CN108503821A - A kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt and preparation method thereof - Google Patents
A kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt and preparation method thereof Download PDFInfo
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- CN108503821A CN108503821A CN201810474081.7A CN201810474081A CN108503821A CN 108503821 A CN108503821 A CN 108503821A CN 201810474081 A CN201810474081 A CN 201810474081A CN 108503821 A CN108503821 A CN 108503821A
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- Prior art keywords
- polyoxyethylene ether
- parts
- glycine betaine
- polycarboxylic acid
- acid sodium
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/90—Betaines
-
- 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
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/08—After-treatment with organic compounds macromolecular
Abstract
The present invention provides a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salts and preparation method thereof.The wherein described polyoxyethylene ether glycine betaine multi-carboxylate, preparing component includes：0.1 ~ 0.5 part of 60 ~ 75 parts of aliphatic amine polyoxyethylene ether, 25 ~ 30 parts of Carboxylation reagent, 20 ~ 25 parts of quaternizing agent, 40 ~ 50 parts of solvent, 12 ~ 18 parts of alkaline agent, 0.5 ~ 2 part of pH value adjustment agent and phase transfer catalyst.A kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt of the present invention, the beet alkali ampholytic ionic surface active agent contained in it, it is nonirritant to human body, environmentally protective easily biological-degradable so that it is used from the production of raw material, finished product and final discharge realizes whole process environmental protection.
Description
Technical field
The present invention relates to a kind of anti-staining soaping agents that textile dyeing and finishing industry uses, and are used for textile printing and dyeing or stamp side
Face.
Background technology
It is known that dyeing is the important composition one's duty of textile industry, and it is the row that energy consumption is higher, quantity of wastewater effluent is larger
Industry.And constantly advancing with society, environmental problem is increasingly paid attention to by society, accordingly for environmental protection
Cry is also higher and higher, and therefore, requirement of the official for industry energy conservation environmental emission reduction is also higher and higher.
For dyeing, carries out energy-saving and emission-reduction work and develop and push away in addition to researching and developing efficient, water-saving, energy-saving equipment
Outside wide applicating energy-saving, water-saving practical new technology；It is having of most going at this stage using efficient, environmentally friendly, water-saving, energy-efficient dye material
The method of effect, and less investment, it is quick.
For wherein for contaminating the anti-staining soaping agent in material, cotton fiber needed after vital staining or stamp through
It crosses and largely soaps, wash away the not fixed loose colour in surface to promote fastness, but remained in cloth cover after dyeing or stamp
A large amount of alkali, slurry can to form crosslinking fixed or secondary to not forming covalently bound hydrolised dye and non-hydrolytic dyestuff with cloth cover
Fixation, the strong influence vividness of true qualities and the whiteness of white background.Therefore it needs to be added during soaping a certain amount of
Releasing soaping agent, the staining again of white background or background can be effectively prevented while soaping.
Releasing soaping agent used at present is divided into three kinds on the market, the first is polycarboxylic acid acid sodium；Second is polycaprolactam polyamine
Such as PVP（Polyvinylpyrrolidone）；The third is the surfactant based on cation.Wherein carboxylic acid sodium is cheating components, is gathered
Polyamines and cation form are lived as the releasing component of the charge attraction to dyestuff, and usual releasing soaping agent is above-mentioned one or more
The common compounding of mixture.
As China Patent Publication No. CN103642600A discloses a kind of anti-staining soaping agent for printing of an activated dye and its system
Preparation Method, the preparation method is quaternized to aliphatic amine polyoxyethylene ether progress using benzyl chloride or chlorethanol, then compounds 2% ~ 10%
Pvp（Polyvinylpyrrolidone）, there is releasing effect.
But this anti-staining soaping agent due to the fact that, make its do not meet instantly society to environment-friendly and green surface-active
The trend of agent demand：
1, benzyl chloride smell is extremely heavy, and chlorethanol has stronger toxicity to human body；
2, after raw material is quaternized, due to ionic relatively strong, it is made easily to generate color dot with the dyestuff of anion in use；
3, not easily biological-degradable after discharging.
Therefore, it is necessory to develop a kind of releasing soaping agent of the environmentally protective Mobyneb monomer of novel whole process,
To cope with instantly increasingly stringent environmental requirement.
Invention content
The purpose of the present invention is to provide a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salts, and environmentally protective, function is more,
Anti-staining soaping agent can be used as textile printing and dyeing or stamp processing aspect, while a kind of environment-friendly type surface-active can be used as again
In terms of agent is for dyeing level dyeing and water process.
To achieve the goals above, the technical solution adopted by the present invention is as follows：
A kind of polyoxyethylene ether glycine betaine multi-carboxylate, preparing component includes：
60 ~ 75 parts of aliphatic amine polyoxyethylene ether；
25 ~ 30 parts of Carboxylation reagent；
20 ~ 25 parts of quaternizing agent；
40 ~ 50 parts of solvent；
12 ~ 18 parts of alkaline agent；
0.5 ~ 2 part of pH value adjustment agent；And
0.1 ~ 0.5 part of phase transfer catalyst.
Wherein the aliphatic amine polyoxyethylene ether structure is CXH2X+3N(EO)Y(EO)Z, wherein X=12 or 18；Y+Z=2~
30；Wherein each group distribution ratio amount of attaching most importance to matches.
Further, in different embodiments, wherein the Carboxylation reagent include in maleic anhydride, phthalic anhydride at least
It is a kind of.
Further, in different embodiments, wherein the Carboxylation reagent includes maleic anhydride and phthalic anhydride, the two it
Between weight proportion be（1.5~3）:1.
Further, in different embodiments, wherein the quaternizing agent include in sodium chloroacetate, monoxone extremely
Few one kind.
Further, in different embodiments, wherein the solvent include ethylene glycol monobutyl ether, deionized water, ethyl alcohol,
At least one of cyclohexanone.
Further, in different embodiments, wherein the alkaline agent includes at least one in sodium hydroxide, potassium hydroxide
Kind.
Further, in different embodiments, wherein the PH conditioning agents include at least one in citric acid, sodium carbonate
Kind.
Further, in different embodiments, wherein the phase transfer catalyst includes dodecyl dimethyl bromination
At least one of ammonium, tetrabutylammonium bromide.
Further, another embodiment of the invention, which provides, a kind of preparing the polyoxyethylene of the present invention
The preparation method of ether glycine betaine polycarboxylic acid sodium salt.It includes the following steps：
By the metered fatty amine polyoxy ether ether in the four-hole boiling flask for taking thermometer, condensing reflux pipe, it is warming up to
55 ~ 65 DEG C, being sufficiently stirred makes it uniformly；
The Carboxylation reagent is added, is to slowly warm up to 80 ~ 95 DEG C, 2 ~ 5h of isothermal reaction；
After the deionized water in 20 ~ 30 parts of solvents is added, the alkaline agent is added, the PH of regulation system is eventually adding
Conditioning agent so that the pH value of whole system is controlled 11 ~ 8, is eventually adding the phase transfer catalyst, is stirred evenly；
It is slowly added into the four-hole boiling flask with the alcohol dissolving quaternizing agent in 5 ~ 10 parts of solvents；
It is slowly heated the four-hole boiling flask so that whole system is to slowly warm up to 140 ~ 160 DEG C of progress back flow reactions；And
After whole system constant temperature 4 ~ 8 hours, 35 ~ 45 DEG C are cooled to, 10 ~ 15 parts of ethylene glycol monobutyl ether in the solvent is added,
It can be obtained the polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt.
Further, in different embodiments, wherein it is to use oil bath heating mode to be slowly heated the four-hole boiling flask
It carries out.
Compared with the existing technology, the beneficial effects of the invention are as follows：A kind of polyoxyethylene ether glycine betaine of the present invention is more
Carboxylic acid sodium salt, the beet alkali ampholytic ionic surface active agent inside contained is nonirritant to human body, environmentally protective easy biology drop
Solution has accomplished whole process environmental protection to make it be used from the production of raw material, finished product to final discharge.
Further, it uses and the cheating components in releasing soaping agent is grafted onto the same knot jointly with releasing component
Structure plays the chelation to metal ion, during soaping so as to improve releasing as a composite multifunction monomer
The hardness of water；Absorption can be generated to hydrolysed reactive dye by charge again, play the role of releasing, thus, accomplish efficiently again
Multipotency can substitute at present the releasing soaping agent of cation form work class on the market, there is good market large-scale promotion to make comprehensively
Use foreground.
Specific implementation mode
Below with reference to embodiment, to a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt of the present invention and its preparation
The technical solution of method is described in further detail.
Embodiment 1
An embodiment of the invention provides a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt, and raw material components include：
65 parts of aliphatic amine polyoxyethylene ether, 26 parts of Carboxylation reagent, 23 parts of quaternizing agent, 43 parts of solvent, 15 parts of alkaline agent, pH value adjustment
0.3 part of 1 part of agent and phase transfer catalyst.
Wherein the aliphatic amine polyoxyethylene ether structure is CXH2X+3N(EO)Y(EO)Z, wherein X=12；Y+Z=15；It is described
Carboxylation reagent be maleic anhydride；The quaternizing agent is monoxone；The solvent include deionized water, ethyl alcohol,
Ethylene glycol monobutyl ether；The alkaline agent is sodium hydroxide；The PH conditioning agents are citric acid, sodium carbonate；The phase transfer
Catalyst is tetrabutylammonium bromide.
Preparation method includes the following steps：
Thermometer is being taken, the fatty amine polyoxy ether ether is added in the four-hole boiling flask of condensing reflux pipe, is warming up to 60 DEG C, fills
Stirring is divided to make it uniformly；
The Carboxylation reagent is added, is to slowly warm up to 90 DEG C, isothermal reaction 3h；
After 20 ~ 30 parts of deionized waters are added, the alkaline agent is added, is eventually adding the PH conditioning agents of regulation system by system
PH value control 11 ~ 8, be eventually adding the phase transfer catalyst, stir evenly；
It is slowly added into the four-hole boiling flask after dissolving the quaternizing agent with 5 ~ 10 parts of ethyl alcohol；
It is slowly heated the four-hole boiling flask with bath oiling so that its interior system is to slowly warm up to 140 ~ 160 DEG C of progress back flow reactions；
After system constant temperature 8 hours, 40 DEG C are cooled to, 10 ~ 15 parts of ethylene glycol monobutyl ethers are added, you can obtain institute of the present invention
State polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt.
Embodiment 2
The another embodiment of the present invention provides a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt, raw material components packet
It includes：72 parts of aliphatic amine polyoxyethylene ether, 27 parts of Carboxylation reagent, 21 parts of quaternizing agent, 45 parts of solvent, 16 parts of alkaline agent, pH value
1 part of conditioning agent, 0.3 part of phase transfer catalyst.
The wherein described aliphatic amine polyoxyethylene ether structure is CXH2X+3N(EO)Y(EO)Z, wherein X=18；Y+Z=20；Described
Carboxylation reagent is by 2:The maleic anhydride and phthalic anhydride of 1 weight proportion mixing；The quaternizing agent is sodium chloroacetate；It is described
Solvent include ethyl alcohol, deionized water, ethylene glycol monobutyl ether；The alkaline agent is sodium hydroxide；The PH conditioning agents are lemon
Acid, sodium carbonate；The phase transfer catalyst is tetrabutylammonium bromide.
Preparation method includes the following steps：
The fatty amine polyoxy ether ether is added in the four-hole boiling flask for taking thermometer, condensing reflux pipe, is warming up to 60 DEG C, fills
Stirring is divided to make it uniformly；
The Carboxylation reagent is added, is to slowly warm up to 90 DEG C, isothermal reaction 3h；
After 20 ~ 30 parts of deionized waters are added, the alkaline agent is added, is eventually adding the PH conditioning agents of regulation system by system
PH value control 11 ~ 8, be eventually adding the phase transfer catalyst, stir evenly；
It is slowly added into the four-hole boiling flask after dissolving the quaternizing agent with 5 ~ 10 parts of ethyl alcohol；
It is slowly heated the four-hole boiling flask with bath oiling so that its interior system is to slowly warm up to 140 ~ 160 DEG C of progress back flow reactions；
After system constant temperature 8 hours, 40 DEG C are cooled to, 10 ~ 15 parts of ethylene glycol monobutyl ethers are added, you can obtain institute of the present invention
State polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt.
A kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt of the present invention, the beet alkali ampholytic ion table inside contained
Face activating agent, environmentally protective easily biological-degradable nonirritant to human body, to make it be used from the production of raw material, finished product to most
Whole process environmental protection has been accomplished in whole discharge.
Further, it uses and the cheating components in releasing soaping agent is grafted onto the same knot jointly with releasing component
Structure plays the chelation to metal ion, during soaping so as to improve releasing as a composite multifunction monomer
The hardness of water；Absorption can be generated to hydrolysed reactive dye by charge again, play the role of releasing, thus, accomplish efficiently again
Multipotency can substitute at present the releasing soaping agent of cation form work class on the market, there is good market large-scale promotion to make comprehensively
Use foreground.
The technical scope of the present invention is not limited solely to the content in above description, and those skilled in the art can not take off
Under the premise of from technical thought of the invention, many variations and modifications are carried out to above-described embodiment, and these deformations and modification should all
When being within the scope of the present invention.
Claims (10)
1. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt；It is characterized in that, its preparation component includes：
60 ~ 75 parts of aliphatic amine polyoxyethylene ether；
25 ~ 30 parts of Carboxylation reagent；
20 ~ 25 parts of quaternizing agent；
40 ~ 50 parts of solvent；
12 ~ 18 parts of alkaline agent；
0.5 ~ 2 part of pH value adjustment agent；And
0.1 ~ 0.5 part of phase transfer catalyst；
Wherein the aliphatic amine polyoxyethylene ether structure is CXH2X+3N(EO)Y(EO)Z, wherein X=12 or 18；Y+Z=2~30；Its
In the ratio of each component is weight proportion.
2. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that the wherein described carboxylic
Acidizing reagent includes at least one of maleic anhydride, phthalic anhydride.
3. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that the wherein described carboxylic
Acidizing reagent includes maleic anhydride and phthalic anhydride, and weight proportion between the two is（1.5~3）:1.
4. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that the wherein described season
Ammonium reagent includes at least one of sodium chloroacetate, monoxone.
5. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that wherein described molten
Agent includes at least one of ethylene glycol monobutyl ether, deionized water, ethyl alcohol, cyclohexanone.
6. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that the wherein described alkali
Agent includes at least one of sodium hydroxide, potassium hydroxide.
7. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that the wherein described PH
Conditioning agent includes at least one of citric acid, sodium carbonate.
8. a kind of polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt according to claim 1, which is characterized in that the wherein described phase
Transfer catalyst includes at least one of Dodecydimethylammonium bronides, tetrabutylammonium bromide.
9. a kind of preparation method being used to prepare polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt described in claim 1, feature exist
In comprising following steps：
By the metered fatty amine polyoxy ether ether in the four-hole boiling flask for taking thermometer, condensing reflux pipe, it is warming up to
55 ~ 65 DEG C, being sufficiently stirred makes it uniformly；
The Carboxylation reagent is added, is to slowly warm up to 80 ~ 95 DEG C, 2 ~ 5h of isothermal reaction；
After the deionized water in 20 ~ 30 parts of the solvent is added, the alkaline agent is added, the described of regulation system is eventually adding
PH conditioning agents so that the pH value of whole system is controlled 11 ~ 8, is eventually adding the phase transfer catalyst, is stirred evenly；
It is slowly added into the four-hole boiling flask with the ethyl alcohol dissolving quaternizing agent in 5 ~ 10 parts of solvents；
It is slowly heated the four-hole boiling flask so that whole system is to slowly warm up to 140 ~ 160 DEG C of progress back flow reactions；And
After whole system constant temperature 4 ~ 8 hours, 35 ~ 45 DEG C are cooled to, the ethylene glycol monobutyl ether in 10 ~ 15 parts of solvents is added,
It can be obtained the polyoxyethylene ether glycine betaine polycarboxylic acid sodium salt.
10. preparation method according to claim 9, which is characterized in that it is to use wherein to be slowly heated the four-hole boiling flask
What oil bath heating mode carried out.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112457927A (en) * | 2020-11-27 | 2021-03-09 | 苏州联胜化学有限公司 | Cotton fiber hair dust washing and removing agent and preparation method thereof |
| CN115403750A (en) * | 2022-09-29 | 2022-11-29 | 山东宝斯泰医用材料有限公司 | Carboxylic acid betaine end group-containing polyethylene glycol-polyester block copolymer and preparation method thereof |
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| CN102304067A (en) * | 2011-06-23 | 2012-01-04 | 河南省道纯化工技术有限公司 | Method for preparing gydroxysulfobetaine amphoteric surface active agent including polyether chain segment |
| CN105566174A (en) * | 2015-11-17 | 2016-05-11 | 中国石油天然气股份有限公司 | Method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures |
| CN105625061A (en) * | 2016-01-12 | 2016-06-01 | 浙江雀屏纺织化工股份有限公司 | Anionic dye anti-staining saponifying agent and production method thereof |
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2018
- 2018-05-17 CN CN201810474081.7A patent/CN108503821B/en active Active
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| CN102304067A (en) * | 2011-06-23 | 2012-01-04 | 河南省道纯化工技术有限公司 | Method for preparing gydroxysulfobetaine amphoteric surface active agent including polyether chain segment |
| CN105566174A (en) * | 2015-11-17 | 2016-05-11 | 中国石油天然气股份有限公司 | Method for synthesizing betaine from long-chain tertiary amine by means of anhydrous quaternization under normal pressures |
| CN105625061A (en) * | 2016-01-12 | 2016-06-01 | 浙江雀屏纺织化工股份有限公司 | Anionic dye anti-staining saponifying agent and production method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112457927A (en) * | 2020-11-27 | 2021-03-09 | 苏州联胜化学有限公司 | Cotton fiber hair dust washing and removing agent and preparation method thereof |
| CN115403750A (en) * | 2022-09-29 | 2022-11-29 | 山东宝斯泰医用材料有限公司 | Carboxylic acid betaine end group-containing polyethylene glycol-polyester block copolymer and preparation method thereof |
| CN115403750B (en) * | 2022-09-29 | 2023-04-18 | 山东宝斯泰医用材料有限公司 | Carboxylic acid betaine end group-containing polyethylene glycol-polyester block copolymer and preparation method thereof |
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| CN108503821B (en) | 2020-12-15 |
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