Bleaching and dyeing; fluid treatment and chemical modification – Multiple chemically diverse fibers or fibers with different...
Reexamination Certificate
2000-02-17
2002-07-02
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Multiple chemically diverse fibers or fibers with different...
C008S566000, C008S654000, C008S657000, C008S917000, C008S930000
Reexamination Certificate
active
06413281
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel 2-(p-sulphophenyl) amino-1,3,5-triazine derivatives and to their use in dyeing animal protein fibers (such as wool, cony hair, camel hair and natural silk) and their textile fabric as a cationic dye auxiliary agent.
BACKGROUND OF THE INVENTION
For a long time it has been known to use acid dyes (including weak acid dyes), acid mordant dyes or reactive dyes to dye animal protein fibers, such as wool, natural silk and so on. For example, CN1040643A disclosed that acid mordant dyes were used to dye textile fabric, that mordant NaCN was used for the mordant dyeing process, and that compound of formula [10] was used to partially replace NaCN for the mordant dyeing process. In CN1035536A, it was mentioned that acid mordant was used to dye protein fibers with the addition of mixed chlorinates of rare elements, formic acid, etc.
Up to now, the methods of dyeing animal protein fibers by use of acid dyes (including weak acid dyes), acid mordant dyes or reactive dyes still exhibit the following shortcomings. 1) The method cannot achieve high dyeing quality, i.e., the color is not bright enough and the color fastness is not sufficient. 2) In the dyeing and finishing process, use of a great amount of strong acids and hypertoxic chemicals (for example, NaCN) heavily impairs the environment and human health. 3) During the dyeing and finishing process, the cost increases by using varied dye auxiliary agents, such as penetrating agents, diffusing agents, softeners and so on, which, at the same time, cause heavy environmental pollution.
The cationic dyes developed afterwards are especially for acrylic fibers. The dyes are bonded together with fibers mainly through ionic bonding and/or covalent bonding. Although cationic dyes have a complete range of color spectra, a satisfactory variety of color, and bright color and high color fastness, they could not be used to dye and finish animal protein fibers.
Due to the aforementioned reasons, the stage-dyeing process should be used for dyeing blended yarn or blended fabric which contains animal protein fiber and synthetic fiber by using different kinds of dyes, i.e., dyeing the synthetic fiber and then dyeing the animal protein fiber, or dyeing the animal protein fiber first and then dyeing the synthetic fiber. The process needs a long time to complete by using a large amount of dyes with a subsequent high cost.
The object of the present invention is to provide a cationic dye auxiliary agent so that it is possible to use cationic dyes for dyeing and finishing animal protein fibers.
The present invention further provides a process for preparing the cationic dye auxiliary agent.
The invention further provides the application of such a cationic dye auxiliary agent when cationic dyestuffs are used to dye and finish animal protein fibers.
This invention also provides a process for dyeing and finishing animal protein fibers by using cationic dyestuffs through the cationic dye auxiliary agent.
DESCRIPTION OF THE INVENTION
The objects of the invention are achieved by providing novel 2-(p-sulphophenyl) amino-1,3,5-triazine derivatives of formula [1] and salts thereof, preferably their sodium salts
wherein R
1
, represents halogen, preferably Cl, F, R
2
, is &agr;- or &bgr;-naphthylamino, &agr;- or &bgr;-naphthoxy.
The cationic dye auxiliary agent according to the present invention can be selected from the group of the following compounds (a)~(g) and sodium salt thereof:
This invention further provides the method for synthesizing the above-described 2-(p-sulphophenyl) amino-1,3,5-triazine derivatives.
The compound of formula [1] can be synthesized according to the following procedures:
In the above procedures, the compounds of formula [1] are prepared with cyanuric trihalide [3], p-aminobenzene sulfonic acid [2] (or salt thereof) and amino-naphthalene (or naphthol) HR
3
, as raw materials by a two-step reaction.
Reaction (1): Cyanuric trihalide as formula [3] is dissolved into ice water in a reaction vessel, then p-aminobenzene sulfonic acid as formula [2] or its salt is slowly added into the solution and the reaction is initiated. The temperature is controlled at −3~10° C., and the pressure is between 0 and 0.05 MPa. Then the catalyst, i. e., a mixed solution of sodium hydroxide and phosphoric acid, is added into the reaction solution. The reaction is sustained for 3~5 hrs. When the pH value of the reaction solution exceeds 5 and the amount of free amine is less than 0.8%, the intermediate as formula [4] is obtained.
Reaction (2): The intermediate as formula [4] is moved into another reaction vessel, then a solution of compound HR
2
(&agr;- or &bgr;-naphthylamino, or &agr;- or &bgr;-naphtol) as well as a catalyst, i. e., a mixed solution of sodium hydroxide and phosphoric acid, are added into the same vessel. The reaction is sustained for 4~5 hrs. at a temperature of 15~50° C., under a pressure of 0~0 03 MPa, with pH value of 5~10. When the pH value is adjusted to around 7 by using acetic acid, the compound as formula [1] is finally obtained through discharging, filtering, drying and grinding.
In the above synthetic processes, molar ratios of the three raw materials are controlled within the range as: cyanuric trihalide: p-aminobenzene sulfonic acid or its salt: naphthylamino (or naphthol)=1.0: (1.10~1.3): (1.0-1.25). For reaction (1), the yield of the intermediate as formula [4] is between 87% and 92%, and the yield of product of formula [1] for reaction (2) is 91%-97%.
There is an essential difference between the dye agent according to the present invention and other ones used in the prior art in the dyeing and finishing industry. The dye auxiliary agent used in the prior art only plays a certain role as a dyeing promoter, but does not participate in the chemical reaction of the molecular chain. However, the dye auxiliary agent according to the present invention participates in the chemical reaction of the molecular chain, i.e., one end group of molecules of the dye auxiliary agent chemically reacts with the fiber molecules and the other group reacts with the cationic dye molecules, thus the cationic dye is firmly bonded to the fiber molecule to achieve coloration. The compound according to the present invention plays a role as a link arm. The cationic dye, which formerly could not bind with the protein fiber, thus bonds to the protein fiber by the aid of said link arm.
The present invention further provides the application of the compounds as formula [1] as a cationic dye auxiliary agent when cationic dyestuffs are used for dyeing and finishing animal protein fiber or its fabric as well as blended yarn or its fabric containing animal protein fiber. Herein, said animal protein fibers are such hairs as wool, cashmere, cony hair, and camel hair, as well as natural silk. Blended yarn means a combination of the animal protein fiber with synthetic fiber, such as wool combining with acrylic fiber, or combining natural silk with rayon. Said fiber means top or yarn.
The method of dyeing hairs (such as wool, cony hair, camel hair, cashmere) or its yarn or fabric by using cationic dyes according to the present invention comprises the steps of:
1) circulating a bath containing said fibers or fabrics with water at a temperature of 20~30° C., in which the bath ratio is between 1:30 and 1:50, and the pH value is adjusted to 3~6; adding the compound as formula [1] as a cationic dyeing auxiliary agent in an amount of 1~8 wt. % on the basis of the total weight of the fibers or fabrics, then circulating the bath for 15~20 minutes;
2) introducing cationic dyes into the bath in an amount of 0.01~3 wt. % on the basis of the weight of the fibers or fabrics; after cycling the bath with a pump for 10~15 minutes at ambient temperature, heating the bath to 98~100° C. at a rate of 1~2° C./min, then boiling the bath for 40~60 minutes; cooling the bath to a temp
Einsmann Margaret
Hogan & Hartson L.L.P.
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