CN105125415A - Preparation method for low-polymerization-shrinkage-ratio dental composite resin material - Google Patents
Preparation method for low-polymerization-shrinkage-ratio dental composite resin material Download PDFInfo
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- CN105125415A CN105125415A CN201510373172.8A CN201510373172A CN105125415A CN 105125415 A CN105125415 A CN 105125415A CN 201510373172 A CN201510373172 A CN 201510373172A CN 105125415 A CN105125415 A CN 105125415A
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Abstract
The invention discloses a preparation method for a low-polymerization-shrinkage-ratio dental composite resin material, and belongs to the technical field of dental restoration materials. The material compositions are an acrylate monomer, filling materials and an initiator. The method comprises preparation of a composition filling material and preparation of the composite resin material. The first step comprises adding a nanometer silicon powder into a disperse medium for pre-dispersing, and adding other filling materials; and mixing with a part of a mixture of the acrylate monomer and the initiator, steaming out the disperse medium, performing illumination solidification, and crushing to obtain the composite filling material. The second step comprises adding the composite filling material into the disperse medium for pre-dispersing; adding the residual mixture of the acrylate monomer and the initiator, stirring, mixing, steaming out the disperse medium so as to obtain the dental composite resin material. The usage mass ratio of the mixture of the acrylate monomer and the initiator in the first step and in the second step is 65-85:15-35. By using the pre-coating method divided into two steps, the polymerization shrinkage of the dental composite resin material is obviously reduced, and the pre-dispersing processing enables the filling materials and the composite filling material to be uniformly dispersed in the monomer.
Description
Technical field:
The invention belongs to the technical field of teeth repairing material, be specifically related to a kind of to there is dentistry compound resin material of oligomerization shrinkage factor and preparation method thereof.
Background technology:
The composite that resin and inorganic filler are made is not only all close with dermal tooth in intensity, hardness, wearability, throwing optical activity, color etc., and fluorine release function can be endowed, photochromic diagnostic function, the light of similar dermal tooth thoroughly and the several functions such as scattering property, be applied to the repairing of tooth increasingly extensively and remake. can predict, due to the comprehensive advantage in attractive in appearance and performance, resin composite materials will replace traditional inorganic, metal material comprehensively.
Itself there is deadly defect in resin composite materials, namely material, when being polymerized, volume contraction and the polymerization stress that causes thus occurs.If bonding plane can not bear this stress, by producing the contraction gap of size about 2 to 10 μm, causing recurrent caries and bringing out irritated odontopathy.In addition, shrinkage stress also may make enamel tear, and destroys healthy dental tissue.Therefore, reduce the volume contraction in resin composite materials polymerization process, be the major subjects of dental materials research always.
At present, the work about the volume contraction reducing polymerization process mainly concentrates in three: 1, use dissimilar resin monomer; 2, different polymerizations is adopted; 3, the reactivity point in unit volume is reduced, as: double key number.Generally realize by increasing monomer molecule amount and reducing monomer consumption in the composite.
Up to now, business-like dental composite mainly uses acrylic monomer.Wherein, methyl methacrylate polymerization shrinkage factor is 22.5%.Bisphenol-A 2-glycidyl dimethylacrylate (BisGMA) shrinkage factor of high molecular is 8%.Although add a large amount of inorganic fillers, the shrinkage factor of commercial resins composite is still generally 2.2 to 3.5%.
One of new progress introduces liquid crystal monomer (US Patent No. 7094358), disordered structure can be transformed into by orderly molecular crystal (as nematic crystal) after its polymerization, produce volumetric expansion to offset the volume contraction produced in acrylic monomer polymerization process.Hygroscopicity value is high because existing for such system, toxicity, with the problems such as the poor compatibility of other bonding agent, have no industrialization.
3M develops a based epoxy resin monomer, and such monomer has lower polymerization shrinkage and polymerization stress, be proved and had feasibility, but overall performance still can not exceed common methyl acrylic ester complex resin.
The up-to-date novel lower shrinkage monomer of a class is (Thio-Ene), but application is restricted because of its toxicity and abnormal smells from the patient, is still in development at present.
Summary of the invention:
The technical problem to be solved in the present invention is, adopts pre-coated method, a certain amount of acrylic ester monomer is polymerized in advance, to reduce the polymerization shrinkage of dental resin material.
Filler of the present invention mixes with acrylic ester monomer (and initiator) and carries out in two steps.First make filler mix with a certain amount of acrylic ester monomer-initiator mixture, obtain compounded mix through solidification pulverizing; Compounded mix mixes with remaining acrylic ester monomer-initiator mixture again, obtains dentistry composite resin.
Concrete technical scheme is as follows.
A preparation method for the dentistry compound resin material of oligomerization shrinkage factor, in dentistry compound resin material, the consumption of each composition is acrylic ester monomer in mass ratio: filler: initiator=29 ~ 69: 30 ~ 70: 0.5 ~ 2; Described filler, mainly nano silica fume; It is characterized in that, divide to prepare compounded mix and prepare composite resin material two step and carry out; Described prepares compounded mix, is nano silica fume is added ultrasonic disperse in disperse medium, adds other fillers; Mix with part acrylic acid esters monomer-initiator mixture, be stirred to and be uniformly dispersed, steam disperse medium, illumination curing, pulverize, obtain compounded mix; Described prepares composite resin material, is compounded mix to be added in disperse medium ultrasonic disperse to evenly; Add remaining acrylic ester monomer-initiator mixture and be stirred to mix homogeneously, steam disperse medium, obtain the dentistry compound resin material of oligomerization shrinkage factor; Wherein the consumption mass ratio of acrylic ester monomer-initiator mixture in two steps is 65 ~ 85: 15 ~ 35.
Described filler comprises, and accounts for the nano silica fume of dentistry compound resin material gross mass 5 ~ 25%, accounts for the silicon dioxide powder of dentistry compound resin material gross mass 0 ~ 40%, accounts for the strontium glass powder of dentistry compound resin material gross mass 0 ~ 20%, accounts for the barium glass powder of dentistry compound resin material gross mass 0 ~ 20% and account for the fluorine-containing glass powder of dentistry compound resin material gross mass 0 ~ 40%.
Other described fillers are silicon dioxide powder, strontium glass powder, barium glass powder, fluorine-containing glass powder; They are through silanization treatment.The silanization treatment of filler is undertaken by method disclosed in ZL200910217908.7.
Wherein, the mean diameter 20 ~ 50nm of nano silica fume, specific surface area is 20 ~ 200m
2/ g; The mean diameter of silicon dioxide powder is 0.2 ~ 20 μm; The mean diameter of strontium glass powder is 0.1 ~ 20 μm, and specific surface area is 2 ~ 20m
2/ g; The mean diameter of barium glass powder is 0.080 μm ~ 5 μm, and specific surface area is 8 ~ 30m
2/ g; Fluorine-containing glass powder by the component of quality is, F is 10% ~ 20%, SiO
2be 35%, SrO be 25% ~ 30%, Al
2o
3be 20% ~ 25%, fluorine-containing glass powder particle size distribution is 0.1 ~ 10 μm, and mean diameter is 1 ~ 2 μm.
Prepare in composite resin material process of the present invention, can also dyestuff be added.
Described disperse medium is that inertia and acrylic ester monomer dissolve each other and the low boiling organic compound not generating azeotropic mixture with acrylic ester monomer to initiator; It can be 1 ~ 5 kind in ethanol, propanol, isopropyl alcohol, acetone, butanone, chloroform, dichloromethane, oxolane, ethyl acetate, hexane, thiacyclohexane.
Described pulverizing is crushed to particle diameter to be not more than 10 μm.
Described acrylic ester monomer is substantially same as the prior art, comprise monomer A, monomers B and monomer C, wherein monomer A is a kind of low-molecular-weight simple function group or bifunctional monomer, and its consumption is 10% ~ 70% of acrylic ester monomer-initiator mixture gross mass; Monomers B is the monomer of the difunctional with higher molecular weight, or polyfunctional monomer, and its consumption is 20% ~ 80% of acrylic ester monomer-initiator mixture gross mass; Monomer C is low-molecular-weight polymer, and its consumption is 0 ~ 20% of acrylic ester monomer-initiator mixture gross mass.
Described initiator is camphorquinone, hydroxy-cyclohexyl acetophenone, two oxygen base acetophenone, two (2,4,6-trimethyl benzoyl) phenylphosphine oxide, 2,4,6-(trimethyl benzoyl) diphenyl phosphate oxidation, 2,4,5, the iodo-3 hydroxyl-10-cyano group-6-fluorones of 7-tetra-, 5,7-bis-iodo-3-butoxy-6-fluorones or 2,4, the iodo-3-hydroxyl of 5,7-tetra--6-fluorone.For some initiators, for accelerating light-initiated speed, also need the tertiary amine adding some, as light triggers such as 4-dimethyl amine ethyl benzoate.
The present invention's monomer A used can be methacrylic acid beta-hydroxy ethyl ester, tetrahydrofurfuryl acrylate, methacrylic acid 3-hydroxy propyl ester, 2-Propenoic acid, 2-methyl-, octyl ester, isodecyl methacrylate, dodecanol methacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate ester, triethylene-glycol dimethylacrylate, tetraethylene-glycol dimethylacrylate, 1, 4-butanediol dimethylacrylate, 1, 6-hexanediol dimethacrylate, 1, 10-decanediol dimethylacrylate, dimethacrylate, glycol dimethacrylate, tripropylene glycol dimethylacrylate, three contracting four dimethacrylate, tetradecane diols dimethylacrylate, methacrylic acid ten ethoxy ethyl ester, 1, 4-cyclohexane dimethyl carbinol dimethylacrylate, neopentylglycol dimethacrylate, dipropoxy neopentylglycol dimethacrylate.Wherein, with methacrylic acid beta-hydroxy ethyl ester, tetrahydrofurfuryl acrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate ester, triethylene-glycol dimethylacrylate, tetraethylene-glycol dimethylacrylate, three contracting four dimethacrylate, 1,4-butanediol dimethylacrylate, 1,6-hexanediol dimethacrylate, Isosorbide-5-Nitrae-cyclohexane dimethyl carbinol dimethylacrylate, neopentylglycol dimethacrylate are good.
The present invention's monomers B used can be bisphenol-A 2-glycidyl dimethylacrylate, bisphenol a dimethacrylate, methacrylic acid benzoyl ethyl ester, two-2-methylacryoyloxyethyl-2,2,4-trimethyls hexane diurethane (UDMA), two-2-methylacryoyloxyethyl 2,4 (or 2,6)-toluencediamine carbamates, 1,12-dodecanediol dimethacrylate, methacrylic acid dipropoxy allyl ester, octacosanol dimethylacrylate, 30 ethoxylated bisphenol A dimethylacrylates, ten ethoxylated bisphenol A dimethylacrylates, eight ethoxylated bisphenol A dimethylacrylates, tetraethoxy bisphenol a dimethacrylate, triethoxy bisphenol a dimethacrylate, trimethylol-propane trimethacrylate, triethoxy trimethylol-propane trimethacrylate, six ethyoxyl trimethylol-propane trimethacrylates, nine ethyoxyl trimethylol-propane trimethacrylates, 15 ethyoxyl trimethylol-propane trimethacrylates, nine propoxyl group trimethylol-propane trimethacrylates, new penta triol trimethyl acrylic ester, tripropoxy glycerol trimethyl acrylic ester, tripropoxy trimethylol-propane trimethacrylate, three (2-ethoxy) isocyanuric acid ester trimethyl acrylic ester, dipentaerythritol pentamethacrylates, tetramethoxy pentaerythritol tetramethylacrylate, tetraethoxy pentaerythritol tetramethylacrylate.Wherein with bisphenol-A 2-glycidyl dimethylacrylate, bisphenol a dimethacrylate, two-2-methylacryoyloxyethyls-2, 2, 4-trimethyl hexane diurethane (UDMA), ten ethoxylated bisphenol A dimethylacrylates, eight ethoxylated bisphenol A dimethylacrylates, tetraethoxy bisphenol a dimethacrylate, triethoxy bisphenol a dimethacrylate, trimethylol-propane trimethacrylate, triethoxy trimethylol-propane trimethacrylate, six ethyoxyl trimethylol-propane trimethacrylates, 15 ethyoxyl trimethylol-propane trimethacrylates, tripropoxy glycerol trimethyl acrylic ester, tripropoxy trimethylol-propane trimethacrylate, three (2-ethoxy) isocyanuric acid ester trimethyl acrylic ester, dipentaerythritol pentamethacrylates, tetramethoxy pentaerythritol tetramethylacrylate is good.
The present invention monomer C used can be polyethylene glycol dimethacrylate, 30 ethoxylated bisphenol A dimethylacrylates, polypropylene glycol dimethacrylate, methoxy polyethylene glycol methacrylate-styrene polymer, methoxyl group methacrylates or ethyoxyl methacrylates.
The bulk composition of dentistry compound resin material of the present invention is acrylic ester monomer and filler.During solidification, monomer polymerization reaction take place, causes volume contraction.In the present invention, the preparation of dentistry composite resin adopts pre-coated method, that is, preparation process is carried out in two steps.The first step, mixes filler with a certain amount of monomer-initiator mixture, prepares filler-monomer complex, and filler-monomer complex, through illumination curing, pulverizing, obtains compounded mix; Above-mentioned compounded mix mixes with remaining monomer-initiator mixture by second step, obtains described dentistry composite resin.First step monomer used, completes polyreaction in compounded mix preparation process, no longer produces volume contraction when dentistry composite resin solidifies, thus, reduce the polymerization shrinkage of dentistry compound resin material.
For making filler and prepared compounded mix be uniformly dispersed in monomer, have employed pre-dispersion method.Described is pre-dispersed, is the ultrasonic disperse of nano silica fume in disperse medium, and the ultrasonic disperse of compounded mix in disperse medium that the first step obtains.
Detailed description of the invention
Embodiment 1 ~ 12 gives the mass ratio of acrylic ester monomer and consumption thereof, and what obtain is acrylic ester monomer-initiator mixture.Embodiment 13 ~ 28 gives the composition of the dentistry compound resin material of oligomerization shrinkage factor and the ratio in quality thereof.Wherein embodiment 13 ~ 20 adopts pre-coated method, i.e. secondary mixing method.Embodiment 21 ~ 28 is conventional mixing method, i.e. mixed once method.Embodiment 29 gives the testing result of the dentistry compound resin material that embodiment 13 ~ 28 obtains.
In each embodiment, initiator is camphorquinone, hydroxy-cyclohexyl acetophenone, two oxygen base acetophenone, two (2,4,6-trimethyl benzoyl) phenylphosphine oxide, 2,4,6-(trimethyl benzoyl) diphenyl phosphate oxidation, 2,4,5, the iodo-3 hydroxyl-10-cyano group-6-fluorones of 7-tetra-, 5,7-bis-iodo-3-butoxy-6-fluorones, 2,4,1 ~ 3 kind in the iodo-3-hydroxyl of 5,7-tetra--6-fluorone, 4-dimethyl amine ethyl benzoate.
Embodiment 1
Embodiment 2
Embodiment 3
Embodiment 4
Embodiment 5
Embodiment 6
Embodiment 7
Embodiment 8
Embodiment 9
Embodiment 10
Embodiment 11
Embodiment 12
In following embodiment 13 ~ 20, adopt pre-coated legal system of the present invention for dentistry compound resin material.
Embodiment 13
Embodiment 14
Embodiment 15
Embodiment 16
Embodiment 17
Embodiment 18
Embodiment 19
Embodiment 20
In following embodiment 21 ~ 28, prior art is adopted to prepare dentistry compound resin material.That is, mixed once legal system is for dentistry compound resin material.
Embodiment 21
Embodiment 22
Embodiment 23
Embodiment 24
Embodiment 25
Embodiment 26
Embodiment 27
Embodiment 28
Embodiment 29
The performance of the dentistry compound resin material of the oligomerization shrinkage factor that embodiment 13 ~ 20 obtains for cladding process of the present invention.As a comparison, also provide the performance of the dentistry compound resin material that embodiment 21 ~ 28 prior art obtains.Wherein, bending strength and bending modulus adopt three-point bending method to measure (YY1042-2011 " odontology polymer repair materials "), and polymerization shrinkage adopts video control methods to measure (video-controlledprocedure).Concrete outcome is in table 1.
Table 1
| Embodiment | Bending strength/MPa | Bending modulus/GPa | Polymerization shrinkage/% |
| 13 | 122 | 9.8 | 1.5 |
| 14 | 131 | 10.9 | 1.6 |
| 15 | 134 | 11.8 | 1.7 |
| 16 | 138 | 11.1 | 1.6 |
| 17 | 139 | 12.1 | 1.9 |
| 18 | 141 | 11.5 | 1.6 |
| 19 | 137 | 10.3 | 1.6 |
| 20 | 128 | 10.0 | 1.2 |
| 21 | 124 | 9.9 | 4.2 |
| 22 | 129 | 11 | 3.8 |
| 23 | 138 | 12.0 | 3.3 |
| 24 | 136 | 11.0 | 4.1 |
| 25 | 142 | 12.2 | 3.3 |
| 26 | 140 | 11.7 | 4.0 |
| 27 | 135 | 10.3 | 3.9 |
| 28 | 126 | 10.1 | 3.7 |
。
Claims (8)
1. a preparation method for the dentistry compound resin material of oligomerization shrinkage factor, in dentistry compound resin material, the consumption of each composition is acrylic ester monomer in mass ratio: filler: initiator=29 ~ 69: 30 ~ 70: 0.5 ~ 2; Described filler, mainly nano silica fume; It is characterized in that, divide to prepare compounded mix and prepare composite resin material two step and carry out;
Described prepares compounded mix, is nano silica fume is added ultrasonic disperse in disperse medium, adds other fillers; Mix with part acrylic acid esters monomer-initiator mixture, be stirred to and be uniformly dispersed, steam disperse medium, illumination curing, pulverize, obtain compounded mix;
Described prepares composite resin material, is compounded mix to be added in disperse medium ultrasonic disperse to evenly; Add remaining acrylic ester monomer-initiator mixture and be stirred to mix homogeneously, steam disperse medium, obtain the dentistry compound resin material of oligomerization shrinkage factor;
Wherein the consumption mass ratio of acrylic ester monomer-initiator mixture in two steps is 65 ~ 85: 15 ~ 35.
2. according to the preparation method of the dentistry compound resin material of oligomerization shrinkage factor according to claim 1, it is characterized in that, described filler comprises, and accounts for the nano silica fume of dentistry compound resin material gross mass 5 ~ 25%, accounts for the silicon dioxide powder of dentistry compound resin material gross mass 0 ~ 40%, accounts for the strontium glass powder of dentistry compound resin material gross mass 0 ~ 20%, accounts for the barium glass powder of dentistry compound resin material gross mass 0 ~ 20% and account for the fluorine-containing glass powder of dentistry compound resin material gross mass 0 ~ 40%.
3. according to the preparation method of the dentistry compound resin material of the oligomerization shrinkage factor described in claim 1 or 2, it is characterized in that, other described fillers, silicon dioxide powder, strontium glass powder, barium glass powder and fluorine-containing glass powder are through silanization treatment.
4. according to the preparation method of the dentistry compound resin material of oligomerization shrinkage factor according to claim 3, it is characterized in that, preparing in composite resin material process, adding dyestuff.
5. according to the preparation method of the dentistry compound resin material of oligomerization shrinkage factor according to claim 1, it is characterized in that, described disperse medium is 1 ~ 5 kind in ethanol, propanol, isopropyl alcohol, acetone, butanone, chloroform, dichloromethane, oxolane, ethyl acetate, hexane, thiacyclohexane.
6. according to the preparation method of the dentistry compound resin material of oligomerization shrinkage factor according to claim 1, it is characterized in that, described pulverizing, is be crushed to granularity≤10 μm.
7. according to the preparation method of the dentistry compound resin material of the oligomerization shrinkage factor described in claim 1,2,5 or 6, it is characterized in that, described acrylic ester monomer, is monomer A, monomers B and monomer C; Wherein monomer A is a kind of low-molecular-weight simple function group or bifunctional monomer, and its consumption is 10% ~ 70% of acrylic ester monomer-initiator mixture gross mass; Monomers B is the monomer of the difunctional with higher molecular weight, or polyfunctional monomer, and its consumption is 20% ~ 80% of acrylic ester monomer-initiator mixture gross mass; Monomer C is low-molecular-weight polymer, and its consumption is 0 ~ 20% of acrylic ester monomer-initiator mixture gross mass.
8. according to the preparation method of the dentistry compound resin material of the oligomerization shrinkage factor described in claim 1,2,5 or 6, it is characterized in that, described initiator, it is camphorquinone, hydroxy-cyclohexyl acetophenone, two oxygen base acetophenone, two (2,4,6-trimethyl benzoyl) phenylphosphine oxide, 2,4,6-(trimethyl benzoyl) diphenyl phosphate oxidation, 2,4,5, the iodo-3 hydroxyl-10-cyano group-6-fluorones of 7-tetra-, 5,7-bis-iodo-3-butoxy-6-fluorones or 2,4, the iodo-3-hydroxyl of 5,7-tetra--6-fluorone.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108542791A (en) * | 2018-04-12 | 2018-09-18 | 安徽皖东树脂科技有限公司 | The preparation method of dental repair resin material |
| CN108578249A (en) * | 2018-04-12 | 2018-09-28 | 华南理工大学 | One kind is double containing long oxyalkyl chain（Methyl）Lower shrinkage stress dentistry composite resin of acrylate and preparation method thereof |
| CN117064765A (en) * | 2023-10-16 | 2023-11-17 | 长春新斯达科技有限公司 | Dental adhesive restorative material composition and application thereof |
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| CA2570341C (en) * | 2004-06-15 | 2012-12-18 | Dentsply International Inc. | Radical polymerizable macrocyclic resin compositions with low polymerization stress |
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| CA2570341C (en) * | 2004-06-15 | 2012-12-18 | Dentsply International Inc. | Radical polymerizable macrocyclic resin compositions with low polymerization stress |
| CN103126908A (en) * | 2012-03-16 | 2013-06-05 | 中新棠国业（北京）科技有限责任公司 | Dental prepolymerized resin filler type composite resin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108542791A (en) * | 2018-04-12 | 2018-09-18 | 安徽皖东树脂科技有限公司 | The preparation method of dental repair resin material |
| CN108578249A (en) * | 2018-04-12 | 2018-09-28 | 华南理工大学 | One kind is double containing long oxyalkyl chain（Methyl）Lower shrinkage stress dentistry composite resin of acrylate and preparation method thereof |
| CN108578249B (en) * | 2018-04-12 | 2019-08-20 | 华南理工大学 | A kind of lower shrinkage stress dentistry composite resin and preparation method thereof of bis- (methyl) acrylate Han long oxyalkyl chain |
| CN117064765A (en) * | 2023-10-16 | 2023-11-17 | 长春新斯达科技有限公司 | Dental adhesive restorative material composition and application thereof |
| CN117064765B (en) * | 2023-10-16 | 2023-12-29 | 长春新斯达科技有限公司 | Dental adhesive restorative material composition and application thereof |
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