32 and X42 in the reactive red dye can respectively be Cl, Br or I, and m is 1 or 2. In one embodiment, X32 and X42 are respectively Cl, and m is 2.
In one embodiment of the present disclosure, the reactive red dye of the formula (II) can be represented by the following formula (II-1):
wherein R12, X32, X42 and m are defined as above.
In another embodiment of the present disclosure, the reactive red dye of the formulas (II) or (II-1) can be represented by the following formula (II-2):
wherein R12 is defined as above.
In another embodiment of the present disclosure, the reactive red dye of the formulas (II), (II-1) or (II-2) can be a compound represented by anyone of the following formulas (II-3) to (II-6):
In the present disclosure, the reactive yellow dye can be represented by the following formula (III):
wherein R13 is H, —C2H4SO3H, —C2H4OC2H4OH or
In one embodiment of the present disclosure, the yellow chromophore in the reactive yellow dye can be
wherein R2 is —CONH2 or —COCH3, and p is 1, 2 or 3.
In one embodiment of the present disclosure, X33 and X43 in the reactive yellow dye can respectively be Cl, Br or L in one embodiment, X33 and X43 are respectively Cl, R2 is —CONH2 or —COCH3, and p is 1, 2 or 3.
In one embodiment of the present disclosure, the reactive yellow dye of the formula (III) can be represented by the following formula (III-I):
wherein R13, X33, X43, R2 and p are defined as above.
In another embodiment of the present disclosure, the reactive yellow dye of the formulas (III) or (III-1) can be represented by the following formula (III-2):
wherein R13, X33, X43 and p are defined as above.
In another embodiment of the present disclosure, the reactive yellow dye of the formulas (III), (III-1) or (III-2) can be represented by the following formula (III-3):
wherein R13, X33 and X43 are defined as above.
In another embodiment of the present disclosure, the reactive yellow dye of the formulas (III), (III-1), (III-2) or (III-3) can be represented by the following formula (III-4):
wherein R13 is defined as above.
In another embodiment of the present disclosure, the reactive yellow dye of the formulas (III), (III-1), (III-2), (III-3) or (III-4) can be represented by the following formulas (III-5) or (III-6):
In one embodiment of the present disclosure, the component (B) may comprise both the reactive red dye or a salt thereof, and the reactive yellow dye or a salt. Thus, the reactive black dye composition of the present disclosure comprises the reactive blue dye, the reactive red dye and the reactive yellow dye. Herein, all the reactive blue dye, the reactive red dye and the reactive yellow dye may respectively comprise two MCT reactive groups. When the reactive black dye composition comprises the reactive blue dye with two MCT reactive groups, the reactive red dye with two MCT reactive groups and the reactive yellow dye with two MCT reactive groups, the reactivity of the reactive black dye composition can be greatly increased. Therefore, the dye uptake of dyes on the fibers can be improved, and the purpose of high fixing rate can be achieved. In another embodiment of the present disclosure, the reactive blue dye can comprises two MCT reactive groups, but the reactive red dye and the reactive yellow dye can selectively comprise two MCT reactive groups, one MCT reactive group, or one or more other reactive groups, respectively.
In the present disclosure, the ratio of the reactive blue dye, the reactive red dye and the reactive yellow dye in the reactive black dye composition is not particularly limited, and can be adjusted according to the desired color. In one embodiment of the present disclosure, a content of the reactive blue dye is between 40 parts by weight and 90 parts by weight, a content of the reactive red dye is between 5 parts by weight and 30 parts by weight, and a content of the reactive yellow dye is between 5 parts by weight and 50 parts by weight. In another embodiment of the present disclosure, a content of the reactive blue dye is between 55 parts by weight and 85 parts by weight, a content of the reactive red dye is between 10 parts by weight and 20 parts by weight, and a content of the reactive yellow dye is between 15 parts by weight and 30 parts by weight. In further another embodiment of the present disclosure, a content of the reactive blue dye is between 60 parts by weight and 75 parts by weight, a content of the reactive red dye is between 12 parts by weight and 17 parts by weight, and a content of the reactive yellow dye is between 18 parts by weight and 25 parts by weight. However, the present disclosure is not limited thereto.
In one embodiment of the present disclosure, the reactive blue dye or the salt thereof comprises: the reactive blue dye itself, a lithium salt of the reactive blue dye, or a sodium salt of the reactive blue dye. The reactive red dye or the salt thereof comprises: the reactive red dye itself, a lithium salt of the reactive red dye, or a sodium salt of the reactive red dye. Similarly, the reactive yellow dye or the salt thereof comprises: the reactive yellow dye itself, a lithium salt of the reactive yellow dye, or a sodium salt of the reactive yellow dye. However, the present disclosure is not limited thereto.
The reactive black dye composition of the present disclosure can be applied to dying various fibers by digital printing or textile printing. For example, the reactive black dye composition of the present disclosure can be applied to digital printing or textile printing for dying cellulose fibers, synthesized polyamide fibers, sheepskin, leather or other mixed fibers to obtain dyed materials with high fixing rate, high depth and excellent fastness.
Hence, the present disclosure further provides a use of the aforesaid reactive black dye composition for digital printing (also called as jet printing) or textile printing (also called as traditional printing). In addition, the present disclosure further provides a method for dying fibers, which comprises: dying fibers with the aforesaid reactive black dye composition by digital printing or textile printing.
Other novel features of the disclosure will become more apparent from the following detailed description when taken in conjunction with the accompanying drawings.
The following embodiments when read with the accompanying drawings are made to clearly exhibit the above-mentioned and other technical contents, features and/or effects of the present disclosure. Through the exposition by means of the specific embodiments, people would further understand the technical means and effects the present disclosure adopts to achieve the above-indicated objectives. Moreover, as the contents disclosed herein should be readily understood and can be implemented by a person skilled in the art, all equivalent changes or modifications which do not depart from the concept of the present disclosure should be encompassed by the appended claims.
Unless specified otherwise, singular words “a” and “the” used in the present specification and claims include one or plural objects.
Unless specified otherwise, term “or” used in the present specification and claims include meaning of and/or.
The present disclosure is explained by the following embodiments, which are not used to limit the scope of the present disclosure. Unless specified otherwise, in the following preparation examples, examples and comparative examples, the unit of the temperature is Celsius (° C.), parts and % used herein are respectively referred to parts by weight and weight percentage. The relation between parts by weight and volumes by weight is similar to that between kilogram (kg) and liter (L).
9.8 parts by weight of 2,4-diaminobenzenesulfonic acid was added into 80 parts by weight of water, and 45 wt % of alkali solution was added therein to dissolve the compounds. The obtained solution was maned A solution. In addition, 9.8 parts by weight of cyanuric chloride was dispersed in iced water by stirring. The A solution was added into the disparsion solution dropwise, sodium carbonate was used to adjust the pH of the mixing solution between 6 and 6.5, and the mixing solution was kept stirring until the condensation reaction was completed. Then, 3.7 parts by weight of NaNO2 was added therein and stirred, followed by adding 12 parts by weight of HCl aqueous solution (32 wt %). The mixing solution was kept stirring at 10° C. or less until the diazotization reaction was completed. The obtained solution was named B solution.
On the other hand, 13.9 parts by weight of aniline-2,5-disulfonic acid was added into 40 parts by weight of water, and 45 wt % of alkali solution was added therein to dissolve the compounds. Then, 3.9 parts by weight of NaNO2 was added therein and stirred, and the obtained solution was added to 15 parts by weight of iced HCl aqueous solution (32 wt %) dropwise. The mixing solution was kept stirring at 10° C. or less until the diazotization reaction was completed. Then, 15.95 parts by weight of an aqueous solution of H acid (1-amino-8-naphthol-3,6-disulfonic acid) was added into the above mixing solution obtained after the diazotization reaction to perform a coupling reaction. The solution obtained after the coupling reaction was added into the B solution, and 15 wt % of alkali aqueous solution was added therein to adjust the pH of the obtained solution to 6 or more. The obtained solution was kept stirring at 15° C. or less until the reaction was completed. Then, 9.4 parts by weight of 2,4-diaminobenzenesulfonic acid powders was added therein, and 15 wt % of alkali aqueous solution was added therein to adjust the pH of the obtained solution to 6 or more. The obtained solution was kept stirring until the condensation reaction was completed. After the obtained solution was cooled down, 9.7 parts by weight of cyanuric chloride was added therein, and 15 wt % of alkali aqueous solution was added therein to adjust the pH of the obtained solution to 6 or more. The obtained solution was kept stirring until the condensation reaction was completed, and a product (a) is obtained. Then, 7 parts by weight of ammonia was added therein, and the temperature of the solution was increased to 35° C. or more. 45 wt % of alkali solution was used to control the pH of the solution, and the solution was kept stirring to obtain the product of the formula (I-2).
15.2 parts by weight of 2-naphthylamine-1,5-disulfonic acid was added into 150 parts by weight of iced water, followed by adding 14 parts by weight of HCl aqueous solution (32 wt %) and stirring. Then, an aqueous solution containing 3.5 parts by weight of NaNO2 was added into the mixing solution, and the obtained solution was kept stirring at 0° C. to 5° C. until the diazotization reaction was completed. The obtained solution was named diazotization solution.
15.95 parts by weigh of 1-naphthol-8-amino-3,6-disulfonic acid was added into 40 parts by weight of water, and 45 wt % of alkali solution was added therein to dissolve the compounds. The obtained solution was named C solution. 9.8 parts by weight of cyanuric chloride was dispersed in iced water by stirring. The C solution was added into the disparsion solution dropwise, sodium carbonate aqueous solution (15 wt %) was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring until the condensation reaction was completed. The above diazotization solution was added into the mixing solution obtained after the condensation solution, and an alkali solution was used to adjust the pH of the mixing solution to 6 or more. Next, 9.4 parts by weight of 2,4-diaminobenzenesulfonic acid powders were added therein, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring until the condensation reaction was completed. After the mixing solution was cooled down, 9.7 parts by weight of cyanuric chloride was added therein, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring until the condensation reaction was completed and a produce (b) was obtained. Then, 8.7 parts by weight of m-aminobenzenesulfonic acid was added therein, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring to obtain the product of the formula (II-3).
19.15 parts by weight of 2-naphthylamine-3,6,8-trisulfonic acid was uniformly dispersed in 75 parts by weight of iced water, and 45% of an alkali solution was used to dissolve the compound. Then 3.55 parts by weight of NaNO2 was was added therein, and the obtained solution was added into 13 parts by weight of iced HCl aqueous solution (32 wt %). The mixing solution was stirred at 8° C. to 15° C. until the diazotization reaction was completed. Next, the obtained solution was added into a solution containing 7.6 parts by weight of 1-(3-aminophenyl)urea, and 15 wt % of sodium carbonate aqueous solution was used to keep the pH of the mixing solution between 4.5 and 5.5. The mixing solution was stirred at 20° C. or less until the coupling reaction was completed. Ice was added to cool down the mixing solution. 9.7 parts by weight of cyanuric chloride was added therein, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 4.5 or more. After the reaction was completed and the mixing solution was filtered, 9.4 parts by weight of 2,4-diaminobenzenesulfonic acid powders was added therein, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the obtained solution to 6 or more. The mixing solution was kept stirring until the condensation reaction was completed. After the mixing solution was cooled down, 9.7 parts by weight of cyanuric chloride was added therein, and 15 wt % of alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring until the condensation reaction was completed, and a product (c) was obtained. Then, 8.7 parts by weight of m-aminobenzenesulfonic acid was added therein, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring and the product of the formula (III-5) can be obtained.
8.7 parts by weight of m-aminobenzenesulfonic acid was added into the product (a) of Preparation example 1, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring to obtain the product of the formula (I-3).
5.8 parts by weight of 2-(2-aminoethoxy)ethanol was added into the product (a) of Preparation example 1, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 8 or more. The mixing solution was kept stirring to obtain the product of the formula (I-4).
5.8 parts by weight of 2-(2-aminoethoxy)ethanol was added into the product (b) of Preparation example 2, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring to obtain the product of the formula (II-4).
5.8 parts by weight of 2-(2-aminoethoxy)ethanol was added into the product (c) of Preparation example 3, and 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring to obtain the product of the formula (III-6).
11 parts by weight of ammonia was added into the product (b) of Preparation example 2, followed by heating to 35° C. or more. 45 w % of an alkali solution as used to control the pH of the mixing solution. The mixing solution was kept stirring to obtain the product of the formula (II-5).
15.2 parts by weight of 2-naphthylamine-1,5-disulfonic acid was dispersed in 150 parts by weight of iced water, followed by adding 14 parts by weight of HCl aqueous solution (32 wt %) and stirring. Then, 3.5 parts by weight of NaNO2 aqueous solution was added therein, and the mixing solution was kept stirring at 0° C. to 5° C. until the diazotization reaction was completed.
15.95 parts by weight of 1-naphthol-8-amino-3,6-disulfonic acid was added into 40 parts by weight of water, and 45 wt % of alkali solution was added therein to dissolve the compounds. The obtained solution was maned C solution. In addition, 9.8 parts by weight of cyanuric chloride was dispersed in iced water by stirring. The C solution was added into the disparsion solution dropwise, 15 wt % of an alkali aqueous solution was used to adjust the pH of the mixing solution to 6 or more. The mixing solution was kept stirring until the condensation reaction was completed. The above product obtained after the diazotization reaction was added into the mixing solution obtained after the condensation solution. The mixing solution was kept stirring until the condensation reaction was completed, and an alkali was used to adjust the pH of the mixing solution to 6 or more. The obtained mixing solution was named D solution. Next, 13.8 parts by weight of cyanuric chloride was dispersed in iced water by stirring, followed by adding 7 parts by weight of ammonia (24 wt %). 45 wt % of an alkali solution was used to adjust the pH of the mixing solution to 9 or more. The mixing solution was kept stirring until the condensation reaction was completed to obtain a product (d). Then, 18.8 parts by weight of 2,4-diaminobenzenesulfonic acid powders were added into 150 parts by weight of water, and 15 wt % of an alkali solution was used to adjust the pH of the mixing solution to 6 or more. The obtained solution was named E solution. The product (d) was added into the E solution, followed by heating to 35° C. or more. 15 wt % of an alkali aqueous solution was used to control the pH of the mixing solution to obtain F solution. The F solution was added into the D solution, and 15 wt % of an alkali aqueous solution was used to control the pH of the mixing solution to natural. The mixing solution was heated to 50° C. and kept stirring to obtain the product of the formula (II-6).
75 parts by weight of the reactive blue dye of the formula (I-2), 17 parts by weight of a reactive brown dye 11 and 8 parts by weight of a reactive orange dye 12 was mixed well to obtain a dye composition.
71 parts by weight of the reactive blue dye of the formula (I-2), 15 parts by weight of the reactive red dye of the formula (II-3) and 14 parts by weight of the reactive orange dye 12 was mixed well to obtain a dye composition.
67 parts by weight of the reactive blue dye of the formula (I-2), 17 parts by weight of the reactive red dye of the formula (II-3), 1 parts by weight of a reactive brown dye 11 and 15 parts by weight of a reactive orange dye 12 was mixed well to obtain a dye composition.
65 parts by weight of the reactive blue dye of the formula (I-2), 14 parts by weight of the reactive red dye of the formula (II-3) and 21 parts by weight of the reactive yellow dye of the formula (III-5) was mixed well to obtain a dye composition.
65 parts by weight of the reactive blue dye of the formula (I-3), 15 parts by weight of the reactive red dye of the formula (II-3) and 20 parts by weight of the reactive yellow dye of the formula (III-6) was mixed well to obtain a dye composition.
62.5 parts by weight of the reactive blue dye of the formula (I-2), 12.5 parts by weight of the reactive red dye of the formula (II-5) and 25 parts by weight of the reactive yellow dye of the formula (III-6) was mixed well to obtain a dye composition.
63.5 parts by weight of the reactive blue dye of the formula (I-2), 13.5 parts by weight of the reactive red dye of the formula (II-6) and 23 parts by weight of the reactive yellow dye of the formula (III-6) was mixed well to obtain a dye composition.
Commercial available reactive black dye P-GR was used.
63 parts by weight of reactive blue dye 171, 11 parts by weight of reactive red dye 141 and 26 parts by weight of reactive yellow dye 84 was mixed well to obtain a dye composition.
The dye paste was prepared according to the textile printing. In brief, 3 parts by weight of the reactive black dye composition shown in Table 1 was added into 50 parts by weight of a thickener, which comprises 2.8 parts by weight of sodium alginate, 38 parts by weight of water, 7 parts by weight of urea and 1.5 parts by weight of NaHCO3. The obtained dye paste was used to dye cotton fabrics. After a drying process, the dyed cotton fabrics was steamed with saturated steam at 102° C. for 10 min. After washing, soaping, rinsing and drying, the dying strength was examined by DATACOLOR 400.
The results of the present testing example are listed in the following Table 2.
In addition, cotton fabrics were dyed through a pad dying process. After steaming, a fixed amount (500 ml) of water was used to wash the dyed cotton fabrics, and the waste water before and after the washing process was compared. The results are listed in the following Table 3.
Fixing rate(%)=(ABS value before washing−ABS value after washing)/ABS value before wasing×100%
The results indicate that the color of the waste water obtained by washing the cotton fabrics dyed with the reactive black dye composition of Example 4 is much lighter than the color of the waste water obtained by washing the cotton fabrics dyed with the reactive black dye composition of Comparative example 1. In addition, according to the results shown in Table 3, the fixing rate of the reactive black dye composition of Example 4 is much better than the fixing rate of the reactive black dye composition of Comparative example 1.
Herein, a printer Epson XP-202 was used to perform the digital printing test. The method used herein is briefly illustrated as follows. A dye solution was prepared according to the following Table 4 and printed onto cotton fabrics. After drying for 10 min and then steaming for 10 min, the cotton fabrics were placed in 500 g of water and heated to boil to perform a washing process for 10 min. Then, the dye concentration in the waste water (b) was measured. The fixing rate was calculated by the following equations.
Dye concentration used in the printing process(a)−dye concentration in the waste water=dye concentration on the cotton fabrics(a-b)
Fixing rate(%)=dye concentration on the cotton fabrics(a-b)/dye concentration used in the printing process(a)×100%
After the digital printing process, a fixed amount (500 ml) of water was used to wash the dyed cotton fabrics, and the waste water before and after the washing process was compared. The results are listed in the following Table 5.
Fixing rate(%)=(ABS value before washing−ABS value after washing)/ABS value before washing×100%
According to the results shown above, when the cotton fabrics were dyed through either the pad printing process or the digital printing process, after the washing process with the fixed amount of water, the dye contained in the waste water when the black dye composition containing two MCT reactive groups is used is much less than the dye contained in the waste water when the dye composition of Comparative example 1 is used. The fixing rate of the traditional P-type Black P-GR (Comparative example 1) is only about 61%, and the fixing rate of the reactive black dye composition of the present disclosure can be increased to 85% or more. in particular, the fixing rate of the reactive black dye composition of Example 4 can be increased to 90% or more. The reactive black dye composition of the present disclosure has high fixing rate, and the problem of the waste water generated by the dying process can be relieved. Hence, for the environmental protection issue, the usage rate of the dye can be improved when using the reactive black dye composition of the present disclosure, and therefore the chemical oxygen demand (COD) of the waste water can be reduced.
Although the present disclosure has been explained in relation to its embodiment, it is to be understood that many other possible modifications and variations can be made without departing from the spirit and scope of the disclosure as hereinafter claimed.
| Number | Date | Country | Kind |
|---|---|---|---|
| 106124887 | Jul 2017 | TW | national |
| 107110024 | Mar 2018 | TW | national |
