CN105536049A - Preparation method of fixed-point qualitative medicament-encapsulated artificial bone bracket - Google Patents
Preparation method of fixed-point qualitative medicament-encapsulated artificial bone bracket Download PDFInfo
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- CN105536049A CN105536049A CN201610028688.3A CN201610028688A CN105536049A CN 105536049 A CN105536049 A CN 105536049A CN 201610028688 A CN201610028688 A CN 201610028688A CN 105536049 A CN105536049 A CN 105536049A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/02—Inorganic materials
- A61L27/12—Phosphorus-containing materials, e.g. apatite
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/20—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/54—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/56—Porous materials, e.g. foams or sponges
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/23—Carbohydrates
- A61L2300/232—Monosaccharides, disaccharides, polysaccharides, lipopolysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
- A61L2300/406—Antibiotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/62—Encapsulated active agents, e.g. emulsified droplets
- A61L2300/624—Nanocapsules
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
Abstract
The invention discloses a preparation method of a fixed-point qualitative medicament-encapsulated artificial bone bracket. According to the method, degradable chitosan with high biocompatibility and a pharmacological remission effect is used as a medicament-encapsulated carrier, and etimicin serving as a new aminoglycoside medicament is used as an encapsulating medicament. The preparation method adopts a quick forming method of biological ceramic microspheres; due to atomization spraying, nano-level hydroxyapatite and the micron-level chitosan-encapsulated etimicin microspheres are uniformly mixed as per the ratio, thus achieving the effects of controllable mechanical property and controllable curing time. According to the preparation method, the chitosan is used as the carrier to prepare a medicament-supported bone scaffold by a biological quick forming method, so that the bone bracket has an infection resistance characteristic; meanwhile, the cost and the time for preparing a die are reduced during preparation, and the preparation efficiency is improved.
Description
Technical field
The present invention relates to the technical field of medical artificial bone transplantation material, be specifically related to a kind of preparation method of artificial bone scaffold of qualitative medicine embedding of fixing a point.
Background technology
At field of orthopaedics, the Cranial defect caused by the many reasons such as severe trauma, bone tumor, osteomyelitis is very common.Bone renovating material conventional at present comprises autologous bone and allograph bone.Autologous bone limited source, post-operative complication is more, adds wound and the misery of patient; Allograph bone causes body to produce rejection due to exogenous meeting, and exist loosen, the problem such as fracture, transplanting succeed rate is low.Traumatic bone is damaged in repair process, very easily cause infection, whether replacement bone is transplanted success or not and is infected closely related, and patient's bone grafting under Infection Status or under high infection risk mostly in a lot of real work, so period needs a large amount of Antibiotic prophylaxis, at present much research all focuses on the compatibility of bone support, the aspect such as induced activity and biomechanics characteristic, but seldom notices in the infection of adopted bone holder material and the characteristic for the treatment of infection.Consider the infection characteristic needed for bone support, antibiotic is added in nano bone, rely on the characteristic of nano material, both can ensure that medicaments uniformity distributed, medicine slow release effect in vivo can be reached again.Artificial bone is as osteoblastic carrier, and play as Oesteoblast growth provides sufficient nutrient substance and the important function of vivosphere, the drug-loaded artificial bone with infection characteristic can reduce patient infection's risk.
Desirable bone substitute should meet following requirement: 1, have good biocompatibility with tissue, without immunogenic reaction, has anti-infective effect; 2, with people's biomechanics of bone similar nature seemingly, and there is certain intensity and support force; 3, excellent three-dimensional microstructures, ensures that culture fluid and blood can enter bone internal stent, and is easy to molding; 4, good osteoinductive; 5, there is suitable surface physicochemical property, and can be absorbed by host bone tissue alternative; 6, draw materials conveniently, be easy to a large amount of making.Therefore, ensureing that under the prerequisite that the bearing function (elastic modelling quantity) of artificial bone meets the demands, artificial bone needs to make loose structure, namely meets certain porosity, thus promote biocompatibility in artificial diaphysis, ensure osteocyte and the transmission of nutritional solution material in support.
As can be seen from the design data of domestic and international artificial bone scaffold, although there is numerous researcheres to propose the design principle of support, it is also proposed many manufacture methods, but great majority are all devoted to the research of pore. the implantation of bone support will have the compatibility with organism, to reduce premised on patient suffering, if the usual selective sintering method of the hydroxyapatite powder containing ingredient is made threedimensional model, may in preparation process, medicine be caused to burn, affect the activity of medicine, do not reach the object of expection.And itself have pollution to bone support, the mechanical property of uncontrollable bone support and microstructure, and obtained bone support is not easily degraded.
In addition, in order to promote biocompatibility in artificial diaphysis, ensure osteocyte and the flowing of nutritional solution material in support, artificial bone often needs to make loose structure.But the bearing function of artificial bone also should not be underestimated, if the artificial bone scaffold implanted does not mate with the original osseous tissue of human body, wearing and tearing can be caused, loosen and implant in conjunction with insecure, particularly in holding capacity situation, convalescent period is longer, and may need second operation.
Chitosan is also known as chitosan, be that the chitin extensively existed by nature obtains through deacetylation, the premium properties such as the biological functionality of this natural polymer and the compatibility, blood compatibility, safety, microbic resolvability are by all trades and professions extensive concern.The semi-synthetic water soluble antibiotics of etimicin system, belongs to aminoglycoside.In vitro activity shows: this product has a broad antifungal spectrum, better antibacterial action is had to multiple pathogen, wherein there is higher anti-viable bacteria property to Escherichia coli, Klebsiella Pneumoniae, Enterobacter, Serratia, proteus mirabilis, salmonella and staphylococcus etc., to part Pseudomonas alba etc., there is certain antibacterial activity, to the staphylococcus aureus of part gentamycin, micronomicin and cefazolin sodium drug resistance, escherichia coli and Klebsiella pneumoniae, its external MIC value is still within the scope of the blood drug level of this product therapeutic dose.
There is no report at present and etimicin granule is done carrier with nanometer hydroxyapatite microsphere powder for raw material with Nano chitosan, utilize biological ceramic microsphere quick molding method, produce the artificial bone scaffold that the property of medicine was learnt, had to Biological Strength well.
Summary of the invention
For the problems referred to above, applicant carried out large quantity research, propose a kind of good biocompatibility, easily degraded, biomechanical property controlled and there is the artificial bone scaffold preparation method of infection effectiveness.
Artificial bone scaffold of the present invention is the composite bondd by biological ceramic microsphere biogum.The method not only can ensure the porosity of gained artificial bone scaffold, also by regulating the effective modulus of elasticity of the performance change artificial bone scaffold of biological adhesive, accomplishes the artificial bone scaffold making dual extension-compression modulus according to individual variation.Having suitable microcellular structure makes porous artificial bone scaffold can play optimum skeletonization effect.
The present invention adopts biological ceramic microsphere quick molding method, by nano-grade hydroxy apatite, the chitosan imbedded etimicin microsphere of micron order mutual mix homogeneously in proportion, utilize computer disposal artificial bone scaffold three-dimensional CAD model, with biological adhesive, every layer of powder mixing is cohered, obtain one and meet individual patient bone porosity, there is infection characteristic, the bone stent model that biomechanics is controlled.
Technical scheme of the present invention is:
The preparation method of the artificial bone scaffold of described a kind of qualitative medicine embedding of fixing a point, is characterized in that: comprise the following steps:
Step 1: prepare mixed-powder material:
Step 1.1: chitosan being dissolved in mass fraction is in the acetum of 3% ~ 5%, preparation mass fraction is the chitosan solution of 0.95%, stirs chitosan solution transparent to solution;
Step 1.2: add etimicin and be stirred to etimicin in the chitosan solution that step 1.1 obtains and dissolve, then leave standstill chitosan etimicin mixed solution to solution-stabilized;
Step 1.3: add the sodium tripolyphosphate solution that mass concentration is 0.85% in chitosan etimicin mixed solution, and stir, after chitosan bag medicine is completely heavy poly-, stops adding sodium tripolyphosphate solution;
Step 1.4: add NaOH solution to PH neutrality in the suspension that step 1.3 obtains; Again centrifugal treating is carried out to the neutral suspension obtained, and gained precipitate is carried out lyophilization, then pulverize, the chitosan imbedded etimicin granule of obtained granular size 60 ~ 100nm;
Step 1.5: by the chitosan imbedded etimicin granule of step 1.4 gained, is the hydroxyapatite micro-sphere material of 60 ~ 80nm with granular size, is 1:20 ~ 1:10 mix homogeneously in mass ratio, obtains mixed-powder material;
Step 2: the liquid storage cylinder biological adhesive being loaded biological 3D printer, stores artificial bone scaffold threedimensional model in the control system of described biological 3D printer; Biological 3D printer layering is adopted to print artificial bone scaffold; Every one deck print procedure is: the mixed-powder material that uniform spreading one deck step 1 obtains on forming worktable, then on mixed-powder material, sprays biological adhesive by biological 3D printer.
Further preferred version, the preparation method of the artificial bone scaffold of described a kind of qualitative medicine embedding of fixing a point, is characterized in that: biological adhesive adopts cyanoacrylate.
Beneficial effect
The invention has the beneficial effects as follows:
(1) artificial bone scaffold preparation process of the present invention is without the need to burn off, but make use of biological microsphere degradable character soluble in water and process, which ensure that the pure of bioceramic material, decrease the contaminated probability of bioceramic, simultaneously can also the accurate control treatment time.
(2) drug-loaded artificial bone support of the present invention, making bone support have certain anti-infection property by adding antibiotic, alleviating patient suffering, effectively reducing or avoid the possibility of superinfection.And can the difference of bone support needed for different patient, the hydroxyapatite mixed-powder of the medicine carrying chitosan microball containing different proportion can be spread, reach feature qualitatively of fixing a point.
(3) the present invention sets up artificial bone scaffold cad model according to sufferer individual character, and this model is imported three-dimensional printer, by a certain percentage Homogeneous phase mixing biological ceramic microsphere and biological medicine carrying microballoons; Then spray biological adhesive bonding mixing ball by three-dimensional printer, realize the preparation of artificial bone scaffold.In order to overcome in prior art porous ceramics scaffold preparation process the weakness that may cause due to sintering polluting, present invention utilizes biological binding agent successively to bond mixing microsphere, avoid the pollution that sintering in preparation process and chemical reaction bring to artificial bone scaffold.
(4) the invention solves artificial bone scaffold and biocompatible, degradability problem on traditional preparation methods, simultaneously medicine carrying chitosan add the susceptible problem in bone grafting link that solves.After implantation, biological tissue can depend on bone grafting growth sooner, has higher appreciation rate.
(5) manufacture method of the present invention is simple, and raw material is easy to obtain, and implants artifact expression power and is greatly improved, be more similar to the effect that nature bone support is played in vivo.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described:
The preparation method of artificial bone scaffold of qualitative medicine embedding of fixing a point in the present embodiment comprises the following steps:
Step 1: prepare mixed-powder material:
Step 1.1: chitosan being dissolved in mass fraction is in the acetum of 3% ~ 5%, preparation mass fraction is the chitosan solution of 0.95%, stirs chitosan solution transparent to solution;
Step 1.2: add etimicin and be stirred to etimicin in the chitosan solution that step 1.1 obtains and dissolve, then leave standstill chitosan etimicin mixed solution to solution-stabilized;
Step 1.3: add the sodium tripolyphosphate solution that mass concentration is 0.85% in chitosan etimicin mixed solution, and stir, after chitosan bag medicine is completely heavy poly-, stops adding sodium tripolyphosphate solution;
Step 1.4: add NaOH solution to PH neutrality in the suspension that step 1.3 obtains; Again the neutral suspension obtained is carried out centrifugal treating on the centrifuge of 3500r/min, and gained precipitate is carried out lyophilization, then pulverize, the chitosan imbedded etimicin granule of obtained granular size 60 ~ 100nm;
Step 1.5: by the chitosan imbedded etimicin granule of step 1.4 gained, with the hydroxyapatite micro-sphere material that granular size is 60 ~ 80nm, be uniformly mixed for the proportionate relationship of 1:20 ~ 1:10 is poured in V-mixer in mass ratio, obtain mixed-powder material;
After obtaining above-mentioned mixed-powder material, prepare artificial bone scaffold below by biological 3D printing technique, the process of the present embodiment is:
Step 2.1: set up artificial bone scaffold three-dimensional CAD model according to sufferer individual character, is divided into the two-dimensional section model of spacing 0.6mm from the bottom to top by artificial bone scaffold three-dimensional CAD model;
Step 2.2: the liquid storage cylinder biological adhesive cyanoacrylate being loaded biological 3D printer, two-dimensional section model layers after the layering adopting biological 3D printer to set up according to step 2.1 prints artificial bone scaffold, every layer of print procedure is: the mixed-powder material that uniform spreading one deck step 1 obtains on forming worktable, then on mixed-powder material, spraying biological adhesive by biological 3D printer, is wherein 0.0004ml/mm by sprinkler biological adhesive cyanoacrylate adhesive average dose
2.
Although illustrate and describe embodiments of the invention above, be understandable that, above-described embodiment is exemplary, can not be interpreted as limitation of the present invention, those of ordinary skill in the art can change above-described embodiment within the scope of the invention when not departing from principle of the present invention and aim, revising, replacing and modification.
Claims (2)
1. a preparation method for the artificial bone scaffold of the qualitative medicine embedding of fixed point, is characterized in that: comprise the following steps:
Step 1: prepare mixed-powder material:
Step 1.1: chitosan being dissolved in mass fraction is in the acetum of 3% ~ 5%, preparation mass fraction is the chitosan solution of 0.95%, stirs chitosan solution transparent to solution;
Step 1.2: add etimicin and be stirred to etimicin in the chitosan solution that step 1.1 obtains and dissolve, then leave standstill chitosan etimicin mixed solution to solution-stabilized;
Step 1.3: add the sodium tripolyphosphate solution that mass concentration is 0.85% in chitosan etimicin mixed solution, and stir, after chitosan bag medicine is completely heavy poly-, stops adding sodium tripolyphosphate solution;
Step 1.4: add NaOH solution to PH neutrality in the suspension that step 1.3 obtains; Again centrifugal treating is carried out to the neutral suspension obtained, and gained precipitate is carried out lyophilization, then pulverize, the chitosan imbedded etimicin granule of obtained granular size 60 ~ 100nm;
Step 1.5: by the chitosan imbedded etimicin granule of step 1.4 gained, is the hydroxyapatite micro-sphere material of 60 ~ 80nm with granular size, is 1:20 ~ 1:10 mix homogeneously in mass ratio, obtains mixed-powder material;
Step 2: the liquid storage cylinder biological adhesive being loaded biological 3D printer, stores artificial bone scaffold threedimensional model in the control system of described biological 3D printer; Biological 3D printer layering is adopted to print artificial bone scaffold; Every one deck print procedure is: the mixed-powder material that uniform spreading one deck step 1 obtains on forming worktable, then on mixed-powder material, sprays biological adhesive by biological 3D printer.
2. the preparation method of the artificial bone scaffold of a kind of qualitative medicine embedding of fixing a point according to claim 1, is characterized in that: biological adhesive adopts cyanoacrylate.
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| CN105833341A (en) * | 2016-06-06 | 2016-08-10 | 西安博恩生物科技有限公司 | Method for preparing artificial bone scaffolds with transverse mechanical structures |
| WO2018022785A1 (en) * | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Three-dimensional printing processes using 1,1-di-activated vinyl compounds |
| CN107670117A (en) * | 2017-11-17 | 2018-02-09 | 迈海新型材料科技（固安）有限公司 | A kind of manufacture method of 3D printing artificial bone |
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| CN107823702A (en) * | 2017-11-17 | 2018-03-23 | 迈海新型材料科技（固安）有限公司 | A kind of manufacture method of 3D printing artificial bone |
| CN108379654A (en) * | 2018-05-06 | 2018-08-10 | 西北工业大学 | A kind of more gradients carry the preparation method of concentration artificial bone scaffold |
| CN109501255A (en) * | 2018-11-30 | 2019-03-22 | 孟兵 | A kind of production method using 3D printing technique production materials for use in skull-fixing |
| CN110025822A (en) * | 2019-04-21 | 2019-07-19 | 西北工业大学 | A kind of preparation method of the bone bracket with anti-infective characteristic |
| US10934411B2 (en) | 2016-09-30 | 2021-03-02 | Ppg Industries Ohio, Inc. | Curable compositions containing 1,1-di-activated vinyl compounds that cure by pericyclic reaction mechanisms |
| US10961403B2 (en) | 2016-07-26 | 2021-03-30 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds |
| US10987697B2 (en) | 2016-07-26 | 2021-04-27 | Ppg Industries Ohio, Inc. | Multi-layer curable compositions containing 1,1-di-activated vinyl compound products and related processes |
| US11078376B2 (en) | 2016-07-26 | 2021-08-03 | Ppg Industries Ohio, Inc. | Polyurethane coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
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| CN105833341A (en) * | 2016-06-06 | 2016-08-10 | 西安博恩生物科技有限公司 | Method for preparing artificial bone scaffolds with transverse mechanical structures |
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| US11466159B2 (en) | 2016-07-26 | 2022-10-11 | Ppg Industries Ohio, Inc. | Particles having surfaces functionalized with 1,1-di-activated vinyl compounds |
| US11634524B2 (en) | 2016-07-26 | 2023-04-25 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1 di-activated vinyl compounds and related coatings and processes |
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| US11136469B2 (en) | 2016-07-26 | 2021-10-05 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| CN109476081A (en) * | 2016-07-26 | 2019-03-15 | Ppg工业俄亥俄公司 | Use the three-dimensional printing method of the vinyl compound activated of 1,1- bis- |
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