CN119113206A - An antibacterial bone cement modified with isobornyl acrylate - Google Patents
An antibacterial bone cement modified with isobornyl acrylate Download PDFInfo
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- CN119113206A CN119113206A CN202411293501.3A CN202411293501A CN119113206A CN 119113206 A CN119113206 A CN 119113206A CN 202411293501 A CN202411293501 A CN 202411293501A CN 119113206 A CN119113206 A CN 119113206A
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- bone cement
- isobornyl acrylate
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- 239000002639 bone cement Substances 0.000 title claims abstract description 111
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical group C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 43
- 239000007791 liquid phase Substances 0.000 claims abstract description 21
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 17
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 17
- 239000007790 solid phase Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract description 4
- 239000000523 sample Substances 0.000 description 10
- 206010018910 Haemolysis Diseases 0.000 description 9
- 230000008588 hemolysis Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 7
- 239000002504 physiological saline solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000006143 cell culture medium Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 244000137852 Petrea volubilis Species 0.000 description 1
- 206010067268 Post procedural infection Diseases 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000003519 biomedical and dental material Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 238000002784 cytotoxicity assay Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
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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
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- 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
- A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
-
- 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
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
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Abstract
本发明属于生物医学材料领域，公开了一种丙烯酸异冰片酯改性的抗菌骨水泥。本发明将丙烯酸异冰片酯(BA)作为一种新型单体，用于骨水泥的液相改性，最终制备出一种BA改性的抗菌骨水泥(BA骨水泥)，这是一种新型抗菌NLBC，抗菌活性、抗压强度和生物相容性俱佳，其优异的性能表明其在临床应用中具有广阔的前景。
The present invention belongs to the field of biomedical materials and discloses an antibacterial bone cement modified with isobornyl acrylate. The present invention uses isobornyl acrylate (BA) as a new monomer for liquid phase modification of bone cement, and finally prepares a BA-modified antibacterial bone cement (BA bone cement), which is a new antibacterial NLBC with excellent antibacterial activity, compressive strength and biocompatibility. Its excellent performance shows that it has broad prospects in clinical applications.
Description
Technical Field
The invention relates to the field of biomedical materials, in particular to isobornyl acrylate modified antibacterial bone cement.
Background
Polymethyl methacrylate (PMMA) bone cement is used as a common biomedical material and is widely applied to joint replacement, vertebroplasty and other surgical procedures. However, insufficient antimicrobial activity has been a concern. Staphylococcus aureus is the most common pathogenic bacteria in orthopaedics, and can cause postoperative infection, delayed healing and even failure of operation, and seriously affect prognosis and life quality of patients. To address this serious challenge, a traditional modification is to mix antibiotics into bone cement to make antibiotic-loaded bone cement (ALBC). Since Buchholz in 1969 added antibiotics to bone cements for the first time, studies on antibiotic-loaded bone cements (ALBC) have attracted considerable attention. However, this approach has problems of explosive release of antibiotics and bacterial resistance, limiting its further use in clinical applications. Against this background, the development of novel antibacterial bone cements has become one of the hot spots in the orthopaedics field.
The non-leaching antibacterial bone cement (NLBC) fixes the group with antibacterial activity on the bone cement through covalent connection or physical adsorption, so as to prepare the modified bone cement with long-term antibacterial activity and good contact bactericidal activity. However, there is currently no NLBC with excellent antimicrobial activity, mechanical strength, and biocompatibility, and a compromise is often required in other ways to prioritize certain properties, limiting further research and application of NLBC.
Disclosure of Invention
The invention aims to overcome the defects of the background technology and provide isobornyl acrylate modified antibacterial bone cement. The invention takes the isobornyl acrylate (BA) as a novel monomer for liquid phase modification of bone cement, and finally prepares the BA-modified antibacterial bone cement (BA bone cement), which is novel antibacterial NLBC, has excellent antibacterial activity, compressive strength and biocompatibility, and the excellent performance shows that the antibacterial bone cement has wide prospect in clinical application.
In order to achieve the aim of the invention, the isobornyl acrylate modified antibacterial bone cement is obtained by adding isobornyl acrylate into bone cement.
Further, in some embodiments of the invention, the bone cement is Polymethylmethacrylate (PMMA) bone cement.
Further, in some embodiments of the invention, the polymethylmethacrylate bone cement comprises a solid phase and a liquid phase, the mass ratio of the solid phase to the liquid phase being 1.5-2.5:1.
Further, in some embodiments of the invention, the mass ratio of solid phase to liquid phase in the polymethyl methacrylate bone cement is 1.6 to 2.2:1.
Further, in some embodiments of the invention, the mass ratio of solid phase to liquid phase in the polymethyl methacrylate bone cement is 1.65 to 2.05:1.
Further, in some embodiments of the invention, the concentration of isobornyl acrylate in the bone cement is 10.0% or more, for example 15.0% or more, and as another example 20.0% or more, preferably 25.0% or more, more preferably 30.0% or more, wherein the concentration of isobornyl acrylate in the bone cement is calculated as the mass ratio of isobornyl acrylate in the bone cement liquid phase.
Further, in some embodiments of the invention, the step of adding isobornyl acrylate to bone cement comprises the steps of adding isobornyl acrylate to a liquid phase of bone cement, and uniformly mixing the isobornyl acrylate with a solid phase of bone cement to prepare a bone cement sample.
Isobornyl acrylate (BA) is a liquid readily soluble in MMA, and the invention reports isobornyl acrylate (BA) modified non-leaching antibacterial bone cement (BA bone cement) for the first time. The bone cement has excellent antibacterial activity and mechanical strength, the compressive strength meets the ISO5833 standard, has no hemolytic activity, low in-vitro cytotoxicity and good application potential.
Drawings
FIG. 1 is a mechanical strength test result of the BA bone cement of the invention, wherein A is a stress-strain graph in which the slope represents the elastic modulus, the parallel lines represent the compressive strength, B is a statistical histogram of the compressive strength data, and C is a histogram of the elastic modulus data.
Detailed Description
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. Additional aspects and advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. It is to be understood that the following description is intended to be illustrative of the invention and not restrictive.
When an equivalent, concentration, or other value or parameter is expressed as a range, preferred range, or a range bounded by a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when ranges of "1 to 5" are disclosed, the described ranges should be construed to include ranges of "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a numerical range is described herein, unless otherwise indicated, the range is intended to include its endpoints and all integers and fractions within the range.
The indefinite articles "a" and "an" preceding an element or component of the invention are not limited to the requirement (i.e. the number of occurrences) of the element or component. Thus, the use of "a" or "an" should be interpreted as including one or at least one, and the singular reference of an element or component includes the plural reference unless the amount clearly dictates otherwise.
Furthermore, the descriptions of the terms "one embodiment," "some embodiments," "examples," "particular examples," or "some examples," etc., described below mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms are not necessarily for the same embodiment or example. The technical features of the respective embodiments of the present invention may be combined with each other as long as they do not collide with each other.
Isobornyl acrylate (BA) is a commercial reagent, and the structure is shown as follows:
Example 1
The preparation method of the BA bone cement comprises the following steps of preparing the formula and the grouping of the bone cement as shown in table 1. 10wt% and 30wt% represent mass proportions of the antibacterial monomer BA added to the liquid phase agent. Commercial PMMA bone cement without any antibacterial monomer added was used as a blank. The Polymethylmethacrylate (PMMA) bone cements referred to in the present invention may be selected from commercially available Eurofix brand, including solid and liquid phases, with a solid to liquid ratio of about 2:1.
Table 1 isobornyl acrylate modified antibacterial bone cements with different ratios
Preparation of bone cement standards according to Table 1, antibacterial monomer BA was mixed into the liquid phase in the corresponding proportions. And uniformly mixing the solid phase agent and the liquid phase agent at room temperature to prepare a cylindrical bone cement sample. The sample length was 12.0.+ -. 0.1mm and the diameter was 6.0.+ -. 0.1mm. And fixing the mould by using a woodworking clamp, taking out the mould after the bone cement is completely solidified, and polishing the mould by using sand paper, wherein the total mass is controlled to be 0.40+/-0.01 g so as to ensure that the top surface and the bottom surface of the bone cement are smooth. Finally, all samples were sterilized by ethylene oxide.
Example 2
BA bone Cement antibacterial Activity test A BA bone cement sample was immersed in physiological saline at a ratio of 0.1g/mL for 24 hours at room temperature to remove monomers whose surface did not participate in polymerization. The sample is then removed, sterilized, and set aside for use. Staphylococcus aureus (s.aureus) was first recovered and passaged to obtain a concentration of 0.5 x 10 8 CFU/mL. Subsequently, each set of bone cement samples was placed in a test tube containing 1mL of this concentration of bacterial solution. The CO 2 incubator was set at 37 ℃ and incubated for 6 hours. After the incubation, the samples were slowly rinsed with pure water to remove non-adhering or poorly adhering s.aureus on the bone cement surface. Then, the sample was placed in a test tube containing 5mL of physiological saline and subjected to shaking washing at a controlled time of 2 minutes using an ultrasonic shaking washer to remove tightly adhered s.aureus from the bone cement surface. After washing, the bone cement sample was removed and the sample solution was shaken thoroughly. 40. Mu.L of the sample solution was diluted 1:100 with 0.9% NaCl solution for plate coating. Incubated in a 37℃CO 2 incubator for 24 hours, the colony count was calculated, and the surface antibacterial rate was calculated. Experiments were repeated five times for each set of bone cement samples. The antibacterial rate of PMMA bone cement was set to 0.
The antibacterial activity of the BA bone cement disclosed by the invention is positively correlated with the content of BA, wherein the antibacterial rate of 10wt% of BA bone cement to staphylococcus aureus is 41.0+/-10.8%, and the antibacterial rate of 30wt% of BA bone cement is 81.0+/-3.1%. As shown in table 2 below.
TABLE 2 antibacterial efficacy of BA bone cements against Staphylococcus aureus
| Bone cement | Antibacterial rate |
| PMMA bone cement | 0% |
| 10% BA bone cement | 41.0±10.8% |
| 30% BA bone cement | 81.0±3.1% |
Example 3
Mechanical strength testing was performed by incubating bone cement samples (5 per group) for 24 hours at 37 ℃ and 100% humidity. The deformation-load curve of the bone cement samples was plotted at room temperature using a materials tester (MTS 809, bose Co., U.S.A.) at a loading rate of 20 mm/min. From these curves, compressive strength and elastic modulus of each bone cement sample were calculated. All operations are performed according to the requirements and standards of ISO 5833. The test results are shown in figure 1.
Example 4
Preparation of bone Cement extract A bone cement standard sample was placed in cell culture medium (DMEM/F12 medium) and physiological saline (0.9% NaCl solution), respectively, and the ratio of sample to liquid was set to 0.2g/mL according to GB/T16886 standard. The cell culture media was incubated for 24 hours at 37℃in a 5% CO 2 incubator, and the saline set was incubated for 30 minutes under the same conditions. The obtained cell culture medium extract was used for in vitro cytotoxicity assay, while physiological saline extract was used for hemolysis assay.
Determination of the haemolysis Rate according to GB/T16886 standard, the bone cement extract is placed in a sterile centrifuge tube and 200. Mu.L of a 2% rabbit red blood cell suspension are added. Further, 200. Mu.L of a 2% rabbit red blood cell suspension was added to 1.8mL of physiological saline and pure water, respectively, as negative and positive controls. After incubation for 1 hour in a 37℃5% CO 2 incubator, centrifugation was carried out at 3000rpm for 5 minutes. The Optical Density (OD) of the supernatant was measured at 545nm using a spectrophotometer. Hemolysis was assessed by visual inspection of the clarity of the supernatant. Three tests were performed for each set of bone cement samples. The Haemolysis Rate (HR) was calculated using the following formula:
Where OD T1 is the optical density of the experimental group solution, OD N1 is the optical density of the negative control, and OD P is the optical density of the positive control. As shown in the following table, a hemolysis ratio of less than 5% is considered to be that no hemolysis occurred. The BA bone cement obtained by the invention is similar to the bone cement sold in the market, and does not cause hemolysis.
TABLE 3 determination of hemolysis Rate of BA bone cements
| Bone cement | Rate of hemolysis |
| PMMA bone cement | 2.35±1.22% |
| 10% BA bone cement | 2.37±1.24% |
| 30% BA bone cement | 3.13±1.37% |
It will be readily appreciated by those skilled in the art that the foregoing is merely illustrative of the present invention and is not intended to limit the invention, but any modifications, equivalents, improvements or the like which fall within the spirit and principles of the present invention are intended to be included within the scope of the present invention.
Claims (10)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202411293501.3A CN119113206A (en) | 2024-09-14 | 2024-09-14 | An antibacterial bone cement modified with isobornyl acrylate |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202411293501.3A CN119113206A (en) | 2024-09-14 | 2024-09-14 | An antibacterial bone cement modified with isobornyl acrylate |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910259A (en) * | 1988-09-26 | 1990-03-20 | Wolff & Kaaber A/S | Bone cement |
| WO2000047214A1 (en) * | 1999-02-09 | 2000-08-17 | Sloan-Kettering Institute For Cancer Research | Anti-resorptive bone cements and allogeneic, autografic, and xenografic bone grafts |
| US20100256242A1 (en) * | 2009-04-07 | 2010-10-07 | Antonucci Joseph M | Polymerizable biomedical composition |
| CN104231507A (en) * | 2013-06-10 | 2014-12-24 | 贺利氏古萨有限公司 | Moulded parts made of pmma powder as simple dosing aid in the manufacture of dental prostheses |
| US20180303616A1 (en) * | 2017-04-21 | 2018-10-25 | Warsaw Orthopedic, Inc. | 3-d printing of bone grafts |
-
2024
- 2024-09-14 CN CN202411293501.3A patent/CN119113206A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910259A (en) * | 1988-09-26 | 1990-03-20 | Wolff & Kaaber A/S | Bone cement |
| WO2000047214A1 (en) * | 1999-02-09 | 2000-08-17 | Sloan-Kettering Institute For Cancer Research | Anti-resorptive bone cements and allogeneic, autografic, and xenografic bone grafts |
| US20100256242A1 (en) * | 2009-04-07 | 2010-10-07 | Antonucci Joseph M | Polymerizable biomedical composition |
| CN104231507A (en) * | 2013-06-10 | 2014-12-24 | 贺利氏古萨有限公司 | Moulded parts made of pmma powder as simple dosing aid in the manufacture of dental prostheses |
| US20180303616A1 (en) * | 2017-04-21 | 2018-10-25 | Warsaw Orthopedic, Inc. | 3-d printing of bone grafts |
Non-Patent Citations (1)
| Title |
|---|
| XUELI SUN ET AL.: ""Antibacterial Adhesion of Polymethyl Methacrylate Modified by Borneol Acrylate"", 《ACS PUBLICATIONS》, 31 December 2016 (2016-12-31), pages 1 - 22 * |
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