CN114181356B - Photosensitive resin, application thereof and preparation method of tooth holder - Google Patents
Photosensitive resin, application thereof and preparation method of tooth holder Download PDFInfo
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- CN114181356B CN114181356B CN202111495366.7A CN202111495366A CN114181356B CN 114181356 B CN114181356 B CN 114181356B CN 202111495366 A CN202111495366 A CN 202111495366A CN 114181356 B CN114181356 B CN 114181356B
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- 239000011347 resin Substances 0.000 title claims abstract description 36
- 229920005989 resin Polymers 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 18
- 229920001661 Chitosan Polymers 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 14
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 14
- 239000004970 Chain extender Substances 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 9
- 229920005862 polyol Polymers 0.000 claims description 17
- 150000003077 polyols Chemical class 0.000 claims description 17
- 229920005906 polyester polyol Polymers 0.000 claims description 14
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 12
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 11
- 230000006196 deacetylation Effects 0.000 claims description 11
- 238000003381 deacetylation reaction Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
- -1 benzyl dimethyl ketal Chemical compound 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 3
- 238000010146 3D printing Methods 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- 229940035437 1,3-propanediol Drugs 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 4
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 241000894006 Bacteria Species 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- 239000002245 particle Substances 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 15
- 125000003916 ethylene diamine group Chemical group 0.000 description 10
- 150000004676 glycans Chemical class 0.000 description 10
- 229920001282 polysaccharide Polymers 0.000 description 10
- 239000005017 polysaccharide Substances 0.000 description 10
- 238000001723 curing Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000007731 hot pressing Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical compound C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C7/00—Orthodontics, i.e. obtaining or maintaining the desired position of teeth, e.g. by straightening, evening, regulating, separating, or by correcting malocclusions
- A61C7/08—Mouthpiece-type retainers or positioners, e.g. for both the lower and upper arch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dentistry (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The application provides a photosensitive resin, application thereof and a preparation method of a tooth holder, wherein the photosensitive resin comprises the following raw material components in parts by weight: 100 parts of esters, 5-15 parts of photoinitiator, 30-50 parts of isocyanate, 5-25 parts of polyalcohol, 5-15 parts of chitosan oligomer, 3-8 parts of amine catalyst, 5-15 parts of chain extender, 15-25 parts of silicon dioxide particles and 10-15 parts of polyurethane; the esters are mixtures of lauryl acrylate and polyethylene glycol acrylate. The tooth holder printed by the photosensitive resin has the advantages of hardness, strong stretching, good antibacterial and anti-inflammatory effects, and can be used for avoiding the problems of bacteria and inflammation easily caused by long-term wearing of the traditional tooth holder.
Description
Technical Field
The application relates to the field of materials, in particular to a photosensitive resin, application thereof and a preparation method of a tooth holder.
Background
In orthodontic clinical work, a patient who finishes treatment needs to make a retainer in order to maintain the effect of correction to prevent the tendency of the teeth to recover from the original deformity. Therefore, the patient is recommended to wear for a lifetime after the treatment is finished, thereby ensuring the stability of the treatment effect. The retainer type comprises a Harley retainer and a transparent hot pressing retainer, and the transparent hot pressing retainer is mainly used. At present, the transparent hot pressing retainer in clinic is mainly manufactured by stamping, pouring a gypsum model, trimming the model and hot pressing. The transparent hot press holder has a good holding effect, but in clinical investigation, it is found that the membrane press holder patient frequently changes due to the loss, damage and long service time of the holder. Because the plaster model is damaged, the patient is required to get the model from the hospital again to replace the retainer, the traditional model taking has poor sensory impression on the patient, and because of the difference of the consistency and the air temperature of the mixing of the impression material, the material with excessive fluidity is placed in the oral cavity, so that the patient is easy to generate uncomfortable symptoms such as nausea, vomiting and the like.
Therefore, in the post-treatment holding stage, the experience of uncomfortable mold taking, time consumption and tedious flow caused to a patient when the holder is replaced is avoided, and the acquisition of permanently stored end data, the transparent holder with high accuracy and the like become problems to be solved in orthodontic clinic.
Disclosure of Invention
In view of the above-described drawbacks of the prior art, an object of the present application is to provide a photosensitive resin and use and a method for producing a dental retainer, for solving the problems in the prior art.
To achieve the above and other related objects, the present application is achieved by the following technical means.
The application provides a photosensitive resin, which comprises the following raw material components in parts by weight:
the esters are mixtures of lauryl acrylate and polyethylene glycol acrylate.
Preferably, the polyol is 10 to 20 parts by weight.
Preferably, the mass ratio of the lauryl acrylate to the polyethylene glycol acrylate is 1: (1-3).
Preferably, the photoinitiator is selected from one or more of benzyl dimethyl ketal and diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
Preferably, the isocyanate is selected from one or both of toluene diisocyanate and 1, 6-hexamethylene diisocyanate.
Preferably, the polyol is selected from one or more of polyester polyols or polyether polyols.
Preferably, the polyester polyol or polyether polyol has a number average molecular weight of 50000 to 90000.
Preferably, the chain extender is selected from one or more of water, ethylenediamine and 1, 3-propanediol.
Preferably, the chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 1000-20000, and the deacetylation degree is more than 0.5. The chitosan oligomer adopted in the application has good antibacterial and anti-inflammatory purposes, can be used for forming a product meeting the use requirements of the tooth holder together with other raw materials in the photosensitive resin through photocuring, can relieve inflammation in subsequent use, and has antibacterial effect.
Preferably, the amine catalyst is selected from one or more of 2, 2-dimorphine diethyl ether, bis (2-dimethylaminoethyl) ether, N-dimethylethanolamine and N, N '-trimethyl-N' -hydroxyethyl-diaminoethyl ether.
The application also provides a preparation method of the photosensitive resin, which is obtained by mixing the raw material components.
The application also discloses the application of the photosensitive resin as the material for the tooth holder.
The application also discloses a preparation method of the tooth holder, which adopts the photosensitive resin to carry out 3D printing and simultaneously carries out actinic radiation to carry out primary curing, and finally carries out secondary curing under the condition of moisture.
Preferably, the actinic radiation is ultraviolet light with an irradiation intensity of 13-18 mJ/cm 2 。
Preferably, the moisture condition refers to an air condition or a water vapor condition having a humidity of more than 65%.
The technical scheme of the application has the beneficial effects that:
the dental retainer printed and formed by the technical scheme of the application has high accuracy and good wearing comfort, brings convenience for repeatedly manufacturing the retainer in the later period, avoids uncomfortable feeling to a patient caused by repeatedly taking the mold, and shortens the chair side operation time of medical staff; the photosensitive resin material can be cured for multiple times, so that the finally formed tooth holder has hardness meeting the use requirement, has good antibacterial effect, and avoids the problems of bacteria and inflammation easily caused by long-term wearing of the traditional tooth holder.
Detailed Description
Further advantages and effects of the present application will become apparent to those skilled in the art from the disclosure of the present application, which is described by the following specific examples.
Before the embodiments of the application are explained in further detail, it is to be understood that the application is not limited in its scope to the particular embodiments described below; it is also to be understood that the terminology used in the examples of the application is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the application. The test methods in the following examples, in which specific conditions are not noted, are generally conducted under conventional conditions or under conditions recommended by the respective manufacturers.
Where numerical ranges are provided in the examples, it is understood that unless otherwise stated herein, both endpoints of each numerical range and any number between the two endpoints are significant both in the numerical range. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. In addition to the specific methods, devices, materials used in the embodiments, any methods, devices, and materials of the prior art similar or equivalent to those described in the embodiments of the present application may be used to practice the present application according to the knowledge of one skilled in the art and the description of the present application.
The number average molecular weight of the polyurethanes in the examples and comparative examples of the present application was1.0～1.5×10 5 The particle size of the silica particles is 50 to 150 meshes.
Example 1
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:1.
The photoinitiator is benzyl dimethyl ketal.
The isocyanate is toluene diisocyanate.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Example 2
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:2.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The isocyanate is toluene diisocyanate.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Example 3
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:2.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The isocyanate is 1, 6-hexamethylene diisocyanate.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Example 4
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:1.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The isocyanate is toluene diisocyanate.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Example 5
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:2.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Example 6
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:2.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Comparative example 1
The raw material components of the photosensitive resin in this comparative example include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:2.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Comparative example 2
The raw material components of the photosensitive resin in this embodiment include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:2.
The photoinitiator is diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Comparative example 3
This comparative example is a comparative example of example 1, which is different from example 1 in that no chitosan oligomer is added to the raw material components, and this raw material component as a comparative photosensitive resin includes:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:1.
The photoinitiator is benzyl dimethyl ketal.
The isocyanate is toluene diisocyanate.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Comparative example 4
The photosensitive resin in this comparative example is a comparative example of example 1, which is different from example 1 in that the chitosan oligomer and the silica particles are not added to the raw material components, and the raw material components in the comparative example include:
the esters are a mixture of lauryl acrylate and polyethylene glycol acrylate according to a mass ratio of 1:1.
The photoinitiator is benzyl dimethyl ketal.
The isocyanate is toluene diisocyanate.
The polyol is polyester polyol, and the number average molecular weight is 50000.
The chain extender is ethylenediamine.
The chitosan oligomer is O-carboxymethyl deacetylated polysaccharide, the number average molecular weight is 10000, and the deacetylation degree is more than 0.5.
The amine catalyst is bis (2-dimethylaminoethyl) ether or N, N-dimethylethanolamine.
Preparing a dental retainer from the photosensitive resin of any one of examples 1 to 6 and the photosensitive resin of comparative examples 1 to 4, mixing the raw material components of the photosensitive resin, and then performing ultraviolet actinic radiation simultaneously with 3D printing to preliminarily cure the dental retainer at an irradiation intensity of 15mJ/cm 2 And finally, performing secondary curing under the air condition of 85% humidity.
Performance tests on the dental retainers formed after curing of each example and each comparative example are shown in Table 1.
The dental retainers formed after curing of each example and comparative example were tested for antibacterial properties with reference to GB/T31402-2015 plastic surface antibacterial property test method, and the results are shown in table 2 below.
TABLE 1
TABLE 2
It can be seen from the table that the dental retainers formed in examples 1 to 6 of the present application have a certain hardness while having a good antibacterial effect, so that they are not deformed and have good use comfort.
The above embodiments are merely illustrative of the principles of the present application and its effectiveness, and are not intended to limit the application. Modifications and variations may be made to the above-described embodiments by those skilled in the art without departing from the spirit and scope of the application. Accordingly, it is intended that all equivalent modifications and variations of the application be covered by the claims, which are within the ordinary skill of the art, be within the spirit and scope of the present disclosure.
Claims (10)
1. The photosensitive resin is characterized by comprising the following raw material components in parts by weight:
the esters are mixtures of lauryl acrylate and polyethylene glycol acrylate.
2. The photosensitive resin of claim 1, wherein the photoinitiator is selected from one or more of benzyl dimethyl ketal and diphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide.
3. The photosensitive resin according to claim 1, wherein the isocyanate is one or both selected from toluene diisocyanate and 1, 6-hexamethylene diisocyanate.
4. The photosensitive resin of claim 1, wherein the polyol is selected from one or more of a polyester polyol or a polyether polyol.
5. The photosensitive resin according to claim 4, wherein the polyester polyol or polyether polyol has a number average molecular weight of 50000 to 90000.
6. The photosensitive resin of claim 1, wherein said chain extender is selected from one or more of water, ethylenediamine, 1, 3-propanediol.
7. The photosensitive resin of claim 1, wherein the chitosan oligomer is O-carboxymethyl chitosan, the number average molecular weight is 1000-20000, and the degree of deacetylation is greater than 0.5.
8. The photosensitive resin of claim 1, wherein said amine catalyst is selected from one or more of 2, 2-dimorphaned diethyl ether, bis (2-dimethylaminoethyl) ether, and N, N-dimethylethanolamine and N, N '-trimethyl-N' -hydroxyethyl-diaminoethyl ether.
9. Use of the photosensitive resin according to any one of claims 1 to 8 as a material for tooth holders.
10. A method for producing a dental retainer, characterized in that 3D printing is performed using the photosensitive resin according to any one of claims 1 to 8 while actinic radiation is performed for primary curing, and then secondary curing is performed under moisture conditions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111495366.7A CN114181356B (en) | 2021-12-09 | 2021-12-09 | Photosensitive resin, application thereof and preparation method of tooth holder |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111495366.7A CN114181356B (en) | 2021-12-09 | 2021-12-09 | Photosensitive resin, application thereof and preparation method of tooth holder |
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| CN114181356A CN114181356A (en) | 2022-03-15 |
| CN114181356B true CN114181356B (en) | 2023-09-01 |
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| US6075065A (en) * | 1996-12-20 | 2000-06-13 | Takeda Chemical Industries, Ltd. | Photocurable resin composition and a method for producing the same |
| CN111763288A (en) * | 2020-04-29 | 2020-10-13 | 苏州博理新材料科技有限公司 | Dual-curing phase-separated continuous 3D printing high-precision photosensitive resin composition |
| CN112250804A (en) * | 2020-10-23 | 2021-01-22 | 浙江大学 | Secondary curing 3D printing resin |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6075065A (en) * | 1996-12-20 | 2000-06-13 | Takeda Chemical Industries, Ltd. | Photocurable resin composition and a method for producing the same |
| CN111763288A (en) * | 2020-04-29 | 2020-10-13 | 苏州博理新材料科技有限公司 | Dual-curing phase-separated continuous 3D printing high-precision photosensitive resin composition |
| CN112250804A (en) * | 2020-10-23 | 2021-01-22 | 浙江大学 | Secondary curing 3D printing resin |
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