CN101230540A - Antibiotic polymer nano fibre and preparation method thereof - Google Patents
Antibiotic polymer nano fibre and preparation method thereof Download PDFInfo
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Abstract
The invention relates to polymer nanometer fiber and a preparation method thereof, wherein, the surface of plasma grafts high molecule naphthyridine hyamine type cationic antimicrobial. The antimicrobial polymer nanometer fiber is the polymer nanometer fiber, the surface of the antimicrobial polymer nanometer fiber is combined with the high molecule naphthyridine hyamine type cationic antimicrobial through a covalent bond, and the diameter of the antimicrobial polymer nanometer fiber is less than 10 microns. The invention adopts an electrostatic spinning method to obtain the polymer nanometer fiber; the plasma is processed for 10 seconds to 20 minutes; vinylpyridine is grafted under the ultraviolet irradiation; the polymer nanometer fiber after the surface thereof is grafted generates quaterisation with brominated alkanes, to obtain the antimicrobial polymer nanometer fiber, the surface of which is combined with the high molecule naphthyridine hyamine type cationic antimicrobial through the covalent bond. The antimicrobial nanometer fiber can be used in the field of filtration, protection, medical treatment, etc.
Description
Technical field
The present invention relates to a kind of antibiotic polymer nano fibre and preparation method, belong to the technical field of special fibre preparation.
Background technology
The quaternary ammonium salt antiseptic is the more class organic antibacterial agent of research, find the bactericidal action of alkyl-dimethyl ammonium chloride and utilize it to handle military uniform that from nineteen thirty-five German G.Domark the research of quaternary ammonium salt antiseptic is the emphasis that the researcher pays close attention to always with since preventing wound infection.Yet, shortcomings such as volatile, difficult processing that the micromolecule quaternary ammonium salt antiseptic exists, poor chemical stability.Discover that the high molecular quaternary group that has chain alkyl has the excellent antibiotic performance, the high molecular quaternary antiseptic can not penetrate into people's skin, have non-volatile, advantage such as chemical stability is good, and toxicity is little.
Fibrous material is widely used in a lot of fields, can further expand its purposes by the modification endowing antibacterial.Usually anti-bacterial fibre can or adopt the method for surface graft modification to prepare by antiseptic and polyblend spinning.
When antiseptic and polyblend spinning, the distribution relative difficult control in fiber of fibre-forming condition and antiseptic.The antiseptic of the fibrous inside that co-blended spinning obtains can not contact with bacterium, and a large amount of antiseptics do not have antibacterial action, and the utilization ratio of antiseptic is low.Also there are problems such as antiseptic migration in the anti-bacterial fibre that co-blended spinning obtains, and antibacterial effect can not keep good durability, and, because the stripping of antiseptics such as some antibacterial metal easily causes secondary pollution to environment.
Adopting surface graft modification to prepare anti-bacterial fibre is by molecule design method, utilizes copolymerization, grafting, and means such as macromolecular reaction change the chemical constitution of fiber, generate antibiotic group, give fiber new anti-microbial property.Because antibiotic group is to be combined on the fiber surface securely with chemical bond, so the effect of fiber antimicrobial chemical modification has persistence.Chinese patent (ZL 00117568.8 and ZL 01129949.5) carries out amidrazone structuring and basic hydrolysis to polyacrylonitrile fibre, makes graft polypropylene nitrile antibacterial synthetic.Chinese patent (ZL 01129946.0) adopts and contains the method for polyfunctional group polyacrylonitrile functional fibre to the different metal complexing, has prepared a metalloid solvay-type broad-spectrum antiseptic functional fibre.Chinese patent (ZL 02128949.2 and ZL 02130694.X) carries out chemical modification to cellulose fibre or chitin fiber, surface grafting quaternary ammonium salt or halogenated amine, by two classes are had the synergy of different sterilization mechanism monomers, make graft copolymer reach best bactericidal effect.Chinese patent (ZL 200510023301.7) provides a kind of and quarternary ammonium salt compound copolymerization and has added the antibacterial acrylic fibre fiber of a certain amount of nano anti-biotic material.Yet, in some chemical modification processes,, having lost the original functional characteristics of fiber when giving antibacterial ability because the change of body fibre chemistry structure causes the original performance decrease of fiber, practicality reduces greatly.
The plasma graft modification is to make the treatment surface activation earlier and introduce active group by action of plasma, and initiated polymerization carries out surface graft modification then.With respect to chemical modification, plasma surface modification only limits to the surface of macromolecular material, have quick, efficient, pollution-free, simple to operate, save advantages such as the energy, the more important thing is, plasma surface modification only causes the physics or the chemical change on object being treated 50～100nm top layer, do not change the premium properties of fibrous matrix, the durability of modified effect is all better than additive method, can be applicable to the modification of various textile substrates things in theory.
The characteristics of nanofiber maximum are exactly that specific area is big, cause its surface energy and active increase, not only can be used as the high efficiency filter material, and have wide application prospects in fields such as biomedical material, chemical sensor, protective materials, nano composite materials.Develop various functional nano fibers such as antibiotic, fire-retardant, anti-ultraviolet, far infrared, antistatic, electromagnetic shielding, especially hot of research and development both at home and abroad at present.Rising in recent years and the electrostatic spinning technique that is subjected to extensive concern are to make a kind of effective spining technology of nanofiber by apply external electric field in polymer solution, nowadays being acknowledged as a kind of simple, effective nano-fiber material technology of preparing, also is the technical method that is hopeful to realize the nanofiber industrialization most.(US6713011B2 US6743273B2) has designed in order to produce many nozzle continuous electrostatic spinnings device of nanofiber in batches United States Patent (USP) for US6616435B2, US6689374B2.Chinese patent (ZL 200510038562.6) has designed a kind of nanofiber of combined continuous electro-spinning more efficiently film manufacturing device.
United States Patent (USP) (US 20060195142A1, US 20060200232A1) is mixed into antiseptic in the nanofiber, improves the antibiotic property of nanofiber, and the utilization rate of antiseptic is not high in the antibacterial nano fiber that this method obtains.
The present invention prepares nanofiber by electrospinning, then it is carried out graft modification after the plasma treatment, obtains antibacterial nano fiber, is a kind of technical method of general preparation antibiotic polymer nano fibre.
Summary of the invention
Technical problem: the antiseptic utilization ratio that The present invention be directed to present anti-bacterial fibre existence is low, body fibre chemistry structure changes because of chemical modification, make the problems such as practicality reduction of functional fibre, a kind of polymer nanofiber that passes through plasma surface grafting polymer pyridine quaternary ammonium salt type cationic antibacterial agent and preparation method thereof is provided, the antibacterial functions fiber that obtains has kept the premium properties of fibrous matrix, the modified effect good endurance, antibiotic property is strong, it is quick, efficient, pollution-free that whole process of preparation has, simple to operate, save advantages such as the energy.
Technical scheme: antibiotic polymer nano fibre of the present invention is the polymer nanofiber of surface with covalent bonds macromolecule pyridine quaternary ammonium salt type cationic antibacterial agent, the antibiotic polymer nano fibre diameter is below 10 microns, and the polymer nanofiber surface is as follows with the structure of the macromolecule pyridyl quaternary ammonium salt antiseptic of covalent bonds:
Wherein, R is C1～C20 alkyl, and Br is a bromine, []
nBe the degree of polymerization.
Described polymer nanofiber diameter is in 50 nanometers～2 micron.
Described polymer is a kind of in polyolefin, polyalkenyl halides, polysiloxanes, polyethers, polyamide, polyester, Merlon, polyurethane, epoxy resin, polyacrylonitrile, polyacrylic acid family macromolecule, polyphenylene oxide, poly-acid anhydrides, poly--a-amino acid, polyphenylene sulfide, the polyether sulfone or two or more blend wherein; Or biology can absorb synthetic high polymer poly--L-lactic acid, poly--(D, L)-and the copolymer of a kind of or following at least two kinds of monomers in lactic acid, polyglycolic acid, polycaprolactone, poly-butyrolactone, poly-valerolactone, polyester dioxane, poly-acid anhydrides, poly--a-amino acid: L-lactic acid, D, L-lactic acid, glycolic acid, 3-hydroxybutyric acid, 3-hydroxypentanoic acid, caprolactone, butyrolactone, valerolactone, amino acid, or two or more blend wherein.
The preparation method of antibiotic polymer nano fibre may further comprise the steps:
A. polymer solution is added in the storage tank, be connected to one or more injector heads by pump or conduit, injector head connects dc high voltage electric field, and voltage is 3 kilovolts-120 kilovolts of plus or minus, and receiving system ground connection is carried out electrospinning, makes polymer nanofiber;
B. polymer nanofiber was carried out Cement Composite Treated by Plasma 10 seconds～20 minutes, and in air, placed 1 second～10 minutes;
C. polymer nanofiber is mixed glycerol polymerization under ultraviolet light irradiation with vinylpyridine solution;
D. polymer nanofiber behind the surface grafting and bromo alkane reacted 1～100 hour down at 30 ℃～100 ℃, obtained antibiotic polymer nano fibre.
The glycerol polymerization 20 minutes～3 hours under ultraviolet light irradiation of polymer nanofiber after the plasma treatment and vinylpyridine.
Beneficial effect: the present invention compares with prior art, has following advantage:
(1) to have a diameter little for antibacterial nano fiber, specific area is big, characteristics such as anti-microbial property excellence have wide application prospects in fields such as high efficiency filter material, biomedical material, protective materials, nano composite materials, and the incomparable performance advantage of traditional fibre is arranged.
(2) the high molecular quaternary antiseptic has non-volatilely, and chemical stability is good, advantages such as security height.
(3) antibiotic group is arrived fiber surface with covalent bonding, the density of antibiotic group is big, the utilization rate height of antiseptic, and anti-microbial property improves greatly.
(4) using plasma glycerol polymerization, short irradiation carries out the back polymerization in room temperature and obtains higher percent grafting easily, and has advantages such as quick, efficient, pollution-free, simple to operate, the saving energy.
(5) antiseptic and substrate fiber are with covalent bonds, and antibiotic persistence is good, and can carry out surface grafting according to the base material of application choice different performance.Both can utilize the high advantage of fiber mechanics intensity, can only change the character of fiber surface again, and give fibrous material new function.
(6) antibacterial nano fiber material of the present invention can be processed into antibacterial film, long yarn, fabric, or is combined into antimicrobial composite material with general fiber, tunica fibrosa, nonwoven fabric etc.
The specific embodiment
Antibiotic polymer nano fibre be the surface with the polymer nanofiber of covalent bonds macromolecule pyridine quaternary ammonium salt type cationic antibacterial agent, the antibiotic polymer nano fibre diameter is below 10 microns, preferred 50 nanometers～2 microns.Polymer is a kind of in polyolefin, polyalkenyl halides, polysiloxanes, polyethers, polyamide, polyester, Merlon, polyurethane, epoxy resin, polyacrylonitrile, polyacrylic acid family macromolecule, polyphenylene oxide, poly-acid anhydrides, poly--a-amino acid, polyphenylene sulfide, the polyether sulfone or two or more blend wherein; Or biology can absorb synthetic high polymer poly--L-lactic acid, poly--(D, L)-and the copolymer of a kind of or following at least two kinds of monomers in lactic acid, polyglycolic acid, polycaprolactone, poly-butyrolactone, poly-valerolactone, polyester dioxane, poly-acid anhydrides, poly--a-amino acid: L-lactic acid, D, L-lactic acid, glycolic acid, 3-hydroxybutyric acid, 3-hydroxypentanoic acid, caprolactone, butyrolactone, valerolactone, amino acid, or two or more blend wherein.
Polymer is dissolved in the solvent, obtain electric spinning polymer solution, add in the storage tank, be connected to one or more injector heads by pump or conduit, injector head connects dc high voltage electric field, and voltage is 3 kilovolts-120 kilovolts of plus or minus, receiving system ground connection, carry out electrospinning, make polymer nanofiber, the polymer nanofiber diameter is below 10 microns.To polymer nanofiber Cement Composite Treated by Plasma 10 seconds～20 minutes, and in air, place a period of time, with the polymer nanofiber after the Cement Composite Treated by Plasma, vinylpyridine mixes with certain amount of solvent, and glycerol polymerization is 20 minutes～3 hours under ultraviolet light irradiation.Polymer nanofiber behind the surface grafting and bromo alkane (alkyl is the alkyl of C2～C9) obtain antibiotic polymer nano fibre 30 ℃～100 ℃ following quaterisations 10～100 hours.
Embodiment 1
Polyurethane 15g is dissolved in 100mL N, dinethylformamide, this solution is added storage tank, be connected to injector head by pump and conduit, the polymer solution flow velocity 6ml/h of injector head applies positive 15 Kilovolt Direct Currents to injector head and presses, and the polymer solution on injector head top sprays silk under electric field action, receiving system with ground connection is collected polyurethane nanofiber, and the distance between receiving system and the injector head is 15cm.To polyurethane nanofiber Cement Composite Treated by Plasma 2 minutes, placing volumetric concentration was the aqueous isopropanol of 20% 4-vinylpridine, and glycerol polymerization is 1 hour under ultraviolet light irradiation.Polyurethane nanofiber behind the surface grafting and bromohexane obtain the antibacterial polyurethane nanofiber 60 ℃ of following quaterisations 2 hours.
Embodiment 2
Polyacrylonitrile 10g is dissolved in 100mlN, in the dinethylformamide, add storage tank, be connected to injector head by pump and conduit, polymer solution flow velocity 3ml/h applies positive 30 Kilovolt Direct Currents to injector head and presses, and the polymer solution on injector head top sprays silk under electric field action, receiving system with ground connection is collected the polyacrylonitrile nano fiber, and the distance between receiving system and the injector head is 20cm.To the polyacrylonitrile nano fiber Cement Composite Treated by Plasma that makes 5 minutes, put into the aqueous isopropanol that volumetric concentration is the 4-vinylpridine of 10% (v/v), glycerol polymerization is 2 hours under ultraviolet light irradiation.Polyurethane nanofiber behind the surface grafting and N-Propyl Bromide obtain the antibacterial polypropylene nitrile nanofibre at 70 ℃ of following quaterisations.
Embodiment 3
Kynoar 30g is dissolved in 100ml and is dissolved in N, in the N-dimethylacetylamide, this electrospinning solution is added storage tank, be connected to injector head by pump and conduit, polymer solution flow velocity 6ml/h applies positive 10 Kilovolt Direct Currents to injector head and presses, and the polymer solution on injector head top sprays silk under electric field action, receiving system with ground connection is collected the polyvinylidene fluoride nanometer fiber, and the distance between receiving system and the injector head is 10cm.To polyvinylidene fluoride nanometer fiber Cement Composite Treated by Plasma 1 minute, and place after 5 minutes in air and put into the aqueous isopropanol that volumetric concentration is 20% (v/v) 4-vinylpridine, glycerol polymerization is 2 hours under ultraviolet light irradiation.Polyvinylidene fluoride nanometer fiber behind the surface grafting and bromohexane obtain antibiotic polyvinylidene fluoride nanometer fiber at 70 ℃ of following quaterisations.
By the agar plate method for counting colonies, measure the modified polyvinilidene fluoride nano-fiber material respectively to Gram-positive staphylococcus aureus and the Gram-negative Escherichia coli anti-microbial property after effect a period of time, its result such as table 1:
Table 1. polyvinylidene fluoride nanometer fibrous material anti-microbial property
| The one-tenth viable count (staphylococcus aureus, CFU/mL) | ||||
| 0h | 1h | 2h | 4h | |
| Blank | 9.25*10 5 ±0.25*10 5 | 8.43*10 5± 0.07*10 5 | 6.09*10 5± 0.41*10 5 | 3.06*10 5± 0.57*10 5 |
| Antibiotic polyvinylidene fluoride nanometer fiber | 988±25 | 79±5 | 0 | |
| The one-tenth viable count (Escherichia coli, CFU/mL) | ||||
| 0h | 1h | 2h | 4h | |
| Blank | 2.95*10 6 ±0.43*10 6 | 2.71*10 6± 0.33*10 6 | 1.96*10 6± 0.26*10 6 | 1.89*10 6± 0.29*10 6 |
| Antibiotic polyvinylidene fluoride nanometer fiber | 2070±97 | 1398±68 | 675±125 | |
Embodiment 4
The random copolymer PLGA 15g of lactide and glycolide is dissolved in the 50ml acetone, this solution is carried out electrospinning obtain the PLGA nanofiber, through Cement Composite Treated by Plasma 1 minute, putting into volumetric concentration then is the aqueous isopropanol of 30% (v/v) 4-vinylpridine, and glycerol polymerization is 0.5 hour under ultraviolet light irradiation.PLGA nanofiber behind the surface grafting and bromooctane obtain antibiotic PLGA nanofiber at 70 ℃ of following quaterisations.
Embodiment 5
Poly--L-lactic acid PLLA (viscosity average molecular weigh 200,000) 50g is dissolved in 500ml acetone and 500mlN, in the mixed solvent of dinethylformamide, this solution is carried out electrospinning obtain the PLLA nanofiber, the PLLA nanofiber was through Cement Composite Treated by Plasma 2 minutes, putting into volumetric concentration is the aqueous isopropanol of 10% (v/v) 4-vinylpridine, and glycerol polymerization is 1 hour under ultraviolet light irradiation.PLLA nanofiber behind the surface grafting and bromo pentane silane obtain antibiotic PLLA nanofiber at 50 ℃ of following quaterisations.
Embodiment 6
Polycaprolactone 15g is dissolved in 100mL to be dissolved in the hexafluoroisopropanol, this solution is added storage tank, be connected to injector head by pump and conduit, this solution is carried out electrospinning obtain the polycaprolactone nanofiber, to nanofiber Cement Composite Treated by Plasma 2 minutes, and in air, place after 3 minutes and put into the aqueous isopropanol that volumetric concentration is 10% (v/v) 4-vinylpridine, glycerol polymerization is 0.5 hour under ultraviolet light irradiation.Polycaprolactone nanofiber behind the surface grafting and bromohexane obtain antibiotic polycaprolactone nanofiber 20 ℃ of following quaterisations 48 hours.
By the agar plate method for counting colonies, measure modification polycaprolactone nano-fiber material respectively to the anti-microbial property of Gram-positive staphylococcus aureus after effect a period of time, its result such as table 2.
Table 2. polycaprolactone nano-fiber material anti-microbial property
| The one-tenth viable count (staphylococcus aureus, CFU/mL) | ||||
| 0h | 1h | 2h | 4h | |
| Blank | 3.21*10 6 ±0.13*10 6 | 2.64*10 6± 0.04*10 6 | 1.85*10 6± 0.02*10 6 | 6.10*10 5± 0.30*10 5 |
| Antibiotic polycaprolactone nanofiber | 100±9 | 30±5 | 20±3 | |
Embodiment 7
Polyurethane 15g is dissolved in 100mL N, and dinethylformamide adds storage tank with this solution, is connected injector head by pump with conduit, this solution is carried out electrospinning obtain polyurethane nanofiber.To polyurethane nanofiber Cement Composite Treated by Plasma 2 minutes, and place after 5 minutes in air and put into the aqueous isopropanol that volumetric concentration is 20% (v/v) 4-vinylpridine, glycerol polymerization is 2 hours under ultraviolet light irradiation.Polyurethane nanofiber behind the surface grafting and bromohexane are quaternized under 20 ℃, obtain the antibacterial polyurethane nanofiber.
By the agar plate method for counting colonies, measure the modified polyurethane nano-fiber material respectively to Gram-positive staphylococcus aureus and the Gram-negative Escherichia coli anti-microbial property after effect a period of time, its result such as table 3.
Table 3. polyurethane nanofiber material anti-microbial property
| The one-tenth viable count (staphylococcus aureus, CFU/mL) | ||||
| 0h | 0.5h | 1h | 2h | |
| Blank | 1.75*10 7 ±0.25*10 7 | 9.30*10 6± 0.40*10 6 | 9.00*10 6± 0.30*10 6 | 8.07*10 6± 0.53*10 6 |
| The antibacterial polyurethane nanofiber | 80±2 | 50±5 | 10 | |
| The one-tenth viable count (Escherichia coli, CFU/mL) | ||||
| 0h | 0.5h | 1h | 2h | |
| Blank | 3.00*10 7 ±0.44*10 7 | 2.63*10 7± 0.23*10 7 | 2.10*10 7± 0.50*10 7 | 1.36*10 7± 0.04*10 7 |
| The antibacterial polyurethane nanofiber | 100 | 52±7 | 5 | |
Embodiment 8
Poly-s 179 PPES100g is dissolved in the 1000ml methyl-sulfoxide, and this solution is added storage tank, is connected injector head by pump with conduit, this solution is carried out electrospinning obtain the PPES nanofiber.To PPES nanofiber Cement Composite Treated by Plasma 2 minutes, and place after 3 minutes in air and put into the aqueous isopropanol that volumetric concentration is 20% (v/v) 4-vinylpridine, glycerol polymerization is 2 hours under ultraviolet light irradiation.PPES nanofiber behind the surface grafting and bromohexane obtain antibiotic PPES nanofiber 30 ℃ of following quaterisations 48 hours.
Claims (5)
1. antibiotic polymer nano fibre, it is characterized in that this antibiotic polymer nano fibre is the polymer nanofiber of surface with covalent bonds macromolecule pyridine quaternary ammonium salt type cationic antibacterial agent, the antibiotic polymer nano fibre diameter is below 10 microns, and the polymer nanofiber surface is as follows with the structure of the macromolecule pyridyl quaternary ammonium salt antiseptic of covalent bonds:
Wherein, R is C1～C20 alkyl, and Br is a bromine, []
nBe the degree of polymerization.
2. antibiotic polymer nano fibre according to claim 1 is characterized in that described polymer nanofiber diameter is in 50 nanometers～2 micron.
3. antibiotic polymer nano fibre according to claim 1 is characterized in that described polymer is a kind of in polyolefin, polyalkenyl halides, polysiloxanes, polyethers, polyamide, polyester, Merlon, polyurethane, epoxy resin, polyacrylonitrile, polyacrylic acid family macromolecule, polyphenylene oxide, poly-acid anhydrides, poly--a-amino acid, polyphenylene sulfide, the polyether sulfone or two or more blend wherein; Or biology can absorb synthetic high polymer poly--L-lactic acid, poly--(D, L)-and the copolymer of a kind of or following at least two kinds of monomers in lactic acid, polyglycolic acid, polycaprolactone, poly-butyrolactone, poly-valerolactone, polyester dioxane, poly-acid anhydrides, poly--a-amino acid: L-lactic acid, D, L-lactic acid, glycolic acid, 3-hydroxybutyric acid, 3-hydroxypentanoic acid, caprolactone, butyrolactone, valerolactone, amino acid, or two or more blend wherein.
4. preparation method of antibiotic polymer nano fibre according to claim 1 is characterized in that this method may further comprise the steps:
A. polymer solution is added in the storage tank, be connected to one or more injector heads by pump or conduit, injector head connects dc high voltage electric field, and voltage is 3 kilovolts-120 kilovolts of plus or minus, and receiving system ground connection is carried out electrospinning, makes polymer nanofiber;
B. polymer nanofiber was carried out Cement Composite Treated by Plasma 10 seconds～20 minutes, and in air, placed 1 second～10 minutes;
C. polymer nanofiber is mixed glycerol polymerization under ultraviolet light irradiation with vinylpyridine solution;
D. polymer nanofiber behind the surface grafting and bromo alkane reacted 1～100 hour down at 30 ℃～100 ℃, obtained antibiotic polymer nano fibre.
5. the preparation method of antibiotic polymer nano fibre according to claim 4 is characterized in that the glycerol polymerization 20 minutes～3 hours under ultraviolet light irradiation of polymer nanofiber after the plasma treatment and vinylpyridine.
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