CN102875801B - Antibacterial polymer, as well as preparation method and application thereof - Google Patents
Antibacterial polymer, as well as preparation method and application thereof Download PDFInfo
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- CN102875801B CN102875801B CN201210361451.9A CN201210361451A CN102875801B CN 102875801 B CN102875801 B CN 102875801B CN 201210361451 A CN201210361451 A CN 201210361451A CN 102875801 B CN102875801 B CN 102875801B
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- antibacterial polymer
- antibacterial
- piperazine
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- GLUUGHFHXGJENI-UHFFFAOYSA-N C1NCCNC1 Chemical compound C1NCCNC1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention belongs to the field of biological material, in particular to a preparation method and an application of an antibacterial polymer. The preparation method of the antibacterial polymer comprises the specific steps as follows: fully mixing and dissolving piperazine and diamine in dimethyl sulfoxide, so as to obtain dimethyl sulfoxide solution; and reacting for 10 to 48 hours in the dimethyl sulfoxide solutino at 25 to 45 DEG C, so as to obtain the antibacterial polymer. The antibacterial polymer provided by the invention has the characteristics of being high in efficiency, stable, and wide in application. The antibacterial polymer provided by the invention is simple in preparation process, and mild in preparation condition, and has the antibacterial property obtained by the interaction of three materials which are out of antibacterial properties.
Description
Technical field
The invention belongs to technical field of biological material, particularly the preparation method and application of antibacterial polymer.
Background technology
Microorganism, the tiny organism that all naked eyes be cannot see or do not seen, it is simple in structure, individual small, conventionally need to just can see clearly by opticmicroscope or electron microscope.But these small biologies just, in the process of human development, have but played the part of vital role.People are enjoying the benefit that beneficial microorganism brings on the one hand, as fermentation, produce ethanol, food; Prepare microbiotic; Degradative plastics, processes tail gas etc.; Also endure on the other hand the puzzlement that harmful microorganism brings to the fullest extent, as popular, the material of transmissible disease mouldy rots etc.Along with social progress and the raising of people's living standard, interpersonal contacts are more and more closer, thereby transmission of disease is also more and more frequent.How prophylactic propagation, ensure that individual health is just more and more subject to people's attention.
Antiseptic-germicide, a class has the auxiliary agent of antibacterial or bacteria resistance function.It mainly comprises inorganic antiseptic, organic antibacterial agent and complex antimicrobials three classes.Wherein, it is fast that organic antibacterial agent has sterilization speed, and antibacterial effect is remarkable, and the advantage such as easy to process and colour stable, therefore has irreplaceable effect in some field.Further, organic antibacterial agent can be divided into again natural organic antibacterial agent, as chitosan etc.; Low molecule organic antibacterial agent, as quaternary ammonium salt, biguanides, phenols etc.; And polymer organic antibacterial agent.The features such as polymer organic antibacterial agent is with respect to small molecules antiseptic-germicide, and performance is more stable, and it is not volatile, long service life, use range wide, be easy to process, have no side effect, reusable, have become the focus of studying in recent years.
And for the anti-microbial property of polymer organic antibacterial agent, mainly obtain by introduce antibacterial functional group in macromolecular material both at home and abroad at present.Antibacterial functional group can introduce by the homopolymerization with monomer or copolymerization, also can be by the method preparation of grafting.But, no matter be to adopt which kind of way, all there is the defects such as complex process, product be wayward, therefore, try to explore new preparation method's exploitation and synthetic antimicrobial polymer tool and be of great significance.
Summary of the invention
One of object of the present invention is to provide a kind of preparation method of biomaterial, and the method technique is simple, is applicable to scale operation.Two of object of the present invention is to provide a kind of biomaterial, and this material of this biomaterial has good biocompatibility and biological degradability, is applicable to field of tissue engineering technology and medical field.Three of object of the present invention provides a kind of new application of germ resistance polymkeric substance, and this is applied as prepares biological antibiotic material new thinking is provided.
For achieving the above object, technical scheme of the present invention is:
1, the preparation method of antibacterial polymer, concrete steps are:
1) piperazine (molecular formula is as shown in I) and diamines (molecular formula is as shown in II) are placed in to dimethyl sulfoxide (DMSO) and fully mix and dissolve, obtain dimethyl sulphoxide solution;
2) at 25 DEG C-45 DEG C, react 10-48 hour at described dimethyl sulphoxide solution, obtain germ resistance polymkeric substance.
2, according to the preparation method of the antibacterial polymer described in 1, in step 1), described piperazine is Piperazine anhydrous, and described diamines is aliphatie diamine and/or aromatic diamine.
3,, according to the preparation method of the antibacterial polymer described in 2, in step 1), described diamines is quadrol (molecular formula is as shown in III) and/or Putriscine (C
4h
12n
2) (molecular formula is as shown in IV).
4,, according to the preparation method of the antibacterial polymer described in 3, in step 1), described piperazine, described diamines and described ethylene diamine tetra-acetic anhydride are 1-4:1-4:5 in molar ratio.
5, according to the preparation method of the antibacterial polymer described in 1, in step 1), described piperazine and described diamines are placed in to dimethyl sulfoxide (DMSO) and under 20-30 DEG C of condition, stir 0.5-1 hour, it is fully mixed.
6, according to the preparation method of the antibacterial polymer described in 1, step 2) in, in described dimethyl sulphoxide solution, pass into rare gas element, react 10-48 hour at 25 DEG C-45 DEG C,
7, according to the preparation method of the antibacterial polymer described in 1, in step 2) afterwards, gained germ resistance polymkeric substance is placed in to ethanol and precipitates, described precipitation vacuum-drying is to constant weight.
8, according to the preparation method of the antibacterial polymer described in 1, step 2) in, at described 40 DEG C, react 24 hours.
9, the antibacterial polymer that described in 1-8 any one, method obtains.
10, the germ resistance polymkeric substance described in 9 is in the application of preparing in biological antibiotic material.
Beneficial effect of the present invention is: the feature such as germ resistance polymkeric substance provided by the present invention has efficiently, stablizes, wide spectrum; The preparation process of germ resistance polymkeric substance provided by the present invention is simple, mild condition; Germ resistance polymkeric substance provided by the present invention is by three kinds of these germ resistancies that produce without the matter interaction of germ resistance.
Embodiment
In order to make object of the present invention, technical scheme and a little clearer, will be described in detail the preferred embodiments of the present invention below.
Embodiment 1
According to setting; be 4:1 by mol ratio 1; 4-butanediamine 0.708g(0.008mol; Mn=88.5) the Piperazine anhydrous 0.172g(0.002mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO), under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 2
According to setting; be 3:2 by mol ratio 1; 4-butanediamine 0.531g(0.006mol; Mn=88.5) the Piperazine anhydrous 0.344g(0.004mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO), under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 3
According to setting; be 1:1 by mol ratio 1; 4-butanediamine 0.442g(0.005mol; Mn=88.5) the Piperazine anhydrous 0.431g(0.005mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO), under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 4
According to setting; be 2:3 by mol ratio 1; 4-butanediamine 0.354g(0.004mol; Mn=88.5) the Piperazine anhydrous 0.517g(0.006mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO), under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 5
According to setting; be 1:4 by mol ratio 1; 4-butanediamine 0.177g(0.002mol; Mn=88.5) the Piperazine anhydrous 0.689g(0.008mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO), under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 6
According to setting; the quadrol 0.481g(0.008mol that is 4:1 by mol ratio; Mn=60.1) the Piperazine anhydrous 0.172g(0.002mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO); under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24h, make germ resistance polymkeric substance.
Embodiment 7
According to setting; the quadrol 0.361g(0.006mol that is 3:2 by mol ratio; Mn=60.1) the Piperazine anhydrous 0.344g(0.004mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO); under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 8
According to setting; the quadrol 0.301g(0.005mol that is 1:1 by mol ratio; Mn=60.1) the Piperazine anhydrous 0.431g(0.005mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO); under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 9
According to setting; the quadrol 0.240g(0.004mol that is 2:3 by mol ratio; Mn=60.1) the Piperazine anhydrous 0.517g(0.006mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO); under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 10
According to setting; the quadrol 0.120g(0.002mol that is 1:4 by mol ratio; Mn=60.1) the Piperazine anhydrous 0.689g(0.008mol and after vacuum-drying; Mn=86.1) join in the round-bottomed flask of 50ml; add again 10ml dimethyl sulfoxide (DMSO); under nitrogen protection, in room temperature, stir 0.5-1 hour, it is fully mixed.Then, then take ethylene diamine tetra-acetic anhydride 2.560g(0.010mol, Mn=256) be dissolved in 15ml dimethyl sulfoxide (DMSO), after it fully dissolves, above-mentioned two kinds of solution are mixed, and logical nitrogen, at 40 DEG C, react 24 hours, make germ resistance polymkeric substance.
Embodiment 11
Prepared embodiment 1-5 germ resistance polymkeric substance is dissolved in distilled water by the concentration of 6mg/ml respectively, after fully dissolving, it gets respectively 5 μ l on the circle scraps of paper, after dry under room temperature, be placed in the solid medium of inoculating streptococcus aureus and cultivate the fixed time at 37 DEG C, then detect its antibacterial circle diameter with vernier callipers, thereby obtain the killing effect of germ resistance polymkeric substance to microorganism.
Experimental result shows: five kinds of germ resistance polymkeric substance that the present invention obtains are to gram positive bacterium, as streptococcus aureus has good killing effect.
Embodiment 12
Prepared embodiment 6-10 germ resistance polymkeric substance is dissolved in distilled water by the concentration of 6mg/ml respectively, after fully dissolving, it gets respectively 5 μ l on the circle scraps of paper, after dry under room temperature, be placed in the solid medium of inoculating streptococcus aureus and cultivate the fixed time at 37 DEG C, then detect its antibacterial circle diameter with vernier callipers, thereby obtain the killing effect of germ resistance polymkeric substance to microorganism.
Experimental result shows: five kinds of germ resistance polymkeric substance that the present invention obtains are to gram positive bacterium, as streptococcus aureus has good killing effect.
Finally explanation is, above embodiment is only unrestricted in order to technical scheme of the present invention to be described, although the present invention is had been described in detail with reference to preferred embodiment, those of ordinary skill in the art is to be understood that, can modify or be equal to replacement technical scheme of the present invention, and not departing from aim and the scope of technical solution of the present invention, it all should be encompassed in the middle of claim scope of the present invention.
Claims (10)
1. the preparation method of antibacterial polymer, is characterized in that, concrete steps are:
1) by molecular formula, diamines as shown in II of the piperazine as shown in I, molecular formula and ethylene diamine tetra-acetic anhydride are placed in dimethyl sulfoxide (DMSO) and fully mix and dissolve, and obtain dimethyl sulphoxide solution
2) at 25 DEG C-45 DEG C, react 10-48 hour at described dimethyl sulphoxide solution, obtain germ resistance polymkeric substance.
2. the preparation method of antibacterial polymer according to claim 1, is characterized in that, in step 1), described piperazine is Piperazine anhydrous, and described diamines is aliphatie diamine and/or aromatic diamine.
3. the preparation method of antibacterial polymer according to claim 2, is characterized in that, in step 1), described diamines is quadrol and/or Putriscine.
4. the preparation method of antibacterial polymer according to claim 3, is characterized in that, in step 1), described piperazine, described diamines and described ethylene diamine tetra-acetic anhydride are 1-4:1-4:5 in molar ratio.
5. the preparation method of antibacterial polymer according to claim 1, is characterized in that, in step 1), described piperazine and described diamines is placed in to dimethyl sulfoxide (DMSO) and under 20-30 DEG C of condition, stirs 0.5-1 hour, and it is fully mixed.
6. the preparation method of antibacterial polymer according to claim 1, is characterized in that step 2) in, in described dimethyl sulphoxide solution, pass into rare gas element, react 10-48 hour at 25 DEG C-45 DEG C.
7. the preparation method of antibacterial polymer according to claim 1, is characterized in that, in step 2) afterwards, gained germ resistance polymkeric substance is placed in to ethanol and precipitates, described precipitation vacuum-drying is to constant weight.
8. the preparation method of antibacterial polymer according to claim 1, is characterized in that step 2) in, at 40 DEG C, react 24 hours.
9. the antibacterial polymer that described in claim 1-8 any one, method obtains.
10. antibacterial polymer claimed in claim 9 is in the application of preparing in biological antibiotic material.
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