CN112647323B - Dyeing promoter, preparation thereof and dyeing method - Google Patents
Dyeing promoter, preparation thereof and dyeing method Download PDFInfo
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- CN112647323B CN112647323B CN202011328829.6A CN202011328829A CN112647323B CN 112647323 B CN112647323 B CN 112647323B CN 202011328829 A CN202011328829 A CN 202011328829A CN 112647323 B CN112647323 B CN 112647323B
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
- D06P1/228—Indigo
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
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Abstract
The invention relates to dyeingAn accelerator comprising a di-reactive quaternary ammonium salt compound having an ethyl sulfone group and a monohalos-triazine group, the compound having the structural formula (I)
Wherein M is H or an alkali metal ion, preferably Na or K; y each independently represents H, halogen or straight-chain or branched C1‑12Alkyl of (a), preferably H; each X independently represents halogen, preferably Cl or F; and R1And R2Each represents a quaternary ammonium group, identical or different, selected from:
or (R)3)3N+‑R4-, wherein R3Independently of one another, represents a linear or branched C1‑12Preferably methyl, ethyl or propyl, R4Denotes straight-chain or branched C1‑12Alkylene of (B), preferably ethylene, propylene or butylene, and R0Represents optionally one or more substituents selected from halogen or C on the phenyl ring1‑8A substituent of the alkyl group of (1). In addition, the invention also relates to a method for preparing the compound, a dyeing promoter composition containing the compound and a dyeing method, in particular to dyeing jean grey cloth.
Description
Technical Field
The application relates to printing and dyeing technology in textile industry, in particular to a novel dyeing promoter, a preparation method thereof and a dyeing method, in particular to a method for dyeing fiber fabrics such as jean grey cloth.
Background
Fiber fabrics are widely used in the textile industry and in the apparel field. In addition to the conventional and common cotton fibers, various natural fibers such as hemp, ramie, flax, silk, wool, etc. are widely used as well as regenerated fibers of viscose, tencel, modal, etc. or synthetic fiber chemical fibers such as polyester, polyamide, acrylic, spandex, etc.
In order to provide rich colors and aesthetic feeling of clothes and fabrics, it is necessary to dye the fiber fabric with dyes. These dyes include, for example, various reactive dyes or indigo. The reactive dye is an anionic dye, also called reactive dye, the molecule of which contains chemically active groups and can react with fibers such as cotton, wool and the like in aqueous solution to form a co-bond. It is popular because of its characteristics of good brilliance, convenient use and good color fastness. However, the reactive dyes are very easy to hydrolyze while being covalently bonded to the fibers, so that there is a problem that the dye uptake and fixation rate are low. In the traditional dyeing process, a large amount of inorganic salt is usually required to be added to shield negative charge aggregation on the surface of the fiber and improve the dye adsorption performance. But doing so can produce high salt content wastewater that can impact the environment or cause wastewater treatment problems.
Indigo is an ancient vat dye and is also widely used for dyeing pure cotton fabrics. The process of indigo dyeing mainly comprises the following steps: dye reduction, leuco body dip dyeing, oxidation, water washing, soaping and drying. Indigo dyes are generally insoluble in water, have no affinity for fibers, cannot be used directly for dyeing, and can be used for dyeing only after being reduced into a leuco body which is slightly soluble in water by a strong reducing agent under an alkaline condition. But the reduction rate of indigo dye is slower. Indigo dyeing rate is slow and the dye uptake is low, typically around 10%, compared to other vat dyes. This is considered to be due to the poor molecular planarity of indigo leuco, and the low affinity for fibers. Indigo belongs to low-temperature dyeing type dye, dyeing is generally carried out at normal temperature, and the color yield is reduced on the contrary when the temperature is higher; meanwhile, indigo belongs to a dyeing dye with low alkalinity, and the higher the alkalinity is, the lower the color yield is.
Therefore, in the textile industry, a large amount of dyeing wastewater is generated and difficult to treat in the dyeing process of fiber fabrics such as denim fabric, and excessive dyeing materials such as reducing agents and alkaline agents, sodium hydroxide and the like are used, thereby generating a large amount of inorganic salts and waste dyes, and increasing the COD of sewage. In addition, the processing stability is not good, the dyeing is affected by seasons, the environmental influence is great, the reproducibility is poor, and the change of color and tone is caused by slight change of conditions. In particular, for the commonly used commercial indigo, it is difficult to dye deep and bright colors and the color fastness is poor when dyeing denim with indigo, especially the rubbing fastness and washing fastness, and other fabrics are easily stained during washing.
The above technical problem is solved in CN110004742A, which provides a salt-free dyeing method of cation-modified cotton fabric to improve level-dyeing property, color fastness, etc., wherein a modification treatment liquid comprising a modifier selected from one of N-methylolacrylamide NMA, N-dimethylazetidinium chloride DMAC, and polyaminocarboxylic acid PACA is particularly used.
In addition, CN107740295A provides a dyeing method based on cotton fabric reactive dye cationic modifier, wherein the cotton fiber is modified, and the modified aqueous solution is glutamate aqueous solution or phenylalanine aqueous solution.
However, there is still room for improvement with respect to those technical problems mentioned above, and there is also a need to further explore suitable accelerators for improving the dyeing process.
Disclosure of Invention
In view of the above technical problems, the inventors of the present application have developed a novel dyeing promoter, which can significantly improve the affinity between the indigo leuco body or the reactive dye and the fiber, reduce the residual amount of the indigo dye or the reactive dye in the dye bath and the COD pollution, improve the dye utilization rate, stabilize the dyeing quality, and improve the fastness such as color fastness and rubbing fastness, after the pretreatment of the fiber fabric, especially the cotton and blended fabric such as jean grey cloth, thereby reducing the environmental stress.
Accordingly, a first aspect of the present application relates to a dyeing promoter comprising a di-active-group quaternary ammonium salt compound having an ethylsulfone group and a monohalos-triazine group, said compound having the structural formula (I) shown below
Wherein
M is H or an alkali metal ion, preferably Na or K;
y each independently represents H, halogen or straight-chain or branched C1-12Alkyl of (a), preferably H;
each X independently represents halogen, preferably Cl or F, more preferably Cl; and
R1and R2Each represents a quaternary ammonium group, identical or different, selected from:
Wherein R is3Independently of one another, represents a linear or branched C1-12Preferably methyl, ethyl or propyl,
R4denotes straight-chain or branched C1-12Alkylene, preferably ethylene, propylene or butylene, and
R0represents optionally one or more, such as 1, 2, 3 or 4, substituents selected from halogen or C on the phenyl ring1-8A substituent of the alkyl group of (1).
A second aspect of the present application relates to a process for the preparation of a compound of formula (I) as described above, comprising the steps of:
(1) one or more R is selected from optionally substituted by one or more R0The group-substituted m-phenylhydroxyalkyl trialkyl ammonium salt, p-phenylhydroxyalkyl trialkyl ammonium salt or trialkyl ammonium salt of hydroxyalkyl trialkyl ammonium salt are subjected to ring closure reaction under alkaline conditions to obtain corresponding epoxy derivatives;
(2) carrying out ammoniation reaction on the epoxy derivative obtained in the step (1) to obtain a corresponding amino derivative; and
(3) reacting the amine derivative obtained in step (2) with 1,3, 5-trihalos-triazine and optionally substituted with one or more R0Reaction of a group-substituted p- (beta-sulfate ethyl sulfone) aniline.
A third aspect of the present application relates to a method of dyeing a fibrous web, comprising the steps of:
(1) providing an optionally desized fibrous facing;
(2) applying a dyeing promoter solution comprising a compound of formula (I) as described above onto the fibrous web; and
(3) the fiber fabric applied with the dyeing promoter is dyed with a reactive dye or an indigo dye.
In the context of the present application, the term "alkali metal" denotes a metal element of main group I of the periodic table of the elements, including Li, Na and K, etc., preferably Na or K.
In the context of the present application, the term "alkyl" preferably denotes a compound having 1 to 12, preferably 1 to 8 orStraight or branched alkyl of 1 to 4 carbon atoms, and one or more H on a carbon atom may be substituted with a halogen such as F, Cl or Br. In a preferred embodiment, said alkyl group represents unsubstituted C1-8More preferably C1-4Such as methyl, ethyl, propyl or butyl.
In the context of the present application, the term "halogen" preferably comprises F, Cl and Br, more preferably represents Cl.
Radical R0Represents optionally one or more substituents selected from halogen or C on the phenyl ring1-8A substituent of the alkyl group of (1). In a preferred embodiment according to the invention, the individual phenyl rings of formula (I) do not have a substituent R0I.e. the phenyl ring is unsubstituted.
According to the invention, in preferred compounds of formula (I):
m is Na or K;
y represents H;
x represents Cl;
R3independently of one another, represents a linear or branched C1-8More preferably C1-6Particularly preferably methyl or ethyl;
R4denotes straight-chain or branched C1-8Alkylene of (3), more preferably C2-6Alkylene groups of (a), particularly preferably propylene groups; and/or
The benzene ring does not contain a substituent R0。
A second aspect of the present application relates to a process for the preparation of a compound of formula (I) as described above.
In step (1) of the process a ring closure reaction is involved. It is apparent that the three trialkylammonium salts of m-phenylalkyltrialkylammonium, p-hydroxyalkyltrialkylammonium, or hydroxyalkyltrialkylammonium correspond to R, respectively1And R2I.e. ammonium salts of substances having the structure wherein R is3And R4As defined above, and R5Denotes straight-chain or branched C1-8Preferably methylene group:
(R3)3N+-R4-OH。
furthermore, the ammonium salt may preferably be formed from a cationic structure as described above with an organic or inorganic acid, such as hydrochloric acid, nitric acid or sulfuric acid. Preferably, all three ammonium salts are hydrochloride salts.
In an exemplary embodiment of the ring-closure reaction, an alkaline solution such as NaOH or KOH may be added to the trialkylammonium salt to perform the reaction. After a certain period of time of the reaction, salts formed in the reaction, such as NaCl, are optionally filtered off, and the pH is adjusted, for example, to 6.0 to 7.5, particularly 6.5 to 7, to give the epoxy derivative of trialkylammonium salt. The pH adjusting agent may be selected from acidic compounds, such as hydrochloric acid. The reaction temperature may be controlled at room temperature (e.g., about 23 ℃).
In the step (2), the epoxy derivative obtained in the step (1) is aminated to obtain the corresponding amino derivative. The amination reaction can be carried out by adding the resulting epoxide derivative to an excess of ammonia. Here, concentrated ammonia can be used. The reaction is maintained for a period of time, e.g. 3-4h, after the addition. Excess ammonia is then removed at elevated temperature (e.g., at 80 ℃) to yield the amine-based derivative.
In step (3), the amine derivative obtained in step (2) is reacted with 1,3, 5-trihalos-triazine and optionally substituted with one or more R0Reaction of a group-substituted p- (beta-sulfate ethyl sulfone) aniline.
Depending on the desired stoichiometry of the particular compound of formula (I), the amine derivative obtained as described above can be reacted with 1,3, 5-trihalos-triazine and p- (. beta. -sulfate ethyl sulfone) aniline in a molar ratio of 2:1: 1. For example, it is clear that if two different amine-based derivatives are used, the molar ratio of the three reactions is 1:1:1: 1.
In this reaction stepThe solution comprising 1,3, 5-trihalos-triazine and p- (. beta. -sulfate ethyl sulfone) aniline is mixed with the amine derivative obtained above, usually at a low temperature such as 0-10 deg.C, more preferably 0-5 deg.C. Suitable solvents for dissolving the 1,3, 5-trihalos-triazine and the p- (. beta. -sulfate ethyl sulfone) aniline are, for example, acetone. In an exemplary embodiment employing two amine-based derivatives, one amine-based derivative may be first mixed and reacted with a solution comprising 1,3, 5-trihalos-triazine and p- (. beta. -sulfate ethyl sulfone) aniline, followed by mixing the other amine-based derivative at an elevated temperature (e.g., to 25-50 deg.C, preferably 35-40 deg.C) to provide the desired accelerator compound. During the reaction in this step, a pH adjusting agent may preferably be added to control the pH of the reaction to 6 to 7, for example, around 6.5. Suitable pH regulators are, for example, Na here2CO3。
A third aspect of the present application relates to a method of dyeing a fibrous web.
The dyeing promoter according to the invention is particularly suitable for dyeing fiber fabrics, especially for denim grey fabrics. A previously desized fibrous web is advantageous. The desizing treatment of the fabric is known per se to the person skilled in the art. Taking a jean grey fabric as an example, the desizing treatment can be performed as follows: padding in desizing enzyme liquid at 50-60 ℃, stacking for 3-4 hours, washing with hot water at more than 60 ℃ (such as 90 ℃), washing with normal temperature water, and drying to obtain the to-be-dyed jean grey fabric.
Subsequently, an accelerator solution comprising a dyeing accelerator of the compound of formula (I) as described above is applied to the fibrous web. Such application may be by means of, for example, double-sided anilox roll coating or double-sided foam coating or padding to apply the dye booster solution uniformly on one or both sides of the facing material. Preferably, the liquid carrying rate of the fiber fabric (preferably jean grey fabric) is more than 20%, such as 25% -50% or 25% -40%.
In one exemplary embodiment, the accelerator solution relates to a dyeing accelerator composition comprising (in weight percent):
3-5% of a dyeing promoter as described above,
2 to 5 percent of a binder,
1-3% of a surfactant,
0-12% of alkaline agent
0.5-2% of leveling agent.
The balance of the dyeing promoter composition may include other suitable additives, conditioners, salts, dispersants, solvents, and the like. Here, preferably, the balance of the dyeing promoter composition is a dispersant or a solvent, such as water.
The binders are components known per se to the person skilled in the art and are generally used as dispersion media, which can adjust to some extent the rheology, viscosity, film-forming properties and coating properties of the system. Such binders may be comprised of, for example, vegetable oils, mineral oils, organic solvents, various natural and synthetic resins, and small amounts of waxes. In a preferred embodiment, the binder is sodium alginate, or guar gum, or synthetic gum, or cellulose and its derivatives, or starch and its derivatives, or a multipolymer of acrylic acid, crotonic acid and its derivatives, or a mixture thereof.
In a preferred embodiment, the surfactant is polyvinylpyrrolidone, or a polyoxyethylenealkylamine, or a fatty alcohol-polyoxyethylene ether, or a silicone, or a mixture thereof.
In a preferred embodiment, the levelling agent is an alkali metal alkyl sulphonate such as sodium alkyl sulphonate, or an alkali metal fatty alcohol sulphate such as sodium higher fatty alcohol sulphate, or a fatty alcohol polyoxyethylene or polyoxypropylene or a mixture thereof.
In a preferred embodiment, the alkaline agent may be an amine compound or an alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide.
After treatment with the dyeing promoter solution, the fibre fabric to which the dyeing promoter has been applied is dyed with a reactive dye, such as a type B reactive dye, or an indigo dye. Such dyeing or printing processes are known.
Finally, the fabric dyed in the way, such as denim, can be dried, subjected to color fixing treatment, water washing and sizing to obtain a finished product.
The inventors of the present application found that the quaternary ammonium salt having both the monohalogen s-triazine and the ethyl sulfone group not only has excellent fixing reaction characteristics for fibers such as cotton fibers in the fiber fabric, but also has significant ecological advantages compared to the conventional indigo dyeing method when the quaternary ammonium salt is used as a dyeing promoter to modify and then dye the fabric, particularly denim fabric. For example, after the compound of formula (I) of the present invention is used as a dyeing promoter, the conventional salt as a dyeing promoter can be greatly reduced or even completely eliminated while the dyeability of the fiber fabric can be maintained or even improved. Thus, the expense, handling difficulties and disposal problems associated with salt addition can be eliminated. In addition, after the dyeing promoter provided by the invention is treated, the dye can be completely combined on fiber tissues to realize high apparent color yield, so that the dye is utilized to the maximum extent, and the use of the dye is obviously reduced. Furthermore, the resulting textile can be dyed uniformly and with good dyefastness, thereby also reducing the need for fixing alkaline agents.
Thus, in a preferred embodiment according to the present invention, the preferred dye booster composition may also comprise other suitable salts such as sodium carbonate, sodium bicarbonate, potassium carbonate and potassium bicarbonate.
However, as one of the advantages of the present invention, in a preferred embodiment of the dyeing process or dyeing promoter composition according to the invention, it is possible to reduce (for example, less than 5%, 2%, 1% or even 0.5% by weight of the promoter composition) or even not to use those alkaline agents which are liable to cause contamination, such as alkali metal hydroxides, in particular also alkaline agents selected from amine compounds, such as organic amines including alkylamines such as triethylamine; and/or no other organic ammonium salt other than the quaternary ammonium salt compound of formula (I) is used.
Drawings
FIG. 1a is a nuclear magnetic resonance (1H-NMR) spectrum of the dyeing promoter synthesized in example 1.
FIG. 1b shows the IR spectrum of the dyeing promoter synthesized in example 1.
FIG. 2a is a nuclear magnetic resonance (1H-NMR) spectrum of the dyeing promoter synthesized in example 2.
Figure 2b infrared spectra of the dye promotors synthesized in example 2.
The following examples are intended to illustrate various embodiments of the invention, but should not be construed as limiting the invention in any way.
Examples
While specific embodiments of the invention have been described above for purposes of illustration, it will be evident to those skilled in the art that numerous variations of the details of the present invention may be made without departing from the scope of the invention as defined in the appended claims.
Test method
The fixation degree test described in the following examples was carried out according to the measurement method of GB/T2391 2014 determination of fixation degree of reactive dyes.
The test of dry rubbing fastness and wet rubbing fastness is carried out according to GB/T3920-.
The test of light fastness and soaping resistance color fastness is carried out according to GB/T14575-2009 comprehensive color fastness of textile color fastness test.
Example 1
Reactive dye for pure cotton herringbone oblique jean fabric is dyed by printing instead of dyeing
(1) Preparing the jean grey fabric:
specification: 10 × 10/72 × 44;
weight: 10 OZ;
breadth: 58-60 inches;
comprises the following components: 100% cotton.
(2) And synthesis of a dyeing promoter:
1 molar part by mass of a 40% aqueous NaOH solution was added dropwise to 1 molar part by mass of each of 1 molar part by mass of m-xylylene trimethylammonium hydrochloride (purchased from Sigma-Aldrich, analytical grade) and 1 molar part by mass of hydroxypropyl trimethylammonium hydrochloride (purchased from Sigma-Aldrich, analytical grade) placed in a reaction vessel with stirring at room temperature. And after the dropwise addition is finished, continuously reacting for 30-60 minutes. Filtering NaCl generated in the reaction, and adjusting the pH value of the solution to 6.5-7 by using hydrochloric acid, thereby respectively preparing the corresponding epoxy derivatives.
Then, an excess of 32% strength concentrated aqueous ammonia was added dropwise to each of the two above-described reaction vessels containing the freshly prepared epoxy derivative. After the dropwise addition is finished, the reaction is continued for 3 to 4 hours. Then removing excessive ammonia in vacuum at 80 ℃ to obtain two corresponding amino derivatives with yield of more than 85%.
Then, slowly dripping acetone solution dissolved with 1,3, 5-monochlorotriazine and p- (beta-sulfate ethyl sulfone) aniline into the amino derivative of the m-phenylmethylol trimethylammonium hydrochloric acid under the condition of 0-5 ℃ and a uniform stirring environment, wherein Na is used for the amino derivative of the m-phenylmethylol trimethylammonium hydrochloric acid at any time2CO3The pH value of the reaction is regulated and controlled to be 6.5 by the aqueous solution until the reaction is finished to obtain a primary product. At this point, Na is no longer added2CO3The pH value of the aqueous solution is kept unchanged at 6.5. Heating the reaction system containing the primary product to 35-40 deg.C, and adding dropwise the amino derivative of hydroxypropyl trimethylammonium hydrochloride while stirring, wherein Na is still used2CO3And regulating and controlling the pH value of the reaction to be 6.5 by using an aqueous solution until the reaction is finished to obtain the denim fabric dyeing promoter. At this time, Na is not added2CO3The pH of the aqueous solution was maintained at 6.5.
The dyeing promoter obtained has the following molecular formula and its nuclear magnetic resonance spectrum and infrared spectrum are shown in FIGS. 1a and 1 b:
wherein
X is Cl; and
R1、R2are respectively as
(3) Dyeing process
A dyeing promoter solution comprising the following components was first prepared on the basis of the dyeing promoter compound prepared as described above:
padding the prepared jean gray fabric in desizing enzyme liquid at 50-60 ℃, piling for 3-4 hours, then washing with hot water at 90 ℃, washing with normal-temperature water, drying and waiting for printing. And then coating the prepared dyeing promoter solution on the front and back surfaces of the jean grey cloth through double-sided anilox roller coating. Finally, the B-type double-active-group active dye (produced by Zhejiang Runli soil chemical Co., Ltd.) is used for printing and dyeing by adopting the transfer dyeing method described in Chinese patent CN201710048417.9, and the pure cotton herringbone oblique denim printing and dyeing cloth is obtained.
The fabric sample prepared in the embodiment has a printing fixation rate of the reactive dye of 93%, and the prepared stretch cotton jean dyed fabric has dry rubbing fastness of 4-5 grade, wet rubbing fastness of 3.5-4 grade, light fastness of 5 grade, and soaping color fastness of 4-5 grade.
Example 2:
dip dyeing of stretch cotton jean fabric
(1) Preparing the jean grey fabric:
specification: 7X 16/70D;
breadth: 50-52 inches;
weight: 11.5 OZ;
comprises the following components: 97% cotton + 3% spandex.
The synthetic method of the denim fabric dyeing promoter comprises the following steps:
(2) and synthesis of a dyeing promoter:
to 1 part by mol of each p-methylol trimethylammonium hydrochloride (purchased from Sigma-Aldrich, analytical grade) placed in two reaction kettles, 1 part by mol of a 40% NaOH aqueous solution was added dropwise with stirring at room temperature. And continuing to react for 30-60 minutes after the dripping is finished. Filtering NaCl generated in the reaction, and adjusting the pH value of the solution to 6.5-7 by using hydrochloric acid to obtain 2 parts of the same epoxy derivative.
Then, the epoxy derivative was added dropwise to an excess of 32% strength concentrated ammonia water, respectively, to a reaction vessel containing the epoxy derivative under stirring at room temperature. After the dropwise addition is finished, the reaction is continued for 3 to 4 hours. Excess ammonia was then removed in vacuo at 80 ℃ to give two identical amino derivatives of p-methylol trimethylammonium hydrochloride.
Then, slowly dripping acetone solution dissolved with 1,3, 5-monochlorotriazine and p- (beta-sulfate ethyl sulfone) aniline in a molar ratio of 1:1 into the obtained amino derivative by using Na at any time in a uniform stirring environment at the temperature of 0-5 DEG C2CO3And regulating the pH value of the reaction to be 6.5 by using an aqueous solution until the reaction is finished to obtain a primary product. At this point, Na is no longer added2CO3The pH value of the aqueous solution is kept constant at 6.5. Heating the reaction system containing the primary product to 35-40 deg.C, and adding a second portion of the resulting amine derivative dropwise while stirring, wherein Na is still used2CO3And regulating the pH value of the reaction to be 6.5 by using an aqueous solution until the reaction is finished to obtain the dyeing promoter. At this time, Na is not added2CO3The pH value of the aqueous solution is still kept at 6.5.
The prepared dyeing promoter compound has the following structural formula, and the nuclear magnetic resonance spectrum and the infrared spectrum of the compound are shown in figures 2a and 2 b:
wherein
R1 and R2 are both
And
and X is Cl.
(3) Dyeing process
A dyeing promoter solution comprising the following components was first prepared on the basis of the dyeing promoter compound prepared as described above:
padding the jean grey cloth in desizing enzyme liquid at 50-60 ℃, stacking for 3-4 hours, then washing with hot water at 90 ℃, washing with normal temperature water, drying and waiting for printing. And then coating the prepared dyeing promoter solution on the front and back surfaces of the jean grey cloth through a double-sided anilox roller. Finally, dyeing and printing are carried out by using indigo dye by a dip dyeing method (such as the methods in review documents: Yangui li, Pencheng jean dyeing and quality control [ J ] Tianjin textile technology, 2011 (3): 7-9) which is well known by the professionals in the field) to obtain the stretch cotton jean dyed fabric.
The dyeing fixation rate of the indigo dye of the fabric sample prepared in the embodiment is 90%, the dry rubbing fastness of the prepared stretch cotton jean dyed fabric is 4-5 grade, the wet rubbing fastness is 3.5-4 grade, the light fastness is 5 grade, and the soaping color fastness is 4-5 grade.
Claims (28)
1. A dyeing promoter comprising a di-reactive quaternary ammonium salt compound having an ethylsulfone group and a monohalos-triazine group, said compound having the structural formula (I) shown below
Wherein
M is H or an alkali metal ion;
y each independently represents H, halogen or straight-chain or branched C1-12Alkyl groups of (a);
each X independently represents a halogen; and
R1and R2Each represents a quaternary ammonium group, identical or different, selected from:
Wherein R is3Independently of one another, represents a linear or branched C1-12The alkyl group of (a) is,
R4denotes straight-chain or branched C1-12Alkylene of (a), and
R0represents optionally one or more substituents selected from halogen or C on the phenyl ring1-8A substituent of the alkyl group of (1).
2. Dyeing promoter according to claim 1, characterized in that M is Na or K.
3. Dyeing promoter according to claim 1, characterized in that Y represents H.
4. Dyeing promoter according to claim 1, characterized in that X represents Cl or F.
5. Dyeing promoter according to claim 1, characterized in that X represents Cl.
6. Dyeing promoter according to claim 1, characterized in that R3Independently of one another, represents methyl, ethyl or propyl.
7. Dyeing promoter according to claim 1, characterized in that R4Represents ethylene, propylene or butylene.
8. Dyeing promoter according to claim 1, characterized in that in the formula (I) R3Independently of one another, represents a linear or branched C1-8Alkyl groups of (a);
R4denotes straight-chain or branched C1-8An alkylene group of (a); and/or
The benzene ring does not contain a substituent R0。
9. Dyeing promoter according to claim 1, characterized in that R is4Is represented by C2-6An alkylene group of (a).
10. Dyeing promoter according to claim 1, characterized in that R is4Represents a propylene group.
11. Dyeing promoter according to claim 1, characterized in that R is3Independently of one another, represents a linear or branched C1-8Alkyl group of (1).
12. A process for preparing a dyeing promoter as claimed in any one of claims 1 to 11, comprising the steps of:
(1) one or more R is selected from optionally substituted by one or more R0The group-substituted m-phenylhydroxyalkyl trialkyl ammonium salt, p-phenylhydroxyalkyl trialkyl ammonium salt or trialkyl ammonium salt of hydroxyalkyl trialkyl ammonium salt are subjected to ring closure reaction under alkaline conditions to obtain corresponding epoxy derivatives;
(2) carrying out ammoniation reaction on the epoxy derivative obtained in the step (1) to obtain a corresponding amino derivative; and
(3) reacting the amine derivative obtained in step (2) with 1,3, 5-trihalos-triazine and optionally substituted with one or more R0Reaction of a group-substituted p- (beta-sulfate ethyl sulfone) aniline.
13. The method according to claim 12, wherein a pH adjusting agent is added in the step (3) to control the pH of the reaction to 6 to 7.
14. The method of claim 13, wherein the pH is 6.5.
15. The method for dyeing the fiber fabric comprises the following steps:
(1) providing an optionally desized fibrous facing;
(2) applying a dyeing promoter solution comprising a compound of formula (I) according to any one of claims 1 to 11 on the fibrous web; and
(3) the fiber fabric applied with the dyeing promoter is dyed with a reactive dye or an indigo dye.
16. The method according to claim 15, wherein the fibrous fabric is a denim fabric.
17. The method according to claim 15 or 16, wherein no compounds selected from the group consisting of amines; and/or no other organic ammonium salt other than the quaternary ammonium salt compound of formula (I) is used.
18. The method of claim 17, wherein the amine compound comprises an organic amine.
19. The method of claim 17, wherein the amine compound comprises an alkylamine.
20. The method of claim 17, wherein the amine compound comprises triethylamine.
21. The method according to claim 15 or 16, wherein the denim blank is dyed with indigo dye.
22. A dyeing promoter composition comprising, by total weight of the composition:
3-5% of a dyeing promoter as claimed in any of claims 1 to 11,
2 to 5 percent of a binder,
1-3% of a surfactant,
0-12% of an alkaline agent, and
0.5-2% of leveling agent.
23. Dyeing promoter composition according to claim 22, characterized in that the balance is water.
24. Dyeing promoter composition according to claim 22 or 23, characterized in that the binder is sodium alginate, or guar gum, or synthetic dragon gum, or cellulose and its derivatives, or starch and its derivatives, or multipolymers of acrylic acid, crotonic acid and its derivatives, or mixtures thereof.
25. Dyeing promoter composition according to claim 22 or 23, characterized in that the surfactant is a polyvinylpyrrolidone, or a polyoxyethylenealkylamine, or a fatty alcohol-polyoxyethylene ether, or a polysiloxane, or a mixture thereof.
26. Dyeing promoter composition according to claim 22 or 23, characterized in that the levelling agent is an alkali metal alkylsulfonate, or an alkali metal fatty alcohol sulfate, or a fatty alcohol polyoxyethylene or polyoxypropylene or mixtures thereof.
27. Dyeing promoter composition according to claim 26, characterized in that the alkylsulfonate is sodium alkylsulfonate.
28. Dyeing promoter composition according to claim 26, characterized in that the fatty alcohol sulfate is a higher fatty alcohol sodium sulfate.
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| CN202011328829.6A CN112647323B (en) | 2020-11-24 | 2020-11-24 | Dyeing promoter, preparation thereof and dyeing method |
| PCT/CN2021/088991 WO2022110623A1 (en) | 2020-11-24 | 2021-04-22 | Dyeing accelerator, preparation thereof, and dyeing method |
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| CN112832042A (en) * | 2020-12-30 | 2021-05-25 | 长胜纺织科技发展(上海)有限公司 | Suspension dye transfer dyeing method for denim |
| CN116163138A (en) * | 2022-12-30 | 2023-05-26 | 福建省联丰盛漂染植绒有限公司 | Processing technology of strong superfine pure cotton plain cloth with high dye-uptake |
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| CN110382775B (en) * | 2017-04-14 | 2022-09-09 | 日东纺绩株式会社 | Wet rubbing fastness improver for cellulose fiber, method for producing dyed cellulose fiber using the same, and use thereof |
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