CN100379399C - Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material - Google Patents
Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material Download PDFInfo
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- CN100379399C CN100379399C CNB2005100191264A CN200510019126A CN100379399C CN 100379399 C CN100379399 C CN 100379399C CN B2005100191264 A CNB2005100191264 A CN B2005100191264A CN 200510019126 A CN200510019126 A CN 200510019126A CN 100379399 C CN100379399 C CN 100379399C
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Abstract
The present invention relates to a purpose of cyclic carbonate used as an initiator aid of a visible light curing filling composite material for dental filling. The present invention adopts the cyclic carbonate with favorable biocompatibility to substitute tertiary amine in the prior art as a photo initiator aid so as to reduce the biological toxicity of materials and increase the biocompatibility of the materials; the present invention has the advantage of low biological toxicity.
Description
Technical field
The present invention relates to the purposes of cyclic carbonate as the aided initiating of visible light hardened filling composite material for dental filling.
Background technology
The dental prosthetic material kind is a lot, wherein being most widely used with silver amalgam, visible-light curing filling composite.Silver amalgam is owing to be eliminated gradually to the pollution of environment with to the toxicity of human body.Sweden forbids the application of silver amalgam in dental prosthetic in earlier 1990s, then is Australia, and European countries such as Germany restriction silver amalgam is as the application of dental prosthetic material in child and anemia of pregnant woman.In the U.S., the consumption of silver amalgam accounts for 25% at present.In developing country, the application of silver amalgam is also very general.But good, easy to operate owing to the light curing compound material aesthetic property, strong with the caking property of tooth structure, after particularly mechanical and physical performance was updated, it used extensive day by day clinically in recent years.In developing country, presented a kind of photocuring filling composite and substituted silver amalgam trend of application in tooth section reparation field gradually.
The visible-light curing filling composite is proposed in 1963 first by doctor R.L.Bowen, with regard to material itself, it is by polymerisable monomer and oligomer (methyl acrylic ester), inorganic filler (quartz, glass, aerosil etc.), visible light initiator and aided initiating, and other additive is formed.Under visible light radiation, a series of photochemical reaction takes place and generates free radical in initiator and aided initiating, and then causes 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.In business-like dentistry visible-light curing filling composite prescription, most initiator systems are by fragrant diketone (camphorquinone, CQ) and tertiary amine (4-N, N-mesitylenic acid ethyl ester, EDAB) form, the organic material system of using is the double methyl methacrylate that contains aromatic rings or carbamate groups at present.Wherein most popular is bisphenol-A epihydric alcohol methylpropenoic acid ester (BISGMA), ethoxyquin bisphenol-A epihydric alcohol methylpropenoic acid ester (EO-BISGMA) and carbamate double methyl methacrylate (UDMA).But their viscosity is very high, must add polymerizable, low viscous methacrylate monomer such as triethylene glycol double methyl methacrylate (TEGDMA) 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.Thereby in the visible-light curing filling composite, to add certain pigment to adjust the color of material.The selection of organic material is very important in the visible-light curing filling composite, because the performance of material is decided by the organic material system to a great extent, for example: the toxicity of polymerization activity, system stability, material, hardness, intensity, compliance, modulus, vitrification point, color etc.Commercial at present with making light-initiated auxiliary agent with tertiary amine usually in the visible-light curing filling composite system, it is requisite a kind of component in the photocuring packing material tooth dental repair material, but well-known, amine has certain murder by poisoning to human body, especially to the liver of human body.
Summary of the invention
The present invention is exactly at above-mentioned deficiency, and the purposes of cyclic carbonate as the aided initiating of visible light hardened filling composite material for dental filling is provided, and is low with the bio-toxicity that reduces visible light hardened filling composite material for dental filling.
Technical scheme provided by the invention is as follows: cyclic carbonate is as the purposes of the aided initiating of visible light hardened filling composite material for dental filling, and wherein this visible-light curing filling composite contains the camphorquinone photosensitizer.
Above-mentioned cyclic carbonate is:
R, R in the formula
1, R
2Be selected from H, hydroxyl, alkyls substituent groups such as methyl, ethyl, ester group, alkoxyl, vinyl, aromatic substituents such as phenyl, benzyl, p-methoxyphenyl; N=1 or 2.
The present invention adopts the cyclic carbonate with good biocompatibility to replace tertiary amine of the prior art as the light trigger auxiliary agent, to reduce the material bio-toxicity, improves the biocompatibility of material; Has the low advantage of bio-toxicity.
Specific embodiments
Example 1:
CQ is in 38.04g TEGDMA for dissolving 0.1536g visible light initiator, being mixed with the UDMA/TEGDMA proportioning with 114.12g UDMA is 75wt%:25wt%, CQ content is the organic resin system (I) of 0.1wt%, fully stirs and makes the system mix homogeneously, places the darkroom standby.
5-methyl-5-benzyl formate trimethylene the cyclic carbonate ester that takes by weighing 0.0511g then to wherein adding the above-mentioned organic resin system of 9.9012g (I), fully stirs and makes its mix homogeneously in the 25mL beaker, obtains containing 0.5wt% cyclic carbonate ester resin compound.In this mixture, add particle mean size then and be 19 microns barium borosilicate glass (U.S. ESSCHEM company) 10.6846g (volume content be amount of the mixture 40%), fully stir and make its mix homogeneously, obtaining organic resin system and inorganic filler volume ratio is the composite system of 60:40.In the darkroom, this composite system is left standstill after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 with visible lamp irradiation two minutes four minutes, is obtained the milky cured film, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 89.6%.
Example 2:
CQ is in 2.14g 1.6-hexanediol double methyl methacrylate (HDDMA) for dissolving 2.2647g visible light initiator, being mixed with the EO-BISGMA/HDDMA proportioning with 40.66g EO-BISGMA (Mn=1700) is 95wt%: 5wt%, CQ content is the organic resin system (II) of 5wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
The trimethylene cyclic carbonate that takes by weighing 1.41g then to wherein adding the above-mentioned organic resin system of 13.09g (II), fully stirs and makes its mix homogeneously in the 25mL beaker, obtains containing 9.7wt% cyclic carbonate resin compound.In this mixture, add the aerosil filler AEROSIL OX50 that mean diameter is 40 nanometers (German DEGUSSA company) 0.47g (volume content be amount of the mixture 80%) then, 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 after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 with visible lamp irradiation four minutes, is obtained the milky cured film, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 91.5%.
Example 3:
Dissolving 0.3513g CQ is in 14.13g 1.3-butanediol double methyl methacrylate (BDDMA), being mixed with the UDMA/BDDMA proportioning with 56.47g UDMA is 80wt%: 20wt%, CQ content is the organic resin system (III) of 0.5wt%, fully stir and make the system mix homogeneously, place the darkroom standby.
The 5-benzyloxy trimethylene cyclic carbonate that takes by weighing 0.4877g then to wherein adding 23.89g organic resin system (III), fully stirs and makes its mix homogeneously in the 25mL small beaker, obtains containing 2.Owt% cyclic carbonate ester resin compound.The barium borosilicate glass (U.S. ESSCHEM company) 10.5695 that adds particle mean size then and be 12 nano fumed silica filler AEROSIL R711 (German DEGUSSA company) 1.1263g (volume content be amount of the mixture 40%) and particle mean size in this mixture and be 6.5 microns restrains (volume content be amount of the mixture 20%), 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 after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 after four minutes, is obtained the milky cured film with the visible lamp irradiation, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 87.3%.
Example 4:
Dissolving 1.7513g CQ is in 21.35g TEGDMA, being mixed with the BISGMA/TEGDMA proportioning with 21.37g BISGMA is 50wt%: 50wt%, CQ content is the organic resin system (IV) of 3.9wt%, fully stirs and makes the system mix homogeneously, places the darkroom standby.
Take by weighing 5 of 0.5017g, 5-dimethyl trimethylene cyclic carbonate then to wherein adding 9.53g organic resin system (IV), fully stirs and makes its mix homogeneously in the 25mL beaker, obtains containing 5.0wt% cyclic carbonate ester resin compound.The barium silicate glass (U.S. ESSCHEM company) 5.8371 that adds particle mean size then and be 40 nano fumed silica filler AEROSIL OX50 (German DEGUSSA company) 0.1289g (volume content be amount of the mixture 30%) and particle mean size in this mixture and be 13 microns restrains (volume content be amount of the mixture 20%), fully stir and make its mix homogeneously, obtain organic resin system and inorganic filler volume ratio and be 50: 50 composite system.In the darkroom, this composite system is left standstill after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 after four minutes, is obtained the milky cured film with the visible lamp irradiation, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 69.3%.
Example 5:
Dissolving 0.5359g CQ is in 14.08g BDDMA, being mixed with the EO-BISGMA/BDDMA proportioning with 32.86g EO-BISGMA (Mn=1700) is 60wt%: 40wt%, CQ content is the organic resin system (V) of 1.1wt%, fully stirs and makes the system mix homogeneously, places the darkroom standby.
5-methyl-5-Ethyl formate trimethylene the cyclic carbonate compound that takes by weighing 0.1805g is in the 25mL small beaker, then to wherein adding 5.7395g organic resin system (V), fully stir and make its mix homogeneously, obtain containing 3.0wt% cyclic carbonate ester resin compound.The aluminosilicate glass ceramics (U.S. ESSCHEM company) 2.8942 that adds particle mean size then and be 12 nano fumed silica filler AEROSIL R711 (German DEGUSSA company) 0.2704g (volume content be amount of the mixture 40%) and particle mean size in this mixture and be 10.4 microns restrains (volume content be amount of the mixture 30%), 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 after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 after four minutes, is obtained the milky cured film with the visible lamp irradiation, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 80.2%.
Example 6:
Dissolving 0.2359g CQ is in 14.08g TEGDMA, being mixed with the BISGMA/TEGDMA proportioning with 32.86g BISGMA is 70wt%: 30wt%, CQ content is the organic resin system (VI) of 0.5wt%, fully stirs and makes the system mix homogeneously, places the darkroom standby.
The dimethylene cyclic carbonate that takes by weighing 0.2097g to wherein adding above-mentioned organic resin system (VI) 13.8010g for preparing, obtains containing the organic resin system of 1.5wt% cyclic carbonate then in the 25mL beaker, fully stir and make the system mix homogeneously; Adding particle mean size then in this system is the AEROSIL OX50 inorganic filler 0.6127g (volume content is 50%) of 40 nanometers, fully stirs and makes its mix homogeneously, obtains organic resin system and inorganic filler volume ratio and be 50: 50 composite system.In the darkroom, this composite system is left standstill after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 with visible lamp irradiation 200 seconds, is obtained the milky cured film, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 58.2%.
Example 7:
The dimethylene cyclic carbonate that takes by weighing 0.3126g is in the 25mL beaker, organic resin system (VI) 7.5024g that in wherein adding example 6, prepares then, obtain containing the organic resin system of 3.0wt% cyclic carbonate, fully stir and make the system mix homogeneously; Adding particle mean size then in this system is the AEROSIL R711 inorganic filler 1.2991g (volume content is 60%) of 12 nanometers, fully stirs and makes its mix homogeneously, obtains organic resin system and inorganic filler volume ratio and be 40: 60 composite system.In the darkroom, this composite system is left standstill after 12 hours in the politef template of injecting 8mm (diameter) * 1mm (thickness), 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 with visible lamp irradiation 200 seconds, is obtained the milky cured film, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 53.1%.
Example 8:
Dissolving 0.2504g CQ is in 19.9g TEGDMA, being mixed with the BISGMA/TEGDMA proportioning with 29.9g BISGMA is 60wt%: 40wt%, CQ content is the organic resin system (VII) of 0.5wt%, fully stirs and makes the system mix homogeneously, places the darkroom standby.
The dimethylene cyclic carbonate that takes by weighing 0.3102g then to wherein adding 7.7 organic resin systems (VII), fully stirs and makes the system mix homogeneously in the 25mL beaker, obtains containing the organic resin system of 3.0wt% cyclic carbonate; Add AEROSIL R711 filler 0.2240g and AEROSIL OX50 filler 0.0861g (volume ratio is 30: 70) to this organic resin system then, fully stir and make its mix homogeneously, obtain organic resin system and mixed type 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, with infrared instrument tracking and monitoring under the near-infrared condition, calculating final double bond conversion rate is 60.5%.
The present invention adopts the cyclic carbonate compound with good biocompatibility to replace tertiary amine of the prior art as the light trigger auxiliary agent, and prepared visible light hardened filling composite material for dental filling bio-toxicity is low, and has good biocompatibility.
Claims (2)
1. cyclic carbonate is as the purposes of the aided initiating of visible light hardened filling composite material for dental filling, and wherein this visible-light curing filling composite contains the camphorquinone photosensitizer.
2. purposes according to claim 1 is characterized in that: cyclic carbonate is the cyclic carbonate of following structure:
R, R in the formula
1, R
2Be selected from H, hydroxyl, methyl, ethyl, ester group, alkoxyl, vinyl, phenyl, benzyl, p-methoxyphenyl, n=1 or 2.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100191264A CN100379399C (en) | 2005-07-20 | 2005-07-20 | Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100191264A CN100379399C (en) | 2005-07-20 | 2005-07-20 | Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material |
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| CN1723869A CN1723869A (en) | 2006-01-25 |
| CN100379399C true CN100379399C (en) | 2008-04-09 |
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| CNB2005100191264A Expired - Fee Related CN100379399C (en) | 2005-07-20 | 2005-07-20 | Cyclic carbnoic ester used as initiator aid dental filling visible light curing filling compounding material |
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| CN100415200C (en) * | 2006-07-24 | 2008-09-03 | 北京化工大学 | Visible light hardened filling composite material for dental filling and its preparing method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047261A (en) * | 1989-06-29 | 1991-09-10 | Societe Nationale Des Pourdres Et Explosifs | Process for the manufacture of coatings by radiocrosslinking |
| CN1537870A (en) * | 2003-03-13 | 2004-10-20 | ��ʽ�����ɽ | Photoepolymerization initiater |
| CN1543458A (en) * | 2001-08-17 | 2004-11-03 | Ucb公司 | Preparation of a compound containing cyclic and linear carbonate groups |
| US20050059752A1 (en) * | 2002-07-12 | 2005-03-17 | Rhodia Chimie | Stable, cationically polymerizable/crosslinkable dental compositions having high filler contents |
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2005
- 2005-07-20 CN CNB2005100191264A patent/CN100379399C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047261A (en) * | 1989-06-29 | 1991-09-10 | Societe Nationale Des Pourdres Et Explosifs | Process for the manufacture of coatings by radiocrosslinking |
| CN1543458A (en) * | 2001-08-17 | 2004-11-03 | Ucb公司 | Preparation of a compound containing cyclic and linear carbonate groups |
| US20050059752A1 (en) * | 2002-07-12 | 2005-03-17 | Rhodia Chimie | Stable, cationically polymerizable/crosslinkable dental compositions having high filler contents |
| CN1537870A (en) * | 2003-03-13 | 2004-10-20 | ��ʽ�����ɽ | Photoepolymerization initiater |
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