CN111549527A - Protein adsorption resistant polyester fiber and preparation method thereof - Google Patents
Protein adsorption resistant polyester fiber and preparation method thereof Download PDFInfo
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- CN111549527A CN111549527A CN202010544905.0A CN202010544905A CN111549527A CN 111549527 A CN111549527 A CN 111549527A CN 202010544905 A CN202010544905 A CN 202010544905A CN 111549527 A CN111549527 A CN 111549527A
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/48—Polyesters
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/11—Oleophobic properties
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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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
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- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Abstract
The invention discloses an anti-protein adsorption polyester fiber and a preparation method thereof, wherein the preparation method comprises the following steps: 1) 5-vinyl isophthalic acid and tert-butyl alcohol are subjected to esterification reaction to synthesize 5-vinyl isophthalic acid di-tert-butyl ester, and the di-tert-butyl ester is used as a third monomer to be co-condensed with terephthalic acid and ethylene glycol to prepare vinyl grafted polyester fiber; 2) carrying out sulfydryl-alkene click reaction on the vinyl grafted polyester fiber and N-acetylcysteine, and carrying out acidic hydrolysis to obtain cysteine grafted polyester fiber; cysteine is used as zwitterion to greatly improve the hydrophilicity and the protein adsorption resistance of the polyester fiber, and has important application prospect in marine antifouling, medical supplies and membrane separation engineering.
Description
Technical Field
The invention belongs to the field of synthetic fibers, and particularly relates to a protein adsorption resistant polyester fiber and a preparation method thereof.
Background
Polyester fiber, commonly known as "dacron", is a synthetic fiber obtained by spinning polyester obtained by polycondensation of organic dibasic acid and dihydric alcohol, is the most widely used synthetic fiber with the maximum yield at present due to excellent thermal stability, light resistance, wear resistance and chemical stability, and is applied to the fields of membrane separation technology, medical treatment, fishing nets and the like besides textiles. However, polyester has strong oleophylic and hydrophobic properties due to its molecular structure, and is easy to adsorb protein, thus limiting its application. For example, in the field of membrane separation technology, protein adsorption and biomass retention, which often occur in the micropores of a separation membrane, can cause a serious decrease in membrane flux and reduce the working life of the separation membrane; similarly, in the fields of medical treatment, water pollution prevention, and the like, there is a problem that a material fails due to protein adsorption.
In the research on protein-resistant adsorption materials, betaine has received attention from many researchers due to its excellent protein-resistant adsorption and environmental friendliness. Betaine is a zwitterionic compound, and the theory of a hydration layer shows that hydrophilic zwitterionic groups can combine with a large number of water molecules through electrostatic force, hydrogen bond action and the like to form a compact hydration layer, and the hydration layer shields the contact and interaction between protein molecules and the surface of a material in a molecular scale space, so that the adsorption of the protein molecules on the surface is effectively reduced. At present, no report about protein adsorption resistance of polyester fibers is found.
Disclosure of Invention
The third monomer with active groups is introduced to carry out polycondensation with terephthalic acid and ethylene glycol, and the active groups are used for introducing betaine (cysteine in particular) to polyester molecular chains, so that the hydrophilicity and the protein adsorption resistance of the polyester fiber are improved, and the application of the polyester fiber in the aspects of membrane separation, oceans and medical supplies is widened.
The invention aims to provide a protein adsorption resistant polyester fiber.
The invention also aims to provide a preparation method of the protein adsorption resistant polyester fiber.
The above purpose of the invention is realized by the following technical scheme:
an anti-protein adsorption polyester fiber PET-g-Acys, which has the following structural formula:
wherein n is 12-50, and m is 60-170.
The reaction process and the preparation method of the protein adsorption resistant polyester fiber are as follows:
synthesis of di-tert-butyl 1.5-vinylisophthalate (M1)
Adding 5-vinyl isophthalic acid, tert-butyl alcohol, N' -dicyclohexyl carbodiimide (DCC) and N, N-p-Dimethylaminopyridine (DMAP) into a round-bottom flask, dissolving the mixture by using equal-volume dry dichloromethane, reacting the mixture at room temperature for 24 hours, filtering the reaction product to remove insoluble substances, evaporating a filtrate solvent at 50-80 ℃, and separating the filtrate solvent by using dichloromethane as an eluent through silica gel column chromatography to obtain a light yellow liquid M1.
The feeding molar ratio of the 5-vinyl isophthalic acid to the tert-butyl alcohol to the DCC to the DMAP is 1:3:5: 0.2.
The structural formula of M1 is as follows:
2. preparation of vinyl-modified polyester fiber (PET-g-vinyl)
In a 1L double-layer heating reaction kettle, the external temperature of the reaction kettle is set to 250-260 ℃ in advance, M1, terephthalic acid (PTA) and Ethylene Glycol (EG) are added when the internal temperature is about 170-180 ℃, stirring is started until the materials are completely molten, and then antimony acetate is added. And setting the external temperature to be 280-290 ℃, slowly heating, vacuumizing to start esterification for 2 hours when the internal temperature is 250-260 ℃, controlling the polycondensation temperature to be 270-280 ℃, reacting for 3 hours, relieving the vacuum with nitrogen, discharging, cooling, slicing, and spinning according to a conventional spinning process to obtain the PET-g-vinyl fiber.
The feeding molar ratio of M1, PTA and EG is 1: 1.5-4: 3-6, and the feeding amount of antimony acetate is 0.4-1% of the mass of the monomer.
The structural formula of PET-g-vinyl is as follows:
3. preparation of acetylcysteine-grafted polyester fiber (PET-g-Acys)
Putting the PET-g-vinyl fiber into a methanol/tetrahydrofuran mixed solution containing N-acetylcysteine (Acys) in a reaction tank, reacting for 5 hours under the irradiation of 365nm ultraviolet light, taking out the modified polyester fiber, washing for 2 times by using methanol, and drying for 2 hours at 80-100 ℃ to obtain the PET-g-Acys fiber.
The N-acetylcysteine (Acys) methanol/tetrahydrofuran mixed solution is characterized in that the molar concentration of Acys is 1-3 mol/L, and the volume ratio of methanol to tetrahydrofuran is 1:1.
The methanol/tetrahydrofuran mixed solution of the N-acetylcysteine (Acys) also contains 0.3-1 mol/L of catalyst benzoin dimethyl ether (DMPA).
The structural formula of PET-g-Acys is as follows:
4. preparation of cysteine grafted polyester fiber (PET-g-Cys)
And (3) putting the PET-g-Acys into an ethanol solution of hydrochloric acid, heating to 90-100 ℃, stirring at constant pressure for reaction for 5 hours, taking out, washing with water for 2-3 times, and drying at 100-120 ℃ to obtain the PET-g-Cys fiber.
The ethanol solution of the hydrochloric acid is a mixed solution of 3mol/L hydrochloric acid solution and 2:1 ethanol in volume ratio.
The invention has the following advantages and beneficial effects:
the invention provides a protein adsorption resistant polyester fiber and a preparation method thereof, wherein betaine (cysteine in particular) is introduced into the polyester fiber by a chemical grafting method, so that the material can be endowed with lasting hydrophilicity and protein adsorption resistance, the adhesion of protein can be reduced by soaking a polyester product in a natural water area for a long time, and the service life of a separation membrane and a fishing net can be prolonged.
Drawings
FIG. 1 is a graph showing the comparison of fluorescence intensity of the protein adsorption surface of PET-g-Cys fibers at different grafting ratios according to examples 1 to 7.
FIG. 2 is a water absorption curve of PET-g-Cys fibers at different grafting ratios according to examples 1-7.
Detailed Description
The present invention will be described in further detail with reference to specific examples, which are not intended to limit the present invention in any manner. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
The test of the invention comprises the following steps:
water absorption test: washing 50g of fibers with ethanol for 2 times, then placing the fibers into an oven to be dried to constant weight, recording the mass M0, then immersing the fibers into a beaker filled with water, standing for 48 hours, then taking out the fibers, placing the fibers on a 100-mesh standard sieve for standing for 30min until no liquid drops drop, then weighing the fibers, recording the mass M1, and calculating the water absorption according to the following formula:
anti-protein adsorption test: the finished PET-g-Cys fiber textile is cut into pieces of 10cm multiplied by 10cm, dried, put into FITC labeled bovine serum albumin PBS buffer solution (FITC-BSA/PBS, BSA concentration of 1mol/L, pH 7.4), vibrated at room temperature for 2h, washed with PBS solution with pH 7.4 for 3 times, observed with a fluorescence microscope (Inverted Axiovert 200M) for multi-layer membrane protein adsorption, and the anti-protein adsorption capacity is evaluated by fluorescence intensity. The fluorescence intensity of example 7 (pure PET) was set to 1, and the fluorescence intensities of the other samples relative to example 7 are shown in Table 1 and FIG. 1.
Example 1
(1) M1 Synthesis
5-vinyl isophthalic acid, tert-butyl alcohol, N' -dicyclohexyl carbodiimide (DCC) and N, N-p-Dimethylaminopyridine (DMAP) are added into a round-bottom flask and dissolved by equal volume of dry dichloromethane, wherein the feeding molar ratio of the 5-vinyl isophthalic acid, the tert-butyl alcohol, the DCC and the DMAP is 1:3:5: 0.2. After 24 hours of reaction at room temperature, insoluble matter was removed by filtration, the filtrate was rotary-distilled at 60 ℃ to remove the solvent, and separated by silica gel column chromatography using methylene chloride as an eluent to give M1 as a pale yellow liquid with a yield of 50%.
(2) Preparation of PET-g-vinyl fiber
Setting the external temperature of a reaction kettle at 250 ℃ in a 1L double-layer heating reaction kettle, adding M1, terephthalic acid (PTA) and Ethylene Glycol (EG) when the internal temperature is about 175 ℃, stirring until the internal temperature is completely melted, adding antimony acetate, setting the external temperature at 285 ℃, heating at the speed of 10 ℃/h, controlling the pressure at 0.35MPa to start esterification when the internal temperature is 250 ℃, controlling the internal temperature at 275 ℃ after 2h, starting polycondensation at the pressure of 500Pa for 3h, removing vacuum by using nitrogen, discharging, cooling, slicing, putting into a static mixer, feeding into a screw extruder, melting, extruding, filtering impurities by a prefilter, metering by a metering pump and a filter layer of a spinning assembly in sequence, finally spraying from a spinneret plate pore, and blowing and cooling to form a strand silk to obtain the PET-g-vinyl fiber.
The feeding molar ratio of M1 to PTA to EG is 1:1:2.5, and the feeding amount of antimony acetate is 0.5 percent of the mass of the monomer.
(3) Preparation of PET-g-Acys fibers
In a liquid reaction tank, PET-g-vinyl fiber is soaked in a methanol/tetrahydrofuran mixed solution containing N-acetylcysteine (Acys), stirred for 5 hours under the irradiation of 365nm ultraviolet light, then the modified polyester fiber is taken out, washed for 2 times by methanol and dried for 2 hours at 80 ℃, and the PET-g-Acys fiber is obtained.
The N-acetylcysteine (Acys) methanol/tetrahydrofuran mixed solution has the Acys molar concentration of 3mol/L and the volume ratio of methanol to tetrahydrofuran of 1:1.
The methanol/tetrahydrofuran mixed solution of the N-acetylcysteine (Acys) also contains 1mol/L of catalyst benzoin dimethyl ether (DMPA).
(4) Preparation of PET-g-Cys fiber
Padding PET-g-Acys in ethanol solution of hydrochloric acid, heating to 90 ℃, stirring at constant pressure for reaction for 5 hours, taking out, washing with water for 3 times, and drying at 100 ℃ to obtain the PET-g-Cys fiber.
The ethanol solution of the hydrochloric acid is a mixed solution of 3mol/L hydrochloric acid solution and 2:1 ethanol in volume ratio.
Example 2
The synthesis steps are the same as the example 1 except that the feeding molar ratio of M1, PTA and EG in the step (2) is 1:2:4, and the feeding amount of antimony acetate is 0.5 percent of the mass of the monomer.
Example 3
The synthesis steps are the same as the example 1 except that the feeding molar ratio of M1, PTA and EG in the step (2) is 1:3:5, and the feeding amount of antimony acetate is 0.5 percent of the mass of the monomer.
Example 4
The synthesis steps are the same as the example 1 except that the feeding molar ratio of M1, PTA and EG in the step (2) is 1:4:6.5, and the feeding amount of antimony acetate is 0.5 percent of the mass of the monomer.
Example 5
The synthesis steps are the same as example 1 except that the feeding molar ratio of M1, PTA and EG in step (2) is 1:5:7, and the feeding amount of antimony acetate is 0.5 percent of the mass of the monomers.
Example 6
The synthesis steps are the same as the example 1 except that the feeding molar ratio of M1, PTA and EG in the step (2) is 1:6:8, and the feeding amount of antimony acetate is 0.5 percent of the mass of the monomer.
Example 7
The synthesis steps are the same as the example 1 except that the charging molar ratio of M1, PTA and EG in the step (2) is 0:1:1.5, and the charging amount of antimony acetate is 0.5 percent of the mass of the monomer.
The variables for examples 1-7 were the charge ratio of M1 to PTA, the remaining process, procedure, and charge were held constant, and the water absorption and protein adsorption tests were performed on each example, and the results are shown in Table 1.
TABLE 1
| Examples | 1 | 2 | 3 | 4 | 5 | 6 | 7 |
| Water absorption percentage% | 7.3 | 7.1 | 6.7 | 5.8 | 4.9 | 3.5 | 1.5 |
| Anti-protein adhesion | 0.14 | 0.16 | 0.54 | 0.69 | 0.75 | 0.92 | 1.00 |
Claims (3)
1. The protein adsorption resistant polyester fiber is characterized by having a structure shown in a formula (I):
wherein n is 12-50, and m is 60-170.
2. The protein adsorption resistant polyester fiber and the preparation method thereof are characterized by comprising the following steps:
(1) 5-vinyl isophthalic acid and tert-butyl alcohol are subjected to esterification reaction to synthesize 5-vinyl isophthalic acid di-tert-butyl ester (M1), and the structural formula of the compound is shown as (II):
(2) m1, terephthalic acid (PTA) and Ethylene Glycol (EG) are esterified and polymerized into vinyl modified polyester, and spinning is carried out according to a conventional spinning process to obtain PET-g-vinyl fiber, wherein the structural formula of the PET-g-vinyl fiber is shown as (III):
(3) synthesizing the acetylcysteine grafted polyester fiber (PET-g-Acys) by carrying out mercapto-alkene click reaction on the PET-g-vinyl fiber and N-acetylcysteine (Acys), wherein the structural formula of the acetylcysteine grafted polyester fiber (PET-g-Acys) is shown as (IV):
(4) the N-acetyl protection of the PET-g-Acys is removed by acid hydrolysis to obtain the cysteine grafted polyester fiber PET-g-Cys (I).
3. The protein adsorption resistant polyester fiber and the preparation method thereof according to claim 2, wherein the protein adsorption resistant polyester fiber comprises the following components:
the feeding molar ratio of M1, PTA and EG in the step (2) is 1: 1.5-4: 3-6;
the step (4) of acidic hydrolysis refers to hydrolysis in a mixed solution of 3mol/L hydrochloric acid and ethanol with a volume ratio of 2: 1.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112337445A (en) * | 2020-10-16 | 2021-02-09 | 邓颖菁 | Nano polyester film for adsorbing heavy metals and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5171837A (en) * | 1989-02-08 | 1992-12-15 | Kuraray Co., Ltd. | Peptide capable of binding interleukin 6 and an adsorbent comprising the peptide immobilized on a carrier |
| CN104532391A (en) * | 2014-12-31 | 2015-04-22 | 江苏恒力化纤股份有限公司 | High-dye-uptake-rate polyester fiber and preparation method thereof |
| CN107488890A (en) * | 2017-09-29 | 2017-12-19 | 郑州大学第附属医院 | A kind of medical terylene antibacterial fiber containing Nano diamond and preparation method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5171837A (en) * | 1989-02-08 | 1992-12-15 | Kuraray Co., Ltd. | Peptide capable of binding interleukin 6 and an adsorbent comprising the peptide immobilized on a carrier |
| CN104532391A (en) * | 2014-12-31 | 2015-04-22 | 江苏恒力化纤股份有限公司 | High-dye-uptake-rate polyester fiber and preparation method thereof |
| CN107488890A (en) * | 2017-09-29 | 2017-12-19 | 郑州大学第附属医院 | A kind of medical terylene antibacterial fiber containing Nano diamond and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112337445A (en) * | 2020-10-16 | 2021-02-09 | 邓颖菁 | Nano polyester film for adsorbing heavy metals and preparation method thereof |
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Effective date of registration: 20221020 Address after: 317100 Shangkeng Village, Haiyou Street, Sanmen County, Taizhou City, Zhejiang Province Applicant after: Zhejiang Shuangfeng Chemical Fiber Co.,Ltd. Address before: 330100 No.39 Chuangye North Road, Wangcheng New District, Xinjian County, Nanchang City, Jiangxi Province Applicant before: Deng Yingjing |
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