CN114010510B - Dentin bonding pretreatment composition based on DMA (direct memory access) and application thereof - Google Patents

Dentin bonding pretreatment composition based on DMA (direct memory access) and application thereof Download PDF

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CN114010510B
CN114010510B CN202111175851.6A CN202111175851A CN114010510B CN 114010510 B CN114010510 B CN 114010510B CN 202111175851 A CN202111175851 A CN 202111175851A CN 114010510 B CN114010510 B CN 114010510B
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dentin
solution
dopamine
acid etching
dimethyl sulfoxide
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CN114010510A (en
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李鸿波
许荣宸
刘琳
王潇宇
关淼升
刘倩
杨忠良
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First Medical Center of PLA General Hospital
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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
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/15—Compositions characterised by their physical properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/74—Fillers comprising phosphorus-containing compounds
    • 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
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/52—Amides or imides
    • C08F120/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F120/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloyl morpholine

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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)
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  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Dental Preparations (AREA)

Abstract

The invention discloses a dentin bonding pretreatment composition based on DMA (methyl acryl dopamine, dopamine methacrylamide)) and application thereof. In the invention, DMA is used as an adhesive resin monomer, synchronous permeation with phosphoric acid in an acid etching agent can be realized, permeation filling of dentin acid etching ore removal and resin-based adhesive medium is realized integrally, polymerization can be formed by a free radical polymerization mode and adhesive components, dentin collagen structure stability can be effectively improved, degradation risks caused by exogenous mechanical stress, biochemistry and other factors of glue are reduced, and enzymolysis risks of an adhesive interface are reduced. The invention can realize acid etching, collagen crosslinking and adhesive resin permeation, can meet the use requirements of short clinical operation time, simplified steps and increased stability of oral cavity adhesive repair.

Description

Dentin bonding pretreatment composition based on DMA (direct memory access) and application thereof
Technical Field
The invention belongs to the technical field of dental restoration materials, and particularly relates to a dentin bonding pretreatment composition which is used for carrying out acid etching and ore removal treatment on dentin before dentin bonding so as to simplify operation complexity and improve dentin bonding stability.
Background
Dentin bonding technology is an important strategy for treating caries, tooth defect and restoring tooth tissue appearance and beauty. Currently, acid etching treatment is a primary condition for dentin bonding treatment in full acid etching, self acid etching and general acid etching systems. The mineral components in dentin are dissolved by acid etching treatment, and an organic dentin collagen fiber network is exposed, so that space can be provided for penetration of bonding resin, and the bonding resin and dentin collagen form physical combination through micro-mechanical embedding action, so that a bonding structure foundation-mixed layer is constructed.
However, the acid etching technology realizes dentin demineralization and simultaneously leads dentin collagen fibers to be directly exposed in an oral cavity environment, so that the degradation effect of various biochemical factors such as chewing stress, moisture, enzymes, bacteria and the like is faced, and the integrity of a mixed layer is lost. In addition, the micro-mechanical jogged effect formed between the bonding resin and dentin collagen is only single physical combination, so that the clinical requirement of dentin bonding stability cannot be met, and ionic bond effect formed by acid functional monomers in a partial self-acid etching bonding system and hydroxyapatite at the bottom of the mixed layer is also easily hydrolyzed, and finally dentin bonding failure is caused.
In view of the above problems, various improved strategies have been developed in the art of dentin bonding, including wet bonding techniques with ethanol, pretreatment with enzyme inhibitors, collagen cross-linking agents, and the like. However, the above strategies require additional procedures, increase the handling time and complexity of clinical procedures, and also affect the patient's physical sensation and increase the chance of infection.
In addition, there is a study to apply functional monomers simultaneously with the acid etching treatment to achieve improvement of dentin adhesive stability without increasing the clinical treatment time. Although the use of both acetic acid and collagen cross-linking agent procyanidins can increase the adhesive strength, the presence of procyanidins has an inhibitory effect on the polymerization of the resin, and thus an additional rinsing step is required. The enzyme inhibitor chlorhexidine has also been studied for simultaneous application to dentin etching treatment by adding to phosphoric acid, but its enzyme inhibition is reduced due to the presence of moisture in dentin. In addition, the toxicity and resistance of chlorhexidine also limit its clinical application.
Methacrylic dopamine (dopamine methacrylamide, DMA) is an acrylamide modified dopa resin monomer, and dopa in the structure can form stable chemical combination with dentin matrix under water environment. In addition, the synchronous acid etching treatment can realize synchronous permeation of the adhesive resin and phosphoric acid molecules, so that mixed layer defects caused by mismatching of acid etching ore removal depth and resin permeation depth are reduced. The DMA solution is used for the dental adhesive pretreatment agent, so that the dentin adhesive performance can be improved, and the operation flow is as follows: phosphoric acid etching, flushing, DMA pretreatment, light blowing, adhesive coating and light irradiation curing. However, the above strategy still has the following problems:
(1) Compared with the traditional acid etching-flushing-light blowing-adhesive coating-light curing strategy, the operation method increases the clinical treatment time and contradicts the medical requirements for shortening the clinical operation time;
(2) DMA is an acrylic acid modified dopa monomer, the catechol structure in the DMA is easily oxidized into quinone under non-acidic condition, and browning phenomenon is generated, which may affect the beautiful demand of oral cavity adhesion repair;
(3) The asynchronous acid etch process and DMA pretreatment operations still do not address the issue of adhesive penetration not matching the acid etch depth.
Disclosure of Invention
According to the 1 st aspect of the invention, a DMA-based dentin bonding pretreatment composition is disclosed, comprising a binary system comprising a solution of methacrylamide dopamine-dimethyl sulfoxide and a solution of phosphoric acid.
Alternatively, the dentin bonding pretreatment composition comprises a ternary system comprising the solution of the methacrylamide dopamine, the dimethyl sulfoxide and the phosphoric acid.
In some examples, the concentration of the dopamine-dimethyl sulfoxide solution of methacrylamide is 2-10mM, or the concentration of the solution of the dopamine of methacrylamide mixed with dimethyl sulfoxide is 2-10mM.
In some examples, the phosphoric acid solution concentration is 35% to 40%, preferably 35%.
In some examples, the dopamine-dimethyl sulfoxide solution and the phosphoric acid solution of methacrylamide are packaged and stored separately, or the dopamine-dimethyl sulfoxide solution and the phosphoric acid solution of methacrylamide are packaged and stored separately.
According to the 2 nd aspect of the invention, the application of the dentin bonding pretreatment composition for preparing an acid etching agent is also disclosed, wherein the acid etching agent is obtained by mixing and stirring a methacrylamide dopamine-dimethyl sulfoxide solution and a phosphoric acid solution, or the acid etching agent is obtained by mixing a methacrylamide dopamine and a dimethyl sulfoxide to obtain a methacrylamide dopamine-dimethyl sulfoxide solution, and then mixing and stirring the methacrylamide dopamine-dimethyl sulfoxide solution and the phosphoric acid solution; the PH value of the acid etching agent is 1.3-1.6.
Or in the application of preparing the acid etching agent by utilizing the dentin bonding pretreatment composition, mixing and stirring the methyl acrylamide dopamine-dimethyl sulfoxide solution and the phosphoric acid solution according to the volume ratio of 1:1 to obtain the acid etching agent; or mixing the methacrylamide dopamine with dimethyl sulfoxide, and then mixing and stirring the mixed solution and the phosphoric acid solution according to a ratio of 1:1 to obtain the acid etching agent.
Wherein the DMA concentration in the acid etching agent is 1-5mM.
In some examples, DMA is co-infiltrated with phosphoric acid in the acid etchant as the binder resin monomer.
In some examples, the acid etchant is suitable for full acid etching processes.
In some examples, the acid is applied to the caries-free, ex-vivo dentin for a predetermined period of time prior to application of the adhesive, rinsed with deionized water, and blown dry with gas or blotted dry with filter paper.
According to the invention, DMA is used as a resin monomer to synchronously permeate with an acid etching agent, and interaction is formed between the DMA and dentin matrix through stable chemical combination under various water environments, so that the stability of dentin collagen structure is effectively improved, degradation risks caused by exogenous mechanical stress, biochemistry and other factors of glue are reduced, and polymerization can be formed through a free radical polymerization mode and an adhesive.
In addition, because the methyl acrylamide dopamine is difficult to directly generate an interaction with the phosphoric acid solution, the invention adopts the dimethyl sulfoxide to dissolve the methyl acrylamide dopamine at first, and then the methyl acrylamide dopamine-dimethyl sulfoxide solution is dissolved in the phosphoric acid solution, so that the material capable of being used for carrying out acid etching treatment is obtained.
And the acid etching agent is adopted to synchronously realize acid etching, collagen crosslinking and adhesive resin permeation with other pretreatment strategies and the previous DMA application modes, so that the use requirements of short clinical operation time and simplified steps can be met.
Drawings
FIG. 1 is an electron microscope scan of an untreated dentin surface morphology;
FIG. 2 is a scanning image of a dentin surface morphology electron microscope using a 35% phosphoric acid solution for acid etching;
FIG. 3 is an electron microscope scan of the dentin surface morphology of acid etched using the acid etchant of the present invention;
FIG. 4 is a graph showing the comparison of infrared spectra of interactions between different acid etchants and dentin collagen, wherein L1 represents dentin after acid etching treatment with the acid etchant of the present invention, L2 represents dentin acid etched with 35% phosphoric acid solution, and L3 represents non-demineralized dentin;
FIG. 5 is a graph showing the comparison of the strength of an adhesive immediately after various acid etching treatments and aged;
FIG. 6 is a comparison of the activities of the adhesive interfacial enzymes after different treatments of acid etching;
fig. 7 is a comparison of the steps of dentin bonding with conventional bonding strategies using the acid etchant of the present invention.
Detailed Description
Hereinafter, the DMA-based dentin adhesive pretreatment composition and the application thereof disclosed in the present invention will be described in detail with reference to the drawings and examples, but the present invention is not limited to these examples.
Example 1:
a DMA-based dentin bonding pretreatment composition comprises a binary system, wherein the binary system comprises a methacrylamide dopamine-dimethyl sulfoxide solution and a phosphoric acid solution.
Wherein, the concentration of the methyl acrylamide dopamine-dimethyl sulfoxide solution is 2-10mM. And dissolving the methacrylamide dopamine powder by using dimethyl sulfoxide as a solvent to form methacrylamide dopamine-dimethyl sulfoxide solution, wherein the volume molar concentration of the solution is 2-10mM, namely 2-10mmol/L.
In this example, the phosphoric acid solution concentration (mass% concentration) is 35% to 40%, preferably 35%.
In this example, the dopamine-dimethyl sulfoxide solution and phosphoric acid solution of methacrylamide are packaged and stored separately.
Example 2:
a DMA-based dentin bonding pretreatment composition comprises a ternary system, wherein the ternary system comprises methacrylamide dopamine, dimethyl sulfoxide and phosphoric acid solution.
Wherein the concentration of the methyl acrylamide dopamine-dimethyl sulfoxide solution after the methyl acrylamide dopamine and the dimethyl sulfoxide are mixed is 2-10mM. The concentration of the phosphoric acid solution is 35% -40%, preferably 35%.
Wherein, the methyl acrylamide dopamine, dimethyl sulfoxide and phosphoric acid solution are respectively and independently packaged and stored.
Example 3:
use of the DMA-based dentin adhesive pretreatment composition of example 1 for the preparation of a dentin adhesive pretreatment comprising: mixing and stirring the methacrylamide dopamine-dimethyl sulfoxide solution and the phosphoric acid solution according to the volume ratio of 1:1, and obtaining the mixed solution with the concentration of 1-5mM.
The dentin adhesive pretreatment is used as an acid etching agent, especially for full acid etching. The DMA concentration of the acid etching agent is 1-5mM.
Example 4:
use of the DMA-based dentin adhesive pretreatment composition of example 1 for the preparation of a dentin adhesive pretreatment comprising: mixing and stirring the methyl acrylamide dopamine-dimethyl sulfoxide solution and the phosphoric acid solution, wherein the pH value of the obtained mixed solution is 1.3-1.6.
The dentin adhesive pretreatment agent is used as an acid etching agent, in particular for full acid etching treatment. The DMA concentration of the acid etching agent is 1-5mM.
Example 5:
use of the DMA-based dentin adhesive pretreatment composition of example 2 for the preparation of a dentin adhesive pretreatment comprising: mixing the methacrylamide dopamine powder with dimethyl sulfoxide to obtain a methacrylamide dopamine-dimethyl sulfoxide solution with the concentration of 2-10mM, and then mixing and stirring the methacrylamide dopamine-dimethyl sulfoxide solution and a phosphoric acid solution according to the ratio of 1:1, wherein the concentration of the obtained mixed solution is 1-5mM.
The dentin adhesive pretreatment agent is used as an acid etching agent, in particular for full acid etching treatment. The DMA concentration of the acid etching agent is 1-5mM.
Example 6:
use of the DMA-based dentin adhesive pretreatment composition of example 2 for the preparation of a dentin adhesive pretreatment comprising: mixing the methacrylamide dopamine powder with dimethyl sulfoxide to obtain a methacrylamide dopamine-dimethyl sulfoxide solution with the concentration of 2-10mM, and then mixing and stirring the methacrylamide dopamine-dimethyl sulfoxide solution with a phosphoric acid solution, wherein the pH value of the obtained mixed solution is 1.3-1.6.
The dentin adhesive pretreatment agent is used as an acid etching agent, in particular for full acid etching treatment. The DMA concentration of the acid etching agent is 1-5mM.
The acid etching agents prepared in examples 3 to 6 were applied to caries-free in-vitro dentin for 15 seconds, rinsed with deionized water for 10 seconds, blown dry with gas or sucked dry with filter paper, applied with an adhesive and cured by light irradiation.
FIGS. 1-3 show dentin surface morphology after various treatments with acid etching. As shown in the figure, the dentin surface mineral can be effectively removed by adopting the dentin acid etching strategy of the invention, dentin collagen and dentin tubules are exposed, and space is provided for the penetration of bonding resin. And after acid etching, the dentin surface is similar to the traditional phosphoric acid etching dentin surface structure, and the residual small amount of mineral substances do not influence the permeation of the adhesive resin.
FIG. 4 is an infrared spectrum of the interaction of different acid etchants with dentin collagen. As shown in the figureCompared with an untreated dentin surface infrared spectrogram, the dentin surface treated by phosphoric acid etching and the acid etching strategy of the acid etching agent is located at 1007cm -1 The phosphate characteristic peak of (C) disappeared, and the surface mineral was confirmed to be dissolved, at 1638cm -1 The presence of characteristic peaks (carbon-carbon double bonds) of (i) demonstrate that DMA adheres effectively to dentin collagen surfaces.
In addition, the peak value of dentin collagen amide I bond after being subjected to acid etching treatment by the acid etching agent is 1632cm -1 The presence of hydrogen bonds was confirmed by the shift of the peak of the dentin collagen amide I bond to the low wave number direction compared with that after phosphoric acid etching.
Fig. 5 shows the immediate and aged bond strengths after various acid treatments. As shown in the figure, the dentin adhesive stability after the acid etching treatment by the acid etching agent of the invention, namely the adhesive strength after aging is obviously improved, wherein the adhesive stability of the acid etching group containing 5mM is most obvious (ph=1.36).
FIG. 6 is a graph showing comparison of interfacial enzyme activities after various acid etching treatments. Wherein, FIG. 6 (A) shows the result of 35% phosphoric acid etching treatment, and FIG. 6 (B) shows the result of phosphoric acid+dimethyl sulfoxide combined acid etching treatment; FIGS. 6 (C) to (E) show the results of acid etching treatment with a combination of phosphoric acid, dimethyl sulfoxide and DMA at different concentrations, wherein FIG. 6 (C) shows the result of acid etching treatment with a DMA concentration of 1mM, FIG. 6 (D) shows the result of acid etching treatment with a DMA concentration of 3mM, and FIG. 6 (E) shows the result of acid etching treatment with a DMA concentration of 5mM.
As can be seen from the figure, the adhesive interfacial enzyme activity was sufficiently inhibited after the acid etching treatment with the acid etching agent of the present invention, wherein the enzyme inhibition ability of the DMA acid etching agent containing a concentration of 5mM was optimal.
In the acid etching agent prepared by the invention, DMA is used as a bonding resin monomer, synchronous permeation with phosphoric acid in the acid etching agent can be realized, permeation filling of dentin acid etching ore removal and resin-based bonding medium is realized integrally, and polymerization can be formed with the bonding agent component in a free radical polymerization mode. Meanwhile, DMA can form interaction with dentin matrixes through stable chemical combination under various water environments, so that the stability of dentin collagen structures is effectively improved, and degradation risks caused by exogenous mechanical stress of glue reasons, biochemistry and other factors are reduced.
In addition, the introduction of DMA can also effectively inhibit collagenase activity in the bonding interface, and reduce the enzymolysis risk of the bonding interface.
Therefore, compared with other pretreatment strategies and the prior DMA application modes, the acid etching agent is adopted to synchronously realize acid etching, collagen crosslinking and adhesive resin permeation, thereby meeting the requirements of short clinical operation time, simplified steps and increased stability of oral cavity adhesive repair. As shown in fig. 7, the bonding operation can be simplified by using the acid etchant of the present invention, compared to the conventional acid etching strategy.
The above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same. Although the invention has been described in detail with reference to the foregoing embodiments, those skilled in the art will understand that modifications may be made to the technical solutions described in the foregoing embodiments, or equivalents may be substituted for some or all of the technical features thereof, without departing from the spirit of the technical solutions of the embodiments of the invention.

Claims (12)

1. The dentin bonding pretreatment composition based on DMA comprises a binary system, and is characterized in that the binary system comprises a methacrylamide dopamine-dimethyl sulfoxide solution and a phosphoric acid solution; wherein, the concentration of the methyl acrylamide dopamine-dimethyl sulfoxide solution is 2-10mM, and the concentration of the phosphoric acid solution is 35-40%.
2. The dentin bonding pretreatment composition according to claim 1, wherein the dopamine-dimethyl sulfoxide solution and the phosphoric acid solution of methacrylamide are packaged and stored separately.
3. The dentin bonding pretreatment composition based on DMA comprises a ternary system, and is characterized in that the ternary system comprises methacrylamide dopamine, dimethyl sulfoxide and phosphoric acid solution; wherein, the concentration of the solution after the mixture of the methyl acrylamide dopamine and the dimethyl sulfoxide is 2-10mM, and the concentration of the phosphoric acid solution is 35-40%.
4. The dentin adhesive pretreatment composition according to claim 3, wherein the dopamine methacrylamide, the dimethyl sulfoxide and the phosphoric acid solution are packaged and stored separately.
5. The dentin adhesive pretreatment composition according to any of claims 1 to 4, wherein the concentration of the phosphoric acid solution is 35%.
6. The use of the dentin bonding pretreatment composition according to claim 1 for preparing an acid etching agent, characterized in that a solution of dopamine-dimethyl sulfoxide of methacrylamide and a solution of phosphoric acid are mixed and stirred to obtain the acid etching agent, and the pH value of the acid etching agent is 1.3-1.6.
7. The use of the dentin bonding pretreatment composition according to claim 3 for preparing an acid etching agent, wherein the acid etching agent is obtained by mixing the methacrylamide dopamine with dimethyl sulfoxide to obtain a methacrylamide dopamine-dimethyl sulfoxide solution, and then mixing and stirring the methacrylamide dopamine-dimethyl sulfoxide solution with a phosphoric acid solution; the pH value of the acid etching agent is 1.3-1.6.
8. The use of the dentin bonding pretreatment composition according to claim 1 for preparing an acid etching agent, characterized in that the acid etching agent is obtained by mixing and stirring a methyl acrylamide dopamine-dimethyl sulfoxide solution and a phosphoric acid solution according to a volume ratio of 1:1.
9. Use of the dentin bonding pretreatment composition according to claim 3 for preparing an acid etching agent, characterized in that the acid etching agent is obtained by mixing the methyl acrylamide dopamine with dimethyl sulfoxide, and then mixing and stirring the mixed solution with phosphoric acid solution according to a ratio of 1:1.
10. The use according to any one of claims 6 to 9, wherein the DMA concentration in the acid etch is 1 to 5mM.
11. Use according to any one of claims 6 to 9, characterized in that DMA is co-penetrating as a binder resin monomer with phosphoric acid in the acid etchant.
12. The use according to any one of claims 6 to 9, wherein the acid etching agent is applied to the caries-free in-vitro dentin for a predetermined time before the application of the adhesive, rinsed with deionized water and dried with air or sucked through filter paper.
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