CN109512679B - Bi-component composition for dental root canal filling, preparation method and application thereof - Google Patents
Bi-component composition for dental root canal filling, preparation method and application thereof Download PDFInfo
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- CN109512679B CN109512679B CN201811424104.XA CN201811424104A CN109512679B CN 109512679 B CN109512679 B CN 109512679B CN 201811424104 A CN201811424104 A CN 201811424104A CN 109512679 B CN109512679 B CN 109512679B
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/50—Preparations specially adapted for dental root treatment
- A61K6/54—Filling; Sealing
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/76—Fillers comprising silicon-containing compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/77—Glass
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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Abstract
The present invention provides a two-component composition for dental root canal filling, comprising: a matrix component and a curing component; the matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent; the curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent. The composition obtained by the epoxy resin system, the specific curing agent and other additives in the specific proportion has high bonding strength and high flexural strength. Experimental results show that the composition has the advantages that the initial setting time is within 30min, the dentin bonding strength is greater than 5MPa, the flexural strength is greater than 70MPa, bonding defects and material cracking are avoided, and the composition is favorable for the lasting stability of dental root canal filling.
Description
Technical Field
The invention relates to the technical field of materials, in particular to a bi-component composition for dental root canal filling, a preparation method and application thereof.
Background
Various kinds of cement have been used in dentistry as a prosthetic filling material and to fix a prosthesis or an appliance in the oral cavity.
The existing common commercially available dental cement comprises zinc oxide, zinc phosphate, zinc polycarboxylate, glass ion, resin modified glass ion cement and the like. The main defects of the glass ion and resin modified glass ion cement are low strength, high water absorption value and dissolution value after curing; the zinc oxide cement material has the defects that the bonding strength is low (less than 3MPa), the bonding is not firm, the bonding defect is easy to generate, the risk of bacterial invasion is caused, the material cracking is easy to cause, the risk of bacterial invasion is caused, and the long-term stability of dental root canal filling is not facilitated.
Therefore, it is necessary to develop a dental root canal filling system having high bonding strength and high flexural strength.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide a two-component composition for dental root canal filling, which has high bonding strength and high flexural strength.
The present invention provides a two-component composition for dental root canal filling, comprising:
a matrix component and a curing component;
the matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent;
the curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent.
Preferably, the matrix component comprises: 40-70 parts of epoxy resin, 10-40 parts of toughening agent, 5-15 parts of developing agent, 10-30 parts of filler and 2-8 parts of thickening agent.
Preferably, the curing component comprises: 35-70 parts of curing agent, 10-60 parts of filler, 2-8 parts of thickening agent and 1-4 parts of coupling agent.
Preferably, the volume ratio of the matrix component to the curing component is 1: 1.
Preferably, in the matrix component:
the epoxy resin is selected from one or more of 3, 4-epoxy cyclohexyl methyl 3, 4-epoxy cyclohexyl formate and bis ((3, 4-epoxy cyclohexyl) methyl) adipate;
the toughening agent is selected from one or more of polyester resin and polysulfide rubber;
the developer is selected from one or more of barium sulfate, bismuth subcarbonate and calcium tungstate;
the filler is selected from one or more of strontium glass powder, barium glass powder, calcium oxide and calcium silicate;
the thickening agent is nano silicon dioxide.
Preferably, in the curing component:
the curing agent is selected from one or more of polyether amine, alicyclic amine, polythiol, amantadine, adamantane diamine and triethanolamine;
the filler is selected from one or more of strontium glass powder, barium glass powder, calcium oxide and calcium silicate;
the thickening agent is nano silicon dioxide;
the coupling agent is selected from one or more of KH550, KH560 and KH 570.
The present invention provides a method for preparing a two-component composition for dental root canal filling according to any one of the above aspects, comprising:
mixing epoxy resin, a toughening agent, a developing agent, a filler and a thickening agent to obtain a matrix component;
and mixing the curing agent, the filler, the thickening agent and the coupling agent to obtain the curing component.
Preferably, the mixing time is respectively and independently selected from 3-8 h; the mixing temperatures are respectively and independently selected from 20-35 ℃.
The invention provides an application of the composition in any one of the technical schemes in preparing a dental root canal filling material.
Compared with the prior art, the invention provides a two-component composition for dental root canal filling, which comprises: a matrix component and a curing component; the matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent; the curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent. The two-component composition for dental root canal filling of the present invention obtained by the above-mentioned auxiliaries such as the epoxy resin system, the specific curing agent and the like in the specific ratio has high bonding strength and high flexural strength. Experimental results show that the composition has the dentin bonding strength of more than 5MPa and the flexural strength of more than 70MPa within 30min of initial setting time (at 37 ℃), does not generate bonding defects and material cracking, and is favorable for the lasting stability of dental root canal filling.
Detailed Description
The invention provides a two-component composition for dental root canal filling, a preparation method and application thereof, and a person skilled in the art can realize the two-component composition by appropriately improving process parameters by referring to the content. It is expressly intended that all such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the scope of the invention. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the methods and applications described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of this invention without departing from the spirit and scope of the invention.
The present invention provides a two-component composition for dental root canal filling, comprising:
a matrix component and a curing component;
the matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent;
the curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent.
The components of the invention are all in parts by weight, and when the total amount is 100, the mass percentage is equal to.
The present invention provides a two-component composition for dental root canal filling comprising a matrix component.
The matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent;
the matrix component comprises 30-80 parts by weight of epoxy resin; preferably 40 to 70 parts by weight of an epoxy resin; more preferably 45 to 69 parts by weight of an epoxy resin; and most preferably 50 to 69 parts by weight of an epoxy resin.
According to the present invention, the epoxy resin is preferably selected from one or more of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexyl formate and bis ((3, 4-epoxycyclohexyl) methyl) adipate; more preferably, it comprises both 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexyl formate and bis ((3, 4-epoxycyclohexyl) methyl) adipate.
The specific ratio of the two is not limited in the present invention, and preferably (30 to 38): (20-31).
The invention creatively adopts the specific epoxy resin to be compounded with other components, particularly the specific two epoxy resins are compounded, and the bonding strength is better.
The matrix component comprises 5-50 parts by weight of a toughening agent; preferably 10 to 40 parts by weight of a toughening agent; more preferably 10 to 30 parts by weight of a toughening agent; the toughening agent is most preferably 10-25 parts by weight.
The toughening agent is selected from one or more of polyester resin and polysulfide rubber; the present invention is not limited in its source, and may be commercially available.
The matrix component comprises 2-20 parts by weight of a developer; preferably 5 to 15 parts by weight of a developer; more preferably 6 to 14 parts by weight of a developer; most preferably, the developer comprises 7 to 12 parts by weight of the developer.
According to the invention, the developer is selected from one or more of barium sulfate, bismuth subcarbonate and calcium tungstate; the present invention is not limited in its source, and may be commercially available.
The matrix component of the invention comprises 10-40 parts by weight of filler; preferably 10 to 30 parts by weight of a filler; more preferably 10 to 25 parts by weight of a filler; most preferably 10 to 20 parts by weight of a filler;
the filler is preferably selected from one or more of strontium glass powder, barium glass powder, calcium oxide and calcium silicate; the present invention is not limited in its source, and may be commercially available.
The matrix component comprises 1-10 parts by weight of a thickening agent; preferably, the thickener comprises 2 to 8 parts by weight; more preferably 2 to 6 parts by weight of a thickener; most preferably 2 to 4 parts by weight of a thickener.
The thickening agent is nano silicon dioxide. The present invention is not limited in its source, and may be commercially available.
According to the invention, the matrix component is finally prepared by matching the specific epoxy resin with the specific toughening agent, the developer, the filler and the thickener, and the matrix component is matched with the curing component to achieve the technical effects of good bonding strength and flexural strength.
The present invention provides a two-component composition for dental root canal filling comprising a curing component.
The curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent.
The curing component comprises 30-80 parts by weight of a curing agent; preferably 35 to 70 parts by weight of a curing agent; more preferably 40 to 65 parts by weight of a curing agent; most preferably 35 to 60 parts by weight of a curing agent; most preferably 40 to 55 parts by weight of a curing agent.
The curing agent is preferably selected from one or more of polyether amine, alicyclic amine, polythiol, amantadine, adamantane diamine and triethanolamine; more preferably two or more selected from the group consisting of polyetheramine, alicyclic amine, polythiol, amantadine, adamantanediamine and triethanolamine; most preferably three or more selected from polyetheramine, alicyclic amine, polythiol, amantadine, adamantanediamine and triethanolamine; most preferably four or more of polyetheramine, alicyclic amine, polythiol, amantadine, and triethanolamine.
The invention is not limited to any four of the above combinations, and as described in the examples, the combination of polyetheramine, polythiol, amantadine, and triethanolamine; may be a combination of alicyclic amines, polythiols, amantadine, and adamantanediamine; can be a combination of polythiol, amantadine, and triethanolamine.
The present invention is not limited to the ratio.
The invention selects the specific curing agent to participate in the curing reaction, so that the composition of the invention achieves the technical effects of good bonding strength and flexural strength.
The curing component comprises 10-40 parts by weight of filler; preferably 15 to 38 parts by weight of a filler; more preferably 20 to 36 parts by weight of a filler; most preferably 25 to 35 parts by weight of a filler;
the filler is preferably selected from one or more of strontium glass powder, barium glass powder, calcium oxide and calcium silicate; the present invention is not limited in its source, and may be commercially available.
The curing component comprises 1-10 parts by weight of a thickening agent; preferably, the thickener comprises 2 to 8 parts by weight; more preferably 2 to 7 parts by weight of a thickener; most preferably 3 to 6 parts by weight of a thickener.
The thickening agent is nano silicon dioxide. The present invention is not limited in its source, and may be commercially available.
The curing component comprises 0.5-5 parts by weight of a coupling agent; preferably 1 to 4 parts by weight of a coupling agent; more preferably 1 to 3 parts by weight of a coupling agent; most preferably 1-2 parts by weight of a coupling agent.
The coupling agent of the invention is preferably selected from one or more of KH550, KH560 and KH 570. The present invention is not limited in its source, and may be commercially available.
According to the invention, the volume ratio of the matrix component to the curing component is 1: 1.
According to the invention, the matrix component and the curing component are innovatively adopted to be matched, and particularly the synergistic effect of the specific epoxy resin, the curing agent and the rest components ensures that the finally prepared composition has high bonding strength and high flexural strength, does not generate bonding defects and material cracking, is favorable for the lasting stability of dental root canal filling, and fills up the industrial blank.
The present invention provides a method for preparing a two-component composition for dental root canal filling according to any one of the above aspects, comprising:
mixing epoxy resin, a toughening agent, a developing agent, a filler and a thickening agent to obtain a matrix component;
and mixing the curing agent, the filler, the thickening agent and the coupling agent to obtain the curing component.
The specific components and proportions of the epoxy resin, the toughening agent, the developer, the filler and the thickener are clearly described above and are not described herein any more, and the specific mixing and stirring manner of the present invention is not limited and is well known to those skilled in the art; the stirring time is preferably 6-8 h; stirring at normal temperature. The mixing temperature is selected from 20-35 ℃.
The concrete components and proportions of the curing agent, the filler, the thickening agent and the coupling agent are clearly described above, and are not described again, and the concrete mixing and stirring modes of the invention are not limited and are well known to those skilled in the art; the stirring time is preferably 6-8 h; stirring at normal temperature. The mixing temperature is selected from 20-35 ℃.
The invention provides an application of the composition in any one of the technical schemes in preparing a dental root canal filling material.
The present invention provides a two-component composition for dental root canal filling, comprising: a matrix component and a curing component; the matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent; the curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent. The two-component composition for dental root canal filling of the present invention obtained by the above-mentioned auxiliaries such as the epoxy resin system, the specific curing agent and the like in the specific ratio has high bonding strength and high flexural strength. Experimental results show that the composition has the dentin bonding strength of more than 5MPa and the flexural strength of more than 70MPa within 30min of initial setting time (at 37 ℃), does not generate bonding defects and material cracking, and is favorable for the lasting stability of dental root canal filling.
In order to further illustrate the present invention, a two-component composition for dental root canal filling, a method for preparing the same, and applications thereof according to the present invention will be described in detail with reference to examples.
Example 1
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is within 30min (at 37 ℃), dentin bonding strength is 6 +/-1 MPa, and flexural strength is 75 +/-5 MPa.
Example 2
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is within 30min (at 37 ℃), dentin bonding strength is 6 +/-1 MPa, and flexural strength is 70 +/-5 MPa.
Example 3
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is within 30min (at 37 ℃), dentin bonding strength is 6 +/-1 MPa, and flexural strength is 75 +/-5 MPa.
Example 4
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is within 30min (at 37 ℃), dentin bonding strength is 4 +/-1 MPa, and flexural strength is 50 +/-5 MPa.
Example 5
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is within 30min (at 37 ℃), dentin bonding strength is more than 4 +/-1 MPa, and flexural strength is 60 +/-5 MPa.
Comparative example 1
The following components were stirred together to form a catalyst liquid (% by mass)
Polycarboxylic acid 50
Aqueous solution 50
The following components were mixed together to form a base powder (% by mass)
And (3) testing results: the initial setting time is within 30min (at 37 ℃), the dentin bonding strength is less than 3MPa, the flexural strength is less than 15MPa, and the cured material is easy to be pulverized to generate medical risks.
Comparative example 2
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is within 30min (at 37 ℃), dentin bonding strength is more than 4 +/-1 MPa, and flexural strength is more than 55 +/-5 MPa. And bisphenol epoxy resins have the potential risk of estrogen aberration.
Comparative example 3
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is more than 90min (at 37 ℃), dentin bonding strength is more than 4 +/-1 MPa, and flexural strength is 50 +/-5 MPa.
Comparative example 4
The following components were stirred together to form the matrix component (% by mass):
the following components were stirred together to form the curing agent component (mass%):
and (3) mixing the raw materials of the matrix component and the curing agent component in proportion for 3-8 hours at normal temperature respectively through a mixing kettle.
And (3) testing results: initial setting time is 30-60 min (at 37 ℃), dentin bonding strength is more than 5 +/-1 MPa, and flexural strength is 45 +/-5 MPa.
Compared with comparative examples 1 to 4, the compositions provided in examples 1 to 5 all show significant improvement (p <0.05) in dentin bonding and flexural strength effects, which indicates that the composition of each component has significant synergistic effect.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. A two-component composition for dental root canal filling comprising:
a matrix component and a curing component; the volume ratio of the matrix component to the curing component is 1: 1;
the matrix component comprises: 30-80 parts of epoxy resin, 5-50 parts of toughening agent, 2-20 parts of developing agent, 10-40 parts of filler and 1-10 parts of thickening agent; the epoxy resin is selected from one or more of 3, 4-epoxy cyclohexyl methyl 3, 4-epoxy cyclohexyl formate and bis ((3, 4-epoxy cyclohexyl) methyl) adipate;
the toughening agent is selected from one or more of polyester resin and polysulfide rubber;
the developer is selected from one or more of barium sulfate, bismuth subcarbonate and calcium tungstate;
the filler is selected from one or more of strontium glass powder, barium glass powder, calcium oxide and calcium silicate;
the thickening agent is nano silicon dioxide;
the curing component comprises: 30-80 parts of curing agent, 10-40 parts of filler, 1-10 parts of thickening agent and 0.5-5 parts of coupling agent; the curing agent is selected from one or more of polyether amine, alicyclic amine, polythiol, amantadine, adamantane diamine and triethanolamine;
the filler is selected from one or more of strontium glass powder, barium glass powder, calcium oxide and calcium silicate;
the thickening agent is nano silicon dioxide;
the coupling agent is selected from one or more of KH550, KH560 and KH 570.
2. The composition of claim 1, wherein the matrix component comprises: 40-70 parts of epoxy resin, 10-40 parts of toughening agent, 5-15 parts of developing agent, 10-30 parts of filler and 2-8 parts of thickening agent.
3. The composition of claim 1, wherein the curing component comprises: 35-70 parts of curing agent, 10-20 parts of filler, 2-8 parts of thickening agent and 1-4 parts of coupling agent.
4. A method for preparing the two-component composition for dental root canal filling according to any one of claims 1 to 3, comprising:
mixing epoxy resin, a toughening agent, a developing agent, a filler and a thickening agent to obtain a matrix component;
and mixing the curing agent, the filler, the thickening agent and the coupling agent to obtain the curing component.
5. The method of claim 4, wherein the mixing time is independently selected from 3 to 8 hours; the mixing temperatures are respectively and independently selected from 20-35 ℃.
6. Use of the composition according to any one of claims 1 to 3 for preparing a dental root canal filling material.
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| JP7471870B2 (en) * | 2020-03-09 | 2024-04-22 | キヤノン株式会社 | Adhesive Composition |
| CN113304056B (en) * | 2021-05-21 | 2022-07-12 | 桂林市啄木鸟医疗器械有限公司 | Premixed strontium-doped calcium silicate-based bioactive preparation and preparation method and application thereof |
| CN115645605B (en) * | 2022-12-05 | 2024-04-26 | 苏州大学 | Developed bone cement and preparation method and application thereof |
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| CN101412896A (en) * | 2007-10-17 | 2009-04-22 | 比亚迪股份有限公司 | Bicomponent epoxy adhesive and preparation thereof |
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| CN101209228A (en) * | 2006-12-27 | 2008-07-02 | 华东理工大学 | Antibiotic dental prosthetic materials and preparation method thereof |
| CN101412896A (en) * | 2007-10-17 | 2009-04-22 | 比亚迪股份有限公司 | Bicomponent epoxy adhesive and preparation thereof |
| CN107537061A (en) * | 2016-06-23 | 2018-01-05 | 辽宁爱尔创生物材料有限公司 | A kind of preparation method of dental composite resin material and its product of preparation |
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