CN115161795B - Antibacterial fabric and preparation process thereof - Google Patents
Antibacterial fabric and preparation process thereof Download PDFInfo
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- CN115161795B CN115161795B CN202210812308.0A CN202210812308A CN115161795B CN 115161795 B CN115161795 B CN 115161795B CN 202210812308 A CN202210812308 A CN 202210812308A CN 115161795 B CN115161795 B CN 115161795B
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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
- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/54—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polymers of unsaturated nitriles
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
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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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
- D01F1/103—Agents inhibiting growth of microorganisms
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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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention relates to the technical field of fabric fibers, and discloses an antibacterial fabric, which is prepared by modifying a quaternary ammonium salt compound to a side chain of a PAN copolymer, and finally weaving the antibacterial fabric into acrylic fiber through spinning, wherein the hydrophilic dicarboxyl functional group introduced can improve the hydrophilicity of the acrylic fiber fabric, and hydrophilic hydroxyl and imino are generated when amino and epoxy groups undergo an addition reaction, so that the hydrophilicity and water absorption rate of the fiber fabric are further improved; and the antibacterial quaternary ammonium salt group is grafted into the acrylic fiber, so that the grafting fastness is high, the stability is good, and the excellent antibacterial performance of the acrylic fiber fabric is provided.
Description
Technical Field
The invention relates to the technical field of fabric fibers, in particular to an antibacterial fabric and a preparation process thereof.
Background
The fiber is one of three macromolecular materials, wherein the acrylic fiber has wide application, and has wide application in the aspects of fiber fabrics, clothing, apparel and the like. The fiber can be made into a fabric through electrostatic spinning, wet spinning and the like, and then the fabric is processed into a fabric through textile weaving and the like, wherein the fiber fabric comprises chemical fiber, cotton cloth, silk, leather and the like, and the fabric is generally required to have the performances of hygroscopicity, comfort, warmth retention, antibacterial property and the like.
The invention aims to graft the quaternary ammonium salt antibacterial agent into acrylic fiber, thereby endowing the fiber with continuous and efficient antibacterial performance.
Disclosure of Invention
(one) solving the technical problems
Aiming at the defects of the prior art, the invention provides the antibacterial fabric and the preparation process thereof, and the hydrophilicity and antibacterial property of the acrylic fiber fabric are improved.
(II) technical scheme
In order to achieve the above purpose, the present invention provides the following technical solutions: the antibacterial fabric is formed by spinning, weaving and braiding functional PAN spinning solution, and the functional PAN spinning solution is prepared by the following process
S1, adding 100 parts by weight of acrylonitrile, 0.5-3 parts by weight of glycidyl methacrylate and 0.5-0.8 part by weight of azodiisobutyronitrile into N, N-dimethylformamide, heating to 50-70 ℃ in a nitrogen atmosphere, and stirring and reacting for 18-30 hours to obtain a P (AN-GMA) copolymer.
S2, adding 100 parts by weight of P (AN-GMA) copolymer into N, N-dimethylformamide, stirring and dissolving, adding 1-5 parts by weight of dicarboxyl dibenzoyl iminoethylamine quaternary ammonium salt compound, heating and stirring for reaction to obtain functionalized PAN, adding the functionalized PAN into the N, N-dimethylformamide, stirring, standing and defoaming to obtain the functionalized PAN spinning solution.
Preferably, the reaction control temperature in the step S2 is 60-90 ℃ and the reaction time is 6-24h.
Preferably, the dicarboxyl dibenzoiminoethylamine quaternary ammonium salt compound in the S2 is prepared by the following process:
s3, adding 100 parts by weight of 4,4' -dimethylbenzophenone and 80-105 parts by weight of titanium tetrachloride into methylene dichloride in an ice bath, then adding 60-90 parts by weight of N, N-dimethylethylenediamine, stirring at 20-35 ℃ for reaction for 6-12 hours, concentrating under reduced pressure after the reaction, and washing and purifying with diethyl ether to obtain the dimethyl diphenyl imine dimethylethylenediamine.
S4, adding 100 parts by weight of dimethyl diphenyl imine dimethyl ethylenediamine into pyridine and distilled water solvent, then dropwise adding 350-520 parts by weight of potassium permanganate, heating to 90-100 ℃, stirring and refluxing for 6-12 hours, and obtaining dicarboxyl diphenyl imine dimethyl ethylenediamine.
S5, adding 35-50 parts by weight of 2-chloroethylamine hydrochloride into a solvent, then dropwise adding sodium hydroxide for neutralization, then adding 100 parts by weight of dicarboxyl diphenyl imine dimethyl ethylenediamine, heating, stirring and carrying out reflux reaction to obtain the dicarboxyl diphenyl imine ethylamine quaternary ammonium salt compound.
Preferably, the volume ratio of pyridine to distilled water in the S4 is 0.7-1:1.
Preferably, the solvent in S5 includes methanol, ethanol, and isopropanol.
Preferably, the reaction control temperature in the step S5 is 70-100 ℃ and the reaction time is 18-48h.
(III) beneficial technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
according to the antibacterial fabric, a novel dicarboxyl dibenziminoethylamine quaternary ammonium salt compound is synthesized by taking cheap and easily available 4,4' -dimethylbenzophenone, N-dimethylethylenediamine and 2-chloroethylamine hydrochloride as reaction principles, and contains two hydrophilic carboxyl groups, amino groups and antibacterial quaternary ammonium salt functional groups, and the amino groups of the novel dicarboxyl dibenziminoethylamine quaternary ammonium salt compound and the epoxy groups of a P (AN-GMA) copolymer are utilized to carry out ring-opening addition reaction, so that the dicarboxyl dibenziminoethylamine quaternary ammonium salt compound is modified to the side chains of a PAN copolymer, and finally, the acrylic antibacterial fabric is woven through spinning, the hydrophilic dicarboxyl functional groups introduced into the acrylic antibacterial fabric can improve the hydrophilicity of the acrylic fabric, and hydrophilic hydroxyl groups and imino groups are generated during the addition reaction of the amino groups and the epoxy groups, so that the hydrophilicity and the water absorption rate of the acrylic fabric are further improved; and the antibacterial quaternary ammonium salt group is grafted into the acrylic fiber, so that the grafting fastness is high, the stability is good, and the excellent antibacterial performance of the acrylic fiber fabric is provided.
Drawings
Fig. 1 is an SEM image of a functionalized PAN fiber.
Fig. 2 is a chart of antibacterial test of the antibacterial fabric against escherichia coli.
Detailed Description
To achieve the above object, the present invention provides the following embodiments and examples:
example 1
(1) Adding 2g of 4,4' -dimethylbenzophenone and 1.8g of titanium tetrachloride into 50mL of dichloromethane under ice bath, then adding 1.6g of N, N-dimethylethylenediamine, stirring at 35 ℃ for reaction for 6 hours, concentrating under reduced pressure after reaction, and washing and purifying with diethyl ether to obtain dimethyl diphenyl imine dimethyl ethylenediamine; 1 H NMR(400MHz，CDCl 3 )：δ8.02-7.87 (d, 2H), 7.82-7.69 (d, 2H), 7.42-7.30 (m, 4H), 3.82-3.59 (t, 2H), 2.70-2.62 (t, 2H), 2.72 (s, 6H), 2.21 (s, 6H); the reaction formula is:
(2) Adding 1g of dimethyl diphenyl imine dimethyl ethylenediamine into 50mL of pyridine and 50mL of distilled water solvent in a volume ratio, then dropwise adding 5.2g of potassium permanganate, heating to 100 ℃, stirring and refluxing for 6 hours, adding ethyl acetate and distilled water for extraction after reaction, concentrating an organic phase under reduced pressure, and washing with distilled water and diethyl ether to obtain dicarboxyl diphenyl imine dimethyl ethylenediamine; 1 H NMR(400MHz，CDCl 3 ): delta 12.65-12.31 (m, 2H), 8.52-8.36 (m, 4H), 8.10-7.82 (m, 4H), 3.75-3.46 (t, 2H), 2.76-2.65 (t, 2H), 2.65 (s, 6H); the reaction formula is:
(3) Adding 0.5g of 2-chloroethylamine hydrochloride into 50mL of methanol solvent, then dropwise adding sodium hydroxide for neutralization, then adding 1g of dicarboxyl diphenyl imine dimethyl ethylenediamine, heating to 70 ℃, stirring and refluxing for reaction for 48 hours, concentrating under reduced pressure after reaction, and washing a product with diethyl ether to obtain dicarboxyl diphenyl imine quaternary ammonium salt compound; 1 H NMR(400MHz，CDCl 3 ): delta 12.75-12.58 (m, 2H), 8.53-8.44 (m, 2H), 8.32-7.90 (m, 6H), 4.12-4.01 (t, 2H), 3.51-3.08 (t, 4H), 3.04-2.95 (t, 2H); 2.91 (s, 6H); 1.62 (s, 2H); the reaction formula is:
(4) 20g of acrylonitrile, 0.1g of glycidyl methacrylate and 0.1g of azobisisobutyronitrile were added to 100mL of N, N-dimethylformamide, the temperature was raised to 60℃under a nitrogen atmosphere, the mixture was stirred and reacted for 18 hours, methanol was added after the reaction to precipitate, and the mixture was washed with distilled water and ethanol to obtain a P (AN-GMA) copolymer.
(5) Adding 20g of P (AN-GMA) copolymer into N, N-dimethylformamide, stirring and dissolving, adding 0.2g of dicarboxyl dibenzoyl iminoethylamine quaternary ammonium salt compound, heating to 70 ℃, stirring and reacting for 12 hours, adding methanol to precipitate, washing with distilled water and ethanol to obtain functionalized PAN, adding the functionalized PAN into the N, N-dimethylformamide, stirring, standing and defoaming to obtain functionalized PAN spinning solution, carrying out electrostatic spinning, and obtaining the functionalized PAN fiber by a spinning voltage of 18kV and a spinning solution flow rate of 0.8mL/h, and weaving and braiding to obtain the antibacterial fabric PAN-1.
Example 2
(1) 2g of 4,4' -dimethylbenzophenone and 2.1g of titanium tetrachloride are added into 60mL of dichloromethane under ice bath, then 1.4g of N, N-dimethylethylenediamine is added, then the mixture is stirred at 35 ℃ for reaction for 8 hours, and after the reaction, the mixture is concentrated under reduced pressure and washed and purified by diethyl ether, so that the dimethyl diphenylimine dimethyl ethylenediamine is obtained.
(2) 1g of dimethyl diphenyl imine dimethyl ethylenediamine is added into pyridine and distilled water solvent with the volume ratio of 50mL, 3.5g of potassium permanganate is added dropwise, the mixture is heated to 90 ℃ and is stirred and refluxed for 6 hours, ethyl acetate and distilled water are added for extraction after reaction, an organic phase is concentrated under reduced pressure, and distilled water and diethyl ether are washed, so that dicarboxyl diphenyl imine dimethyl ethylenediamine is obtained.
(3) Adding 0.5g of 2-chloroethylamine hydrochloride into 40mL of isopropanol solvent, then dropwise adding sodium hydroxide for neutralization, then adding 1g of dicarboxyl diphenyl imine dimethyl ethylenediamine, heating to 80 ℃, stirring and refluxing for reaction for 18h, concentrating under reduced pressure after reaction, and washing the product with diethyl ether to obtain the dicarboxyl diphenyl imine quaternary ammonium salt compound.
(4) 20g of acrylonitrile, 0.3g of glycidyl methacrylate and 0.14g of azobisisobutyronitrile were added to 150mL of N, N-dimethylformamide, the temperature was raised to 50 ℃ under nitrogen atmosphere, the mixture was stirred and reacted for 24 hours, methanol was added after the reaction to precipitate, and the mixture was washed with distilled water and ethanol to obtain a P (AN-GMA) copolymer.
(5) Adding 20g of P (AN-GMA) copolymer into N, N-dimethylformamide, stirring and dissolving, adding 0.6g of dicarboxyl dibenzoyl iminoethylamine quaternary ammonium salt compound, heating to 90 ℃, stirring and reacting for 24 hours, adding methanol to precipitate, washing with distilled water and ethanol to obtain functionalized PAN, adding the functionalized PAN into the N, N-dimethylformamide, stirring, standing and defoaming to obtain functionalized PAN spinning solution, carrying out electrostatic spinning, spinning voltage of 15kV, and spinning solution flow rate of 0.8mL/h to obtain functionalized PAN fibers, and weaving and braiding to obtain the antibacterial fabric PAN-2.
Example 3
(1) 2g of 4,4' -dimethylbenzophenone and 1.6g of titanium tetrachloride are added into 40mL of methylene dichloride under ice bath, then 1.2g of N, N-dimethylethylenediamine is added, then the mixture is stirred at 35 ℃ for reaction for 8 hours, and after the reaction, the mixture is concentrated under reduced pressure and washed and purified by diethyl ether, so that the dimethyl diphenylimine dimethyl ethylenediamine is obtained.
(2) 1g of dimethyl diphenyl imine dimethyl ethylenediamine is added into pyridine and 50mL of distilled water solvent with the volume ratio of 35mL, then 4.3g of potassium permanganate is added dropwise, the mixture is heated to 100 ℃ and is stirred and refluxed for 6 hours, ethyl acetate and distilled water are added for extraction after the reaction, an organic phase is concentrated under reduced pressure, and distilled water and diethyl ether are washed, so that dicarboxyl diphenyl imine dimethyl ethylenediamine is obtained.
(3) Adding 0.35g of 2-chloroethylamine hydrochloride into 20mL of ethanol solvent, then dropwise adding sodium hydroxide for neutralization, then adding 1g of dicarboxyl diphenyl imine dimethyl ethylenediamine, heating to 90 ℃, stirring and refluxing for reaction for 18h, concentrating under reduced pressure after reaction, and washing the product with diethyl ether to obtain the dicarboxyl diphenyl imine quaternary ammonium salt compound.
(4) 20g of acrylonitrile, 0.6g of glycidyl methacrylate and 0.16g of azobisisobutyronitrile were added to 200mL of N, N-dimethylformamide, the temperature was raised to 70℃under a nitrogen atmosphere, the mixture was stirred and reacted for 18 hours, methanol was added after the reaction to precipitate, and the mixture was washed with distilled water and ethanol to obtain a P (AN-GMA) copolymer.
(5) Adding 20g of P (AN-GMA) copolymer into N, N-dimethylformamide, stirring and dissolving, adding 1g of dicarboxyl dibenzoyl iminoethylamine quaternary ammonium salt compound, heating to 70 ℃, stirring and reacting for 12 hours, adding methanol to precipitate, washing with distilled water and ethanol to obtain functionalized PAN, adding the functionalized PAN into the N, N-dimethylformamide, stirring, standing and defoaming to obtain functionalized PAN spinning solution, and then carrying out electrostatic spinning at a spinning voltage of 20kV and a spinning solution flow rate of 0.5mL/h to obtain functionalized PAN fibers, and weaving and braiding to obtain the antibacterial fabric PAN-3.
Comparative example 1
(1) 20g of acrylonitrile, 0.3g of glycidyl methacrylate and 0.13g of azobisisobutyronitrile were added to 150mL of N, N-dimethylformamide, the temperature was raised to 50℃under a nitrogen atmosphere, the mixture was stirred and reacted for 30 hours, methanol was added after the reaction to precipitate, and the mixture was washed with distilled water and ethanol to obtain a P (AN-GMA) copolymer.
(2) Adding the P (AN-GMA) copolymer into N, N-dimethylformamide, stirring, standing and defoaming to obtain PAN spinning solution, then carrying out electrostatic spinning to obtain PAN fibers, and weaving and braiding to obtain the fabric P (AN-GMA).
The antibacterial property of the antibacterial fabric against Escherichia coli is tested by an oscillation method with reference to GB/T20944.3-2008 standard
The antibacterial fabric has excellent antibacterial property for escherichia coli with different inoculation concentrations.
Weight m 0 The PAN fabric of (2) was added to distilled water, stirred at room temperature for 4 hours, then taken out, weighed m when no significant water drops were dropped, and the water absorption Q was calculated.
| Sample of | m 0 (g) | m(g) | W(g/g) |
| PAN-1 | 0.1 | 0.38 | 2.8 |
| PAN-2 | 0.1 | 0.45 | 3.5 |
| PAN-3 | 0.1 | 0.48 | 3.8 |
| P(AN-GMA) | 0.1 | 0.19 | 0.9 |
The antibacterial fabric has better water absorption rate and hydrophilicity.
Claims (5)
1. An antibacterial fabric is formed by spinning, weaving and braiding functional PAN spinning solution, and is characterized in that: the functional PAN spinning solution is prepared by the following process:
s1, adding 100 parts by weight of 4,4' -dimethylbenzophenone and 80-105 parts by weight of titanium tetrachloride into methylene dichloride in an ice bath, then adding 60-90 parts by weight of N, N-dimethylethylenediamine, and then stirring and reacting for 6-12 hours at 20-35 ℃ to obtain dimethylbenzeneimine dimethylethylenediamine;
s2, adding 100 parts by weight of dimethyl diphenyl imine dimethyl ethylenediamine into pyridine and distilled water solvent, then dropwise adding 350-520 parts by weight of potassium permanganate, heating to 90-100 ℃, stirring and refluxing for 6-12 hours, and obtaining dicarboxyl diphenyl imine dimethyl ethylenediamine;
s3, adding 35-50 parts by weight of 2-chloroethylamine hydrochloride into a solvent, then dropwise adding sodium hydroxide for neutralization, then adding 100 parts by weight of dicarboxyl diphenyl imine dimethyl ethylenediamine, heating, stirring and refluxing for reaction to obtain dicarboxyl diphenyl imine ethylamine quaternary ammonium salt compound with a structural formula of
S4, adding 100 parts by weight of acrylonitrile, 0.5-3 parts by weight of glycidyl methacrylate and 0.5-0.8 part by weight of azodiisobutyronitrile into N, N-dimethylformamide, heating to 50-70 ℃ in a nitrogen atmosphere, and stirring and reacting for 18-30 hours to obtain a P (AN-GMA) copolymer;
s5, adding 100 parts by weight of P (AN-GMA) copolymer into N, N-dimethylformamide, stirring and dissolving, adding 1-5 parts by weight of dicarboxyl dibenzoyl iminoethylamine quaternary ammonium salt compound, heating and stirring for reaction to obtain functionalized PAN, adding the functionalized PAN into the N, N-dimethylformamide, stirring, standing and defoaming to obtain the functionalized PAN spinning solution.
2. The antibacterial fabric of claim 1, wherein: the volume ratio of pyridine to distilled water in the S2 is 0.7-1:1.
3. The antibacterial fabric of claim 1, wherein: the solvent in the step S3 comprises methanol, ethanol and isopropanol.
4. The antibacterial fabric of claim 1, wherein: the reaction control temperature in the step S3 is 70-100 ℃ and the reaction time is 18-48h.
5. The antibacterial fabric of claim 1, wherein: and in the step S5, the reaction temperature is controlled to be 60-90 ℃ and the reaction time is controlled to be 6-24 hours.
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