CN100415200C - Visible light hardened filling composite material for dental filling and its preparing method - Google Patents
Visible light hardened filling composite material for dental filling and its preparing method Download PDFInfo
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- CN100415200C CN100415200C CNB2006100888846A CN200610088884A CN100415200C CN 100415200 C CN100415200 C CN 100415200C CN B2006100888846 A CNB2006100888846 A CN B2006100888846A CN 200610088884 A CN200610088884 A CN 200610088884A CN 100415200 C CN100415200 C CN 100415200C
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Abstract
The visible light hardened filling composite material for dental filling and its preparation process belongs to the field of dental repair material making technology. The composite material is prepared through mixing polymerisable dimethylacrlyate resin comprising dimethylacrlyate pre-polymer and active dimethylacrlyate diluent, visible light initiator cyclic pepper compound or its derivative, and inorganic filler of quartz and/or glass, and irradiation with visible light. The composite material has the features of high initiating efficiency, high mechanical performance, good use performance, low toxicity and good biocompatibility.
Description
Technical field
The invention belongs to the tooth dental repair material and make field, the particularly preparation of visible light hardened filling composite material for dental filling.
Background technology
Because silver amalgam is to the pollution of environment and to the toxic and side effects of human body, tradition is replaced by the visible-light curing filling composite gradually based on the tooth dental repair material of silver amalgam.
The visible-light curing filling composite is made up of polymerisable monomer, prepolymer (methyl acrylic ester), inorganic filler (quartz is or/and glass etc.), visible light initiator and aided initiating, other additive.Under visible light radiation, a series of photochemical reactions take place and generate free radical in visible light initiator and aided initiating, and then cause methyl acrylic ester organic facies polymerization and form highly cross-linked macromolecule.The main effect of inorganic filler is the mechanical and physical performance that improves material, reduces the volume contraction of system, and reinforcing material is ornamental simultaneously, reduces material cost.
Current business-like tooth section visible-light curing filling composite, most polymerizable double methyl methacrylate resinoids of forming by double methyl methacrylate prepolymer and double methyl methacrylate reactive diluent, with visible light initiator virtue diketone (camphorquinone, abbreviation CQ) and after aided initiating fully mixes, add the inorganic filler of forming by quartz, glass or both mixture again, cause polymerizable double methyl methacrylate resinoid monomer polymerization through illumination and make.Its initiator system is by visible light initiator virtue diketone (CQ) and aided initiating tertiary amine (4-N, N-mesitylenic acid ethyl ester, EDMAB or 2-N, N-dimethylaminoethyl methacrylate, DMEM) composition.The organic material system is the double methyl methacrylate that contains aromatic rings or carbamate groups, and wherein most popular is bisphenol-A epihydric alcohol methylpropenoic acid ester (BISGMA) and carbamate double methyl methacrylate (UDMA).But the organic material viscosity of Huo Deing is very high like this, must add polymerizable, low viscous methacrylate monomer such as triethylene glycolbismethyl-acrylate (TrEGDMA) but to improve the operational readiness of material, increase follow-up loadings of filler simultaneously.
The visible-light curing filling composite is mainly used in to be repaired because the injury of teeth that a variety of causes causes.It also will have good aesthetic property except needing good mechanical and physical performance, especially to the reparation of nipper, very important with the color that former tooth maintenance is same.And visible light initiator virtue diketone (CQ) is a yellow solid, and in order to keep aesthetic property, the consumption of fragrant diketone (CQ) is restricted in the reparation system.In the clinical repair process, the operating time is an important parameter, considers doctor and the patient comfortableness when clinical repair, is generally 30-40 second the hardening time of material, and therefore must strengthen the aided initiating consumption improves curing rate.Commerce, can not be incorporated into again in the crosslink polymer network because the tertiary amine molecule is little with using tertiary amine to do aided initiating in the visible-light curing filling composite at present, and therefore easily being drunk fluid extraction enters human body.Because the amine in the tertiary amine is to human body, especially liver has certain toxic action, therefore, uses the visible-light curing filling composite of this initiator system to have certain bio-toxicity, and biocompatibility is poor.
Chinese patent CN200510019126.4, " cyclic carbonate is as the purposes of the aided initiating of visible light hardened filling composite material for dental filling " (applying date is on July 20th, 2005), with Chinese patent CN200510019127.9, " the ring acetal is as the purposes of the aided initiating of visible light hardened filling composite material for dental filling " (applying date is on July 20th, 2005) discloses the technology of using cyclic carbonate and ring acetal to do aided initiating in the visible-light curing filling composite.On the basis of these two patents with commercial visible-light curing filling composite prescription, use cyclic carbonate/ring acetal to substitute tertiary amine and make aided initiating, and change the proportioning of other materials, avoid the extraction of amine, the purpose that realize reducing the material bio-toxicity, improves the biocompatibility of material.But these two kinds of prepared solidfied materials of method, mechanical performance are lower than the mechanical performance of using tertiary amine to make aided initiating gained solidfied material, cause serviceability to reduce; In addition, trigger rate is also not ideal enough.
Summary of the invention
The object of the present invention is to provide a kind of trigger rate higher, when guaranteeing the material serviceability, can effectively reduce bio-toxicity, have visible light hardened filling composite material for dental filling of good biocompatibility and preparation method thereof.
Technical scheme of the present invention is as follows:
Visible light hardened filling composite material for dental filling is the polymerizable double methyl methacrylate resin that will be made up of double methyl methacrylate prepolymer and double methyl methacrylate reactive diluent, visible light initiator virtue diketone (CQ), aided initiating, the inorganic filler of being made up of quartz, glass or both mixture fully mixes, and obtains through the radiation of visible light after fixing.
The mass percent of double methyl methacrylate prepolymer is 50～95% in polymerizable double methyl methacrylate resin, and the mass percent of double methyl methacrylate reactive diluent is 5～50%; Virtue diketone (CQ) content is 0.1～5.0% of the two methylacrylic acid ester resin qualities of polymerizable; The volume content of inorganic filler is 35～80% of a described visible-light curing filled composite materials cumulative volume; Aided initiating is cyclic piperonyl compound and the derivant thereof shown in general formula (1)～(8) are arbitrary, and its content is 0.1～5.0% of polymerizable double methyl methacrylate resin quality,
Above-mentioned double methyl methacrylate prepolymer is bisphenol-A epihydric alcohol methylpropenoic acid ester (BISGMA) or carbamate double methyl methacrylate (UDMA); The double methyl methacrylate reactive diluent is a triethylene glycolbismethyl-acrylate (TrEGDMA), 1,3-butanediol double methyl methacrylate (BDDMA), 1,6-hexanediol double methyl methacrylate (HDDMA) or tetraethylene-glycol double methyl methacrylate (TTEGDMA).
Particle diameter is that the components contents of 7～40 nanometers is 5～60% of a visible-light curing filling composite volume in the above-mentioned inorganic filler
The double methyl methacrylate resin causes radical polymerization by light initiation system among the present invention under radiation of visible light, generates highly cross-linked polymer rapidly.Its trigger rate ratio improves when using ring acetal or cyclic carbonate to make aided initiating greatly.See accompanying drawing 1, therefrom as can be seen, at resin system is carbamate double methyl methacrylate (UDMA)/tetraethylene-glycol double methyl methacrylate (TTEGDMA)=70/30wt%, virtue diketone (CQ) is 0.5wt%, 3,4-methylenedioxyphenyl methanol (piperitol) and ring acetal 2-methyl isophthalic acid, the concentration of 3-dioxolane (MDO) is 1.0wt%, and light intensity is 20mW/cm
2Under the condition, the trigger rate of piperitol will improve a lot.
See accompanying drawing 2,3, do not adding (UDMA: TEGDMA: CQ=70: 30: 0.5wt%) under the situation of filler, at oral temperature condition (0～50 ℃), use methacrylic acid-3 respectively, 4-methylenedioxyphenyl methyl ester (MDBMM), 2-N, N-dimethylaminoethyl methacrylate (DMEM) and 4-N, N-mesitylenic acid ethyl ester (EDMAB) are during as aided initiating, and measured mechanical property of materials index is more or less the same.The solidfied material that this data declaration obtains after solidifying in the oral temperature scope, its physical property are not less than or do a little more than corresponding use DMEM and EDMAB the solidfied material of aided initiating gained.
Cyclic piperonyl compound and derivant thereof are used plant from edible natural, and inanimate object toxicity has excellent biological compatibility.
Description of drawings
Accompanying drawing 1, piperitol and ring acetal 2-methyl isophthalic acid, 3-dioxolane (MDO) trigger rate comparison diagram, used resin system is carbamate double methyl methacrylate (UDMA)/tetraethylene-glycol double methyl methacrylate (TTEGDMA)=70/30wt%, virtue diketone (CQ) is 0.5wt%, the concentration of piperitol and ring acetal (MDO) is 1.0wt%, and light intensity is 20mW/cm
2
Accompanying drawing 3, do not add under the situation of filler, use methacrylic acid-3 respectively, 4-methylenedioxyphenyl methyl ester (MDBMM), 2-N, N-dimethylaminoethyl methacrylate (DMEM) and 4-N, N-mesitylenic acid ethyl ester (EDMAB) is during as aided initiating, the comparison diagram of storage modulus-temperature.Used resin system is carbamate double methyl methacrylate (UDMA)/tetraethylene-glycol double methyl methacrylate (TTEGDMA)=70/30wt%, and fragrant diketone (CQ) is 0.5wt%.
Specific embodiments
Following examples are embodiment preferred, but the embodiment that provided should be provided in actual applications.
Example 1:
Dissolving 0.3771g light trigger virtue diketone (CQ) is in 18.62g triethylene glycolbismethyl-acrylate (TrEGDMA), the proportioning that is mixed with BISGMA/TrEGDMA with 56.85g bisphenol-A epihydric alcohol methylpropenoic acid ester (BISGMA) is 75wt%: 25wt%, CQ content is the organic resin system (I) of 0.5wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
Take by weighing 3 shown in the 0.1203g general formula (1), 4-methylenedioxyphenyl methanol (piperitol) is in the 25mL beaker, and then to wherein adding 12.0014g organic resin system (I), mix homogeneously obtains containing the organic resin mixture of 1.0wt% piperitol.In this system, add the aerosil filler AEROSIL R 202 that the aerosil filler AEROSIL R 711 that particle mean size is 12 nanometers (German DEGUSSA company) 1.0116g (volume content be amount of the mixture 40%) and average particle size are 7 nanometers (German DEGUSSA company) 0.04864g (volume content be amount of the mixture 5%) then, fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 55: 45 composite system.In the darkroom, this composite system is left standstill in the politef template of 8mm (the diameter) * 1mm (thickness) that reinjects after 12 hours, after upper and lower surface clamps with glass slide, to be tested when leaving standstill to no bubble.Under the room temperature, in the air atmosphere, be 100mW/cm with sample light intensity to be tested
2Visible lamp irradiation 120 seconds, obtain the milky cured film of visible-light curing filling composite, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 73.6%.
Example 2:
Dissolving 0.9126g light trigger virtue diketone (CQ) is in 36.50g tetraethylene-glycol double methyl methacrylate (TTEGDMA), being mixed with the UDMA/TTEGDMA proportioning with 54.73g carbamate double methyl methacrylate (UDMA) is 60wt%: 40wt%, CQ content is the organic resin system (II) of 1.0wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
Get 3 shown in the 0.0105g general formula (2), 4-methylenedioxyphenyl formic acid (piperic acid) is in the 25mL beaker, and then to wherein adding organic resin system (II) 10.2013g, mix homogeneously obtains containing the organic resin mixture of 0.1wt% piperic acid.In this system, add the aerosil filler A 380 (the beneficial auspicious new material company limited in GuangZhou, China city) that the aerosil filler AEROSIL OX 50 that particle mean size is 40 nanometers (German DEGUSSA company) 0.4622g (volume content be amount of the mixture 40%) and particle mean size are 7 nanometers (volume content be amount of the mixture 20%) 0.2300g then, fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 40: 60 composite system.In the darkroom, this composite system is left standstill in the politef template of 8mm (the diameter) * 1mm (thickness) that reinjects after 12 hours, after upper and lower surface clamps with glass slide, to be tested when leaving standstill to no bubble.Under the room temperature, in the air atmosphere, sample to be tested was shone 3 minutes with visible lamp, obtain the milky cured film of visible-light curing filling composite, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 78.1%.
Example 3:
Dissolving 0.6678g light trigger virtue diketone (CQ) is in 1 of 13.23g, in the 6-hexanediol double methyl methacrylate (HDDMA), being mixed with the UDMA/HDDMA proportioning with 53.50g carbamate double methyl methacrylate (UDMA) is 80wt%: 20wt%, CQ content is the organic resin system (III) of 0.1wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
Take by weighing 3 shown in the general formula (7) of 0.1264g, shown in 4-methylenedioxyphenyl methyl formate (methyl piperate) or the general formula (3) 3,4-methylenedioxyphenyl Ethyl formate (piperic acid ethyl ester) is in the 25mL beaker, then to wherein adding organic resin system (III) 6.3327g, fully stir and make the system mix homogeneously, obtain containing the organic resin mixture of 2.0wt% methyl piperate.In this system, add particle mean size then and be the aerosil filler AEROSIL OX 50 that 12.5 microns silicic-boric acid barium glass (U.S. ESSCHEM company) 8.1045g (volume content be amount of the mixture 30%) and particle mean size be 40 nanometers (German DEGUSSA company) 0.0224 and restrain (volume content be amount of the mixture 5%), fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 65: 35 composite system.In the darkroom, this composite system is left standstill in the politef template of 8mm (the diameter) * 1mm (thickness) that reinjects after 12 hours, after upper and lower surface clamps with glass slide, to be tested when leaving standstill to no bubble.Under the room temperature, in the air atmosphere, sample to be tested was shone 3 minutes with visible lamp, obtain the milky cured film of visible-light curing filling composite, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 80.7%.
Example 4:
Dissolving 1.2520g light trigger virtue diketone (CQ) is in 1 of 12.5245g, in the 6-hexanediol double methyl methacrylate (HDDMA), being mixed with the BISGMA/HDDMA proportioning with 12.5243g bisphenol-A epihydric alcohol methylpropenoic acid ester (BISGMA) is 50wt%: 50wt%, CQ content is the organic resin system (IV) of 5.0wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
Take by weighing the acetic acid-3 shown in the 0.1238g general formula (5), 4-methylenedioxyphenyl methyl ester is in the 25mL beaker, then to wherein adding organic resin system (IV) 8.2902g, fully stir and make the system mix homogeneously, obtain containing 1.5wt% acetic acid-3, the organic resin mixture of 4-methylenedioxyphenyl methyl ester.In this mixture, add particle mean size then and be the aerosil filler AEROSIL OX50 that 10.4 microns aluminosilicate glass ceramics (U.S. ESSCHEM company) 15.9128 grams (volume content is an amount of the mixture 30%) and particle mean size be 40 nanometers (German DEGUSSA company) 0.5665 and restrain (volume content be amount of the mixture 40%), fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 30: 70 composite system.In the darkroom, this composite system is left standstill in the politef template of 8mm (the diameter) * 1mm (thickness) that reinjects after 12 hours, after upper and lower surface clamps with glass slide, to be tested when leaving standstill to no bubble.Under the room temperature, in the air atmosphere, sample to be tested was shone four minutes with visible lamp, obtain the milky cured film of visible-light curing filling composite, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 87.5%.
Example 5:
Dissolving 0.8493g light trigger virtue diketone (CQ) is in 1 of 2.2001g, in the 3-butanediol double methyl methacrylate (BDDMA), being mixed with the UDMA/BDDMA proportioning with 40.2773g carbamate double methyl methacrylate (UDMA) is 95wt%: 5wt%, CQ content is the organic resin system (V) of 2.0wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
Take by weighing the methacrylic acid-3 shown in the 0.3131g general formula (4), methacrylic acid-3 shown in 4-methylenedioxyphenyl methyl ester or the general formula (6), 4-methylenedioxyphenyl ester is in the 25mL beaker, then to wherein adding organic resin system (V) 6.2594g, obtain containing 5.0wt% methacrylic acid-3,4-methylenedioxyphenyl methyl ester or methacrylic acid-3, the organic resin system of 4-methylenedioxyphenyl ester fully stirs and makes the system mix homogeneously; In this system, add particle mean size then and be the aerosil filler AEROSIL OX50 that 6.5 microns silicic-boric acid barium glass (U.S. ESSCHEM company) 13.6043g (volume content be product total amount 20%) and particle mean size be 40 nanometers (German DEGUSSA company) 0.8365g (volume content be product total amount 60%), fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 20: 80 composite system.In the darkroom, this composite system is left standstill in the politef template of 8mm (the diameter) * 1mm (thickness) that reinjects after 12 hours, after upper and lower surface clamps with glass slide, to be tested when leaving standstill to no bubble.Under the room temperature, in the air atmosphere, sample to be tested was shone four minutes with visible lamp, obtain the milky cured film of visible-light curing filling composite, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 89.4%.
Example 6:
Dissolving 0.4521g light trigger virtue diketone (CQ) is in the triethylene glycolbismethyl-acrylate (TrEGDMA) of 15.0694g, being mixed with the UDMA/TrEGDMA proportioning with 35.1612g carbamate double methyl methacrylate (UDMA) is 70wt%: 30wt%, CQ content is the organic resin system (VI) of 0.9wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
Take by weighing the acetic acid-3 shown in the 0.1061g general formula (8), 4-methylenedioxyphenyl ester to wherein adding organic resin system (VI) 5.2970g, obtains containing 2.0wt% acetic acid-3 then in the 25mL beaker, the organic resin system of 4-methylenedioxyphenyl ester fully stirs and makes the system mix homogeneously; In this system, add the aerosil filler R-972 that particle mean size is 16 nanometers (the auspicious new material company limited of GuangZhou, China city benefit) 0.1591g (volume content be product total amount 40%) then, fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 60: 40 composite system.In the darkroom, this composite system is left standstill in the politef template of 8mm (the diameter) * 1mm (thickness) that reinjects after 12 hours, after upper and lower surface clamps with glass slide, to be tested when leaving standstill to no bubble.Under the room temperature, in the air atmosphere, sample to be tested is shone 180s with visible lamp, obtain the milky cured film of visible-light curing filling composite, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 87.8%.
The present invention adopts from edible natural and replaces tertiary amine of the prior art as the light trigger auxiliary agent with chemical constituent and the derivant thereof of plant, prepared visible light hardened filling composite material for dental filling, and bio-toxicity is low, and has the biocompatibility of getting well.As can be seen from the above embodiments, in useful clinically light application time, double bond conversion rate is higher than 80% mostly, this value explanation initiator system efficiency of initiation height of the present invention, and the degree of cross linking height of the product that generates, good mechanical property can guarantee serviceability.
Claims (3)
1. visible light hardened filling composite material for dental filling, it is the polymerizable double methyl methacrylate resin that to form by double methyl methacrylate prepolymer and double methyl methacrylate reactive diluent, visible light initiator virtue diketone, aided initiating, by quartz, the inorganic filler that glass or both mixture are formed fully mixes, obtain through the radiation of visible light after fixing, it is characterized in that: the mass percent of double methyl methacrylate prepolymer is 50～95% in the polymerizable double methyl methacrylate resin, and the mass percent of double methyl methacrylate reactive diluent is 5～50%; Virtue diketone content is 0.1～5.0% of polymerizable double methyl methacrylate resin quality; The volume content of inorganic filler is 35～80% of a described visible-light curing filled composite materials cumulative volume; Aided initiating is cyclic piperonyl compound and the derivant thereof shown in general formula (1)～(8) are arbitrary, and its content is 0.1～5.0% of polymerizable double methyl methacrylate resin quality,
2. visible light hardened filling composite material for dental filling according to claim 1 is characterized in that: described double methyl methacrylate prepolymer is bisphenol-A epihydric alcohol methylpropenoic acid ester or carbamate double methyl methacrylate; The double methyl methacrylate reactive diluent is triethylene glycolbismethyl-acrylate, 1,3 butylene glycol double methyl methacrylate, 1,6-hexanediol double methyl methacrylate or tetraethylene-glycol double methyl methacrylate.
3. visible light hardened filling composite material for dental filling according to claim 1 and 2 is characterized in that: particle diameter is that the components contents of 7～40 nanometers is 5～60% of a visible-light curing filling composite volume in the described inorganic filler.
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| CN108014021B (en) * | 2016-11-29 | 2022-03-04 | 北京安泰生物医用材料有限公司 | Tooth filling and repairing material and preparation method thereof |
| CN109897161B (en) * | 2019-03-04 | 2021-03-02 | 武汉科技大学 | Heat-repairing polyurethane elastomer containing ketal structure and preparation method thereof |
| CN109971294B (en) * | 2019-04-03 | 2020-11-10 | 广州五行材料科技有限公司 | Self-initiated organic/inorganic hybrid material and preparation method and application thereof |
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| JPH06336417A (en) * | 1993-03-31 | 1994-12-06 | Shiseido Co Ltd | Ultraviolet light absorber and external preparation for skin mixed with the same |
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| CN1196923A (en) * | 1997-03-31 | 1998-10-28 | 可乐丽股份有限公司 | Resinous composition for dental use |
| US20050059752A1 (en) * | 2002-07-12 | 2005-03-17 | Rhodia Chimie | Stable, cationically polymerizable/crosslinkable dental compositions having high filler contents |
| CN1723870A (en) * | 2005-07-20 | 2006-01-25 | 武汉大学 | Cyclic aldehyde acetal used as initiator aid of dental filling visible light curing filling compounding material |
| CN1723869A (en) * | 2005-07-20 | 2006-01-25 | 武汉大学 | Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material |
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2006
- 2006-07-24 CN CNB2006100888846A patent/CN100415200C/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091001A (en) * | 1992-11-04 | 1994-08-24 | 英国技术集团有限公司 | The compositions of command-curable |
| JPH06336417A (en) * | 1993-03-31 | 1994-12-06 | Shiseido Co Ltd | Ultraviolet light absorber and external preparation for skin mixed with the same |
| JPH07238275A (en) * | 1994-02-28 | 1995-09-12 | Shiseido Co Ltd | Ultraviolet light absorber and skin external preparation containing the same blended therein |
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| US20050059752A1 (en) * | 2002-07-12 | 2005-03-17 | Rhodia Chimie | Stable, cationically polymerizable/crosslinkable dental compositions having high filler contents |
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| CN1723869A (en) * | 2005-07-20 | 2006-01-25 | 武汉大学 | Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material |
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