CN109651644A - A kind of method that grafted by beta cyclodextrin modified wick grass removes disperse dyes in colored terylene - Google Patents
A kind of method that grafted by beta cyclodextrin modified wick grass removes disperse dyes in colored terylene Download PDFInfo
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- CN109651644A CN109651644A CN201811508094.8A CN201811508094A CN109651644A CN 109651644 A CN109651644 A CN 109651644A CN 201811508094 A CN201811508094 A CN 201811508094A CN 109651644 A CN109651644 A CN 109651644A
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- grafted
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- beta cyclodextrin
- colored terylene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
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- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
The present invention relates to colored terylene recycling fields, disclose a kind of method that grafted by beta cyclodextrin modified wick grass removes disperse dyes in colored terylene.Method includes the following steps: beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water by (1), it is stirred to obtain mixed solution, rush is added in the mixed solution, is reacted at a reflux temperature, grafted by beta cyclodextrin modified wick grass is obtained；(2) in the presence of active metal and/or active metal salt, at 25-150 DEG C, colored terylene waste material is dissolved in organic solvent, is then filtered, obtains filtrate；(3) the grafted by beta cyclodextrin modified wick grass is mixed with the filtrate.The disperse dyes in colored terylene can be sufficiently removed according to the method described in the present invention, to realize the recycling of colored terylene waste material.
Description
Technical field
The present invention relates to colored terylene recycling fields, and in particular to a kind of grafted by beta cyclodextrin modified wick grass removing
The method of disperse dyes in colored terylene.
Background technique
Terylene is that yield is maximum in the world, most widely used synthetic fibers kind, in recent years, as domestic economy continues
The continuous improvement of rapid growth and domestic consumption of resident ability, the demand of polyester staple fiber constantly increase, be largely used to dress material,
The textiles such as bedding, various trimming cloth, defence and military particular fabric and other industrial fibre products.However due to
The tensile strength of terylene is high, elasticity is good, and wear-resisting, heat-resisting, fast light and acidproof, so that polyester fiber or dacron waste material
Recycling and reusing becomes very difficult.
Currently, terylene waste material recycling and reusing is mainly by crushing melting to pure polyester fiber or pure polyester fabric shoddy
Afterwards, thickening chain extender is added and carries out liquid-phase tackifying, is eventually fabricated polyester slice and is used again, such as patent application
CN200910196653.0 and CN201010190044.7.It is given up in addition, patent application CN97181632.8 is described using terylene
Material recycles terephthalic acid (TPA) and ethylene glycol under the action of weak base and alkali metal；CN200910196653.0 is mainly for low viscosity
The recovery processing of polyester fiber or dacron waste material；CN201010190044.7 need to be first by discarded same color terylene clothes
Then the non-terylene part of artificial removal crushes and is handled, produces a large amount of human cost；And the main mesh of CN97181632.8
It is recycling terephthalic acid (TPA) and ethylene glycol, if this is carried out polymerization spinning again, operation is too cumbersome, and wastes a large amount of energy
Source and cost.In addition, for how to remove disperse dyes therein, being technology reality in the removal process of colored terylene waste material
The difficult point applied, in the prior art even without relevant report.
Summary of the invention
The purpose of the invention is to overcome in the removal process of existing colored terylene waste material to be difficult to remove disperse dyes
The problem of, a kind of method that grafted by beta cyclodextrin modified wick grass removes disperse dyes in colored terylene is provided.
To achieve the goals above, the present invention provides in a kind of grafted by beta cyclodextrin modified wick grass removing colored terylene
The method of disperse dyes, method includes the following steps:
(1) beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water, are stirred to obtain mixed solution, it will
Rush is added in the mixed solution, is reacted at a reflux temperature, and grafted by beta cyclodextrin modified wick grass is obtained；
(2) in the presence of active metal and/or active metal salt, at 25-150 DEG C, colored terylene waste material is dissolved
It in organic solvent, is then filtered, obtains filtrate；
(3) the grafted by beta cyclodextrin modified wick grass is mixed with the filtrate.
Preferably, in the mixed solution described in step (1), the concentration of beta-cyclodextrin is 30-100g/L, citric acid it is dense
Degree is 30-100g/L, and the concentration of sodium hypophosphite is 5-50g/L, and the concentration of ethyl alcohol is 1-10g/L.
It is further preferred that the concentration of beta-cyclodextrin is 60-80g/L, lemon in the mixed solution described in step (1)
The concentration of acid is 60-80g/L, and the concentration of sodium hypophosphite is 20-40g/L, and the concentration of ethyl alcohol is 2-3g/L.
Preferably, reaction described in step (1) carries out under ultrasonic agitation, and the time of reaction is 3-60 minutes.
Preferably, in step (1), the volume ratio of the rush and the mixed solution is 1:3-10.
Preferably, in step (2), the organic solvent is DMF, dimethyl sulfoxide, o-chlorphenol, parachlorophenol, benzene
At least one in phenol, formic acid, pyridine, ethylene glycol, acetamide, diethylene glycol (DEG), tetrachloroethanes, benzyl alcohol, trichloroethanes and nitrobenzene
Kind.
Preferably, in step (2), the active metal is sodium, magnesium, aluminium or zinc.
Preferably, in step (3), process that the grafted by beta cyclodextrin modified wick grass and the filtrate are mixed
It is carried out under ultrasonic agitation.
Preferably, in step (3), the volume ratio of the grafted by beta cyclodextrin modified wick grass and the filtrate is 1:3-
15。
In grafted by beta cyclodextrin modified wick grass of the present invention removing colored terylene the method for disperse dyes have with
Lower advantage:
(1) rush and beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are subjected to hybrid reaction, during the reaction,
Cellulose components in citric acid and rush are crosslinked, and the carboxyl in citric acid molecule and the hydroxyl in beta-cyclodextrin molecule are sent out
Raw esterification forms the modified rush of grafted by beta cyclodextrin.
(2) rush has hollow structure, and side wall is loose reticular structure (as shown in Figure 1), thus rush has
There is biggish specific surface area, so that the modified wick grass has biggish adsorption capacity.
(3) it is washed using grafted by beta cyclodextrin modified wick grass of the present invention to the coloured of disperse dyes is wherein dispersed with
Synthetic fibre solution is adsorbed, and the disperse dyes in colored terylene can be sufficiently removed, to realize the recycling benefit of colored terylene waste material
With.
Detailed description of the invention
Fig. 1 is the electron scanning micrograph in rush section.
Specific embodiment
Below in conjunction with attached drawing, detailed description of the preferred embodiments.It should be understood that this place is retouched
The specific embodiment stated is merely to illustrate and explain the present invention, and is not intended to restrict the invention.
The endpoint of disclosed range and any value are not limited to the accurate range or value herein, these ranges or
Value should be understood as comprising the value close to these ranges or value.For numberical range, between the endpoint value of each range, respectively
It can be combined with each other between the endpoint value of a range and individual point value, and individually between point value and obtain one or more
New numberical range, these numberical ranges should be considered as specific open herein.
In grafted by beta cyclodextrin modified wick grass of the present invention removing colored terylene the method for disperse dyes include with
Lower step:
(1) beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water, are stirred to obtain mixed solution, it will
Rush is added in the mixed solution, is reacted at a reflux temperature, and grafted by beta cyclodextrin modified wick grass is obtained；
(2) in the presence of active metal and/or active metal salt, at 25-150 DEG C, colored terylene waste material is dissolved
It in organic solvent, is then filtered, obtains filtrate；
(3) the grafted by beta cyclodextrin modified wick grass is mixed with the filtrate.
In method of the present invention, in step (1), by making rush and beta-cyclodextrin, citric acid, hypophosphorous acid
Sodium and ethyl alcohol carry out hybrid reaction, and the cellulose components in citric acid and rush are crosslinked, and the carboxyl in citric acid molecule with
Hydroxyl in beta-cyclodextrin molecule is esterified, and forms the modified rush of grafted by beta cyclodextrin.
In step (1), in the mixed solution, the concentration of beta-cyclodextrin can be 30-100g/L, preferably 60-
80g/L；The concentration of citric acid can be 30-100g/L, preferably 60-80g/L；The concentration of sodium hypophosphite can be 5-50g/L,
Preferably 20-40g/L；The concentration of ethyl alcohol can be 1-10g/L, preferably 2-3g/L.
In step (1), the reaction is preferably carried out under ultrasonic agitation.The time of the reaction can be 3-60 points
Clock, preferably 5-20 minute.
In step (1), the volume ratio of the rush and the mixed solution can be 1:3-10, preferably 1:5-7.
In method of the present invention, in step (2), in the presence of active metal and/or active metal salt, institute
Colored terylene waste material is stated to be dissolvable in water in organic solvent, it is available wherein to disperse then by filtering to remove solid impurity
There is the colored terylene liquid of disperse dyes.
In step (2), the process that the colored terylene waste material is dissolved in the organic solvent can be at 25-150 DEG C
It carries out, in a particular embodiment, the temperature of dissolution can be 25 DEG C, 30 DEG C, 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C, 80 DEG C, 90
DEG C, 100 DEG C, 110 DEG C, 120 DEG C, 130 DEG C, 140 DEG C or 150 DEG C.In the preferred case, the temperature of the dissolution is 50-120
℃。
In the present invention, as long as the organic solvent can dissolve terylene.In a particular embodiment, described to have
Solvent be DMF, dimethyl sulfoxide, o-chlorphenol, parachlorophenol, phenol, formic acid, pyridine, ethylene glycol, acetamide, diethylene glycol (DEG),
At least one of tetrachloroethanes, benzyl alcohol, trichloroethanes and nitrobenzene.It is described organic molten in more preferably embodiment
Agent is the mixed solvent of the o-chlorphenol perhaps mixed solvent or ethylene glycol of phenol and dimethyl sulfoxide and diethylene glycol (DEG).
In the present invention, the active metal can be sodium, magnesium, aluminium or zinc.The active metal salt can be sodium,
Magnesium, the sulfate of aluminium or zinc, nitrate, hydrochloride etc..
In method of the present invention, in step (3), make the grafted by beta cyclodextrin modified wick grass and the filter
Liquid is mixed, the disperse dyes in the filtrate described in the grafted by beta cyclodextrin modified wick grass adsorbing and removing, to realize
The reuse of terylene waste material.
In more preferably embodiment, grafted by beta cyclodextrin modified wick grass described in step (3) and the filtrate are mixed
The process of splice grafting touching carries out under ultrasonic agitation, enables the disperse dyes in filtrate (i.e. colored terylene solution) more abundant
Ground is adsorbed in the grafted by beta cyclodextrin modified wick grass.
In more preferably embodiment, in step (3), the grafted by beta cyclodextrin modified wick grass and filtrate are (i.e.
Colored terylene solution) volume ratio be 1:3-15, preferably 1:8-12.
In the present invention, in order to realize the reuse of terylene waste material, the method can also include: after step (3), will
Removing disperse dyes after terylene liquid crystallized, melted, wire drawing, cooling, it is spare to be then wound into spun polyester thread.
The present invention will be described in detail by way of examples below, but scope of protection of the present invention is not limited thereto.
Embodiment 1
Beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water, in a heated condition, is stirred, is mixed
Close solution, wherein the concentration of beta-cyclodextrin is 70g/L, and the concentration of citric acid is 70g/L, and the concentration of sodium hypophosphite is 30g/L,
The concentration of ethyl alcohol is 2.5g/L.Then rush is added in the mixed solution, under ultrasonic agitation, at a reflux temperature instead
It answers 8 minutes, obtains grafted by beta cyclodextrin modified wick grass S1.
Colored terylene waste material is placed in reaction kettle, sodium is added, is subsequently added into o-chlorphenol as solvent, is stirred at 50 DEG C
It mixes, is dissolved in colored terylene waste material in solvent, then catalyst and other solid matters are taken out in filtering, obtain filtrate.
Under ultrasonic agitation, the grafted by beta cyclodextrin modified wick grass S1 is added in the filtrate, the two volume ratio
It for 1:10, is mixed 2 hours, takes out modified wick grass, the terylene liquid A 1 decolourized.
Embodiment 2
Beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water, in a heated condition, is stirred, is mixed
Close solution, wherein the concentration of beta-cyclodextrin is 60g/L, and the concentration of citric acid is 60g/L, and the concentration of sodium hypophosphite is 20g/L,
The concentration of ethyl alcohol is 3g/L.Then rush is added in the mixed solution, under ultrasonic agitation, is reacted at a reflux temperature
5 minutes, obtain grafted by beta cyclodextrin modified wick grass S2.
Colored terylene waste material is placed in reaction kettle, sodium is added, the mixture for being subsequently added into phenol and dimethyl sulfoxide is (mixed
Close volume ratio 1:1) it is used as solvent, it is stirred at 80 DEG C, is dissolved in colored terylene waste material in solvent, then catalysis is taken out in filtering
Agent and other solid matters, obtain filtrate.
Under ultrasonic agitation, the grafted by beta cyclodextrin modified wick grass S2 is added in the filtrate, the two volume ratio
It for 1:8, is mixed 2 hours, takes out modified wick grass, the terylene liquid A 2 decolourized.
Embodiment 3
Beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water, in a heated condition, is stirred, is mixed
Close solution, wherein the concentration of beta-cyclodextrin is 80g/L, and the concentration of citric acid is 80g/L, and the concentration of sodium hypophosphite is 40g/L,
The concentration of ethyl alcohol is 2g/L.Then rush is added in the mixed solution, under ultrasonic agitation, is reacted at a reflux temperature
12 minutes, obtain grafted by beta cyclodextrin modified wick grass S3.
Colored terylene waste material is placed in reaction kettle, sodium is added, is subsequently added into ethylene glycol and (is mixed with the mixture of diethylene glycol (DEG)
Volume ratio 1:1) it is used as solvent, it is stirred at 120 DEG C, is dissolved in colored terylene waste material in solvent, then catalysis is taken out in filtering
Agent and other solid matters, obtain filtrate.
Under ultrasonic agitation, the grafted by beta cyclodextrin modified wick grass S3 is added in the filtrate, the two volume ratio
It for 1:12, is mixed 2 hours, takes out modified wick grass, the terylene liquid A 3 decolourized.
Comparative example 1
The disperse dyes in colored terylene are removed according to the method for embodiment 1, the difference is that directly with non-modified
Rush replaces the grafted by beta cyclodextrin modified wick grass S1, thus the terylene liquid D 1 decolourized.
Comparative example 2
The disperse dyes in colored terylene are removed according to the method for embodiment 1, the difference is that preparing modified wick grass
During, it is added without beta-cyclodextrin, thus the terylene liquid D 2 decolourized.
Comparative example 3
The disperse dyes in colored terylene are removed according to the method for embodiment 1, the difference is that connecing preparing beta-cyclodextrin
During branch modified wick grass, it is added without ethyl alcohol, thus the terylene liquid D 3 decolourized.
Comparative example 4
Colored terylene liquid and removing disperse dyes, institute are prepared according to the method implementation of step (2) and (3) in embodiment 1
Unlike, during removing disperse dyes, the grafted by beta cyclodextrin modified wick grass S1 is replaced with active carbon, thus
The terylene liquid D 4 decolourized.
Test case
Detect the content of dyestuff in the terylene liquid of above-described embodiment and colored terylene liquid and decoloration in comparative example, tool
The detection mode of body is: colored terylene liquid and the terylene liquid of decoloration being diluted, dissolves, separates and filtered, is then adopted
With high performance liquid chromatography detection treated terylene liquid, washing of decolourizing is gone out by the high performance liquid chromatography calculated by peak area measured
Dyestuff accounts for the weight percent (X%) of dyestuff in the colored terylene liquid before decoloration in synthetic fibre liquid, as a result as shown in table 1 below.
Table 1
| Embodiment number | X% |
| Embodiment 1 | 4.3% |
| Embodiment 2 | 4.1% |
| Embodiment 3 | 4.9% |
| Comparative example 1 | 31.8% |
| Comparative example 2 | 22.4% |
| Comparative example 3 | 21.7% |
| Comparative example 4 | 8.1% |
It can be seen that point that can be sufficiently removed in colored terylene according to the method described in the present invention by the result of table 1
Dyestuff is dissipated, to realize the recycling of colored terylene waste material.
The preferred embodiment of the present invention has been described above in detail, and still, the present invention is not limited thereto.In skill of the invention
In art conception range, can with various simple variants of the technical solution of the present invention are made, including each technical characteristic with it is any its
Its suitable method is combined, and it should also be regarded as the disclosure of the present invention for these simple variants and combination, is belonged to
Protection scope of the present invention.
Claims (9)
1. a kind of method of disperse dyes in grafted by beta cyclodextrin modified wick grass removing colored terylene, which is characterized in that the party
Method the following steps are included:
(1) beta-cyclodextrin, citric acid, sodium hypophosphite and ethyl alcohol are added to the water, are stirred to obtain mixed solution, by wick
Grass is added in the mixed solution, is reacted at a reflux temperature, and grafted by beta cyclodextrin modified wick grass is obtained；
(2) in the presence of active metal and/or active metal salt, at 25-150 DEG C, colored terylene waste material has been dissolved in
Then solvent is filtered, obtain filtrate；
(3) the grafted by beta cyclodextrin modified wick grass is mixed with the filtrate.
2. the method according to claim 1, wherein in the mixed solution described in step (1), beta-cyclodextrin
Concentration is 30-100g/L, and the concentration of citric acid is 30-100g/L, and the concentration of sodium hypophosphite is 5-50g/L, and the concentration of ethyl alcohol is
1-10g/L。
3. according to the method described in claim 2, it is characterized in that, in the mixed solution described in step (1), beta-cyclodextrin
Concentration is 60-80g/L, and the concentration of citric acid is 60-80g/L, and the concentration of sodium hypophosphite is 20-40g/L, and the concentration of ethyl alcohol is 2-
3g/L。
4. method described in any one of -3 according to claim 1, which is characterized in that reaction described in step (1) is in ultrasound
Stirring is lower to be carried out, and the time of reaction is 3-60 minutes.
5. method described in any one of -3 according to claim 1, which is characterized in that in step (1), the rush with
The volume ratio of the mixed solution is 1:3-10.
6. method described in any one of -3 according to claim 1, which is characterized in that in step (2), the organic solvent
For DMF, dimethyl sulfoxide, o-chlorphenol, parachlorophenol, phenol, formic acid, pyridine, ethylene glycol, acetamide, diethylene glycol (DEG), four chloroethenes
At least one of alkane, benzyl alcohol, trichloroethanes and nitrobenzene.
7. method described in any one of -3 according to claim 1, which is characterized in that in step (2), the active metal
For sodium, magnesium, aluminium or zinc.
8. the method according to claim 1, wherein in step (3), the grafted by beta cyclodextrin modified wick
The careless process being mixed with the filtrate carries out under ultrasonic agitation.
9. method according to claim 1 or 8, which is characterized in that in step (3), the grafted by beta cyclodextrin is modified
The volume ratio of rush and the filtrate is 1:3-15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811508094.8A CN109651644B (en) | 2018-12-11 | 2018-12-11 | Method for removing disperse dye in colored terylene by beta-cyclodextrin graft modification of rush |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811508094.8A CN109651644B (en) | 2018-12-11 | 2018-12-11 | Method for removing disperse dye in colored terylene by beta-cyclodextrin graft modification of rush |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110407267A (en) * | 2019-08-08 | 2019-11-05 | 中国石油集团渤海钻探工程有限公司 | A kind of filters pressing liquid processing method |
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| CN108404679A (en) * | 2018-05-16 | 2018-08-17 | 芜湖市艾德森自动化设备有限公司 | A kind of preparation method of decolorizing printing and dyeing waste water film |
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| RU2307706C1 (en) * | 2006-02-20 | 2007-10-10 | Государственное учреждение Волгоградский научно-исследовательский технологический институт мясо-молочного скотоводства и переработки продукции животноводства Россельхозакадемии (ГУ ВНИТИ ММС и ППЖ Россельхозакадемии) | Method of production of the sorbent on the basis ot the natural polymer |
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