CN107162981A - The antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation and its preparation method and application - Google Patents
The antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation and its preparation method and application Download PDFInfo
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- CN107162981A CN107162981A CN201710370647.7A CN201710370647A CN107162981A CN 107162981 A CN107162981 A CN 107162981A CN 201710370647 A CN201710370647 A CN 201710370647A CN 107162981 A CN107162981 A CN 107162981A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/288—Halogen containing polymers
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/60—Agents for protection against chemical, physical or biological attack
- C04B2103/67—Biocides
Abstract
The invention discloses the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation and its preparation method and application.The present invention is prepared for the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation, such monomer can as acrylate bone cement antibacterial additives.The monomer is characterized in that can assign acrylate bone cement very strong anti-microbial property, and the hardening time influence on the acrylate bone cement of self-solidifying is relatively low, and can significantly shorten the dough time of bone cement, while the bone cement good mechanical properties containing the monomer.
Description
Technical field
The present invention relates to a series of polymerisable monomers that can be used as acrylate bone cement additive, and in particular to containing halogenation
The antibiotic property polymerisable monomer and its preparation method of imidazole salts structure and application.
Background technology
China just moves towards aging society at present, and the orthopaedics degenerative disease related to elderly population is continuously increased.And
The incidence of disease of Cranial defect maintains higher level for a long time caused by industrial accident, traffic accident, orthopaedic disease etc..Therefore use
It is very necessary that artificial material carries out Bone Defect Repari.
Acrylate bone cement be a kind of clinical practice most widely be used for bone surgery bone renovating material, its mainly into
It is polymethyl methacrylate (PMMA) to divide, with biologically inert.Acrylate bone cement is generally by pulvis and liquor two parts
Composition, at room temperature mixes it by a certain percentage, then is placed on the position for needing to change joint or filling, in certain time
It is i.e. curable after interior generation polymerisation, thus realize joint prosthesis fix or Cranial defect repairing.
Due to operation sterilizing, not there is the reasons such as original infection focus in thorough, apparatus contamination or patient, and some patientss exist
Bacterium infection can occur at articular prosthesis, bone cement dummy and in bone tissue and soft tissue.Infection easily triggers
Cause the serious problems such as prosthetic loosening and bone dissolving, need to carry out revision procedure after infection, the painful and negative of patient is significantly greatly increased
Load.
Acrylate bone cement lacks antibacterial activity.It is main at present to add antibiotic into acrylate bone cement to prevent
Infection, the antibiotic property bone cement formula containing gentamicin is clinically made extensively as disclosed in patent US4059684
With.Make bone cement mechanical properties decrease however, the bone cement containing antibiotic is present, lack long-term antimicrobial efficiency and be also easy to produce drug resistance
The problem of.In order to find the substitute of antibiotic, someone introduces containing silver material or other organic antibacterial agents to make into bone cement
The standby bone cement with antibiotic property, such as patent CN102380126 and patent CN102218158 individually disclose a kind of argentiferous and contained
The antibacterial bone cement formula of chitosan quaternary ammonium salt.But the implant of argentiferous has been found to that the nervous system disease may be caused, and shell gathers
The transportable organic antibacterial agent of the class of sugared quaternary ammonium salt etc. one can not also assign bone cement long-term antimicrobial efficiency.Therefore, new third is developed
Olefin(e) acid ester bone cement antibacterial additives have triggered increasing concern.
The content of the invention
It is an object of the invention to can cause bone cement mechanical properties decrease, antibiotic property for the existing antibiotic-loaded bone cement that contains
Persistently and the shortcomings of bacterium can be made to produce drug resistance acrylate bone cement long acting antibiotic performance can not be assigned there is provided a series of
The preparation method of antibiotic property methacrylate monomers and its application.
It is a further object to provide above-mentioned antibiotic property methacrylate monomers in acrylate bone cement
Application.
The above-mentioned purpose of the present invention is realized by the following method.
The antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation, shown in its structural formula such as formula (I)；
N takes any one integer in 1~5 in formula (I)；R in formula (I)1Any one in modus ponens methyl or (II)；
I in structural formula (II) is any one numerical value in 0~26；
Any one in formula (I) X modus ponens (III)；
X=F, Cl, Br, I (III).
A kind of preparation method of the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation, comprises the following steps：
N- hydroxyalkyls imidazoles and solvent are added in reaction vessel, methacrylic acid isocyano group second is added under stirring
Ester, reacts 0.5~12 hour at 5 DEG C~60 DEG C, isocyanate groups is reacted completely, and it is 50 DEG C then to adjust reaction temperature
~100 DEG C, alkyl halide is added, is reacted 5~100 hours, product is generated, purification processes then are carried out to reaction product, contained
The antibiotic property polymerisable monomer of imidazolium halide salt structure.
In the above method, the amount of the material of the isocyanatoethyl and the amount of the material of N- hydroxyalkyl imidazoles
Ratio be 1:1.0~1:1.5；The ratio of the amount of the material of alkyl halide and the amount of the material of N- hydroxyalkyl imidazoles is 1:1.0~
1:3.0。
In the above method, in the step, the N- hydroxyalkyls imidazoles include N- hydroxy methylimidazoles, N- hydroxyethyl imidazoles,
N- hydroxypropyls imidazoles, N- hydroxyls butyl imidazole or N- hydroxyl amyl group imidazoles；The type of the solvent includes acetone, butanone, cyclohexanone, four
Hydrogen furans, dimethyl sulfoxide (DMSO), DMF, 1-METHYLPYRROLIDONE, dichloromethane or chloroform.
In the above method, in the step, the alkyl halide includes：Fluoromethane, 1- fluoroethanes, 1- fluoro-propanes, 1- fluorine fourths
Alkane, 1- amyl fluorides, 1- fluorine hexane, 1- fluorine heptane, n octyl fluoride, 1- fluorine nonane, 1- fluorine decane, 1- fluorine hendecane, 1- fluorine 12
Alkane, 1- fluorine tridecane, the 1- fluorine tetradecane, 1- fluorine pentadecane, 1- fluorine hexadecane, 1- fluorine heptadecane, 1- fluorine octadecane, 1- fluorine 19
Alkane, 1- fluorine eicosanes, 1- fluorine heneicosane, 1- fluorine docosane, 1- fluorine tricosane, 1- fluorine lignocerane, 1- fluorine 25
Alkane, 1- fluorine hexacosane, 1- fluorine heptacosane, 1- fluorine octacosane, chloromethanes, 1- chloroethanes, n-propyl chloride, 1-chlorobutane,
1-chloropentane, 1- chlorohexanes, 1- chloroheptanes, 1- chloro-octanes, 1- chlorononanes, 1- chlorodecanes, 1- chloro-undecanes, 1- chlorododecanes,
1- chlorine tridecane, the 1- chlorine tetradecane, 1- chlorine pentadecane, 1- chlorine hexadecane, 1- chlorine heptadecane, 1- chlorine octadecane, 1- chlorine nonadecane,
1- chlorine eicosanes, 1- chlorine heneicosane, 1- chlorine docosane, 1- chlorine tricosane, 1- chlorine lignocerane, 1- chlorine pentacosane,
1- chlorine hexacosane, 1- chlorine heptacosane, 1- chlorine octacosane, bromomethane, 1- bromoethanes, 1- N-Propyl Bromides, 1- NBBs, 1- bromines
Pentane, hexyl bromide 1 bromohexane, 1- heptyl bromides, 1- bromooctanes, 1- bromononanes, 1- bromo-decanes, 1- bromo-n-11s, 1- bromo-dodecanes, 1- bromines
Tridecane, 1- bromo-tetradecanes, pe-ntadecyl bromide, 1- bromines hexadecane, 1- bromines heptadecane, 1- bromo-octadecanes, 1- bromines nonadecane, 1- bromines
Eicosane, 1- bromines heneicosane, 1- bromines docosane, 1- bromines tricosane, 1- bromines lignocerane, 1- bromines pentacosane, 1- bromines
Hexacosane, 1- bromines heptacosane, 1- bromines octacosane, iodomethane, 1- iodoethane, 1- iodopropanes, 1- iodobutanes, 1- iodine penta
Alkane, 1- iodohexanes, 1- iodine heptane, 1- iodo-octanes, nonyl iodide, 1- iodine decane, 1- iodine hendecane, 1- iodine dodecane, 1- iodine ten
Three alkane, the 1- iodine tetradecane, 1- iodine pentadecane, Cetyl Iodide, 1- iodine heptadecane, 1- iodine octadecane, 1- iodine nonadecane, 1- iodine two
Ten alkane, 1- iodine heneicosane, 1- iodine docosane, 1- iodine tricosane, 1- iodine lignocerane, 1- iodine pentacosane, 1- iodine two
Hexadecane, 1- iodine heptacosane or 1- iodine octacosanes.
So that raw material is N- hydroxyethyl imidazoles, isocyanatoethyl and bromine hexadecane as an example, the change of above-mentioned reaction
Learn equation as follows：
The polymerizate of the polymerisable monomer of the present invention has broad-spectrum efficient antibacterial properties, can partly replace during concrete application
Methyl methacrylate in acrylate bone cement is used to prepare antibiotic property acrylate bone cement.
Compared with prior art, the present invention has the advantages that：
The remarkable advantage of the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation prepared by the present invention is high with wide spectrum
The antibiotic property of effect, can participate in the solidification process of acrylate bone cement, assign the long-acting pre- aseptic function of bone cement.Cause
This, the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation prepared by the present invention resists with acrylate bone cement is developed to
The potential of bacterium property additive.
Brief description of the drawings
Fig. 1 is example A2BnF is with the methyl methacrylate in 5% mass fraction part substituted acrylate bone cement
The anti-microbial property comparison diagram of prepared bone cement.
Embodiment
The present invention is further described through with reference to specific embodiment, but specific embodiment is not appointed to the present invention
What is limited.
The antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation of the invention, shown in its structural formula such as formula (I)；
N takes any one integer in 1~5 in formula (I)；R in formula (I)1Any one in modus ponens methyl or (II)；
I in structural formula (II) is any one numerical value in 0~26；
Any one in formula (I) X modus ponens (III)；
Embodiment 1
The present embodiment prepares A2B12F monomers, key step is as follows：
1.12g N- hydroxyethyl imidazoles and 50mL tetrahydrofurans is added in reaction vessel, with 20 drops under stirring
1.55g isocyanatoethyl is added dropwise in speed per minute, is reacted 12 hours at 45 DEG C, makes isocyanate groups
Reaction completely, it is 65 DEG C then to adjust reaction temperature, adds 2.49g bromo-dodecanes, is reacted 72 hours, generates product, Ran Houjin
Row purification processes, obtain A2B12F type monomers, product is characterized with proton nmr spectra：
1H-NMR (DMSO-d6,600MHz)：δ 0.85 [3H, t], 1.24 [18H, s], 1.79 [2H, m], 1.87 [3H, s],
3.24 [2H, q], 4.07 [2H, t], 4.20 [2H, t], 4.32 [2H, t], 4.45 [2H, t], 5.68 [1H, s], 6.05 [1H, s],
7.52 [1H, t], 7.80 [1H, s], 7.85 [1H, s], 9.29 [1H, s]
Embodiment 2
The present embodiment prepares A2B16F monomers, key step is as follows：
1.12g N- hydroxyethyl imidazoles and 50mL tetrahydrofurans is added in reaction vessel, with 20 drops under stirring
1.55g isocyanatoethyl is added dropwise in speed per minute, is reacted 12 hours at 45 DEG C, makes isocyanate groups
Reaction completely, it is 65 DEG C then to adjust reaction temperature, adds 3.05g bromine hexadecanes, is reacted 72 hours, generates product, Ran Houjin
Row purification processes, obtain A2B16F type monomers, product is characterized with proton nmr spectra：
1H-NMR (DMSO-d6,600MHz)：δ 0.85 [3H, t], 1.23 [26H, s], 1.77 [2H, m], 1.87 [3H, s],
3.24 [2H, q], 4.07 [2H, t], 4.19 [2H, t], 4.32 [2H, t], 4.44 [2H, t], 5.68 [1H, s], 6.04 [1H, s],
7.49 [1H, t], 7.79 [1H, s], 7.84 [1H, s], 9.26 [1H, s]
Embodiment 3
The present embodiment prepares A2B18F monomers, key step is as follows：
1.12g N- hydroxyethyl imidazoles and 50mL tetrahydrofurans is added in reaction vessel, with 20 drops under stirring
1.55g isocyanatoethyl is added dropwise in speed per minute, is reacted 12 hours at 45 DEG C, makes isocyanate groups
Reaction completely, it is 65 DEG C then to adjust reaction temperature, adds 3.33g bromo-dodecanes, is reacted 72 hours, generates product, Ran Houjin
Row purification processes, obtain A2B18F type monomers, product is characterized with proton nmr spectra：
1H-NMR (DMSO-d6,600MHz)：δ 0.85 [3H, t], 1.24 [30H, s], 1.79 [2H, m], 1.87 [3H, s],
3.25 [2H, q], 4.07 [2H, t], 4.20 [2H, t], 4.32 [2H, t], 4.45 [2H, t], 5.68 [1H, s], 6.05 [1H, s],
7.51 [1H, t], 7.80 [1H, s], 7.85 [1H, s], 9.30 [1H, s]
Embodiment 4
A2B12F、A2B16F and A2B18F mass fraction is operation, curing characteristics and the power of 5% acrylate bone cement
Learn performance.
The present embodiment A for accounting for prepared acrylate bone cement quality 5%2B12F、A2B16F and A2B18F distinguishes part
Methyl methacrylate in substituted acrylate bone cement liquor, the operation of the prepared bone cement of research, curing characteristics and
Mechanical property, its formula is as follows：
Bone cement liquor：Methyl methacrylate：A2BnF：N, N- dimethyl-p-toluidine：Hydroquinones=27.58：5：
0.67：0.05 (n=12,16,18)；Bone cement pulvis：Poly methyl methacrylate particle：Zirconium dioxide：Benzoyl peroxide
=55.37：10：1.33；Bone cement liquor presses 1 with bone cement pulvis：2 mass ratio is mixed with sample.Its operating characteristic and
Curing characteristics result is as shown in table 1.Mechanical property is as shown in table 2.
From Tables 1 and 2, containing A2BnThe F bone cement dough time reduces, and maximum temperature declines, and setting time, which meets, to be made
With requiring, generally operating characteristics has optimized.As known from Table 2, containing A2BnF bone cement good mechanical properties.
Table 1 is containing the A that mass fraction is 5%2BnDough time, setting time and the maximum temperature of F bone cement
Table 2 is containing the A that mass fraction is 5%2BnBending modulus, bending strength and the compression strength of F bone cement
Embodiment 5A2B12F、A2B16F and A2B18F mass fraction is the anti-microbial property of 5% acrylate bone cement
The present embodiment A for accounting for prepared acrylate bone cement quality 5%2B12F、A2B16F and A2B18F distinguishes part
Methyl methacrylate in substituted acrylate bone cement liquor, the anti-microbial property of the prepared bone cement of research, it is formulated
It is as follows：
Bone cement liquor：Methyl methacrylate：A2BnF：N, N- dimethyl-p-toluidine：Hydroquinones=27.58：5：
0.67：0.05 (n=12,16,18)；Bone cement pulvis：Poly methyl methacrylate particle：Zirconium dioxide：Benzoyl peroxide
=55.37：10：1.33；Bone cement liquor presses 1 with bone cement pulvis：2 mass ratio is mixed with sample.With without A2BnF's
Bone cement is control, containing the A that mass fraction is 5%2BnThe antibiotic rate of F bone cement is as shown in Figure 1.
As shown in Figure 1, A2BnF addition improves the anti-microbial property of bone cement.Containing 5%A2B12F bone cement is for large intestine
Escherichia has relatively good antibacterial effect.For staphylococcus aureus, containing 5%A2B12F、A2B16F、A2B18F bone water
Mud has a good anti-microbial property.
Claims (6)
1. the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation, it is characterised in that shown in its structural formula such as formula (I)；
N takes any one integer in 1~5 in formula (I)；R in formula (I)1Any one in modus ponens methyl or (II)；
I in structural formula (II) is any one numerical value in 0~26；
Any one in formula (I) X modus ponens (III)；
X=F, Cl, Br, I (III).
2. preparing the method for the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation described in claim 1, its feature exists
In comprising the following steps：
N- hydroxyalkyls imidazoles and solvent are added in reaction vessel, isocyanatoethyl is added under stirring,
At 5 DEG C~60 DEG C react 0.5~12 hour, isocyanate groups is reacted completely, then adjust reaction temperature be 50 DEG C~
100 DEG C, alkyl halide is added, is reacted 5~100 hours, product is generated, purification processes then are carried out to reaction product, obtain halogen
Change the antibiotic property polymerisable monomer of imidazole salts structure.
3. preparation method according to claim 2, it is characterised in that the material of the isocyanatoethyl
The ratio of amount and the amount of the material of N- hydroxyalkyl imidazoles is 1:1.0~1:1.5；The amount of the material of alkyl halide and N- hydroxyalkyl imidazoles
Material amount ratio be 1:1.0~1:3.0.
4. preparation method according to claim 2, it is characterised in that in the step, the N- hydroxyalkyls imidazoles includes
N- hydroxy methylimidazoles, N- hydroxyethyl imidazoles, N- hydroxypropyls imidazoles, N- hydroxyls butyl imidazole or N- hydroxyl amyl group imidazoles；The solvent
Type include acetone, butanone, cyclohexanone, tetrahydrofuran, dimethyl sulfoxide (DMSO), DMF, 1-METHYLPYRROLIDONE,
Dichloromethane or chloroform.
5. preparation method according to claim 2, it is characterised in that in the step, the alkyl halide includes：Fluorine first
Alkane, 1- fluoroethanes, 1- fluoro-propanes, 1- fluorine butane, 1- amyl fluorides, 1- fluorine hexane, 1- fluorine heptane, n octyl fluoride, 1- fluorine nonane, 1-
Fluorine decane, 1- fluorine hendecane, 1- fluorine dodecane, 1- fluorine tridecane, the 1- fluorine tetradecane, 1- fluorine pentadecane, 1- fluorine hexadecane, 1- fluorine
Heptadecane, 1- fluorine octadecane, 1- fluorine nonadecane, 1- fluorine eicosanes, 1- fluorine heneicosane, 1- fluorine docosane, 1- fluorine 23
Alkane, 1- fluorine lignocerane, 1- fluorine pentacosane, 1- fluorine hexacosane, 1- fluorine heptacosane, 1- fluorine octacosane, chloromethanes, 1-
Chloroethanes, n-propyl chloride, 1-chlorobutane, 1-chloropentane, 1- chlorohexanes, 1- chloroheptanes, 1- chloro-octanes, 1- chlorononanes, the 1- chlorine last of the ten Heavenly stems
Alkane, 1- chloro-undecanes, 1- chlorododecanes, 1- chlorine tridecane, the 1- chlorine tetradecane, 1- chlorine pentadecane, 1- chlorine hexadecane, 1- chlorine 17
Alkane, 1- chlorine octadecane, 1- chlorine nonadecane, 1- chlorine eicosanes, 1- chlorine heneicosane, 1- chlorine docosane, 1- chlorine tricosane, 1-
Chlorine lignocerane, 1- chlorine pentacosane, 1- chlorine hexacosane, 1- chlorine heptacosane, 1- chlorine octacosane, bromomethane, 1- bromine second
Alkane, 1- N-Propyl Bromides, 1- NBBs, 1- bromo pentane silanes, hexyl bromide 1 bromohexane, 1- heptyl bromides, 1- bromooctanes, 1- bromononanes, 1- bromo-decanes, 1-
Bromo-n-11,1- bromo-dodecanes, 1- bromine 13s alkane, 1- bromo-tetradecanes, pe-ntadecyl bromide, 1- bromines hexadecane, 1- bromines heptadecane, 1-
Bromo-octadecane, 1- bromines nonadecane, 1- bromines eicosane, 1- bromines heneicosane, 1- bromines docosane, 1- bromines tricosane, 1- bromines two
The tetradecane, 1- bromines pentacosane, 1- bromines hexacosane, 1- bromines heptacosane, 1- bromines octacosane, iodomethane, 1- iodoethane, 1-
Iodopropane, 1- iodobutanes, 1- iodopentanes, 1- iodohexanes, 1- iodine heptane, 1- iodo-octanes, nonyl iodide, 1- iodine decane, 1- iodine ten
One alkane, 1- iodine dodecane, 1- iodine tridecane, the 1- iodine tetradecane, 1- iodine pentadecane, Cetyl Iodide, 1- iodine heptadecane, 1- iodine ten
Eight alkane, 1- iodine nonadecane, 1- iodine eicosane, 1- iodine heneicosane, 1- iodine docosane, 1- iodine tricosane, 1- iodine 24
Alkane, 1- iodine pentacosane, 1- iodine hexacosane, 1- iodine heptacosane or 1- iodine octacosanes.
6. the antibiotic property polymerisable monomer of the structure of imidazole salts containing halogenation described in claim 1 as acrylate bone cement can
It polymerize the application in antibacterial additives.
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| CN108484487B (en) * | 2018-03-23 | 2021-10-22 | 华南理工大学 | Antibacterial (methyl) acrylate monomer containing quaternary pyridinium salt and carbamate structure and preparation method and application thereof |
| CN117327422A (en) * | 2023-09-07 | 2024-01-02 | 厦门欧化实业有限公司 | Synthesis process of UV (ultraviolet) curing polyurethane ink |
| CN117327422B (en) * | 2023-09-07 | 2024-03-08 | 厦门欧化实业有限公司 | Synthesis process of UV (ultraviolet) curing polyurethane ink |
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