CN109602615A - A kind of resin and its preparation method and application - Google Patents

A kind of resin and its preparation method and application Download PDF

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Publication number
CN109602615A
CN109602615A CN201910012914.2A CN201910012914A CN109602615A CN 109602615 A CN109602615 A CN 109602615A CN 201910012914 A CN201910012914 A CN 201910012914A CN 109602615 A CN109602615 A CN 109602615A
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CN
China
Prior art keywords
resin
dmaddm
infiltration
infiltration resin
dental
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Pending
Application number
CN201910012914.2A
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Chinese (zh)
Inventor
程磊
于金钊
周学东
李继遥
李好
李明云
彭显
任彪
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Sichuan University
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Sichuan University
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Priority to CN201910012914.2A priority Critical patent/CN109602615A/en
Publication of CN109602615A publication Critical patent/CN109602615A/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/60Preparations for dentistry comprising organic or organo-metallic additives
    • A61K6/69Medicaments

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)

Abstract

The present invention provides a kind of resins, it contains infiltration resin and 12 chain quaternary ammonium salt dimethylamino dodecyl methyl acrylate (DMADDM).In the present invention, a kind of condition antibacterial agent is introduced in infiltration resin --- DMADDM, it can be in oral environment, improve the anti-microbial property of material itself, it reduces the bacterial biof iotalm amount of material surface and reduces the metabolic activity and lactic acid production acid amount of bacterium simultaneously, solve the problems, such as that traditional penetration resin causes dental caries to continue to progress due to a lack of antibiotic property.

Description

A kind of resin and its preparation method and application
Technical field
The present invention provides a kind of novel dental material containing quaternary ammonium salt infiltration resin, solves traditional penetration resin The problem of causing dental caries to continue to progress due to a lack of antibiotic property.
Background technique
Infiltration resin is dental material emerging in recent years.It is mainly used in the early stage of dental caries, it can be by penetrating into morning In the gap of phase dental caries demineralization enamel, and then dead air space, prevent bacteriogenic acid from entering the further hair for inhibiting dental caries Exhibition.
Early-stage study discovery inhibits dental caries progress aspect in closing demineralization enamel, and infiltration resin is better than fluoride and bonding Agent.However, although infiltration resin be it is generally acknowledged at present apply the material best in incipient dental caries, it still cannot terminate dental caries completely The progress of disease.Studies have found that incipient dental caries patient use infiltration resin, after 18 months X-ray film discovery 7% patient occur dental caries into Exhibition.Also there is research that Icon infiltration resin is coated in the grinding of demineralization enamel, be put into volunteer oral cavity, while being ground daily It can impregnate 2 times, 30 minutes every time, be put by the way that cross-section microradiography and individual wavelengths are micro- in 10% sucrose solution Photography observation is penetrated using dental caries progress after infiltration resin, the speed of dental caries progress occurs in the environment for being susceptible to suffer from dental caries for discovery sample Slowly, but below Icon infiltration resin still there is a small amount of demineralization, illustrate that Icon infiltration resin cannot completely inhibit dental caries progress.
Summary of the invention
The drawbacks described above for how improving infiltration resin is the main contents that the present invention studies.
Based on the above issues, the present invention provides a kind of resins, it contains infiltration resin and 12 chain quaternary ammonium salt dimethylaminos Dodecyl methyl acrylate (DMADDM).
In the present invention, a kind of condition antibacterial agent is introduced in infiltration resin --- DMADDM, can in oral environment, The anti-microbial property for improving material itself, reduces the bacterial biof iotalm amount of material surface and reduces the metabolic activity and cream of bacterium simultaneously Acid produces acid amount, solves the problems, such as that traditional penetration resin causes dental caries to continue to progress due to a lack of antibiotic property.
The working principle of infiltration resin: the tubule system by permeating enamel penetrate into acid can not, to terminate incipient dental caries Progress, and reinforce the intensity of dental hard tissue.
Wherein, the quality of 12 chain quaternary ammonium salt dimethylamino dodecyl methyl acrylate (DMADDM) accounts for gross mass 2.5%-10%.It is become apparent from the research of the invention finds that DMADDM accounts for gross mass 5%-10% (mass fraction) effect.
Wherein, the infiltration resin is selected from Icon infiltration resin.
The present invention also provides the preparation methods of above-mentioned resin, it includes following content:
(1) DMADDM is taken;
(2) infiltration resin is taken;
(3) component of (1) and (2) is taken to mix.
The present invention also provides a kind of joint dental materials, it includes Icon infiltration resin and 12 chain quaternary ammonium salt diformazan ammonia Two kinds of components of base dodecyl methyl acrylate (DMADDM).
The present invention also provides the application methods of above-mentioned dental material, before the material is used for dental treatment, by each group Part mixing.
Above-mentioned joint dental material the links such as is producing and selling, is not needing to mix two kinds of components, can disperse every It opens, independent packaging or unitizing are remixed before dental treatment.
The present invention also provides above-mentioned resin or joint dental materials, are being used to prepare with antibacterial or/and treatment dental caries Purposes in the product of disease.
The present invention also provides above-mentioned resin or joint dental material is stated, in the production for being used to prepare antibacterium biomembrane Purposes in product.
Wherein, the bacterium is cariogenic bacterium.Cariogenic bacterium includes but is not limited to Streptococcus mutans, Gordon streptococcus, blood One of streptococcus is a variety of.
Resin provided by the present invention or joint dental material, not only can treat incipient dental caries, applied to white after correction The buccal labial surfaces such as spot incipient dental caries and proximal surface incipient dental caries etc., while dental caries can also be inhibited further to develop.
Detailed description of the invention
Fig. 1 aesthetics experiment sample
Fig. 2 antibiotic property experiment sample
When Fig. 3 leaching liquor Cyto toxic experiment showed illustrates that DMADDM mass fraction is less than or equal to 10% in infiltration resin, material The leaching liquor of material does not have toxicity to HOK cell.When DMADDM mass fraction is more than 10%, material leaching liquor has HOK cell Toxicity.This experimental result can be used as the experimental basis of the determining DMADDM mass fraction upper limit.
When Fig. 4 roughness experimental result illustrates that DMADDM mass fraction is less than or equal to 10% in infiltration resin, the table of material Surface roughness does not have statistical difference.
When Fig. 5 performance attractive in appearance experimental result illustrates that DMADDM mass fraction is less than or equal to 10% in infiltration resin, material changes The performance attractive in appearance of kind incipient dental caries chalk spot will not change.
Fig. 6: MTT colorimetric method result explanation is compared with control group, the infiltration resin bacterial metabolism activity drop containing DMADDM It is low, and the mass fraction correlation of this effect and DMADDM.
Fig. 7: crystal violet staining assay result explanation is compared with control group, the infiltration resin bacterial biof iotalm amount containing DMADDM It reduces, and the mass fraction correlation of this effect and DMADDM.
Fig. 8: lactic acid production measurement result illustrates that the infiltration resin bacterial lactate containing 2.5% (mass fraction) DMADDM produces Amount and control group no significant difference;Containing 5% with the infiltration resin bacterial lactate yield of 10% (mass fraction) DMADDM with it is right It compares and substantially reduces according to group, and the mass fraction correlation of this effect and DMADDM.
Specific embodiment
Below by specific embodiment, the present invention will be further described.Following embodiment is only part of the invention Embodiment, instead of all the embodiments.Based on the embodiment in invention, those of ordinary skill in the art are not making wound Every other embodiment obtained under the premise of the property made labour belongs to the range that the present invention protects.
In the present invention, DMADDM and infiltration resin can be obtained by purchase commercial product, can also be according to the prior art It is prepared.
Such as DMADDM can be prepared with the following method:
It is reacted by tertiary amine groups and organohalogen compounds.By 2- bromoethyl methacrylate (2- Bromoethylmethacrylate, BEMA) be used as organohalogen compounds, 1- dimethylamino dodecane [1- (dimethyla minutes O) dodecane, DMAD] it is used as tertiary amine.By the DMAD of 10mmol (TokyoChemicalIndustry, Japan), 10mmol BEMA (Monomer-PolymerandDajacLabs, the U.S.) and 3g ethyl alcohol are added in the reagent bottle of 20mL.Reagent bottle envelope Mouthful, 70 DEG C of stirrings are for 24 hours.Ethanol evaporation solvent after fully reacting finally obtains limpid colourless viscous fluid DMADDM.
Embodiment 1
DMADDM is mixed with infiltration resin: being mixed DMADDM with infiltration resin according to certain mass score 2.5%, room temperature Under be protected from light shaking table mixing.
Embodiment 2
DMADDM is mixed with infiltration resin: being mixed DMADDM with infiltration resin according to certain mass score 5%, at room temperature It is protected from light shaking table mixing.
Embodiment 3
DMADDM is mixed with infiltration resin: being mixed DMADDM with infiltration resin according to certain mass score 10%, room temperature Under be protected from light shaking table mixing.
Following experimental study has been carried out to such compound in the present invention, with illustrate the compound the utility model has the advantages that
1. sample preparation
(1) aesthetics experiment sample: the fresh young baurodont pulled out, it is molten to be stored in 0.1% thymol for immersion after cleaning In liquid;Low speed cutting machine-cut is cut into crown root two parts, abandons root of the tooth part, and corona part is stand-by.Sample is observed under Stereo microscope This, rejects defective and crackle baurodont sample;After sample drying, enamel placed face down is in silica gel hole, with resin packet It buries after resin thoroughly solidifies, is polished using polishing machine.Successively surface is polished off using the sand paper of 600 mesh, 1200 mesh, 2500 mesh The adamantine layer of 150um, the exposure at least windowing face of 4*4mm, the region except windowing face is coated on using antiacid nail polish.
(2) production of antibiotic property experiment sample: the fresh young baurodont pulled out impregnates after cleaning and is stored in 0.1% Moschus In careless phenol solution;Low speed cutting machine-cut is cut into crown root two parts, abandons root of the tooth part, and corona part is stand-by.Under Stereo microscope Sample is observed, defective and crackle baurodont sample is rejected;Sample is fabricated to the glaze mass sample of 8*8mm on low speed polishing machine This, successively polishes off the adamantine layer of surface 150um using the sand paper of 600 mesh, 1200 mesh, 2500 mesh, is finally made 8*8*1mm's Enamel specimens.
2. demineralization Demineralization solutions are made of 50mM acetate solution, wherein containing 1.28mM Ca (NO3)2·4H2O, 0.74mM NaH2PO4·2H2O and 0.03ppm villiaumite.Adjust pH value be 5.0, sample 37.8 DEG C, do not stir in environment and impregnate 16 hours.The total measurement (volume) of the solution used is to use 2ml/mm2Enamel areal calculation come out.
3. filling the preparation of sample
Grouping: in the infiltration resin darkroom of mass fraction 0,2.5,5,10%DMADDM, by the DMADDM of corrresponding quality and Infiltration resin is added in ep pipe, is protected from light the dissolution on shaking table and is mixed 24 hours.
4. three strain bio films construct
Streptococcus mutans UA159, Gordon streptococcus DL1 and Streptococcus sanguis ATCC 10556 are (by mouth disease research country Key lab provides), BHI culture medium, 37 DEG C of recoveries, BHI Solid agar culture stroke plate, 4 DEG C of preservations, picking single colonie gram It is grand, 37 DEG C of amphimicrobian (90%N2,5%H2,5%CO2) cultures, light microscopic microscopy.
With BHI+1% sugar: matching 20% sucrose mother liquor outside super-clean bench;Filter filters in super-clean bench afterwards, takes 20ml that 380ml is added BHI solution in;
Change chain, the blood chain, format streptococcus being incubated overnight are taken out, is centrifuged (2500 turns, 10 minutes), removes supernatant, BHI+1% Sucrose solution is resuspended, and adjusts OD600=0.2, and bacterial concentration is the 108CFU/ml order of magnitude at this time, and then three bacterium solutions are mixed in equal volume It closes.
3) 10 times of mixed liquor are diluted with BHI+1% sucrose solution, be added in 24 orifice plates, had in every hole 2ml orifice plate using not The sample of the infiltration resin of homogenous quantities score (0-10%) DMADDM.
5. leaching liquor safety experiment:
96 orifice plates, each hole are added 5 μ L infiltration resins and laminate, and after DDW impregnates 24 hours, sterilize and supply in West China Hospital Answer center, ethylene oxide cold sterilization.Same group of 10 samples are immersed in 200 μ L cell culture mediums, 37 DEG C, agitate, for 24 hours, To obtain leaching liquor.According to dental surface product and saliva of buccal cavity secretory volume, leaching liquor is diluted to respective concentration, is soaked with containing HOK cell (control group uses the culture medium without leaching liquor that cell is resuspended) is resuspended in the culture medium of extract, with 4000cell/well's 100ul cell suspension inoculation to 96 orifice plates, culture for 24 hours, are replaced the fresh 100 μ L culture mediums containing leaching liquor by concentration, then Cultivate 48h.The 20 μ L of MTT solution that 5mg/mL is added afterwards enters each well, cultivates 4h;Liquid is removed, 150 μ L DMSO are added, OD value under 492nm is surveyed after being protected from light concussion.
5. surface roughness detects
After the completion of infiltration resin fills sample, atomic force microscope, contact mode are sent, constant force spring is set as 0.1N/m progress The test of surface roughness obtains 512*512 pixel image, and obtains 10 μm of * 10 μm of three-dimensional surface morphology image reconstructions, each Sample takes 3 point datas, obtains surface roughness Ra value data and three-dimensional reconstruction image.
6. aesthetics is tested:
After the preparation of aesthetics experiment sample, color data is measured using spectrophotometric colo instrument;Demineralization is carried out later;It is de- Color data is measured after mine again;Coating penetrating resin;Color data is measured again.
7. MTT method (MTT colorimetric method)
Sample is taken out from 24 orifice plates, is softly rinsed using sterile PBS solution by three strain bio Membrance cuitures 48 hours, To remove sample surface planktonic bacteria, 24 new orifice plates are transferred samples to later, and every hole is adherent to be slowly added to 1mL 0.5mg/ The fresh MTT solution of mL, is protected from light, 37 DEG C, and culture is incubated for 1 hour under the conditions of 5%CO2, is later transferred to sample again another In 24 new orifice plates, every hole is slowly added to 1mL DMSO solution, is protected from light and shakes up about 20 minutes, uniform to color, and 3, every hole is parallel Sample, is sucked out 200 μ L into 96 orifice plates respectively, and corresponding absorbance value is measured at 540nm wavelength with microplate reader.8. crystal violet contaminates Color method:
Sample is taken out from 24 orifice plates, is softly rinsed using sterile PBS solution by three strain bio Membrance cuitures 48 hours, To remove sample surface planktonic bacteria, 24 new orifice plates are transferred samples to later, every hole is adherent to be slowly added to 1mL methanol, quiet It sets 15 minutes, with this fixed biofilm.Sample is taken out from 24 orifice plates later, is softly rinsed using sterile PBS solution, and make It is dried, and orifice plate is added in 0.1% gentian violet solution of 1mL, stands 5 minutes.0.1% gentian violet solution is discarded later, gently rinsing life Object film is colourless until rinsing liquid.24 orifice plates are added in 95% ethanol solution of 1mL, place shaking table 30 minutes and decolourize, until observing life Object film decolourizes completely.200 μ L are sucked out into 96 orifice plates in 3, every hole Duplicate Samples respectively, are surveyed at 595nm wavelength with microplate reader Fixed corresponding absorbance value.
9. lactic acid production measures
Biological Membrance cuiture took out each group sample after 48 hours, was gently rinsed using sterile PBS, to remove sample surface Planktonic organism film.24 new orifice plates are put samples into, the BPW buffer that 1.5mL contains 0.2% sucrose is added, is putting it into Temperature is to place that mature biomembrane is made within 3 hours to continue to produce acid in 37 DEG C of amphimicrobian incubators containing 5%CO2.After 3 hours Take out and sample removed and is used the concentration of lactic acid in lactic dehydrogenase enzyme process measurement BPW liquid: by the cream to be measured in 24 orifice plates Acid solution body is transferred in 96 orifice plates with liquid-transfering gun, and the standard lactic acid of various concentration gradient is added as standard curve, in enzyme mark Its light absorption value is measured on instrument under 340nm wavelength;Be then respectively adding after lactic dehydrogenase reflects 1 hour again it is same under the conditions of survey Light absorption value is measured, data are recorded and analyzed.

Claims (10)

1. a kind of resin, it is characterised in that: it contains infiltration resin and dimethylamino dodecyl methyl acrylate (DMADDM)。
2. resin according to claim 1, it is characterised in that: dimethylamino dodecyl methyl acrylate (DMADDM) Quality account for the 2.5%-10% of gross mass;It is further selected from 5-10%.
3. resin according to claim 1, it is characterised in that: the infiltration resin is selected from Icon infiltration resin.
4. the preparation method of resin described in claim 1-3 any one, it is characterised in that: it includes following content:
(1) DMADDM is taken;
(2) infiltration resin is taken;
(3) component of (1) and (2) is taken to mix.
5. the preparation method according to claim 4, it is characterised in that: mixed at 20~30 DEG C;Further, it is protected from light mixed It closes.
6. a kind of joint dental material, it is characterised in that: it includes Icon infiltration resin and dimethylamino dodecyl methyl Two kinds of components of acrylate (DMADDM).
7. the application method of dental material described in claim 6, it is characterised in that:, will before the material is used for dental treatment Each component mixing.
8. the described in any item resins of claims 1 to 3 or material as claimed in claim 6, be used to prepare with antibacterial or/ With the purposes in the product for the treatment of dental caries.
9. the described in any item resins of claims 1 to 3 or material as claimed in claim 6 are being used to prepare antibacterium biology Purposes in the product of film.
10. purposes according to claim 8 or claim 9, it is characterised in that: the bacterium is cariogenic bacterium;Further, described Cariogenic bacterium includes one of Streptococcus mutans, Gordon streptococcus, Streptococcus sanguis or a variety of.
CN201910012914.2A 2019-01-07 2019-01-07 A kind of resin and its preparation method and application Pending CN109602615A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111821200A (en) * 2020-06-03 2020-10-27 四川大学 Dental material and preparation method and application thereof
CN114159314A (en) * 2021-12-08 2022-03-11 四川大学 PH sensitive permeable resin intelligent material, preparation method and application
CN114395075A (en) * 2022-01-20 2022-04-26 上海交通大学医学院附属第九人民医院 Dental zero-filler permeable resin and preparation method thereof
CN114732741A (en) * 2022-04-08 2022-07-12 四川大学 Quaternary ammonium salt monomer modified dental filling composite material, preparation and detection method and application

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
FANG LI等: ""Evaluation of antibacterial and remineralizing nanocomposite and adhesive in rat tooth cavity model"", 《ACTA BIOMATERIALIA》 *
HUI CHEN等: "Heat-Polymerized Resin Containing Dimethylaminododecyl Methacrylate Inhibits Candida albicans Biofilm", 《MATERIALS》 *
德国DMG: "Icon 爱康渗透树脂使用说明书", 《HTTP://WWW.360DOC.COM/CONTENT/16/0325/08/30854438_545059033.SHTML》 *
郑燕丹等: ""渗透树脂治疗前牙唇面白垩斑的美容效果探析"", 《中国医药科学》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111821200A (en) * 2020-06-03 2020-10-27 四川大学 Dental material and preparation method and application thereof
CN114159314A (en) * 2021-12-08 2022-03-11 四川大学 PH sensitive permeable resin intelligent material, preparation method and application
CN114395075A (en) * 2022-01-20 2022-04-26 上海交通大学医学院附属第九人民医院 Dental zero-filler permeable resin and preparation method thereof
CN114732741A (en) * 2022-04-08 2022-07-12 四川大学 Quaternary ammonium salt monomer modified dental filling composite material, preparation and detection method and application

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Application publication date: 20190412