CN115414259B - Customized type fixed denture and manufacturing method thereof - Google Patents
Customized type fixed denture and manufacturing method thereof Download PDFInfo
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- CN115414259B CN115414259B CN202211213963.0A CN202211213963A CN115414259B CN 115414259 B CN115414259 B CN 115414259B CN 202211213963 A CN202211213963 A CN 202211213963A CN 115414259 B CN115414259 B CN 115414259B
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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
- A61K6/802—Preparations for artificial teeth, for filling teeth or for capping teeth comprising ceramics
- A61K6/818—Preparations for artificial teeth, for filling teeth or for capping teeth comprising ceramics comprising zirconium oxide
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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
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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
- A61K6/896—Polyorganosilicon compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
Abstract
The application relates to the technical field of dental denture materials, and particularly discloses a customized fixed denture and a manufacturing method thereof. The customized fixed denture comprises the following components: nanometer zirconia, alumina, modified polysiloxane, quaternary ammonium salt antibacterial agent, 2-hydroxyethyl methacrylate phosphate, toughening agent, dispersing agent and deionized water, wherein the modified polysiloxane is hydroxyl modified polysiloxane; the manufacturing method comprises the following steps: the nanometer zirconia, alumina, dispersant, toughening agent and deionized water are mixed and ball milled to obtain mixed material, which is further mixed with 2-hydroxyethyl methacrylate phosphate, and modified polysiloxane grafted with quaternary ammonium salt group is further added to prepare denture material slurry, and the denture material slurry is printed to form the customized denture. The fixed denture manufactured by the method has good antibacterial property, lasting antibacterial effect and high bending strength.
Description
Technical Field
The application relates to the technical field of dental denture materials, in particular to a customized fixed denture and a manufacturing method thereof.
Background
Tooth and dentition defects are common diseases and frequently-occurring diseases in the treatment of oral diseases, and if the range of the tooth defects is large and the defect degree is serious, the dental defects need to be treated as early as possible by using a fixed denture. The fixed denture is a restoration for restoring one or a plurality of missing teeth in the dentition, and is connected with the prepared abutments or implants on the two sides of the missing teeth by using cement or a fixing device so as to restore the anatomical form and the physiological function of the missing teeth.
At present, the materials for manufacturing the fixed false tooth mainly comprise alloy, all-ceramic, high polymer resin and the like, wherein the all-ceramic material has the best biocompatibility, has no stimulation to gums and no anaphylactic reaction, and is the most widely applied oral cavity repairing material. However, since the temperature and humidity in the oral cavity are suitable for the growth and reproduction of many microorganisms, the denture is easy to grow bacteria in the use process, and the grown bacteria are easy to damage the health of patients and can corrode denture materials, so that the service life of the denture materials is influenced.
In the related art, in order to achieve the antibacterial effect of the denture, an organic antibacterial agent having the antibacterial effect is generally mixed into the original mixture, but the combination is only physical mixing, and the added antibacterial agent is easily decomposed and dissolved, so that the antibacterial effect is not durable. Thus, there is a need to produce a permanent denture with a durable antimicrobial effect.
Disclosure of Invention
In order to improve the antibacterial durability of the fixed denture, the application provides a customized fixed denture and a manufacturing method thereof.
The application provides a customized type fixed denture which adopts the following technical scheme:
the customized fixed denture comprises the following components in parts by weight: 6-8 parts of nano zirconia, 1-1.5 parts of alumina, 1-1.5 parts of modified polysiloxane, 0.6-1 part of quaternary ammonium salt antibacterial agent, 0.2-0.5 part of 2-hydroxyethyl methacrylate phosphate, 0.2-1 part of toughening agent, 0.2-0.4 part of dispersing agent and 3.5-5 parts of deionized water, wherein the modified polysiloxane is hydroxyl modified polysiloxane; by adopting the technical scheme, the quaternary ammonium salt antibacterial agent is introduced to enable the denture material to have antibacterial performance, but the antibacterial agent is simply mixed into the original mixed material, only physical mixing is carried out, the added antibacterial agent is easy to decompose and dissolve, and the antibacterial effect is not durable. The hydroxyl modified polysiloxane is adopted, the hydroxyl modified polysiloxane has hydrophilicity, a quaternary ammonium salt group with sterilizing effect in the quaternary ammonium salt antibacterial agent can be grafted to a modified hydroxyl modified polysiloxane chain to form a stable covalent bond with hydroxyl on the hydroxyl modified polysiloxane, the quaternary ammonium salt antibacterial group is fixed on the hydroxyl modified polysiloxane chain in a covalent bond form, so that the antibacterial effect of the fixed denture material is more stable, the combination is more firm and the antibacterial effect of the fixed denture material is prolonged; meanwhile, the polysiloxane added can be self-crosslinked and solidified to fill the pores of the nano zirconia, and also can form an interpenetrating network transition layer with the toughening agent, so that the problems of fragility and easy ceramic collapse of the full ceramic false tooth are solved; further, 2-hydroxyethyl methacrylate phosphate is selected as a binder, so that the binding force between the nano zirconia and polysiloxane with antibacterial groups is enhanced, and the durability of the antibacterial effect is enhanced.
Optionally, the modified polysiloxane is prepared by the following method:
(1) Mixing vinyl triethoxysilane, diphenyl diethoxysilane and dimethyl diethoxysilane, and sequentially adding deionized water and a catalyst;
(2) And (3) carrying out heat preservation reaction for 4 hours at the temperature of 75 ℃ to obtain a crude product, and removing alcohol and drying to obtain the hydroxyl modified polysiloxane.
Optionally, the reaction ratio of vinyltriethoxysilane, diphenyldiethoxysilane and dimethyldiethoxysilane is (2-7): 1:1.
Alternatively, the catalyst may be acetic acid or hydrochloric acid.
By adopting the technical scheme, when the hydroxyl modified polysiloxane is prepared, the prepared hydroxyl modified polysiloxane has higher hydroxyl mass fraction under the catalysis of the acid catalyst, and when the hydroxyl modified polysiloxane is matched with the quaternary ammonium salt antibacterial agent for use, the grafting efficiency of the quaternary ammonium salt antibacterial group is improved, and the antibacterial effect of the material is enhanced.
Optionally, the nano zirconia is tetragonal zirconia, and the grain size of the nano zirconia is 20-50nm.
By adopting the technical scheme, the tetragonal zirconia is adopted, has high and stable mechanical property, and the tetragonal zirconia with the grain diameter of 20-50nm has better bending strength and fracture toughness, and is suitable for serving as a dental repair material.
Optionally, the toughening agent is an epoxy resin.
By adopting the technical scheme, the epoxy group adopted has higher chemical activity, the hydroxyl modified polysiloxane in the components can open the ring of the epoxy resin, solidify and crosslink the epoxy resin to generate a reticular structure, and improve the toughness and the wear resistance of the denture material.
In a second aspect, the present application provides a method for manufacturing a customized denture, which adopts the following technical scheme:
(1) Preparation of a mixture A: uniformly mixing nano zirconia, alumina, a dispersing agent, epoxy resin and deionized water, and performing ball milling to obtain a mixed material A;
(2) Preparation of a mixed material B: irradiating polysiloxane with irradiation rays under vacuum condition, immersing the irradiated hydroxyl modified polysiloxane into a quaternary ammonium salt antibacterial agent, and reacting for 2-3h under anaerobic condition to obtain a mixed material B;
(3) Adding 2-hydroxyethyl methacrylate phosphate into the mixture A, stirring, and adding the mixture into the mixture B after stirring uniformly to prepare denture material slurry;
(4) Printing and forming the denture material slurry to obtain the customized fixed denture.
By adopting the scheme, firstly, the surface of the nano zirconia is roughened by using the alumina, a micro-concave interface is formed on the surface of the nano zirconia, so that the subsequently added 2-hydroxyethyl methacrylate phosphate can better play a role in adhesion, the binding force between various added substances and the zirconia is enhanced, the groups are more stable, and the prepared denture material has good antibacterial effect, long duration, no fragility and wear resistance.
Optionally, the dispersing agent in the step of mixing A is sodium dodecyl benzene sulfonate.
By adopting the technical scheme, the nano zirconia can be uniformly dispersed in the solvent without agglomerating.
In summary, the present application has the following beneficial effects:
1. because the quaternary ammonium salt antibacterial agent and the modified polysiloxane are added into the fixed denture material prepared by the application, the antibacterial group in the quaternary ammonium salt antibacterial agent can form a covalent bond with the hydroxyl modified polysiloxane, so that the antibacterial effect in the material is more stable, and the antibacterial time is longer; meanwhile, the added hydroxyl modified polysiloxane can be subjected to self-crosslinking, crosslinking and curing, so that the pores of the nano zirconia are filled, an interpenetrating network transition layer can be formed with the toughening agent epoxy resin, and the defects of fragility and wear resistance of the all-ceramic false tooth are overcome; the zirconium oxide and polysiloxane with antibacterial groups are further bonded by adopting 2-hydroxyethyl methacrylate phosphate, the 2-hydroxyethyl methacrylate phosphate with certain fluidity can penetrate into the ultrastructure on the surface of the zirconium oxide, and the embedding is formed after solidification, so that the antibacterial groups are combined more firmly, and the durability of the antibacterial effect of the denture material is enhanced.
2. In the application, epoxy resin is preferably used as a toughening agent, the epoxy resin has higher chemical activity of epoxy groups, and hydroxyl modified polysiloxane in the components contains active hydrogen, so that the epoxy resin can be subjected to ring opening, solidification and crosslinking to generate a reticular structure, and the toughness and the wear resistance of the denture material are improved.
3. According to the method, firstly, the surface of the nano zirconia is roughened by using alumina, a micro-concave interface is formed on the surface of the nano zirconia, so that the subsequently added 2-hydroxyethyl methacrylate phosphate can better play a role in adhesion, the binding force between various added substances and the zirconia is enhanced, the groups are more stable, and the prepared denture material has good antibacterial effect, lasting time and high bending strength.
Detailed Description
The present application is described in further detail below with reference to examples.
The sources of raw materials used in the present application are as follows:
TABLE 1 sources of raw materials
Preparation of modified polysiloxanes
Preparation example 1
The modified polysiloxane is prepared by the following method:
(1) Adding 1kg of vinyltriethoxysilane, 1kg of diphenyldiethoxysilane and 1kg of dimethyldiethoxysilane into deionized water, uniformly mixing, and adding ammonia water as a catalyst;
(2) The reaction was carried out at 75℃for 4 hours under heat preservation to give a crude product, and ethanol and water were removed in a rotary evaporator to give a hydroxy-modified polysiloxane.
Preparation example 2
The difference from preparation 1 is that the catalyst added is acetic acid.
Preparation example 3
The difference from preparation 1 is that the catalyst added is hydrochloric acid.
Preparation example 4
The difference from preparation example 1 is that vinyltriethoxysilane, diphenyldiethoxysilane and dimethyldiethoxysilane are added in a weight ratio of 2:1:1.
Preparation example 5
The difference from preparation example 1 is that vinyltriethoxysilane, diphenyldiethoxysilane and dimethyldiethoxysilane are added in a weight ratio of 7:1:1.
Preparation example 6
The difference from preparation example 1 is that vinyltriethoxysilane, diphenyldiethoxysilane and dimethyldiethoxysilane are added in a weight ratio of 8:1:1.
Examples
Example 1
A customized fixture denture, the preparation comprising the steps of:
(1) Preparation of a mixture A: uniformly mixing nano zirconia, alumina, a dispersing agent, a toughening agent and deionized water, and performing ball milling at 40r/min for 6 hours to obtain a mixed material A;
(2) Preparation of a mixed material B: irradiating the modified polysiloxane with gamma rays under a vacuum condition, immersing the irradiated hydroxyl modified polysiloxane into a quaternary ammonium salt antibacterial agent, and reacting for 2.5 hours under an anaerobic condition to obtain a mixed material B;
(3) Adding 2-hydroxyethyl methacrylate phosphate into the mixture A, stirring, and adding the mixture into the mixture B after stirring uniformly to prepare denture material slurry;
(4) Printing and forming the denture material slurry to obtain the customized fixed denture.
In this example, the modified polysiloxane prepared in preparation example 1 is used as the raw material, sodium dodecyl benzene sulfonate is used as the dispersing agent, and polymethyl methacrylate organosiloxane acrylate core-shell copolymer is used as the toughening agent.
Examples 2 to 3
A customized type fixed denture is different from example 1 in that the raw materials and the corresponding parts by weight are shown in Table 2.
TABLE 2 weight (kg) of the raw materials in examples 1 to 3
Example 4
A customized type of denture differs from example 1 in that the modified polysiloxane prepared in preparation example 2 was used as a raw material.
Example 5
A customized type of denture differs from example 1 in that the modified polysiloxane prepared in preparation example 3 was used as a raw material.
Example 6
A customized type of denture differs from example 1 in that the modified polysiloxane prepared in preparation example 4 was used as a raw material.
Example 7
A customized type of denture differs from example 1 in that the modified polysiloxane prepared in preparation example 5 was used as a raw material.
Example 8
A customized type of denture differs from example 1 in that the modified polysiloxane prepared in preparation example 6 was used as a raw material.
Example 9
A customized type of denture differs from example 1 in that the raw material is epoxy resin as the toughening agent.
Comparative example
Comparative example 1
A customized type denture, which is different from example 1 in that raw materials are unmodified polysiloxanes, the preparation comprises the following steps:
(1) Preparation of a mixture A: uniformly mixing nano zirconia, alumina, a dispersing agent, a toughening agent and deionized water, and performing ball milling at 40r/min for 6 hours to obtain a mixed material A;
(2) Preparation of a mixed material B: uniformly mixing polysiloxane and a quaternary ammonium salt antibacterial agent to obtain a mixed material B;
(3) Adding 2-hydroxyethyl methacrylate phosphate into the mixture A, stirring, and adding the mixture into the mixture B after stirring uniformly to prepare denture material slurry;
(4) Printing and forming the denture material slurry to obtain the customized fixed denture.
Comparative example 2
A customized type of denture was different from example 1 in that no modified polysiloxane was added in this comparative example. The preparation method comprises the following steps:
(1) Preparation of a mixture A: uniformly mixing nano zirconia, alumina, a dispersing agent, a toughening agent and deionized water, and performing ball milling at 40r/min for 6 hours to obtain a mixed material A;
(2) Adding the quaternary ammonium salt antibacterial agent and the 2-hydroxyethyl methacrylate phosphate into the mixture A, and uniformly stirring to prepare denture material slurry;
(3) Printing and forming the denture material slurry to obtain the customized fixed denture.
Comparative example 3
A customized fixture denture is different from example 1 in that 2-hydroxyethyl methacrylate phosphate is not added in this comparative example. The preparation method comprises the following steps:
(1) Uniformly mixing nano zirconia, alumina, a dispersing agent, a toughening agent and deionized water, and performing ball milling at 40r/min for 6 hours to obtain a mixed material A;
(2) Preparation of a mixed material B: irradiating polysiloxane with gamma rays under a vacuum condition, immersing the irradiated hydroxyl modified polysiloxane into a quaternary ammonium salt antibacterial agent, and reacting for 2.5h under an anaerobic condition to obtain a mixed material B;
(3) Mixing and stirring the mixture A and the mixture B uniformly to prepare denture material slurry;
(4) Printing and forming the denture material slurry to obtain the customized fixed denture.
Performance test
Detection method/test method
Experimental samples: the fixed denture materials obtained in examples 1 to 9 and comparative examples 1 to 3 were used.
The experimental method comprises the following steps:
1. the flexural strength of denture materials was tested according to GB 30367-2013/ISO 6872:2008 dental ceramic materials, and the test results are shown in Table 3.
2. Short-term bacteriostasis rate: the antibacterial performance of the denture material is detected according to the method of JC/T897-2014 antibacterial performance of antibacterial ceramic products, and the antibacterial rate is calculated.
3. Long-term bacteriostasis rate: soaking the prepared fixed denture in artificial saliva, and then placing the denture in a constant temperature condition of 36.3-37.2 ℃ for 180 days; then the antibacterial property of the denture material is detected according to the method in JC/T897-2014 antibacterial property of antibacterial ceramic products, and the test result is shown in Table 4.
TABLE 3 Performance test results
TABLE 4 Performance test results
As can be seen from the combination of examples 1-3 and comparative example 1 and the combination of tables 3 and 4, the long-term antibacterial effect of example 1 is significantly better than that of comparative example 1, which shows that the addition of hydroxy-modified polysiloxane to the denture material can make the antibacterial group in the quaternary ammonium salt antibacterial agent more easily form a covalent bond with the hydroxy-modified polysiloxane, and can effectively improve the antibacterial durability of the material.
As can be seen from the combination of examples 1 and 9 and comparative example 2 and the combination of tables 3 and 4, the breaking strength of the denture materials of examples 1 and 9 is obviously better than that of comparative example 2, which indicates that the hydroxyl modified polysiloxane can be self-crosslinked, crosslinked and cured, and fills the pores of the nano zirconia, and the hydroxyl modified polysiloxane contains active hydrogen, so that the epoxy resin can be ring-opened, cured and crosslinked to form a net structure, and the strength of the denture material is improved.
As can be seen from the combination of examples 1-3 and comparative example 3 and the combination of tables 3 and 4, the antibacterial durability of examples 1-3 is significantly better than that of comparative example 3, which shows that the addition of 2-hydroxyethyl methacrylate phosphate bonds zirconia with polysiloxane having antibacterial groups, and that 2-hydroxyethyl methacrylate phosphate can penetrate into the ultrastructure of the zirconia surface, form chimerism after curing, make the antibacterial groups combine more firmly, and enhance the durability of the antibacterial effect of denture materials.
As can be seen by combining examples 1, 4 and 5 and combining table 4, the antibacterial effect of examples 4 to 5 is better than that of example 1, demonstrating that the use of acetic acid or hydrochloric acid as a catalyst in the preparation of the hydroxy-modified polysiloxane can increase the hydroxy content, thereby increasing the grafting efficiency of the antibacterial groups of the quaternary ammonium salt and improving the antibacterial properties of the denture material.
As can be seen from the combination of examples 1 and examples 6 to 8 and the combination of tables 3 and 4, the denture materials prepared in examples 6 to 7 have better strength than those prepared in examples 1 and 8, and the effect of the raw material preparation ratio on the material properties when preparing the hydroxyl-modified polysiloxane is demonstrated, and the weight ratio of the raw materials vinyltriethoxysilane, diphenyldiethoxysilane and dimethyldiethoxysilane is (2 to 7): at 1:1, the material has better breaking strength.
The present embodiment is merely illustrative of the present application and is not intended to be limiting, and those skilled in the art, after having read the present specification, may make modifications to the present embodiment without creative contribution as required, but is protected by patent laws within the scope of the claims of the present application.
Claims (5)
1. The customized fixed denture is characterized by comprising the following components in parts by weight: 6-8 parts of nano zirconia, 1-1.5 parts of alumina, 1-1.5 parts of modified polysiloxane, 0.6-1 part of quaternary ammonium salt antibacterial agent, 0.2-0.5 part of 2-hydroxyethyl methacrylate phosphate, 0.2-1 part of toughening agent, 0.2-0.4 part of dispersing agent and 3.5-5 parts of deionized water, wherein the toughening agent is epoxy resin, the modified polysiloxane is hydroxyl modified polysiloxane, and the hydroxyl modified polysiloxane is prepared by adopting the following method:
(1) Mixing vinyl triethoxysilane, diphenyl diethoxysilane and dimethyl diethoxysilane, and sequentially adding deionized water and a catalyst;
(2) Performing heat preservation reaction for 2-4h at 70-75 ℃ to obtain a crude product, removing alcohol, and drying to obtain hydroxyl modified polysiloxane;
wherein the catalyst in the step (1) is acetic acid or hydrochloric acid.
2. The customized fixture denture of claim 1, wherein the weight ratio of vinyltriethoxysilane, diphenyldiethoxysilane, and dimethyldiethoxysilane is (2-7): 1:1.
3. The customized fixing denture according to claim 1, wherein the nano zirconia is tetragonal zirconia, and the particle size of the nano zirconia is 20-50nm.
4. A method of making a customized permanent denture according to any one of claims 1 to 3, comprising the steps of:
(1) Preparation of a mixture A: uniformly mixing nano zirconia, alumina, a dispersing agent, epoxy resin and deionized water, and performing ball milling to obtain a mixed material A;
(2) Preparation of a mixed material B: irradiating polysiloxane with irradiation rays under vacuum condition, immersing the irradiated hydroxyl modified polysiloxane into a quaternary ammonium salt antibacterial agent, and reacting for 2-3h under anaerobic condition to obtain a mixed material B;
(3) Adding 2-hydroxyethyl methacrylate phosphate into the mixture A, stirring, and adding the mixture into the mixture B after stirring uniformly to prepare denture material slurry;
(4) Printing and forming the denture material slurry to obtain the customized fixed denture.
5. The method of manufacturing a customized permanent denture according to claim 4, wherein: the dispersing agent in the step (1) is sodium dodecyl benzene sulfonate.
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