CN105079883A - Multistage nanofiber composite drug-loaded periodontal tissue material and preparation method thereof - Google Patents
Multistage nanofiber composite drug-loaded periodontal tissue material and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of a medical material, and discloses a multistage nanofiber composite drug-loaded periodontal tissue material and a preparation method thereof. The multistage nanofiber composite drug-loaded periodontal tissue material is composed of a blend fiber, composite fiber or polylactic acid fiber/chitosan microsphere composite structure which is formed from 50-99% of polylactic acid and 1-50% of chitosan in percentage by mass; the preparation method comprises the following steps: firstly preparing a polylactic acid fiber membrane or stent, and combining chitosan fibers or chitosan microspheres on the polylactic acid fiber membrane or stent; or simultaneously preparing polylactic acid fibers and chitosan fibers to form blend fiber or composite fiber, so as to obtain the multistage nanofiber composite drug-loaded periodontal tissue material. According to the material disclosed by the invention, fat-soluble, water-soluble and nanoparticle medicine components can be bound to the composite material during preparing, so that the composite material has a great significance for modification or function improvement of various added medicines in future.
Description
Technical field
The invention belongs to Degradable Biomedical Materials technical field, be specifically related to a kind of multi-stage nano fiber composite medicine-carried periodontal tissue material and preparation method thereof.
Background technology
From Rokkane in 1984 first by PGA (polyglycolic acid) for after Orthopedic Clinical, experiment and the clinical research of biodegradation absorbable material obtain fast development, and obtain certain achievement.In orthopaedic trauma, this kind of material is developed rapidly at present.Periodontal tissue is in the moist microenvironment in oral cavity, constantly oozing out of level in gingival sulcus fluid, pathogenic bacterium a large amount of in periodontal tissue exist many factors, and to cause the treatment of periodontitis and the treatment of wound bone to have different significantly, the main function of wound bone material promotes knitting, therefore, the artificial substituting material for periodontal surgery is higher than the material requirements of wound bone.
Artificial substituting material conventional in periodontal surgery has bone meal and GTR (guide tissue regeneration) film, in periodontal disease, periodontal tissue's Cranial defect is once be formed, to be difficult to return to original degree, after periodontal surgery, organization healing forms epithelium regeneration healing often in addition, and this will improve the relapse rate of periodontal disease.Therefore, how to pass through periodontal tissue's material success load induced material, antibacterial medicines and antibiotics composition, thus promote that periodontal tissue's Cranial defect recovers, suppressing Periodontal Pathogens grow and reduce the relapse rate of periodontal disease, is the problem that researcher in this field needs to solve.
Summary of the invention
In order to solve the shortcoming and defect part of above prior art, primary and foremost purpose of the present invention is to provide a kind of multi-stage nano fiber composite medicine-carried periodontal tissue material.
Another object of the present invention is to the preparation method that above-mentioned multi-stage nano fiber composite medicine-carried periodontal tissue material is provided.
The object of the invention is achieved through the following technical solutions:
A kind of multi-stage nano fiber composite medicine-carried periodontal tissue material is that blended fiber, composite fibre or the acid fiber by polylactic/chitosan microball composite construction that the polylactic acid (PLA) of 50% ~ 99% and the chitosan (CS) of 1% ~ 50% are formed is formed by mass fraction; The form of described blended fiber is that acid fiber by polylactic and chitin fiber are mutually interspersed or stacked together; The form of described composite fibre is that acid fiber by polylactic and chitin fiber form island, core-skin, bias or composite construction arranged side by side; The form of described acid fiber by polylactic/chitosan microball composite construction is that chitosan microball is distributed in polylactic acid fiber surface with graininess.
Preferably, the weight average molecular weight of described polylactic acid is 1 × 10
4~ 9 × 10
7g/mol, the weight average molecular weight of chitosan is 1 × 10
4~ 9 × 10
7g/mol.
Described multi-stage nano fiber composite medicine-carried periodontal tissue material also comprises medicine carrying composition, described medicine carrying composition comprises water solublity medicine carrying composition or nano-particle, and described water solublity medicine carrying composition is carried on inside or the surface of chitin fiber or chitosan microball; Described nano-particle is carried on inside or the surface of chitin fiber, chitosan microball or acid fiber by polylactic.
Preferably, described water solublity medicine carrying composition is at least one in fibroblast growth factor, tetracycline, amoxicillin, first nitre file, LIUWEI DIHUANG WAN, puerarin, Hedysamn polysaccharide and ferrum lactoprotein; Described nano-particle refers at least one in nanometer silver and ZnO.
The preparation method of above-mentioned multi-stage nano fiber composite medicine-carried periodontal tissue material, comprises following preparation process:
First polylactic acid fiber membrane or support is prepared, then recombination chitosan fiber or chitosan microball in polylactic acid fiber membrane or support, or prepare acid fiber by polylactic and chitin fiber simultaneously and form blended fiber or composite fibre, obtain multi-stage nano fiber composite medicine-carried periodontal tissue material.
Above-mentioned periodontal tissue material also loading nano silvery by the following method: through air gun piping and druming evenly and ultrasonic disperse, directly dropping is at material surface, air-dry, obtains multi-stage nano fiber composite loading nano silvery periodontal tissue material for nanometer silver deionized water suspension.
The preparation method of described polylactic acid fiber membrane or support is as follows:
Polylactic acid is dissolved in solvent, is made into the PLA solution that mass fraction is 5 ~ 40%, then split method, meltblown, centrifugal spinning, freeze-drying by method of electrostatic spinning, film, liquid causes split-phase method or flash method obtains polylactic acid fiber membrane or support.
Preferably, described solvent refers to one or more the mixing in chloroform, dichloromethane, dimethyl formamide, dimethyl acetylamide, dimethyl sulfoxide, hexafluoroisopropanol, six cyclopentadiene and oxolane.
The preparation method of described recombination chitosan fiber or chitosan microball in polylactic acid fiber membrane or support is as follows:
Chitosan is dissolved in mass fraction be 30% ~ 90% acetic acid, trifluoroacetic acid, in one or more mixed solvents in trifluoroethanol and hexafluoroisopropanol, be made into the chitosan solution that mass fraction is 5 ~ 30%, then form chitin fiber or chitosan microball by electrostatic spinning, electrostatic spraying, electrostatic dipping or dipping lyophilization in polylactic acid fiber membrane or rack surface.
The preparation method preparing acid fiber by polylactic and chitin fiber formation blended fiber or composite fibre while described is as follows:
Chitosan is dissolved in mass fraction be 30% ~ 90% acetic acid, trifluoroacetic acid, in one or more mixed solvents in trifluoroethanol and hexafluoroisopropanol, be made into the chitosan solution that mass fraction is 5 ~ 30%, then chitosan solution and PLA solution obtained mixed emulsion under the effect of surfactant; Again mixed emulsion is split method, meltblown, centrifugal spinning, freeze-drying by method of electrostatic spinning, film, liquid causes split-phase method or flash method obtains PLA/CS blended fiber or composite fibre.
Described chitosan solution also adds water solublity medicine carrying composition or nano-particle and dissolves and pass through and be uniformly dispersed in process for preparation, obtains chitosan-loaded drug solns.
Preferably, described surfactant refers to one or more the mixing in tween, span, dodecyl sodium sulfate, sodium lauryl sulphate, polyvinyl alcohol (PVA), polyvinylpyrrolidone, carboxymethyl cellulose (CMC) and polyacrylic acid.
Preferably, the concrete preparation process of described mixed emulsion is: the surfactant first adding 1% ~ 10% mass fraction in the solvent of polylactic acid, and stirring and emulsifying forms emulsification system, then add chitosan solution, after stirring and emulsifying, add polylactic acid, dissolve, homogenize, deaeration, obtains mixed emulsion; The solvent of described polylactic acid refers to one or more the mixing in chloroform, dichloromethane, dimethyl formamide, dimethyl acetylamide, dimethyl sulfoxide, hexafluoroisopropanol, six cyclopentadiene and oxolane.
Preparation method of the present invention and the product tool obtained have the following advantages and beneficial effect:
(1) in the preparation process of periodontal tissue of the present invention material, water soluble drug can load in chitosan solution, fat-soluble medicine can load on the molding carrying out nanofiber in PLA material, nano-particle such as nanometer silver directly can be sprayed onto material surface, fat-soluble, water solublity and nanoparticulate drug composition all can be attached on composite, it carries out modifying or function is improved and had very large meaning for adding multi-medicament from now on, has vast potential for future development;
(2) structure of multi-stage nano fiber composite medicine-carried periodontal tissue of the present invention material and the diameter of periodontal membrane collagen and plesiomorphism, be different from wound bone material, promote tissue regeneration after can be used for periodontal surgery, improves operative effect;
(3) multi-stage nano fiber composite medicine-carried periodontal tissue of the present invention material is bicomponent structural, is unfavorable for that the PLA of cell adhesion directly contacts with gingiva tissue; The chitosan being beneficial to cell proliferation contacts with osseous tissue, is beneficial to skeletonization;
(4) the present invention adopts chitosan to carry out modification to polylactic acid, elastic properties of materials step-down, be enough to the space maintaining periodontal tissue's reparation, degradation speed is then by changing the molecular weight of use PLA and regulating the consumption of CS to obtain the requirement that suitable proportioning meets actual use;
(5) preparation method of the present invention adopts multiple forming technique to combine, and products therefrom effectively overcomes the uneven defect of simple method of electrostatic spinning gained fiber felt.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
Polylactic acid (PLA, M
w=3 × 10
5g/mol) (80 DEG C, 10h) after vacuum drying, employing chloroform is solvent, and the mass fraction being mixed with polylactic acid is the solution of 20%, and magnetic agitation 5h, standing and defoaming 4h obtain PLA solution; Method of electrostatic spinning is adopted to prepare PLA film the PLA solution prepared, electrospinning conditions is: the distance 12cm between dash receiver and syringe needle, under 15kV voltage, PLA solution carries out electrospinning with the flow velocity of 0.5ml/h, and fibrous membrane electrospinning obtained carries out vacuum drying, obtains pure PLA film; Chitosan (CS, M
w=8 × 10
4g/mol) adopt concentration be 90% acetic acid solvent be mixed with the CS solution that mass fraction is 3%, then CS solution is sprayed onto on pure PLA film with the flow velocity of 0.6ml/h by the mode of electrostatic spraying, in electrostatic spray process, dash receiver and syringe needle distance are 10cm, voltage between syringe needle and dash receiver is 20kV, vacuum drying again, namely obtains CS-PLA film; Nanometer silver deionized water suspension is blown and beaten evenly through air gun and through ultrasonic disperse, directly drips on CS-PLA film surface, air-dry, obtain multi-stage nano fiber composite load silver periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is that 300 ~ 500nm, CS are distributed in PLA film surface with graininess, and its diameter range is 400 ~ 800nm, and its structure is acid fiber by polylactic/chitosan microball composite construction; The collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber close, suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 2
Polylactic acid (PLA, M
w=9 × 10
7g/mol) (80 DEG C, 10h) after vacuum drying, adopt chloroform: dimethyl formamide weight ratio is the mixed solvent of 1:1 is solvent, and the mass fraction being mixed with polylactic acid is the solution of 14%, stir 5h, standing and defoaming 4h and obtain PLA solution; Method of electrostatic spinning is adopted to prepare PLA film the PLA solution prepared, electrospinning conditions is: the distance 12cm between dash receiver and syringe needle, under 15kV voltage, PLA solution carries out electrospinning with the flow velocity of 0.5ml/h, and fibrous membrane electrospinning obtained carries out vacuum drying, obtains pure PLA film; Chitosan (CSM
w=7 × 10
4g/mol) hexafluoroisopropanol of 90% is adopted: trifluoroacetic acid (1:1) is mixed with the CS solution that mass fraction is 5%, then CS solution is sprayed onto the two sides of pure PLA film by the mode of electrostatic spraying with the flow velocity of 0.6ml/h, distance 10cm in electrostatic spray process between dash receiver and syringe needle, voltage between syringe needle and dash receiver is 20kV, gained sample vacuum drying, obtain CS-PLA composite membrane, this structure of composite membrane is sandwich structure, wherein CS is in the both sides of PLA, take PLA as intermediate layer; Nanometer silver deionized water suspension is blown and beaten evenly through air gun and through ultrasonic disperse, directly drips at CS-PLA composite film surface, air-dry, obtain multi-stage nano fiber composite load silver periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is that 300 ~ 500nm, CS are distributed in PLA film surface with graininess, and its diameter range is 500 ~ 900nm, and its structure is acid fiber by polylactic/chitosan microball composite construction; The collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 3
Polylactic acid (PLA, M
w=2.4 × 10
6g/mol) (80 DEG C, 10h) after vacuum drying, adopt chloroform: dimethyl formamide weight ratio is the mixed solvent of 1:1 is solvent, and the mass fraction being mixed with polylactic acid is the solution of 24%, stir 5h, standing and defoaming 4h and obtain PLA solution; Chitosan (CSM
w=1 × 10
4g/mol) trifluoroacetic acid solution of 90% is adopted to be mixed with the CS solution that mass fraction is 5%; Adopt double needle pattern, namely syringe needle carries out the electrostatic spinning of PLA solution, and another syringe needle carries out the electrostatic spraying of CS solution.Distance 12cm between dash receiver and syringe needle, under 15kV voltage, PLA solution carries out electrospinning with the flow velocity of 0.5ml/h, vacuum drying, obtains pure PLA film; CS solution is with the flow velocity of 0.6ml/h, dash receiver and syringe needle distance are 12cm, between syringe needle and dash receiver, voltage is 20kV molding, by sample vacuum drying, namely CS-PLA composite membrane is obtained, gained structure of composite membrane is the core-sheath composite structure that CS and PLA mixes mutually, and wherein CS is sandwich layer, and PLA is cortex; Nanometer silver deionized water suspension is blown and beaten evenly through air gun and through ultrasonic disperse, directly drips at CS-PLA composite film surface, air-dry, obtain multi-stage nano fiber composite load silver periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is 300 ~ 500nm, CS distribution of fiber diameters scope is 600 ~ 800nm, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 4
Polylactic acid (PLA, M
w=8 × 10
5g/mol) (80 DEG C, 10h) after vacuum drying, employing dimethyl formamide is solvent, and the mass fraction being mixed with polylactic acid is the solution of 28%, stirs 5h, standing and defoaming 4h and obtains PLA solution; Chitosan (CSM
w=4 × 10
4g/mol) adopt the mixed solvent of the hexafluoroisopropanol of 90% mass fraction and trifluoroacetic acid (volume ratio of hexafluoroisopropanol and trifluoroacetic acid is 1:3) to be mixed with the CS solution that mass fraction is 5%, and the first nitre file adding 2wt% in CS solution is uniformly dissolved and obtain CS medicine carrying solution; Adopt double needle pattern, namely syringe needle carries out the electrostatic spinning of PLA solution, another syringe needle carries out the electrostatic spraying of CS solution, method of electrostatic spinning is adopted to prepare PLA film PLA solution, distance 15cm between dash receiver and syringe needle, under 25kV voltage, PLA solution carries out electrospinning with the flow velocity of 0.5ml/h, carries out vacuum drying, obtains pure PLA film; CS medicine carrying solution is with the flow velocity of 0.6ml/h, dash receiver and syringe needle distance are 12cm, between syringe needle and dash receiver, voltage is 20kV molding, by sample vacuum drying, namely multi-stage nano fiber composite load first nitre tooth grinding week organization material is obtained, resulting materials structure is the island composite construction that CS and PLA mixes mutually, and wherein CS is island phase, and PLA is marine facies.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is 500-700nm, CS distribution of fiber diameters scope is 500-800nm, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 5
Polylactic acid (PLA, M
w=3 × 10
6g/mol) after vacuum drying (80 DEG C, 10h), adopt dimethyl formamide: the weight ratio of hexafluoroisopropanol is the mixed solvent of 1:2 is solvent, the mass fraction of preparation polylactic acid is the solution of 50%, stir 5h, standing and defoaming 4h and obtain PLA solution; Chitosan (CSM
w=3 × 10
5g/mol) adopt the mixed solvent of the hexafluoroisopropanol of 60% mass fraction and trifluoroacetic acid (volume ratio of hexafluoroisopropanol and trifluoroacetic acid is 1:3) to be made into the CS solution that mass fraction is 3%, and the ZnO adding 2% in CS solution is uniformly dispersed and obtain CS medicine carrying solution; Adopt double needle pattern, namely syringe needle carries out the electrostatic spinning of PLA solution, another syringe needle carries out the electrostatic spraying of CS solution, method of electrostatic spinning is adopted to prepare PLA film PLA solution, distance 15cm between dash receiver and syringe needle, under 25kV voltage, PLA solution carries out electrospinning with the flow velocity of 0.5ml/h, obtains pure PLA film after vacuum drying; CS medicine carrying solution is with the flow velocity of 0.6ml/h, dash receiver and syringe needle distance are 12cm, between syringe needle and dash receiver, voltage is 20kV molding, by sample vacuum drying, namely multi-stage nano fiber composite loading ZnO periodontal tissue material is obtained, gained structure of composite membrane is the core-sheath composite structure that CS and PLA mixes mutually, and wherein CS is sandwich layer, and PLA is cortex.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is 600-1200nm, CS distribution of fiber diameters scope is 500-800nm, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 6
Polylactic acid (PLA, M
w=6 × 10
5g/mol) (80 DEG C, 10h) after vacuum drying, adopt dimethyl sulfoxide: the weight ratio of dichloromethane is the mixed solvent of 1:2 is solvent, the mass fraction of preparation polylactic acid is the solution of 14%, stirs 5h, standing and defoaming 4h and obtains PLA solution; Adopt centrifugal method of electrostatic spinning to prepare PLA film PLA solution, the distance 20cm between dash receiver and syringe needle, under the voltage of 35kV, PLA solution carries out electrospinning with the flow velocity of 450r/min, 15ml/h, obtains pure PLA film after vacuum drying; Chitosan (CSM
w=2.6 × 10
5g/mol) hexafluoroisopropanol of 60% mass fraction is adopted to be the CS solution that solvent is mixed with that mass fraction is 3%, electrostatic impregnation technology is adopted to stick on pure PLA film CS solution, voltage is 5kV, dipping solid-to-liquid ratio is 1:15, dip time is 5min, and then vacuum drying, namely obtain CS-PLA film, namely acid fiber by polylactic and chitin fiber form eccentric structure; Nanometer silver deionized water suspension is blown and beaten evenly through air gun and through ultrasonic disperse, is directly dripped on CS-PLA film surface, air-dry, obtains multi-stage nano fiber composite load silver periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is 300-500nm, CS distribution of fiber diameters scope is 400-800nm, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 7
Polylactic acid (PLA, M
w=6 × 10
5g/mol) (80 DEG C, 10h) after vacuum drying, adopt dimethyl sulfoxide: the weight ratio of dichloromethane is the mixed solvent of 1:2 is solvent, the mass fraction of preparation polylactic acid is the solution of 14%, stirs 5h, standing and defoaming 4h and obtains PLA solution; Adopt centrifugal method of electrostatic spinning to prepare PLA film PLA solution, the distance 20cm between dash receiver and syringe needle, under the voltage of 35kV, solution carries out electrospinning with the flow velocity of 450r/min, 15ml/h, obtains pure PLA film after vacuum drying; Chitosan (CSM
w=2.6 × 10
5g/mol) the hexafluoroisopropanol aqueous solution of 60% mass fraction is adopted to be the CS solution that solvent is mixed with that mass fraction is 3%, the amoxicillin medicine of 5wt% is added again in CS solution, obtain CS medicine carrying solution, adopted by CS medicine carrying solution dipping postlyophilization technique to stick on pure PLA film, namely obtain multi-stage nano fiber composite load amoxicillin periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is 300-500nm, CS is distributed in PLA film surface with graininess, its diameter Distribution scope is 400-800nm, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 8
Polylactic acid (PLA, M
w=1 × 10
4g/mol) (80 DEG C, 10h) after vacuum drying, adopt meltblown to prepare PLA fibre framework materials, framework material vacuum drying is obtained pure PLA scaffold material; Chitosan (CSM
w=9 × 10
7g/mol) the hexafluoroisopropanol aqueous solution of 90% mass fraction is adopted to be the CS solution that solvent is mixed with that mass fraction is 1%, by the mode of electrostatic spraying, CS solution is sprayed onto in pure PLA scaffold material with the flow velocity of 0.6ml/h, dash receiver and syringe needle distance are 10cm, voltage between syringe needle and dash receiver is 20kV, vacuum drying again, namely obtaining PLA fiber is shelf layer, assorted multi-stage nano fiber composite medicine-carried periodontal tissue material of planting CS fiber in layer.
In the present embodiment gained periodontal tissue material, the fibre diameter of polylactic acid is 800-1400nm, CS distribution of fiber diameters scope is 700-1200nm, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 9
At dimethyl sulfoxide: the weight ratio of dichloromethane is the sorbester p18 adding 1wt% in the mixed solvent of 1:2,3000r/min emulsify at a high speed is after 30 minutes, and adding with the hexafluoroisopropanol aqueous solution of 60% mass fraction is the chitosan (CS.M that solvent is mixed with that mass fraction is 3%
w=2.6 × 10
5g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 14wt% vacuum drying
w=6 × 10
5g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add the tetracycline medicine of 5wt% in CS solution preparation process, form medicine-carried system; Adopt method of electrostatic spinning to prepare PLA/CS composite cellulosic membrane, the distance 20cm between dash receiver and syringe needle, spinning moulding under 35kV voltage PLA/CS mixed emulsion, obtain PLA/CS core-skin multi-stage nano fiber composite load tetracycline periodontal organization material.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS core-skin composite fiber is 600-1500nm, CS with the structure distribution of irregularity at fibrous outer surfaces, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 10
At dimethyl acetylamide: the weight ratio of dichloromethane is the polysorbate60 adding 1wt% in the mixed solvent of 1:2,3000r/min emulsify at a high speed is after 30 minutes, adds with the aqueous solution (volume ratio of hexafluoroisopropanol and trifluoroethanol is 1:1) of the hexafluoroisopropanol of 90% mass fraction and the mixture of trifluoroethanol for mixed solvent is mixed with the chitosan (CS.M that mass fraction is 3%
w=3 × 10
5g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 14wt% vacuum drying
w=6 × 10
5g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add ZnO medicine in CS solution preparation process, form medicine-carried system; Centrifugal method of electrostatic spinning is adopted to prepare PLA/CS composite cellulosic membrane PLA/CS mixed emulsion, distance 20cm between dash receiver and syringe needle, centrifugal rotation speed 400r/min, spinning moulding under 35kV voltage, obtains PLA/CS core-skin multi-stage nano fiber composite loading ZnO periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS core-skin composite fiber is 800-1800nm, CS part with the structure distribution of irregularity at fibrous outer surfaces, part becomes separately threadiness, be separated with PLA, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), the microenvironment of periodontal ligament cell growth can be simulated, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 11
In chloroform solvent, add the PVA aqueous solution (PVA mass concentration is 15%) of 10wt%, 3000r/min emulsify at a high speed is after 30 minutes, and adding with trifluoroacetic acid is the chitosan (CS.M that solvent is mixed with that mass fraction is 15%
w=1.4 × 10
4g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 20wt% vacuum drying
w=4 × 10
5g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add ferrum lactoprotein in CS solution preparation process, form medicine-carried system; PLA/CS mixed emulsion is adopted lyophilization molding, obtains PLA/CS island shape multi-stage nano fiber composite load iron lactoprotein periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS island shape composite fibre is 1000-1600nm, CS part with the structure distribution of irregularity at fibrous outer surfaces, part becomes separately threadiness, be separated with PLA, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 12
At chloroform: the weight ratio of oxolane is the PVA aqueous solution (PVA mass concentration is 20%) adding 10wt% in the solvent of 1:1,3000r/min emulsify at a high speed is after 30 minutes, and adding with trifluoroacetic acid is the chitosan (CS.M that solvent is mixed with that mass fraction is 15%
w=1.8 × 10
5g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 10wt% vacuum drying
w=9 × 10
7g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add Hedysamn polysaccharide in CS solution preparation process, form medicine-carried system; Adopt film to split melt-blown molding PLA/CS mixed emulsion and obtain PLA/CS island shape multi-stage nano fiber composite load Hedysamn polysaccharide periodontal tissue material, meltblown forming temperature is 180 DEG C, spinning pressure 2MPa, ambient temperature 80 DEG C.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS island shape composite fibre is 800-1500nm, CS part with the structure distribution of irregularity at fibrous outer surfaces, part becomes separately threadiness, be separated with PLA, this periodontal tissue's material can simulate the microenvironment of periodontal ligament cell growth, the collagen fiber diameter of PLA fiber and periodontal membrane tissue is close to (the diameter about 200 ~ 1500nm of collagen fiber), this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, often be prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 13
At six cyclopentadiene: the weight ratio of dichloromethane is the sodium lauryl sulphate adding 1wt% in the mixed solvent of 1:2,3000r/min emulsify at a high speed is after 30 minutes, and adding with the hexafluoroisopropanol aqueous solution of 60% mass fraction is the chitosan (CS.M that solvent is mixed with that mass fraction is 3%
w=2.6 × 10
5g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 14wt% vacuum drying
w=6 × 10
5g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add the puerarin solution of 5wt% in CS solution preparation process, form medicine-carried system; Adopt method of electrostatic spinning to prepare PLA/CS composite cellulosic membrane, the distance 20cm between dash receiver and syringe needle, spinning moulding under 35kV voltage PLA/CS mixed emulsion, obtain PLA/CS core-skin multi-stage nano fiber composite load puerarin periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS core-skin composite fiber is 600-1500nm, CS with the structure distribution of irregularity at fibrous outer surfaces, this periodontal tissue's material can simulate the microenvironment of periodontal ligament cell growth, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 14
In dimethylacetamide solvent, add the sodium lauryl sulphate of 1wt%, 3000r/min emulsify at a high speed is after 30 minutes, and adding with the hexafluoroisopropanol aqueous solution of 60% mass fraction is the chitosan (CS.M that solvent is mixed with that mass fraction is 3%
w=2.6 × 10
5g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 14wt% vacuum drying
w=5 × 10
5g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add the fibroblast growth factor of 5wt% in CS solution preparation process, form medicine-carried system; Method of electrostatic spinning is adopted to prepare PLA/CS composite cellulosic membrane PLA/CS mixed emulsion, distance 20cm between dash receiver and syringe needle, spinning moulding under 25kV voltage, obtains PLA/CS parallel type multi-stage nano fiber composite load fibroblast growth factor periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS parallel composite fiber is 600-1500nm, CS and PLA forms bilateral fibre structure, part is present in PLA fiber peripheral with free state, this periodontal tissue's material can simulate the microenvironment of periodontal ligament cell growth, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Embodiment 15
In chloroform solvent, add the Tween 80 of 1wt%, after 3000r/min emulsify at a high speed 30min, add with the hexafluoroisopropanol aqueous solution of 60% mass fraction to be mass fraction that solvent is mixed be 1% chitosan (CS.M
w=9 × 10
7g/mol) solution, in 5000r/min emulsify at a high speed 2h, polylactic acid (PLA, the M of (80 DEG C, 10h) after adding 14wt% vacuum drying
w=5 × 10
5g/mol), stir 5h, standing 4h obtains PLA/CS mixed emulsion; Wherein add 5wt% LIUWEI DIHUANG WAN suspension in CS solution preparation process, form medicine-carried system; Adopt flash method molding to prepare PLA/CS composite membrane PLA/CS mixed emulsion, obtain PLA/CS parallel type multi-stage nano fiber composite load LIUWEI DIHUANG WAN periodontal tissue material.
In the present embodiment gained periodontal tissue material, the fibre diameter of PLA/CS parallel composite fiber is 800-2000nm, CS and PLA forms bilateral fibre structure, part is present in PLA fiber peripheral with free state, this periodontal tissue's material can simulate the microenvironment of periodontal ligament cell growth, this structure is different from wound bone material (tradition wound bone material analog bone organizational structure, in order to better analog bone is organized, be often prepared to the loose structure of similar spongy bone.Spinning fibre structure prepared by the present invention and periodontal membrane fiber are close to suitable paradenlal tissue regeneration).(use derives from the bone marrow stroma stem cell of rat to cell proliferation on the present embodiment gained periodontal tissue material, be numbered RAWMX-01001) obviously faster than blank group (namely cell direct inoculation is in Tissue Culture Plate), it is comparatively obvious that cell mineralization experiments (use derives from the bone marrow stroma stem cell of rat, is numbered RAWMX-01001) shows Mineral nodules.Therefore, the present embodiment gained periodontal tissue material can meet the requirement of induction periodontal tissue growth.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from spirit of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (10)
1. a multi-stage nano fiber composite medicine-carried periodontal tissue material, is characterized in that: be that blended fiber, composite fibre or the acid fiber by polylactic/chitosan microball composite construction that the polylactic acid of 50% ~ 99% and the chitosan of 1% ~ 50% are formed is formed by mass fraction; The form of described blended fiber is that acid fiber by polylactic and chitin fiber are mutually interspersed or stacked together; The form of described composite fibre is that acid fiber by polylactic and chitin fiber form island, core-skin, bias or composite construction arranged side by side; The form of described acid fiber by polylactic/chitosan microball composite construction is that chitosan microball is distributed in polylactic acid fiber surface with graininess.
2. a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 1 material, is characterized in that: the weight average molecular weight of described polylactic acid is 1 × 10
4~ 9 × 10
7g/mol, the weight average molecular weight of chitosan is 1 × 10
4~ 9 × 10
7g/mol.
3. a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 1 material, it is characterized in that: described multi-stage nano fiber composite medicine-carried periodontal tissue material also comprises medicine carrying composition, described medicine carrying composition comprises water solublity medicine carrying composition or nano-particle, and described water solublity medicine carrying composition is carried on inside or the surface of chitin fiber or chitosan microball; Described nano-particle is carried on inside or the surface of chitin fiber, chitosan microball or acid fiber by polylactic.
4. a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 3 material, is characterized in that: described water solublity medicine carrying composition is at least one in fibroblast growth factor, tetracycline, amoxicillin, first nitre file, LIUWEI DIHUANG WAN, puerarin, Hedysamn polysaccharide and ferrum lactoprotein; Described nano-particle refers at least one in nanometer silver and ZnO.
5. the preparation method of a kind of multi-stage nano fiber composite medicine-carried periodontal tissue material described in any one of Claims 1 to 4, is characterized in that comprising following preparation process:
First polylactic acid fiber membrane or support, then recombination chitosan fiber or chitosan microball in polylactic acid fiber membrane or support is prepared; Or prepare acid fiber by polylactic and chitin fiber simultaneously and form blended fiber or composite fibre, obtain multi-stage nano fiber composite medicine-carried periodontal tissue material.
6. the preparation method of a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 5 material, it is characterized in that: described periodontal tissue material also loading nano silvery by the following method: nanometer silver deionized water suspension through air gun piping and druming evenly and ultrasonic disperse, direct dropping is at material surface, air-dry, obtain multi-stage nano fiber composite loading nano silvery periodontal tissue material.
7. the preparation method of a kind of multi-stage nano fiber composite medicine-carried periodontal tissue material according to claim 5 or 6, is characterized in that: the preparation method of described polylactic acid fiber membrane or support is as follows:
Polylactic acid is dissolved in solvent, is made into the PLA solution that mass fraction is 5 ~ 40%, then split method, meltblown, centrifugal spinning, freeze-drying by method of electrostatic spinning, film, liquid causes split-phase method or flash method obtains polylactic acid fiber membrane or support; Described solvent refers to one or more the mixing in chloroform, dichloromethane, dimethyl formamide, dimethyl acetylamide, dimethyl sulfoxide, hexafluoroisopropanol, six cyclopentadiene and oxolane.
8. the preparation method of a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 7 material, is characterized in that: the preparation method of described recombination chitosan fiber or chitosan microball in polylactic acid fiber membrane or support is as follows:
Chitosan is dissolved in mass fraction be 30% ~ 90% acetic acid, trifluoroacetic acid, in one or more mixed solvents in trifluoroethanol and hexafluoroisopropanol, be made into the chitosan solution that mass fraction is 5 ~ 30%, then form chitin fiber or chitosan microball by electrostatic spinning, electrostatic spraying, electrostatic dipping or dipping lyophilization in polylactic acid fiber membrane or rack surface;
The preparation method preparing acid fiber by polylactic and chitin fiber formation blended fiber or composite fibre while described is as follows:
Chitosan is dissolved in mass fraction be 30% ~ 90% acetic acid, trifluoroacetic acid, in one or more mixed solvents in trifluoroethanol and hexafluoroisopropanol, be made into the chitosan solution that mass fraction is 5 ~ 30%, then chitosan solution and PLA solution obtained mixed emulsion under the effect of surfactant; Again mixed emulsion is split method, meltblown, centrifugal spinning, freeze-drying by method of electrostatic spinning, film, liquid causes split-phase method or flash method obtains PLA/CS blended fiber or composite fibre.
9. the preparation method of a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 8 material, it is characterized in that: described chitosan solution in process for preparation, also add water solublity medicine carrying composition or nano-particle dissolves or is uniformly dispersed, and obtains chitosan-loaded drug solns.
10. the preparation method of a kind of multi-stage nano fiber composite medicine-carried periodontal tissue according to claim 8 material, is characterized in that: described surfactant refers to one or more the mixing in tween, span, dodecyl sodium sulfate, sodium lauryl sulphate, polyvinyl alcohol, polyvinylpyrrolidone, carboxymethyl cellulose and polyacrylic acid;
The concrete preparation process of described mixed emulsion is: the surfactant first adding 1% ~ 10% mass fraction in the solvent of polylactic acid, and stirring and emulsifying forms emulsification system, then adds chitosan solution, add polylactic acid after stirring and emulsifying, dissolve, homogenize, deaeration, obtains mixed emulsion; The solvent of described polylactic acid refers to one or more the mixing in chloroform, dichloromethane, dimethyl formamide, dimethyl acetylamide, dimethyl sulfoxide, hexafluoroisopropanol, six cyclopentadiene and oxolane.
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