CN115844736B - Adhesive composition based on pyroelectric principle and application thereof - Google Patents
Adhesive composition based on pyroelectric principle and application thereof Download PDFInfo
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- CN115844736B CN115844736B CN202211670800.5A CN202211670800A CN115844736B CN 115844736 B CN115844736 B CN 115844736B CN 202211670800 A CN202211670800 A CN 202211670800A CN 115844736 B CN115844736 B CN 115844736B
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- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 230000001070 adhesive effect Effects 0.000 title abstract description 54
- 239000000853 adhesive Substances 0.000 title abstract description 53
- 229910052454 barium strontium titanate Inorganic materials 0.000 claims abstract description 36
- 239000011256 inorganic filler Substances 0.000 claims abstract description 31
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 31
- 239000002245 particle Substances 0.000 claims abstract description 29
- 239000003999 initiator Substances 0.000 claims abstract description 20
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 17
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 15
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003479 dental cement Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 claims abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 239000010954 inorganic particle Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 10
- 229910052788 barium Inorganic materials 0.000 claims description 9
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 9
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
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- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- ZYMCJDAUBJFVSM-UHFFFAOYSA-N 6-methylheptyl 4-(dimethylamino)benzoate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 ZYMCJDAUBJFVSM-UHFFFAOYSA-N 0.000 claims description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 2
- SCIGVHCNNXTQDB-UHFFFAOYSA-N decyl dihydrogen phosphate Chemical compound CCCCCCCCCCOP(O)(O)=O SCIGVHCNNXTQDB-UHFFFAOYSA-N 0.000 claims description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 2
- RJUVPCYAOBNZAX-UHFFFAOYSA-N ethyl 3-(dimethylamino)-2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=CN(C)C RJUVPCYAOBNZAX-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- -1 2,4, 6-trimethylbenzoyl phenyl ethyl Chemical group 0.000 claims 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims 1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 6
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
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- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
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- 102000004190 Enzymes Human genes 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
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- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- 239000008272 agar Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- YMCOIFVFCYKISC-UHFFFAOYSA-N ethoxy-[2-(2,4,6-trimethylbenzoyl)phenyl]phosphinic acid Chemical compound CCOP(O)(=O)c1ccccc1C(=O)c1c(C)cc(C)cc1C YMCOIFVFCYKISC-UHFFFAOYSA-N 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 238000002715 modification method Methods 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- GUGNSJAORJLKGP-UHFFFAOYSA-K sodium 8-methoxypyrene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].C1=C2C(OC)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 GUGNSJAORJLKGP-UHFFFAOYSA-K 0.000 description 1
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Landscapes
- Dental Preparations (AREA)
Abstract
The invention discloses an adhesive composition based on a pyroelectric principle and application thereof. The adhesive composition of the present invention comprises urethane dimethacrylate, hydroxyethyl methacrylate, bisphenol a glycidyl methacrylate, an acidic polymerization monomer, an initiator, an inorganic filler and a solvent, wherein the inorganic filler comprises barium strontium titanate particles and/or fibers having pyroelectric properties when the temperature is changed at 20-50 ℃. The dental adhesive composition of the present invention can be applied to repairing and bonding of dental restoration, for example, to bonding restoration of a photocurable composite resin and a tooth, cavity sealing for pretreatment in indirect restoration, bonding treatment of root surface exposure, bonding of a dental crown restoration using a photocurable composite resin, and the like, and simultaneously, the adhesive composition of the present invention is used for rapid and simple restoration and has excellent antibacterial performance.
Description
Technical Field
The invention relates to a dental restorative material, in particular to an adhesive composition based on the pyroelectric principle and application thereof.
Background
At present, dental adhesives are used for repairing enamel, dentin and cementum damaged by caries and the like, and the adhesives can be matched with light-cured composite resin to carry out adhesive repairing of dental crown repairing bodies. Dental adhesives typically include a polymerizable monomer, a filler, and an initiator.
The existing material has higher adhesive property to dentin, so that the repaired prosthesis can be prevented from falling off, secondary caries is prevented, and the antibacterial property is required to be improved. In this regard, several dental adhesives for improving antibacterial performance have been developed, for example, CN101239024a discloses a nano silver fluorine-containing self-etching single-bottle dental adhesive which realizes antibacterial function of the adhesive by introducing antibacterial nano silver, but antibacterial performance is to be improved.
Therefore, there is still a need for a dental adhesive with long-acting antibacterial function, which can meet the requirement of proper mechanical properties to solve the problems of current antibacterial property, mechanical property, biocompatibility and the like.
The information in the background section is only for the purpose of illustrating the general background of the invention and is not to be construed as an admission or any form of suggestion that such information forms the prior art that is well known to those of ordinary skill in the art.
Disclosure of Invention
In order to solve at least part of the technical problems in the prior art, the invention provides a dental antibacterial resin composition based on a pyroelectric principle, a dental restoration material and application thereof. Specifically, the present invention includes the following.
In a first aspect of the present invention, there is provided an adhesive composition based on the principle of pyroelectric, comprising an organic resin matrix, an initiator, an inorganic filler and a solvent, wherein the inorganic filler comprises barium strontium titanate particles having pyroelectric properties when the temperature is changed between 20 and 50 ℃, and the organic resin matrix comprises urethane dimethacrylate, hydroxyethyl methacrylate, phosphoric acid or carbonic acid polymeric monomers and bisphenol a glycidyl methacrylate.
In certain embodiments, the adhesive composition according to the present invention, wherein the adhesive composition further comprises an auxiliary agent comprising at least one of a polymerization inhibitor, a surfactant, and an ultraviolet light absorber.
In certain embodiments, adhesive compositions according to the present invention wherein the acid polymerized monomer comprises the phosphoric acid or carbonic acid polymerized monomer, examples of which include, but are not limited to, monodecyl 10- (2-methacryloyloxy) phosphate.
In certain embodiments, the adhesive composition according to the present invention, wherein the adhesive composition comprises 10 to 60 parts by weight of urethane dimethacrylate, 1 to 60 parts by weight of hydroxyethyl methacrylate, 10 to 60 parts by weight of bisphenol A glycidyl methacrylate, 1 to 20 parts by weight of an acidic polymeric monomer, 20 to 60 parts by weight of barium strontium titanate particles, 10 to 40 parts by weight of a solvent, 0.5 to 10 parts by weight of an initiator, and 0.5 to 10 parts by weight of an auxiliary agent, based on the weight of the adhesive composition.
In certain embodiments, the adhesive composition according to the present invention, wherein the solvent is selected from at least one of ethanol, propanol, n-butanol, acetone, methyl ethyl ketone, ethyl acetate, and water, or a combination thereof.
In certain embodiments, the adhesive composition according to the present invention, wherein the initiator comprises at least one of camphorquinone, ethyl 4-N, N-dimethylaminobenzoate, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO), benzil, ethyl 2,4, 6-trimethylbenzoyl-phenylphosphonate (TPIO-L), 2-methyl-2- (4-morpholino) -1- [4- (methylthio) phenyl ] -1-propanone, 1-hydroxycyclohexylphenyl ketone, ethyl N, N-dimethylaminomethacrylate, isooctyl p-N, N-dimethylaminobenzoate (EHA), 1-phenyl-1, 2-propanedione (PPD), and ethyl p-dimethylaminobenzoate (EDB).
In certain embodiments, the adhesive composition according to the present invention, wherein the barium strontium titanate has a particle size of 0.1-25nm. In certain embodiments, the inorganic filler further comprises silica, zirconia, silanized silica and/or barium glass, preferably the above particles have a particle size of 0.1 to 25nm. It is also preferred that the weight ratio of barium strontium titanate particles to inorganic filler particles is greater than 1:1, such as (10-1): 1.
In certain embodiments, the adhesive composition according to the present invention, wherein the barium strontium titanate has a pyroelectric coefficient of 698 μC.m at 36 DEG C -2 ·K -1 The above.
In a second aspect of the present invention, there is provided a method for preparing the adhesive composition according to the first aspect, comprising the steps of:
(1) Preparing a urethane dimethacrylate, a hydroxyethyl methacrylate and bisphenol a glycidyl methacrylate, a phosphoric acid or carbonic acid polymerization monomer, an initiator and a solvent under non-polymerization conditions;
(2) Preparing barium strontium titanate ferroelectric phase particles with pyroelectric performance at 20-50 ℃ and particle size of 0.1-25nm; and
(3) Mixing the components of steps (1) and (2) to obtain a mixture, wherein the mixture is capable of being cured under curing conditions.
In a third aspect, the present invention provides the use of the dental antibacterial adhesive composition according to the pyroelectric principle in the preparation of a restorative adhesive or dentin adhesive material.
The invention develops a new self-antibacterial dental restoration adhesive composition material which has a long-acting antibacterial function, can meet the requirement of proper mechanical properties, can solve the problems of antibacterial property, mechanical property, biocompatibility and the like of the current dental adhesive, realizes the synergistic promotion of the antibacterial function and mechanical adaptation of the dental restoration material, prolongs the service life of a restoration body, and improves the long-term restoration effect of caries.
The dental adhesive composition of the present invention can be applied to repairing and bonding of dental restorations and dental crowns, for example, repairing of a photocurable composite resin, hole sealing for pretreatment in indirect repairing, bonding treatment of root surface exposure, bonding of a dental crown restoration using a photocurable composite resin, and the like, and at the same time, repairing using the adhesive composition of the present invention is rapid and simple, and has excellent antibacterial properties.
Drawings
The pyroelectric properties of barium strontium titanate inorganic filler in the exemplary binder of fig. 1.
The cure rate of the exemplary adhesive of fig. 2.
Fig. 3 illustrates the bacteriostatic rate of the adhesive.
FIG. 4CCK-8 experimental results.
Detailed Description
Various exemplary embodiments of the invention will now be described in detail, which should not be considered as limiting the invention, but rather as more detailed descriptions of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. In addition, for numerical ranges in the present invention, it is understood that the upper and lower limits of the ranges and each intermediate value therebetween are specifically disclosed. Every smaller range between any stated value or stated range, and any other stated value or intermediate value within the stated range, is also encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control. Unless otherwise indicated, "%" is percent by weight.
Adhesive composition
In a first aspect of the present invention, there is provided a dental antibacterial adhesive composition (sometimes referred to herein simply as "the composition of the present invention") based on the principle of pyroelectric, which is a curable composition, or is a composition before curing. The adhesive composition of the invention comprises an organic resin matrix, an initiator, an inorganic filler, a solvent, an acidic monomer and an auxiliary agent.
In certain embodiments, the urethane methacrylate UDMA component is typically present in an amount of 10 to 60 parts by weight, e.g., 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 parts by weight, etc., based on the weight of the adhesive composition. The content of bisphenol A glycidyl methacrylate bis-GMA is generally 10 to 60 parts by weight, for example 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 parts by weight, etc. The content of hydroxyethyl methacrylate HEMA is generally 1 to 60 parts by weight, for example 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 parts by weight, etc. The content of the acid polymerized monomer 10- (2-methacryloyloxy) phosphoric acid monodecyl ester MDP is generally 1 to 20 parts by weight, for example, 1, 5, 10, 15, 20 parts by weight, etc. The barium strontium titanate is generally used in an amount of 20 to 60 parts by weight, for example, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, etc. The auxiliary is generally used in an amount of 0.5 to 10 parts by weight, for example, 0.5, 2,4,6, 8, 10 parts by weight, etc. The solvent is generally used in an amount of 10 to 40 parts by weight, for example, 10, 20, 30, 40 parts by weight, etc. The initiator is generally used in an amount of 0.5 to 10 parts by weight, for example, 0.5, 1,2, 4,6, 8, 10 parts by weight, etc. The amount of the solvent used is generally 10 to 40 parts by weight, for example, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, etc.
In the present invention, the diluent is used to promote the blending between the polymerizable monomer and the inorganic filler, and to improve the double bond conversion rate during polymerization. The polymerizable monomers and diluents are generally used in amounts of from 0.5 to 2:1 by weight. When the amount of the diluent is too large, the polymerization shrinkage of the obtained cured resin tends to become high, and the water absorption is enhanced, thereby affecting the mechanical properties. On the other hand, if the amount of the diluent is too low, it tends to affect the uniform dispersion of the inorganic filler, thereby affecting the double bond conversion. The diluent is not particularly limited, and any known type of diluent may be used.
In the present invention, the initiator is not particularly limited, and any known initiator type may be used, including a thermal initiator and a photoinitiator, and two initiators may be used in combination to form a dual initiation system. Examples of thermal initiators include, but are not limited to, terephthaloyl peroxide (BPO), preferably further using amine molecules as catalysts. The photoinitiator is preferably a visible light photoinitiator, examples of which include, but are not limited to, camphorquinone (CQ) and ethyl 4-N, N-dimethylaminobenzoate (EDMAB), wherein EDMAB is a co-initiator shared by CQ, having an accelerator and an antioxidant polymerization inhibiting function.
In the present invention, barium strontium titanate particles and/or fibers having pyroelectric properties refer to ferroelectric phase inorganic particles and/or fibers having pyroelectric properties at a temperature range in the oral cavity, such as a temperature change of 20 to 50 ℃. The present inventors have found that by using such particles and/or fibers in place of at least a portion of the inorganic filler in conventional adhesive compositions, the cured resin can be rendered pyroelectric, and further have found that the inorganic particles having pyroelectric properties still enable the adhesive composition to exhibit excellent antibacterial activity.
In the present invention, the inorganic filler may contain nano-sized barium strontium titanate particles having a particle diameter of generally 0.1 to 25nm, preferably 1 to 20nm, more preferably 2 to 20nm, such as 2nm, 4nm, 6nm, 8nm, 10nm, 12nm, 14nm, 16nm, 18nm, 20nm, etc. The particle size in the above range allows the resulting adhesive composition to have a high antibacterial activity while having good wetting properties. If the particle diameter is too small, the polymerization shrinkage tends to become high at the time of large-scale filling, thereby affecting the mechanical strength and also affecting the pyroelectric effect of barium strontium titanate, and thus is preferably 10 to 20nm, more preferably 15 to 20nm. On the other hand, if the particle size is too large, it is disadvantageous to fill or adhere the pores of the collagen fiber network after the dentin etching, for example. It will be appreciated by those skilled in the art that nano-sized barium strontium titanate fibers within the above size ranges may also be used.
In the present invention, the inorganic filler optionally further comprises inorganic particles of 1 to 20nm. In this case, the inorganic filler is a mixed filler. The invention discovers that when different particles are mixed for use, the compressive strength and the three-point bending strength can be improved, and meanwhile, the polishing performance is better. Herein, other particles generally refer to inorganic particles that do not have pyroelectric properties, examples of which include, but are not limited to, silica, zirconia, barium glass frit, and the like. The present invention may use a combination of one or more of the above components. Preferably, the present invention uses inorganic particles that are relatively light transmissive, such as barium glass frit and/or silica.
In the present invention, the amount of barium strontium titanate (or fibers) used with other inorganic particles is generally greater than the amount of barium strontium titanate used with other inorganic particles. Preferably (10-1): 1, more preferably (9-1.5): 1, such as 8:1, 6:1, 5:1, 4:1, 3:1, 2:1, on a weight basis. If the dosage of other inorganic particles is too large, the antibacterial effect is greatly reduced.
In the present invention, the inorganic filler may be modified by surface modification, for example, to improve compatibility with the organic component. Examples of the surface modification method include surface modification of an inorganic filler using a silane coupling agent such as MPTS or the like, to improve the mechanical strength of the composite resin.
In the invention, the auxiliary agent comprises polymerization inhibitor, colorant, color shading agent, photosensitizer, reducer and the like. Examples of polymerization inhibitors include, but are not limited to, 2, 6-di-t-butyl-p-cresol (BHT), p-hydroxyanisole (MEHQ), and the like. Examples of colorants, color masking agents include, but are not limited to, titanium white, aluminum oxide, iron oxide, chrome yellow, and the like.
Preparation method
The invention also provides a preparation method of the adhesive composition, which at least comprises the following steps:
(1) Preparing urethane dimethacrylate, hydroxyethyl methacrylate, bisphenol A glycidyl methacrylate, an initiator, an acidic monomer and a solvent under non-polymerization conditions;
(2) Preparing barium strontium titanate ferroelectric phase particles with pyroelectric performance at 20-50 ℃ and particle size of 0.1-25nm; and
(3) The components in the steps (1) and (2) are mixed and cured under curing conditions to obtain an adhesive composition.
It will be appreciated by those skilled in the art that the steps numbered (1), (2), etc. are for the purpose of distinguishing between different steps and not necessarily for the purpose of indicating the order of the steps. The order of the steps is not particularly limited as long as the object of the present invention can be achieved. Furthermore, more than two of the above steps may be combined and performed simultaneously, e.g. steps (1) and (2) may be performed simultaneously. In addition, it will be appreciated by those skilled in the art that other steps or operations may be included before or after steps (1) - (3) or between any of these steps, such as further optimizing and/or improving the methods described herein.
Use of the same
The invention further provides the use of a dental antibacterial adhesive composition based on pyroelectric principles for the preparation of a dental adhesive material for prosthesis bonding or dentin bonding. Uses herein include the use of the composition to prepare repair materials, as well as the use of adhesives in combination with other materials, such as packaging materials, to form repair materials for clinical use. In the second case, the organic component and the inorganic filler in the composition may be present in a pre-mixed form and stored under non-curing conditions such as light-shielding conditions, or may be present as separate and independent components. In certain embodiments, the polymerizable monomer and initiator are present in the organic component in separate phases, and the two are mixed prior to use.
Example 1
This example is an exemplary adhesive composition, specifically as follows:
1. 80 parts by weight of a premixed composition comprising 23 parts by weight of Bis-GMA, 12 parts by weight of UDMA, 8 parts by weight of HEMA, 8 parts by weight of MDP, 1 part by weight of iron oxide, 0.6 part by weight of CQ, 0.6 part by weight of ethyl 4-N, N-dimethylaminobenzoate (EDMAB), 26.8 parts by weight of acetone/ethanol, was weighed in a beaker;
2. 20 parts by weight of an inorganic filler, which is barium strontium titanate BST, has a particle size of 20nm, a molar ratio of Ba to Sr of 7:3, and a pyroelectric coefficient of 698 mu C.m at body temperature (36 ℃) -2 ·K -1 ；
3. Adding the components obtained in 1 and 2 into a beaker, stirring overnight on a magnetic stirrer, and removing bubbles by ultrasonic for 15 minutes;
4. and (3) sucking a proper amount of mixed liquid, adding the mixed liquid into a silica gel mold, and performing photo-curing by using a dental photo-curing lamp to obtain the pyroelectric antibacterial adhesive composition.
Example 2
This example is an exemplary adhesive composition, specifically as follows:
1. weighing 50 parts by weight of a premixed component in a beaker, wherein the component comprises 20 parts by weight of Bis-GMA, 8 parts by weight of UDMA, 3 parts by weight of HEMA, 3 parts by weight of MDP, 0.8 part by weight of ferric oxide, 0.5 part by weight of CQ, 0.5 part by weight of ethyl 4-N, N-dimethylaminobenzoate (EDMAB) and 14.2 parts by weight of acetone/ethanol;
2. 50 parts by weight of an inorganic filler, which is barium strontium titanate BST, has a particle diameter of 20nm, a molar ratio of Ba to Sr of 7:3, and a pyroelectric coefficient of 698 mu C.m at body temperature (36 ℃) -2 ·K -1 ；
3. Adding the components obtained in 1 and 2 into a beaker, stirring overnight on a magnetic stirrer, and removing bubbles by ultrasonic for 15 minutes;
4. and (3) sucking a proper amount of mixed liquid, adding the mixed liquid into a silica gel mold, and performing photo-curing by using a dental photo-curing lamp to obtain the pyroelectric antibacterial adhesive composition.
Example 3
1. Weighing 60 parts by weight of a premixed component in a beaker, wherein the component comprises 23 parts by weight of Bis-GMA, 10 parts by weight of UDMA, 5 parts by weight of HEMA, 5 parts by weight of MDP, 1 part by weight of ferric oxide, 0.6 part by weight of CQ, 0.6 part by weight of ethyl 4-N, N-dimethylaminobenzoate (EDMAB) and 14.8 parts by weight of acetone/ethanol;
2. 40 parts by weight of an inorganic filler, which is barium strontium titanate BST and commercial barium glass powder in a weight ratio of 2:1, wherein the particle size of the barium strontium titanate is 20nm, the molar ratio of the Ba to the Sr is 7:3, and the bulk pyroelectric coefficient is 698 mu C.m -2 ·K -1 The grain diameter of the commercial barium glass powder is 20nm;
3. adding the components obtained in 1 and 2 into a beaker, stirring overnight on a magnetic stirrer, and removing bubbles by ultrasonic for 15 minutes;
4. and (3) sucking a proper amount of mixed liquid, adding the mixed liquid into a silica gel mold, and performing photo-curing by using a dental photo-curing lamp to obtain the pyroelectric antibacterial adhesive composition.
Comparative example 1
1. Weighing 60 parts by weight of a premixed component in a beaker, wherein the component comprises 23 parts by weight of Bis-GMA, 10 parts by weight of UDMA, 5 parts by weight of HEMA, 5 parts by weight of MDP, 1 part by weight of ferric oxide, 0.6 part by weight of CQ, 0.6 part by weight of ethyl 4-N, N-dimethylaminobenzoate (EDMAB) and 14.8 parts by weight of acetone/ethanol;
2. 40 parts by weight of inorganic filler which is barium strontium titanate BST and commercial barium glass powder with the weight ratio of 1:2, wherein the particle size of the barium strontium titanate is 20nm, and the temperature pyroelectric coefficient is 698 mu C.m -2 ·K -1 And the molar ratio of Ba to Sr is 7:3, and the grain diameter of the commercial barium glass powder is 20nm;
3. adding the components 1 and 2 into a beaker, stirring overnight on a magnetic stirrer, and removing bubbles by ultrasonic for 15 minutes;
4. and (3) sucking a proper amount of mixed liquid, adding the mixed liquid into a silica gel mold, and performing photo-curing by using a dental photo-curing lamp to obtain the pyroelectric antibacterial adhesive composition.
Comparative example 2
1. Weighing 60 parts by weight of a premixed component in a beaker, wherein the component comprises 23 parts by weight of Bis-GMA, 10 parts by weight of UDMA, 5 parts by weight of HEMA, 5 parts by weight of MDP, 1 part by weight of ferric oxide, 0.6 part by weight of CQ, 0.6 part by weight of ethyl 4-N, N-dimethylaminobenzoate (EDMAB) and 14.8 parts by weight of acetone/ethanol;
2. weighing 40 parts by weight of inorganic filler which is commercial barium glass powder and has the particle size of 20nm;
3. adding the components obtained in 1 and 2 into a beaker, stirring overnight on a magnetic stirrer, and removing bubbles by ultrasonic for 15 minutes;
4. and (3) sucking a proper amount of mixed liquid, adding the mixed liquid into a silica gel mold, and performing photo-curing by using a dental photo-curing lamp to obtain the pyroelectric antibacterial adhesive composition.
Test case
1. Cure rate test
Infrared spectra of the uncured resin and the cured resin were detected, and the cure rate DC (%) = (1-R cured/R uncured) ×100, (EqnS 4), r=1638 cm -1 Peak/1608 cm -1 A peak value.
2. Antibacterial rate
Preparing a resin round sample wafer for high-temperature high-pressure sterilization; the resin swatches were incubated with artificial saliva for 30min to simulate an oral acquired membrane. Using a composition containing 1%Mixing sucrose BHI culture medium with artificial saliva at a ratio of 1/9 to obtain micronutrient conditioned medium, and diluting pre-cultured Streptococcus mutans ua159 to 10 4 CFU/ml, 1ml was added per tube. The temperature change interval of the metal bath is set to 25-45 ℃ (multiple temperature mode is set), the temperature is gradually raised to 45 ℃ after the temperature is kept at 25 ℃ for 2min, the temperature is reduced to 25 ℃ by a semiconductor refrigeration module after the temperature is kept at 45 ℃ for 2min, the temperature is changed to be a cold-hot cycle), resin samples are taken out respectively when the 150 th cycle is completed, 1ml of PBS is added to strip bacteria, 100 mu l of the resin samples are taken out and evenly coated on a BHI agar plate, and the resin samples are placed in a carbon dioxide incubator for culturing for 48 hours. Antibacterial ratio= (number of colonies of control bacteria liquid-number of colonies of example)/100% of control bacteria liquid.
3. CCK-8 experiment
Preparing a resin round sample wafer, sterilizing at high temperature and high pressure, soaking in a cell culture medium for 3 days to obtain a resin leaching solution, culturing L929 cells by using the resin leaching solution, adding CCK-8 reagent on the 1 st, 2 nd and 3 rd days of culture, and testing the activity of the cells on an enzyme-labeled instrument.
4. Determination of dentin adhesive Strength of adhesive
The adhesive prepared in example 1 was applied to the tooth surface and cured by light, and the universal tester was connected to the machine, and the loading speed was set to 0.5mm/min, so that the loading head was parallel to the dentin adhesive surface, and the maximum loading force at shear fracture was measured to calculate the shear strength (MPa).
TABLE 1
As is clear from table 1, when the inorganic filler contains nano-sized BST, the higher the content thereof, the higher the antibacterial efficiency. When the amount of other inorganic filler is larger than the amount of BST, the pyroelectric antibacterial activity is lowered, probably because other inorganic particles form a discontinuous phase inside the resin, and the conduction of micro-current generated by pyroelectric is affected. In addition, it was found that when BST alone is used as an inorganic filler, its cure rate is low, and as other inorganic fillers are added, the cure rate increases, a possible cause of this phenomenon being that the refraction of BST is unfavorable for photocuring. But has excellent curing rate and antibacterial rate when the amount of BST and other inorganic fillers is in the range of (10-1): 1 based on weight.
In addition, it was found that the bacteriostatic activity was correlated with the pyroelectric coefficient, and the higher the pyroelectric coefficient was, the higher the bacteriostatic activity of the resulting adhesive composition was.
The adhesive composition of example 1 of the present invention was tested to have an adhesive strength to dentin of 28MPa.
While the invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Various modifications or changes may be made to the exemplary embodiments of the present disclosure without departing from the scope or spirit of the invention. The scope of the claims is to be accorded the broadest interpretation so as to encompass all modifications and equivalent structures and functions.
Claims (4)
1. A dental adhesive composition based on a pyroelectric principle is characterized in that the raw materials of the composition comprise 10-60 parts by weight of dimethyl acrylic carbamate, 1-60 parts by weight of hydroxyethyl methacrylate, 10-60 parts by weight of bisphenol A glycidyl methacrylate, 1-20 parts by weight of acidic polymerization monomer, 20-60 parts by weight of inorganic filler, 10-40 parts by weight of solvent, 0.5-10 parts by weight of initiator and 0.5-10 parts by weight of auxiliary agent, wherein the inorganic filler comprises barium strontium titanate particles and inorganic particles, wherein the barium strontium titanate is 0.1-25nm of barium strontium titanate particles with pyroelectric performance when the temperature is changed at 20-50 ℃, and the pyroelectric number of the barium strontium titanate is 698 [ mu ] C.m at 36 DEG C -2 ·K -1 The molar ratio of Ba to Sr is 7:3, the inorganic particles are 1-20nm silicon dioxide, zirconia, silanized silica and/or barium glass inorganic particles, and the barium strontium titanate and the inorganic particles are not usedThe weight ratio of the machine particles is (10-1) 1, the acidic polymerization monomer is 10- (2-methacryloyloxy) phosphoric acid mono decyl ester, the solvent is ethanol, propanol, N-butanol, acetone, methyl ethyl ketone, ethyl acetate or water, the initiator is camphorquinone, 4-N, N-dimethylamine ethyl benzoate, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, benzil, 2,4, 6-trimethylbenzoyl phenyl ethyl phosphonate, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl]-1-propanone, 1-hydroxycyclohexyl phenyl ketone, ethyl N, N-dimethylaminomethacrylate, isooctyl p-N, N-dimethylaminobenzoate, 1-phenyl-1, 2-propanedione or ethyl p-dimethylaminobenzoate;
the composition is prepared by the following steps:
(1) Preparing urethane dimethacrylate, hydroxyethyl methacrylate, bisphenol A glycidyl methacrylate, an initiator, an acidic polymerization monomer, an auxiliary agent and a solvent under non-polymerization conditions;
(2) Preparing an inorganic filler; and
(3) Mixing the components of steps (1) and (2) to obtain a mixture, wherein the mixture is cured using a dental light curing light.
2. The dental adhesive composition based on the principle of pyroelectric according to claim 1, wherein said auxiliary agent comprises at least one of a polymerization inhibitor, a surfactant and an ultraviolet light absorber.
3. A method for preparing a dental adhesive composition based on the pyroelectric principle according to claim 1 or 2, comprising the steps of:
(1) Preparing urethane dimethacrylate, hydroxyethyl methacrylate, bisphenol A glycidyl methacrylate, an initiator, an acidic polymerization monomer, an auxiliary agent and a solvent under non-polymerization conditions;
(2) Preparing an inorganic filler; and
(3) Mixing the components of steps (1) and (2) to obtain a mixture, wherein the mixture is cured using a dental light curing light.
4. Use of the dental adhesive composition based on pyroelectric principles according to claim 1 or 2 for the preparation of a dental adhesive material for restorative adhesion or dentin adhesion.
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