CN106176251A - A kind of polyurethane dental prosthetic material and preparation and application thereof - Google Patents
A kind of polyurethane dental prosthetic material and preparation and application thereof Download PDFInfo
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- CN106176251A CN106176251A CN201610776730.XA CN201610776730A CN106176251A CN 106176251 A CN106176251 A CN 106176251A CN 201610776730 A CN201610776730 A CN 201610776730A CN 106176251 A CN106176251 A CN 106176251A
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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
- A61K6/893—Polyurethanes
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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
- A61K6/838—Phosphorus compounds, e.g. apatite
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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
- A61K6/84—Preparations for artificial teeth, for filling teeth or for capping teeth comprising metals or alloys
- A61K6/844—Noble metals
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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
- A61K6/887—Compounds obtained 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
- A61K6/80—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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- Oral & Maxillofacial Surgery (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dental Preparations (AREA)
Abstract
The invention belongs to dental prosthetic material technical field, specifically disclose a kind of polyurethane dental prosthetic material and preparation and application thereof.Described polyurethane dental prosthetic material is made up of polyurethane resin, polyvinyl pyrrolidone, modifted-nano-hydroxyapatite, polymerization inhibitor, polyester resin, reactive diluent and light trigger, and each constituent mass number is as follows: polyurethane resin 40～65 mass parts, polyvinyl pyrrolidone 3～5 mass parts, modifted-nano-hydroxyapatite 13～25 mass parts, polymerization inhibitor 1～5 mass parts, polyester resin 8～20 mass parts, reactive diluent 9～20 mass parts, light trigger 1～10 mass parts.The present invention, by adding modifted-nano-hydroxyapatite, polyvinyl pyrrolidone and Polyethylene Glycol, obtains that viscosity is little, curing rate is fast, glossiness is high and the polyurethane dental prosthetic material of excellent antibacterial performance.
Description
Technical field
The invention belongs to dental prosthetic material technical field, be specifically related to a kind of polyurethane dental prosthetic material and preparation thereof
With application.
Background technology
Preferably dental prosthetic material has effectively and durable antibiotic performance, and pre-anticariogenic generation improves repair materials
Durability, the preventing and treating to dental caries and other bacterial infection oral disease has far-reaching influence.The dental prosthetic material of 3M company
Material has almost monopolized the dental prosthetic market of existing whole China, but, as market high share occupant, the material of 3M company
Substantially without antibacterial action.The antibacterial wide spectrum of quaternary ammonium salt, low toxicity, stable performance, low corrosion and there is long-term biological effect, quilt
Extensively application, such as, is bonded to crosslinkable polymeric quaternary antibacterial monomer in dental resin sill, gives resin base material
Material is with anti-microbial property；But, this kind of monomer is less, and complicated process of preparation is expensive.
After the sixties in 20th century, UV-curing technology is used for dental prosthetic material field.Ultraviolet light polymerization is profit
Being the energy with ultraviolet light, initiation has chemically active liquid formulations and realizes being converted into by liquid the rapid-action solidification of solid-state
Process.Quickly, easy and simple to handle, color and luster is good for the solidification of ultraviolet light polymerization dental prosthetic material, and intensity and plasticity are high, adhesive effect
Good, and can sanding and polishing after solidifying so that it is deeply favored by market in Dental Erosion field.
Summary of the invention
In order to overcome the shortcoming of prior art with not enough, the primary and foremost purpose of the present invention is to provide a kind of polyurethane dentistry to repair
Multiple material, described polyurethane dental prosthetic material is by adding modifted-nano-hydroxyapatite, polyvinyl pyrrolidone and gathering
Ethylene glycol, obtains that viscosity is little, curing rate is fast, glossiness is high and the polyurethane dental prosthetic material of excellent antibacterial performance.
Another object of the present invention is to provide the preparation method of above-mentioned polyurethane dental prosthetic material, described preparation method
Step is simple, easy and simple to handle.
It is still another object of the present invention to provide the application of above-mentioned polyurethane dental prosthetic material.
The purpose of the present invention is achieved through the following technical solutions:
A kind of polyurethane dental prosthetic material, it is by polyurethane resin, polyvinyl pyrrolidone, modified Nano hydroxy-apatite
Stone, polymerization inhibitor, polyester resin, reactive diluent and light trigger composition, each constituent mass number is as follows: polyurethane resin 40～
65 mass parts, polyvinyl pyrrolidone 3～5 mass parts, modifted-nano-hydroxyapatite 13～25 mass parts, polymerization inhibitor 1～5
Mass parts, polyester resin 8～20 mass parts, reactive diluent 9～20 mass parts, light trigger 1～10 mass parts.
Described polyurethane resin is polyurethane acrylic resin prepolymer.
Described modifted-nano-hydroxyapatite is made up of nanometer hydroxyapatite, Polyethylene Glycol, nanometer silver and glycerol, each group
Point mass fraction is as follows: nanometer hydroxyapatite 50～80 mass parts, Polyethylene Glycol 10～30 mass parts, nanometer silver 0.01～
0.1 mass parts, glycerol 10～20 mass parts.
Described polymerization inhibitor is hydroquinone or MEHQ.
Described polyester resin is polyester acrylate resin prepolymer.
Described reactive diluent is 2-(Acryloyloxy)ethanol, hydroxyethyl methylacrylate, Hydroxypropyl acrylate, methacrylic acid
Hydroxypropyl acrylate, isobornyl thiocyanoacetate, methyl isobornyl thiocyanoacetate, 1,6-hexanediyl ester, tri (propylene glycol) diacrylate and three
One in hydroxymethyl-propane triacrylate.
Described light trigger is benzophenone, isopropyl thioxanthone, 2-hydroxy-2-methyl-1-phenyl-1-acetone and 1-
One in hydroxy-cyciohexyl phenyl ketone.
The preparation method of a kind of polyurethane dental prosthetic material, described method specifically comprises the following steps that
(1) in first reactor, 50～80 mass parts nanometer hydroxyapatites and 10～30 mass parts Polyethylene Glycol are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.01～0.1 mass parts nanometer silver and 10～
20 mass parts glycerol, under the rotating speed of 2000 revs/min, stir 6 hours at 60 DEG C, after being cooled to room temperature, obtain modification and receive
Rice hydroxyapatite, standby；
(2) in second reactor, 40～65 mass parts polyurethane resins and 3～5 mass parts polyvinylpyrrolidones are added
Ketone, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, add what 13～25 mass parts steps (1) prepared
Modifted-nano-hydroxyapatite and 1～5 mass parts polymerization inhibitors, under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；
Finally, add 8～20 mass parts polyester resin, 9～20 mass parts reactive diluent and 1～10 mass parts light triggers,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C, after being cooled to room temperature, obtain described polyurethane dental prosthetic material
Material.
The application of a kind of polyurethane dental prosthetic material, described application is that polyurethane dental prosthetic material is led in dental prosthetic
Application in territory.
Compared with prior art, the present invention has the following advantages and beneficial effect:
(1) polyurethane dental prosthetic material of the present invention, by being modified nanometer hydroxyapatite, makes nano-hydroxy
Apatite energy Stable distritation is among system；
(2) polyurethane dental prosthetic material of the present invention, by adding polyvinyl pyrrolidone and Polyethylene Glycol, due to
The stably dispersing effect of the polymer of polyvinyl pyrrolidone and Polyethylene Glycol, and mutually adsorb work between active group
With so that nanometer hydroxyapatite and nanometer silver are evenly distributed among system, obtain that viscosity is little, curing rate fast, glossiness
The high polyurethane dental prosthetic material with excellent antibacterial performance.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
Embodiment 1
The polyurethane dental prosthetic material of the present embodiment is prepared by step and prepares:
(1) in first reactor, 50 mass parts nanometer hydroxyapatites and 30 mass parts polyethylene glycol 200s are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.05 mass parts nanometer silver and 20 mass parts are sweet
Oil, under the rotating speed of 2000 revs/min, stirs 6 hours at 60 DEG C, after being cooled to room temperature, obtains modified Nano hydroxy-apatite
Stone, standby；
(2) in second reactor, 48 mass parts polyurethane resins (Changxing chemistry 6143A-80) and the poly-second of 5 mass parts are added
Vinyl pyrrolidone K30, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, 15 mass parts steps are added
(1) modifted-nano-hydroxyapatite prepared and 5 mass parts hydroquinone, under the rotating speed of 2000 revs/min, stir at 60 DEG C
Mix 2 hours；Finally, add 8 mass parts polyester resin (Changxing chemistry 6390F), 9 mass parts 1,6-hexanediyl ester and
10 mass parts benzophenone, under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C, after being cooled to room temperature, obtain institute
The polyurethane dental prosthetic material stated.
The properties of the polyurethane dental prosthetic material that the present embodiment prepares is:
(1) viscosity: 1900 milli pascal seconds；
(2) hardening time: 20 seconds；
(3) outward appearance: transparent, glossiness is fine；
(4) anti-microbial property of the paint film of antimicrobial nano water paint is: to colibacillary antibiotic rate 95%, to Staphylococcus aureus
The antibiotic rate 95% of bacterium.
Embodiment 2
The polyurethane dental prosthetic material of the present embodiment is prepared by step and prepares:
(1) in first reactor, 80 mass parts nanometer hydroxyapatites and 10 mass parts polyethylene glycol 200s are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.01 mass parts nanometer silver and 10 mass parts are sweet
Oil, under the rotating speed of 2000 revs/min, stirs 6 hours at 60 DEG C, after being cooled to room temperature, obtains modified Nano hydroxy-apatite
Stone, standby；
(2) in second reactor, 65 mass parts polyurethane resins (Changxing chemistry 6143A-80) and the poly-second of 3 mass parts are added
Vinyl pyrrolidone K30, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, 13 mass parts steps are added
(1) modifted-nano-hydroxyapatite prepared and 1 mass parts hydroquinone, under the rotating speed of 2000 revs/min, stir at 60 DEG C
Mix 2 hours；Finally, add 8 mass parts polyester resin (Changxing chemistry 6390F), 9 mass parts 1,6-hexanediyl ester and
1 mass parts benzophenone, under the rotating speed of 2000 revs/min, stirs 2 hours at 60 DEG C, after being cooled to room temperature, obtains described
Polyurethane dental prosthetic material.
The properties of the polyurethane dental prosthetic material that the present embodiment prepares is:
(1) viscosity: 1900 milli pascal seconds；
(2) hardening time: 25 seconds；
(3) outward appearance: transparent, glossiness is fine；
(4) anti-microbial property of the paint film of antimicrobial nano water paint is: to colibacillary antibiotic rate 85%, to Staphylococcus aureus
The antibiotic rate 86% of bacterium.
Embodiment 3
The polyurethane dental prosthetic material of the present embodiment is prepared by step and prepares:
(1) in first reactor, 70 mass parts nanometer hydroxyapatites and 18 mass parts PEG400s are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.1 mass parts nanometer silver and 12 mass parts glycerol,
Under the rotating speed of 2000 revs/min, stir 6 hours at 60 DEG C, after being cooled to room temperature, obtain modifted-nano-hydroxyapatite,
Standby；
(2) in second reactor, 45 mass parts polyurethane resins (Changxing chemistry 6143A-80) and the poly-second of 4 mass parts are added
Vinyl pyrrolidone K30, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, 25 mass parts steps are added
(1) modifted-nano-hydroxyapatite prepared and 2 mass parts MEHQ, under the rotating speed of 2000 revs/min, at 60 DEG C
Lower stirring 2 hours；Finally, 9 mass parts polyester resin (Changxing chemistry 6390F), 10 mass parts trimethylolpropane tris third are added
Olefin(e) acid ester and 5 mass parts 2-hydroxy-2-methyl-1-phenyl-1-acetone, under the rotating speed of 2000 revs/min, stir at 60 DEG C
2 hours, after being cooled to room temperature, obtain described polyurethane dental prosthetic material.
The properties of the polyurethane dental prosthetic material that the present embodiment prepares is:
(1) viscosity: 2100 milli pascal seconds；
(2) hardening time: 20 seconds；
(3) outward appearance: transparent, glossiness is fine；
(4) anti-microbial property of the paint film of antimicrobial nano water paint is: to colibacillary antibiotic rate 99%, to Staphylococcus aureus
The antibiotic rate 99% of bacterium.
Embodiment 4
The polyurethane dental prosthetic material of the present embodiment is prepared by step and prepares:
(1) in first reactor, 75 mass parts nanometer hydroxyapatites and 10 mass parts PEG400s are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.02 mass parts nanometer silver and 15 mass parts are sweet
Oil, under the rotating speed of 2000 revs/min, stirs 6 hours at 60 DEG C, after being cooled to room temperature, obtains modified Nano hydroxy-apatite
Stone, standby；
(2) in second reactor, 40 mass parts polyurethane resins (Changxing chemistry 6143A-80) and the poly-second of 3 mass parts are added
Vinyl pyrrolidone K30, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, 13 mass parts steps are added
(1) modifted-nano-hydroxyapatite prepared and 3 mass parts MEHQ, under the rotating speed of 2000 revs/min, at 60 DEG C
Lower stirring 2 hours；Finally, 20 mass parts polyester resin (Changxing chemistry 6390F), 20 mass parts isobornyl thiocyanoacetates and 1 mass are added
Part 2-hydroxy-2-methyl-1-phenyl-1-acetone, under the rotating speed of 2000 revs/min, stirs 2 hours at 60 DEG C, is cooled to
After room temperature, obtain described polyurethane dental prosthetic material.
The properties of the polyurethane dental prosthetic material that the present embodiment prepares is:
(1) viscosity: 1900 milli pascal seconds；
(2) hardening time: 25 seconds；
(3) outward appearance: transparent, glossiness is fine；
(4) anti-microbial property of the paint film of antimicrobial nano water paint is: to colibacillary antibiotic rate 93%, to Staphylococcus aureus
The antibiotic rate 92% of bacterium.
Embodiment 5
The polyurethane dental prosthetic material of the present embodiment is prepared by step and prepares:
(1) in first reactor, 60 mass parts nanometer hydroxyapatites and 25 mass parts polyethylene glycol 200s are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.05 mass parts nanometer silver and 15 mass parts are sweet
Oil, under the rotating speed of 2000 revs/min, stirs 6 hours at 60 DEG C, after being cooled to room temperature, obtains modified Nano hydroxy-apatite
Stone, standby；
(2) in second reactor, 50 mass parts polyurethane resins (Changxing chemistry 6143A-80) and the poly-second of 4 mass parts are added
Vinyl pyrrolidone K30, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, 20 mass parts steps are added
(1) modifted-nano-hydroxyapatite prepared and 3 mass parts MEHQ, under the rotating speed of 2000 revs/min, at 60 DEG C
Lower stirring 2 hours；Finally, 9 mass parts polyester resin (Changxing chemistry 6390F), 9 mass parts trimethylolpropane tris propylene are added
Acid esters and 5 mass parts 2-hydroxy-2-methyl-1-phenyl-1-acetone, under the rotating speed of 2000 revs/min, stir 2 at 60 DEG C
Hour, after being cooled to room temperature, obtain described polyurethane dental prosthetic material.
The properties of the polyurethane dental prosthetic material that the present embodiment prepares is:
(1) viscosity: 2000 milli pascal seconds；
(2) hardening time: 20 seconds；
(3) outward appearance: transparent, glossiness is fine；
(4) anti-microbial property of the paint film of antimicrobial nano water paint is: to colibacillary antibiotic rate 96%, to Staphylococcus aureus
The antibiotic rate 95% of bacterium.
Polyurethane dental prosthetic material described in above-described embodiment is solidified by ultraviolet light irradiation, and ultraviolet light irradiation is at height
Pressure mercury lamp tracked machine is carried out, and the power of high voltage mercury lamp is 3kW, and each performance test methods is as follows:
(1) viscosity test: before solidification, by the rotary viscosity of Brookfield DV-II+PRO viscometer test sample, test temperature
Degree is 25 DEG C；
(2) hardening time: the exposure total time of ultraviolet light；
(3) outward appearance: after solidification, the transparency of range estimation sample and glossiness；
(4) anti-microbial property: antibiotic rate is tested by " measurement of ISO 22196-2007 frosting antibacterial activity ".
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not by above-described embodiment
Limit, the change made under other any spirit without departing from the present invention and principle, modify, substitute, combine, simplify,
All should be the substitute mode of equivalence, within being included in protection scope of the present invention.
Claims (9)
1. a polyurethane dental prosthetic material, it is characterised in that described polyurethane dental prosthetic material is by polyurethane resin, poly-
Vinyl pyrrolidone, modifted-nano-hydroxyapatite, polymerization inhibitor, polyester resin, reactive diluent and light trigger composition, respectively
Constituent mass number is as follows: polyurethane resin 40～65 mass parts, polyvinyl pyrrolidone 3～5 mass parts, modified Nano hydroxyl
Base apatite 13～25 mass parts, polymerization inhibitor 1～5 mass parts, polyester resin 8～20 mass parts, reactive diluent 9～20 mass
Part, light trigger 1～10 mass parts.
Polyurethane dental prosthetic material the most according to claim 1, it is characterised in that described polyurethane resin is polyurethane
Acrylic resin prepolymer.
Polyurethane dental prosthetic material the most according to claim 1, it is characterised in that described modifted-nano-hydroxyapatite
Being made up of nanometer hydroxyapatite, Polyethylene Glycol, nanometer silver and glycerol, each constituent mass number is as follows: nanometer hydroxyapatite
50～80 mass parts, Polyethylene Glycol 10～30 mass parts, nanometer silver 0.01～0.1 mass parts, glycerol 10～20 mass parts.
Polyurethane dental prosthetic material the most according to claim 1, it is characterised in that described polymerization inhibitor be hydroquinone or
MEHQ.
Polyurethane dental prosthetic material the most according to claim 1, it is characterised in that described polyester resin is polyester
Acid resin prepolymer.
Polyurethane dental prosthetic material the most according to claim 1, it is characterised in that described reactive diluent is acrylic acid
Hydroxyl ethyl ester, hydroxyethyl methylacrylate, Hydroxypropyl acrylate, Hydroxypropyl methacrylate, isobornyl thiocyanoacetate, methyl isobornyl thiocyanoacetate,
One in 1,6-hexanediyl ester, tri (propylene glycol) diacrylate and trimethylolpropane trimethacrylate.
Polyurethane dental prosthetic material the most according to claim 1, it is characterised in that described light trigger is hexichol first
One in ketone, isopropyl thioxanthone, 2-hydroxy-2-methyl-1-phenyl-1-acetone and 1-hydroxy-cyciohexyl phenyl ketone.
8. the preparation method of a polyurethane dental prosthetic material, it is characterised in that comprise the steps:
(1) in first reactor, 50～80 mass parts nanometer hydroxyapatites and 10～30 mass parts Polyethylene Glycol are added,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；Then, add 0.01～0.1 mass parts nanometer silver and 10～
20 mass parts glycerol, under the rotating speed of 2000 revs/min, stir 6 hours at 60 DEG C, after being cooled to room temperature, obtain modification and receive
Rice hydroxyapatite, standby；
(2) in second reactor, 40～65 mass parts polyurethane resins and 3～5 mass parts polyvinylpyrrolidones are added
Ketone, under the rotating speed of 500 revs/min, is stirred at room temperature 2 hours；Then, add what 13～25 mass parts steps (1) prepared
Modifted-nano-hydroxyapatite and 1～5 mass parts polymerization inhibitors, under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C；
Finally, add 8～20 mass parts polyester resin, 9～20 mass parts reactive diluent and 1～10 mass parts light triggers,
Under the rotating speed of 2000 revs/min, stir 2 hours at 60 DEG C, after being cooled to room temperature, obtain described polyurethane dental prosthetic material
Material.
9. the application in dental restorative area of the polyurethane dental prosthetic material described in claim 1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117736684A (en) * | 2023-12-15 | 2024-03-22 | 云浮市骏驰新材料科技有限公司 | Nano composite functional hot melt adhesive and manufacturing process thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117736684A (en) * | 2023-12-15 | 2024-03-22 | 云浮市骏驰新材料科技有限公司 | Nano composite functional hot melt adhesive and manufacturing process thereof |
| CN117736684B (en) * | 2023-12-15 | 2024-05-28 | 云浮市骏驰新材料科技有限公司 | Nano composite functional hot melt adhesive and manufacturing process thereof |
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