CN114381953A - Application and high-value recycling method based on m-phthalic acid-5-sodium sulfonate derivative - Google Patents
Application and high-value recycling method based on m-phthalic acid-5-sodium sulfonate derivative Download PDFInfo
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- CN114381953A CN114381953A CN202210047373.9A CN202210047373A CN114381953A CN 114381953 A CN114381953 A CN 114381953A CN 202210047373 A CN202210047373 A CN 202210047373A CN 114381953 A CN114381953 A CN 114381953A
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 24
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 13
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- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical group COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- PDSHIGQYIXZKRO-UHFFFAOYSA-L disodium;3-carboxy-5-sulfonatobenzoate Chemical class [Na+].[Na+].OS(=O)(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 PDSHIGQYIXZKRO-UHFFFAOYSA-L 0.000 claims description 5
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- YXTFRJVQOWZDPP-UHFFFAOYSA-M sodium;3,5-dicarboxybenzenesulfonate Chemical compound [Na+].OC(=O)C1=CC(C(O)=O)=CC(S([O-])(=O)=O)=C1 YXTFRJVQOWZDPP-UHFFFAOYSA-M 0.000 description 8
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- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- 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
- D06P1/62—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 using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/621—Compounds without nitrogen
- D06P1/622—Sulfonic acids or their salts
- D06P1/625—Aromatic
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
The invention relates to an application and high-value recycling method based on an m-phthalic acid-5-sodium sulfonate derivative, wherein the-5-sodium sulfonate derivative is used for removing oligomers generated in a polyester fabric dyeing process, the-5-sodium sulfonate derivative is m-phthalic acid-5-sodium sulfonate or m-phthalic acid dimethyl ester-5-sodium sulfonate or a mixture of m-phthalic acid-5-sodium sulfonate and m-phthalic acid dimethyl ester-5-sodium sulfonate, the oligomers contain two or more than two of cyclic trimer or dimer or linear oligomer or cyclic trimer, dimer and linear oligomer, the-5-sodium sulfonate derivative is from a dangerous waste product with the middle-risk waste code of 900-, the hazardous waste also contains sodium sulfate. The method solves the problem of reducing or removing the oligomer in the dyeing process of the polyester fabric, and has the advantage of cost performance and obvious effect.
Description
Technical Field
The invention belongs to the technical field of recycling of hazardous waste with a hazardous waste code of 900-999-49, and particularly relates to an application and high-value recycling method based on an isophthalic acid-5-sodium sulfonate derivative.
Background
Composition and formation of mono-and oligomers
The terylene oligomer is a low molecular weight byproduct formed in the polycondensation reaction process of terylene monomers, the content of the terylene oligomer is influenced by the polymerization reaction condition and is generally 1 to 3 percent of the fiber mass. The polyester oligomer contains the most main component of cyclic trimer, and the structure is shown in figure 1; goodman and Nesbit studies suggest that the cyclic trimer is formed by transesterification between or within the molecular chains of ethylene terephthalate (FIG. 2); peebles and Ha et al considered the chain-end ring depolymerization mechanism to be more rational (FIG. 3).
As shown in FIG. 1, the structure of the cyclic trimer is highly symmetrical, so that the cyclic trimer is easy to aggregate and crystallize, and the formed crystal has a higher melting point (310 ℃), and thermal stability and chemical stability. The cyclic trimer in dacron is present in a very high proportion of at least 70% of the total oligomers, and even at high temperatures of 130 c, the cyclic trimer has a solubility in water of not more than 2mg/L, and thus it is difficult to remove it during dacron production, dyeing and finishing, or other wet processes.
Linear oligomers are the initial polycondensation products of two monomers, the content of which decreases with the progressive condensation of the monomers. The linear oligomer accounts for about 25% of the total amount of oligomers in the polyester fiber, and the molecular structure has polar end groups, has certain solubility in water and has small influence on the textile processing of the polyester fiber.
Due to the equilibrium competition relationship between the intermolecular and intramolecular esterification reactions during the polyester synthesis, it is impossible to completely eliminate the cyclic trimer by any method, and it is impossible to reduce the trimer content to 0.5% and the total oligomer content to 1% in industrial production. Although oligomers are difficult to remove completely, there is currently no evidence that the textile dye finishing process will produce new oligomers, probably because the probability of rearrangement of the polyester macromolecules in the solid state to form trimers is very low.
2. Effect of oligomers on dyeing and finishing processing
During the dyeing process, the oligomer can gradually migrate from the interior of the fiber to the surface of the fiber after the polyester fiber is heated. It is believed that the oligomers on the surface of the fibers account for more than 0.1% of the fiber mass, causing various problems. Before heat setting and dyeing, the content of the surface oligomer of the terylene is 0.05 to 0.1 weight percent; and 0.2 wt% or more after heat setting or dyeing, and is sufficient to affect the processing and finishing of the polyester fabric in several respects:
(1) the oligomers deposit on the various parts of the dyeing apparatus, hindering the circulation of the dyeing liquor, causing a reduction in the efficiency of the machine; the deposition causes color differences and stains on the fabric.
(2) Oligomers migrate from the interior of the fabric to the surface, affecting product quality, such as appearance, hand, etc.
(3) Oligomers attached to the surface of the polyester fibers increase the friction of the yarn, causing a change in tension during the fabric formation process, and at the same time accelerating the wear of the machine.
(4) Oligomers accumulate on the dyeing equipment, affecting sensors and other functional parts, even causing machine malfunctions leading to machine shutdowns.
(5) The low polymer adhered on the surface of the fiber causes difficult yarn winding, the phenomena of yarn breakage, uneven thickness and the like occur, the spinnability of the fiber is reduced, and the quality of the textile is seriously influenced.
3. Method for controlling oligomers
The problem of the polyester oligomer troubles dyeing workers for a long time, so that the method for removing the oligomer on the surface of the polyester during dyeing has very important significance for dyeing and finishing the polyester. Many scholars at home and abroad research on the problem, and although no method can completely solve the problem of the oligomer so far, the oligomer can be minimized and controlled by the prior art. In the dyeing process of the polyester fiber, factors influencing the content of the oligomer on the surface of the fiber are many, including heat setting temperature and time, dyeing temperature, time, bath ratio, liquid discharge temperature, carrier type and dosage and the like. Therefore, to solve the oligomer problem, it is necessary to consider the influence of various variables in combination from these factors.
Production of dyed oligomers for cheese
In fact, in the production of polyester fiber by chemical fiber spinning, oligomer is produced as a byproduct, the chemical structure of the oligomer is linear and cyclic, and the oligomer can be separated by high-temperature dyeing.
Oligomeric disperse dyes can be classified into E-, SE-and S-types (also called H-type abroad), and the required dyeing temperature is different: the E type is a low temperature type, and the S type is a high temperature type. Generally, when the temperature rises to 125-130 ℃, the color depth obtained in the same heat preservation time (30min) is basically slightly different from that of S-type dyes, and the separation of oligomers can be reduced by adopting lower dyeing temperature for dyeing different dyes.
The problem of common black cheese oligomer dyeing is the most outstanding, 300 percent of domestic most common disperse black EX-SF is dyed at 125-130 ℃, the obtained color is almost the same, and the dyeing heat preservation time is controlled within 30min and is not easy to overlong.
Thirdly, the generation of the dangerous waste with the dangerous waste code of 900-
The domestic production of sodium 5-sulfoisophthalate and sodium 5-sulfoisophthalate was mainly concentrated in the Texas region of Weifang City in Shandong province, wherein the process flow of sodium 5-sulfoisophthalate is shown in FIG. 4, and the process flow of sodium 5-sulfoisophthalate is shown in FIG. 5. The waste liquid generated in the production process of the two products is neutralized by sodium carbonate to obtain a sodium sulfate solution, water and substances of sodium 5-sulfoisophthalate and sodium sulfate which can not be separated are contained in the sodium sulfate solution, and the hazardous waste with the hazardous waste code of 900-999-49 is obtained after dehydration, distillation and drying. If the isophthalic acid-5-sodium sulfonate or the isophthalic acid dimethyl ester-5-sodium sulfonate is completely purified, enterprises need to spend a large amount of cost, which is very uneconomical; if the land is filled, the land area is occupied while the environment is polluted, and the method is not an enterprise intelligence management method under the condition that the land is increasingly scarce at present.
The invention provides an application and a high-value recycling method based on an isophthalic acid-5-sodium sulfonate derivative, in particular to a method for solving the technical problems, which adopts a dangerous waste with a dangerous waste code of 900-999-49 and adds sodium lignosulfonate, aims to reduce the low polymer of polyester cheese dyeing and polyester fabric, and has cost performance advantage and obvious effect.
Disclosure of Invention
The invention aims to provide an application and a high-value recycling method based on an isophthalic acid-5-sodium sulfonate derivative, and aims to solve the technical problems in the background technology.
In one aspect of the present invention, there is provided an application method based on a sodium 5-sulfoisophthalate derivative, which is used for removing oligomers generated in a dyeing process of polyester fabrics.
Further, the-5-sodium sulfonate derivative is isophthalic acid-5-sodium sulfonate or dimethyl isophthalate-5-sodium sulfonate or a mixture of isophthalic acid-5-sodium sulfonate and dimethyl isophthalate-5-sodium sulfonate.
Further, the oligomer contains cyclic trimer or dimer or linear oligomer or a mixture of two or more of cyclic trimer, dimer and linear oligomer.
Further, the sodium-5-sulfonate derivative is from the hazardous waste products with the hazardous waste code of 900-999-49 in national hazardous waste catalogue (2021 edition), and the hazardous waste products also contain sodium sulfate.
In another aspect of the present invention, a high value recycling method based on isophthalic acid-5-sodium sulfonate derivatives is provided, which mainly comprises the following steps:
s1, composition of oligomer remover: mixing and compounding sodium lignosulfonate and hazardous waste according to a certain proportion to obtain an oligomer remover;
s2, use of oligomer remover: when the polyester fabric is dyed, adding a dye at normal temperature, simultaneously adding an oligomer remover according to a certain proportion, and when the temperature is raised to 130-135 ℃, fully contacting the oligomer remover with the oligomer due to the fact that the oligomer is melted out of the fiber at the high temperature of 130-135 ℃ to generate a chemical reaction;
s3, removing oligomers: because the oligomer remover contains the-5-sodium sulfonate derivative and the oligomer contains the cyclic trimer, the-5-sodium sulfonate derivative and the cyclic trimer can generate chemical reaction to generate a water-soluble low molecular compound, and can directly remove and collect the low molecular compound without generating other harmful substances.
Further, the oligomer remover is prepared by mixing sodium lignosulfonate and hazardous waste products according to the proportion of 1: 9, and mixing and compounding the components in a ratio of 9.
Furthermore, the oligomer remover accounts for 0.8-2.5% of the weight of the polyester fabric.
Further, the chemical reaction formula between the sodium-5-sulfonate derivative and the cyclic trimer is as follows:
the invention has the beneficial effects that:
1. the method solves the problem of low polymer reduction or removal in the polyester dyeing process, and has the advantage of cost performance and obvious effect;
2. when the fiber is dyed at the temperature of 130-135 ℃ under the high temperature condition, dimers, tricyclics and other low molecular linear cyclic polymers which are melted from the fiber can chemically react with the-5-sodium sulfonate derivative to generate water-soluble low molecular compounds which can not be attached to equipment or the fiber.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the embodiments or the prior art descriptions will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without inventive exercise.
FIG. 1 is a cyclic trimer structure;
FIG. 2 shows an inter-or intra-molecular transesterification reaction;
FIG. 3 is a chain end ring depolymerization reaction;
FIG. 4 is a process flow diagram of sodium 5-sulfoisophthalate;
FIG. 5 is a process flow diagram of sodium dimethyl isophthalate-5-sulfonate;
FIG. 6 is a graph showing the effect of oligomer removal when an amount of the oligomer removing agent is 0.8 to 1% by weight of a polyester fabric;
FIG. 7 is a graph showing the effect of removing oligomers when the amount of the oligomer removing agent added is 1.5% -2.5% of the weight of the polyester cheese.
Detailed Description
"a" and "the" are used interchangeably and mean one or more; "and/or" is used to indicate that one or both of the recited conditions may occur, e.g., a and/or B includes (a and B) and (a or B). In addition, the recitation of ranges by endpoints herein includes all numbers subsumed within that range (e.g. 1 to 10 includes 1.4, 1.9, 2.33, 5.75, 9.98, etc.).
In addition, the recitation of "at least one" herein includes all numbers of one and more (e.g., at least 2, at least 4, at least 6, at least 8, at least 10, at least 25, at least 50, at least 100, etc.).
The present invention will be further described with reference to the following examples.
Example 1
The embodiment of the invention provides an application method based on an isophthalic acid-5-sodium sulfonate derivative, wherein the-5-sodium sulfonate derivative is a dangerous waste product with a dangerous waste code of 900-49 in national hazardous waste records (2021 edition) implemented on 01/2021, and the dangerous waste product also contains sodium sulfate. As is readily understood by those skilled in the art: the hazardous waste contains sodium-5-sulfonate derivative or sodium sulfate or mixture of sodium-5-sulfonate derivative and sodium sulfate, and is used for removing oligomers generated in the fabric dyeing process.
The "dyeing process of polyester fabric" includes, but is not limited to, the dyeing process of polyester fabric or polyester cheese, and also includes the dyeing process of other polyester fabrics.
The hazardous waste in the process of the embodiment contains a-5-sodium sulfonate derivative and sodium sulfate, wherein the-5-sodium sulfonate derivative is isophthalic acid-5-sodium sulfonate or dimethyl isophthalate-5-sodium sulfonate or a mixture of isophthalic acid-5-sodium sulfonate and dimethyl isophthalate-5-sodium sulfonate.
The oligomer in this embodiment contains a cyclic trimer or dimer or linear oligomer or a mixture of two or more of cyclic trimer, dimer and linear oligomer.
Example 2
The embodiment provides a high-value recycling method based on an isophthalic acid-5-sodium sulfonate derivative, which mainly comprises the following steps:
s1, composition of oligomer remover: mixing sodium lignosulfonate and dangerous waste products according to the proportion of 1: 9 to obtain an oligomer remover;
s2, use of oligomer remover: when the polyester fabric is dyed, adding a dye at normal temperature, simultaneously adding an oligomer remover according to a certain proportion, and melting out a cyclic trimer or a dimer or a linear oligomer or a mixture of two or more of the cyclic trimer, the dimer and the linear oligomer from fibers at the high temperature of 130-135 ℃ when the temperature is raised to 130-135 ℃, so that the oligomer remover can be fully contacted with the cyclic trimer, the dimer and the linear oligomer respectively to generate chemical reaction;
s3, removing oligomers: because the oligomer remover contains sodium lignosulfonate and hazardous waste, the hazardous waste contains a-5-sodium sulfonate derivative, the-5-sodium sulfonate derivative is isophthalic acid-5-sodium sulfonate or isophthalic acid dimethyl ester-5-sodium sulfonate or a mixture of isophthalic acid-5-sodium sulfonate and isophthalic acid dimethyl ester-5-sodium sulfonate, and the oligomer contains two or more than two of a cyclic trimer or a dimer or a linear oligomer or a cyclic trimer, a dimer and a linear oligomer, the isophthalic acid-5-sodium sulfonate or the isophthalic acid dimethyl ester-5-sodium sulfonate can respectively chemically react with the cyclic trimer, the dimer and the linear oligomer under the dispersion action of the sodium lignosulfonate, so that water-soluble low molecular compounds are generated, and can be directly removed and collected without generating other harmful substances.
As is readily understood by those skilled in the art: the sodium lignosulfonate in the oligomer remover functions as a dispersant in the high value recycling method described above for dispersing the formed small molecule compounds into the aqueous solution.
In the course of this example, the chemical reaction between the sodium-5-sulfonate derivative (using sodium 5-sulfoisophthalate as an example) and the oligomer (using the cyclic trimer as an example) is as follows:
in the process of this example, the chemical reaction between the sodium-5-sulfonate derivative (using sodium 5-sulfoisophthalate as an example) and the oligomer (using linear oligomer as an example) is as follows:
as shown in fig. 6, in the case of the dyeing process of the dacron cloth of this embodiment, the optimal amount of the oligomer remover is added when the amount of the oligomer remover is 0.8% to 1% of the weight of the dacron cloth without changing the original process, so that the oligomer is effectively prevented from being generated, the pain in the industry is solved, and the quality is improved.
Meanwhile, sodium sulfate contained in the hazardous waste is easily soluble in water, the dyeing effect is not influenced in the polyester fabric dyeing process, and the sodium sulfate is in the same bath with dyeing, and the skilled person easily understands that: when dye is added in the dyeing process of the terylene cloth, an oligomer remover is also added according to a certain proportion, so that the dyeing effect is not influenced, the same bath can be realized under the condition of not changing the dyeing process, and the generation of oligomer in the dyeing process of the terylene cloth can be solved; in addition, the process that a manufacturer continuously extracts the 5-sodium sulfonate derivative from the sodium sulfate (the hazardous waste) in the hazardous waste is omitted, financial resources, energy and manpower are greatly saved, and the method has cost performance advantages and obvious effects.
Example 3
This example differs from example 2 in that: example 2 is a dyeing process of polyester fabric, and this example is a dyeing process of polyester cheese, and the difference between the two is that: the amount of the added oligomer remover accounts for 1.5 to 2.5 percent of the weight of the polyester cheese.
For the dyeing process of the polyester cheese in the embodiment, as shown in fig. 7, under the condition of not changing the original process, the optimal usage amount is obtained when the amount of the added oligomer remover accounts for 1.5-2.5% of the weight of the polyester cheese, so that the oligomer lime in the dyeing process of the polyester cheese can be effectively removed, the product quality is improved, and the process is simplified.
The invention has the beneficial effects that:
1. the invention solves the problems of the polyester cheese dyeing and the polyester fabric oligomer reduction or removal, and has the cost performance advantage and obvious effect;
2. when the fiber is dyed at the temperature of 130-135 ℃ under the high temperature condition, dimers, tricyclics and other low molecular linear cyclic polymers which are melted from the fiber can chemically react with the-5-sodium sulfonate derivative to generate water-soluble low molecular compounds which can not be attached to equipment or the fiber.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (8)
1. An application method based on isophthalic acid-5-sodium sulfonate derivatives is characterized in that: the-5-sodium sulfonate derivative is used for removing oligomers generated in the polyester fabric dyeing process.
2. The method of claim 1, wherein the method comprises the following steps: the-5-sodium sulfonate derivative is isophthalic acid-5-sodium sulfonate or isophthalic acid dimethyl ester-5-sodium sulfonate or a mixture of isophthalic acid-5-sodium sulfonate and isophthalic acid dimethyl ester-5-sodium sulfonate.
3. The method of claim 1, wherein the method comprises the following steps: the oligomer contains cyclic trimer or dimer or linear oligomer or a mixture of two or more of cyclic trimer, dimer and linear oligomer.
4. The use of a sodium 5-sulfoisophthalate derivative according to any one of claims 1, 2, or 3, wherein: the sodium-5-sulfonate derivative is from hazardous waste products with hazardous waste codes of 900-999 in national hazardous waste catalogue (2021 edition), and the hazardous waste products also contain sodium sulfate.
5. A high-value recycling method based on isophthalic acid-5-sodium sulfonate derivatives is characterized by comprising the following steps: the high-value recycling method mainly comprises the following steps:
s1, composition of oligomer remover: mixing and compounding sodium lignosulfonate and hazardous waste according to a certain proportion to obtain an oligomer remover;
s2, use of oligomer remover: when the polyester fabric is dyed, adding a dye at normal temperature, simultaneously adding an oligomer remover according to a certain proportion, and when the temperature is raised to 130-135 ℃, fully contacting the oligomer remover with the oligomer due to the fact that the oligomer is melted out of the fiber at the high temperature of 130-135 ℃ to generate a chemical reaction;
s3, removing oligomers: because the oligomer remover contains the-5-sodium sulfonate derivative and the oligomer contains the cyclic trimer, the-5-sodium sulfonate derivative and the cyclic trimer can generate chemical reaction to generate a water-soluble low molecular compound, and can directly remove and collect the low molecular compound without generating other harmful substances.
6. The method for recycling high-value sodium 5-sulfoisophthalate derivatives according to claim 5, wherein: the oligomer remover is prepared from sodium lignosulfonate and hazardous waste products in a proportion of 1: 9, and mixing and compounding the components in a ratio of 9.
7. The method for recycling high-value sodium 5-sulfoisophthalate derivatives according to claim 5, wherein: the oligomer remover accounts for 0.8-2.5% of the weight of the polyester fabric.
8. The method for recycling high-value sodium 5-sulfoisophthalate derivatives according to claim 5, wherein: the chemical reaction formula between the sodium-5-sulfonate derivative and the cyclic trimer is as follows:
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| US4211527A (en) * | 1976-12-14 | 1980-07-08 | Ciba-Geigy Corporation | Process for dyeing polyester materials |
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| US4211527A (en) * | 1976-12-14 | 1980-07-08 | Ciba-Geigy Corporation | Process for dyeing polyester materials |
| CN101331267A (en) * | 2006-05-16 | 2008-12-24 | 日华化学株式会社 | Oligomer remover for polyester fiber material |
| JP2009120646A (en) * | 2007-11-12 | 2009-06-04 | Nicca Chemical Co Ltd | Disperse dye composition |
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