CN114409668A - Isosorbide derivative and pit and furrow closing agent based on isosorbide structure - Google Patents
Isosorbide derivative and pit and furrow closing agent based on isosorbide structure Download PDFInfo
- Publication number
- CN114409668A CN114409668A CN202210066012.9A CN202210066012A CN114409668A CN 114409668 A CN114409668 A CN 114409668A CN 202210066012 A CN202210066012 A CN 202210066012A CN 114409668 A CN114409668 A CN 114409668A
- Authority
- CN
- China
- Prior art keywords
- isosorbide
- socket
- sealer
- pit
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical class O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 title claims abstract description 69
- 229960002479 isosorbide Drugs 0.000 claims abstract description 40
- 239000003085 diluting agent Substances 0.000 claims abstract description 29
- 239000011159 matrix material Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 20
- -1 2-methyl-acryloyl Chemical group 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000011256 inorganic filler Substances 0.000 claims description 12
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 12
- 230000000844 anti-bacterial effect Effects 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 5
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 3
- 229940124350 antibacterial drug Drugs 0.000 claims description 3
- 239000001506 calcium phosphate Substances 0.000 claims description 3
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 3
- 235000011010 calcium phosphates Nutrition 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 235000001671 coumarin Nutrition 0.000 claims description 3
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 3
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 claims description 2
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 2
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011775 sodium fluoride Substances 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims 1
- LWLHCZLCSDUDEL-UHFFFAOYSA-O C[N+](C)(C)CC(O)=P(=O)CCOC(=O)C=C Chemical compound C[N+](C)(C)CC(O)=P(=O)CCOC(=O)C=C LWLHCZLCSDUDEL-UHFFFAOYSA-O 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
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- 239000000068 pit and fissure sealant Substances 0.000 description 17
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
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- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
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- CJZGXWURAFVFND-UHFFFAOYSA-N 4-hydroxy-4-oxobutanoate;triethylazanium Chemical compound CCN(CC)CC.OC(=O)CCC(O)=O CJZGXWURAFVFND-UHFFFAOYSA-N 0.000 description 1
- OXJGJKIURHREKH-UHFFFAOYSA-O CC(=C)C(=O)OCCP(=O)=C(O)C[N+](C)(C)C Chemical compound CC(=C)C(=O)OCCP(=O)=C(O)C[N+](C)(C)C OXJGJKIURHREKH-UHFFFAOYSA-O 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/69—Medicaments
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K6/70—Preparations for dentistry comprising inorganic additives
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/74—Fillers comprising phosphorus-containing compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/74—Fillers comprising phosphorus-containing compounds
- A61K6/75—Apatite
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/76—Fillers comprising silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Biophysics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Sealing Material Composition (AREA)
Abstract
The application provides an isosorbide derivative and an isosorbide structure-based nest closing agent, wherein the isosorbide structure-based nest closing agent comprises an isosorbide-based matrix and an isosorbide-based diluent, wherein the isosorbide-based matrix is at least one of isosorbide-bis { succinic acid mono [2- [ (2-methyl-acryloyl) oxy ] ethyl ] ester } ester or isosorbide-bis [ succinic acid mono (2-acryloyloxyethyl) ] ester; the isosorbide-based diluent is at least one of isosorbide-dimethacrylate or isosorbide-bis allyl carbonate. The pit and trench sealant takes low-viscosity high-molecular-weight monomers as a matrix, and the addition proportion of low-molecular-weight diluents is greatly reduced, so that the pit and trench sealant has lower double bond density, and is favorable for reducing polymerization shrinkage in material curing and the micro-leakage degree after curing.
Description
Technical Field
The application belongs to the technical field of medical oral biomaterials, and particularly relates to an isosorbide derivative and a pit and fissure sealant based on an isosorbide structure.
Background
Pit and fissure sealants have been used for decades in clinical applications as one of the important means of preventing breast molar pit caries. 3M ESPE Clinpro widely used in clinic at presentTMThe Sealant is a resin type socket sealing agent which takes Bisphenol A diglycidyl methacrylate (Bis-GMA) as a matrix and Triethylene Glycol Dimethacrylate (TEGDMA) as a diluent, has good fluidity and rapid photocrosslinking effect, can reach fine crack gaps, and forms a barrier between the socket and the oral environment after light curing so as to realize the sealing effect.
However, 3M ESPE Clinpro exerts a high-efficiency blocking effect and simultaneouslyTMSealant also has the disadvantage of micro-leakage between the material-dental tissue after repair. One of the main causes of microleakage is the polymerization shrinkage of the material during curing. Due to the high viscosity of bis-GMA, a large amount of TEGDMA is required to be added in the preparation process of the pit and fissure sealant to endow the product with sufficient fluidity, so that the double bond density of the material is increased, the polymerization shrinkage degree in the sealing process is increased, and the micro-leakage condition is generated. Furthermore, 3M ESPE ClinproTMThe bis-GMA molecule in Sealant also brings about a controversy in terms of biosafety for the product: because the material can not be completely polymerized in the curing process or the repairing material can be degraded in the oral cavity under the action of enzyme in the later period, bis-GMA monomer or degradation product containing bisphenol A structure is released, and the risk of inducing pulpal inflammation is caused; also, when bisphenol A-containing degradation products are swallowed into the human body with saliva, there is a possibility of damaging the reproductive system. Therefore, the research and development of a low polymeric shrinkage and a biologically safe pit and fissure sealant are very important for patients, especially preschool children.
Isosorbide is a safe material structure approved by the U.S. food and drug administration. Isosorbide, as a dehydrated derivative of sorbitol, has a unique double fused ring structure and two alcoholic hydroxyl groups, and exhibits excellent mechanical properties while having good biosafety. In recent years, some attempts have been made to prepare isosorbide-based materials or monomer molecules, for example, Jung-Hwan Lee and Hae-Hyoung Lee project groups prepared the pit and fissure sealant in 2020 by using synthetic isosorbide structure-based molecules ISDB as a matrix and TEGDMA as a diluent, and the fact that the isosorbide molecules do not have estrogen-like effect is proved through cell experiments.
However, this material was prepared by adding a large amount of diluent (ISDB: TEGDMA ═ 29.5: 69.5 (wt%)), which was very disadvantageous in reducing the polymerization shrinkage of the material (dent. mater.2020,36,157); in addition, different structures of isosorbide molecule-based matrix monomers or diluents have been developed and studied, such as isosorbide-bis-glycidyl methacrylate (eur.polym.j.2017,92,338), bis-3, 3-isosorbide-bis-propyl dimethacrylate (eur.polym.j.2019,112,629), isosorbide-bis-urethane methacrylate (j.appl.polym.sci.2017, DOI:10.1002/app.44591), isosorbide-bis-methacrylate (j.mech.behav.biomed.mater.2019,100,103371), but they have remained in the theoretical stage of research and no reports of work related to all-bio-based, oligomeric shrinkage-based pit sealer molded products.
In addition, the current clinical pit and fissure sealants are mainly from 3M company, Nippon Songfeng corporation, Australia SDI company and the like, and the imported materials are expensive, which increases the treatment cost of patients. Therefore, the development of the pit and fissure sealant with high performance and independent intellectual property rights has great significance for benefiting patients and promoting the development of domestic original oral cavity materials.
Disclosure of Invention
The application provides a pit and furrow closing agent based on an isosorbide structure based on the design concept of a low double bond density material, and aims to solve the problems of polymerization shrinkage and biological safety disputes of the existing pit and furrow closing agent.
In order to solve the above-mentioned technical problems, according to an aspect of the present application, there is provided an isosorbide derivative characterized in that the isosorbide derivative has a structure represented by general formula (I):
wherein the A group is
R is H or CH3。
In some embodiments, the isosorbide derivative is a compound of formula (I-1), (I-2), or (I-3):
in some embodiments, the compound of formula (I-1) is named isosorbide-bis { succinic acid mono [2- [ (2-methyl-acryloyl) oxy ] ethyl ] ester } ester or isosorbide-bis [ succinic acid mono (2-acryloyloxyethyl) ] ester.
In some embodiments, the compound of formula (I-2) is designated isosorbide-bis methacrylate and the compound of formula (I-3) is isosorbide-bis allyl carbonate.
According to another aspect of the present application, there is provided a litter box based on isosorbide structures comprising any one or more of the isosorbide derivatives described above.
In some embodiments, the pit and fissure sealant comprises an isosorbide-based base and an isosorbide-based diluent, wherein the isosorbide-based base is a compound having the structure shown in formula (I-1); the isosorbide-based diluent is at least one of a compound having a structure represented by formula (I-2) or a compound having a structure represented by formula (I-3).
In some embodiments, the socket closure agent comprises an isosorbide-based matrix and an isosorbide-based diluent, wherein the isosorbide-based matrix is at least one of isosorbide-bis { succinic acid mono [2- [ (2-methyl-acryloyl) oxy ] ethyl ] ester } ester or isosorbide-bis [ succinic acid mono (2-acryloyloxyethyl) ] ester; the isosorbide-based diluent is at least one of isosorbide-dimethacrylate or isosorbide-bis allyl carbonate.
In some embodiments, the isosorbide-based base is present in an amount of 60 to 85 weight percent based on the total weight of the pit and fissure sealant.
In some embodiments, the isosorbide-based diluent is present in a mass percent of 4 wt% to 27 wt%, based on the total mass of the pit and fissure sealant.
In some embodiments, the pit and trench blocking agent further comprises at least one of a photoinitiator or an inorganic filler, wherein the photoinitiator is at least one of an α -diketone photoinitiator, a ketal photoinitiator, a thioxanthone photoinitiator, an acylphosphine oxide photoinitiator, or a coumarin photoinitiator; the inorganic filler is at least one of silicon dioxide, aluminum oxide, titanium oxide, zirconium oxide, ceramic, hydroxyapatite or calcium phosphate.
In some embodiments, the photoinitiator is, for example, but not limited to, photoinitiators of alpha-diketones such as camphorquinone, ketals such as benzyldimethylaldehyde acetophenone, benzyldiethylaldehyde acetophenone, thioxanthones such as 2-chlorothioxanthone, and acylphosphine oxides, coumarins, and the like. These photoinitiators may be used alone, may be used alone in the present application, or may be used in combination of two or more components.
In some embodiments, the photoinitiator is present in an amount of 0.2 to 2 weight percent, based on the total weight of the pit and trench blocking agent
In some embodiments, the inorganic filler is a dental glass powder such as, but not limited to, silica, alumina, titania, zirconia, ceramic, hydroxyapatite, or calcium phosphate. These inorganic fillers may be used alone or in combination of two or more components.
In some embodiments, the inorganic filler is modified with a silane coupling agent prior to use.
In some embodiments, the inorganic filler has an average particle size of 50nm to 900 nm.
In some embodiments, the inorganic filler is present in an amount of 5 wt% to 20 wt%, based on the total mass of the pit and trench closing agent.
In some embodiments, the socket sealant further comprises a fluoride ion releasing substance that is tetrabutylammonium tetrafluoroborate, potassium fluoride, sodium fluoride, calcium fluoride, or fluoroaluminosilicate glass. These fluoride ion-releasing substances may be used alone or in combination of two or more components.
In some embodiments, the mass percent of the fluoride ion releasing material is less than or equal to 10 wt% based on the total mass of the pit and trench closing agent.
In some embodiments, the pit and fissure sealant further comprises an antibacterial substance which is an organic antibacterial quaternary ammonium salt, an antibacterial nanoparticle, an antibacterial drug, methacryloyloxyethyl phosphorylcholine, silicone, or an organofluoro compound. These antibacterial substances may be used alone or in combination of two or more components in the present application.
In some embodiments, organic antimicrobial quaternary ammonium salts such as, but not limited to, methacryloyloxydodecylbromopyridine or quaternary ammonium methacrylate-based silicate nanoparticles; antibacterial nanoparticles such as, but not limited to, nanosilver; antibacterial drugs such as but not limited to chlorhexidine.
In some embodiments, the mass percent of the antimicrobial substance is less than or equal to 10 wt% based on the total mass of the pit and fissure sealant.
In some embodiments, the pit and fissure sealant further comprises an adjuvant that is at least one of a stabilizer, an accelerator, a colorant, or a color-masking agent.
In some embodiments, the mass percent of the stabilizer, the accelerator, the colorant, or the color-masking agent, respectively, is less than or equal to 10 wt% based on the total mass of the pit and fissure sealant.
In some embodiments, the accelerator is, for example, but not limited to, such as hydroquinone or p-hydroxyanisole; such as, but not limited to, dimethylaminoethyl methacrylate or ethyl 4-dimethylaminobenzoate).
According to a preferred embodiment of the present application: the pit and trench sealing agent based on the isosorbide structure is a fluid which is uniformly mixed and has uniform inorganic filler particle size, and has good fluidity and convenient operation; the solid sample obtained by the pit and furrow closing agent after being cured by illumination has stable color and luster and smooth and flat surface.
The isosorbide structure-based pit and fissure sealants described herein have the effect of point crack fissure sealant to prevent breast molar caries.
With 3M ESPE ClinproTMCompared with bis-GMA (maleic anhydride-maleic anhydride) matrix of Sealant, the isosorbide-based matrix synthesized by the one-step method has larger molecular weight and lower shear viscosity, so that the addition amount of a diluent in the preparation process of a product is greatly reduced, the double bond density of the material is reduced, and the reduction of polymerization shrinkage in curing is facilitated. In addition, the isosorbide-based base and isosorbide-based diluent used herein are both monomer molecules based on the isosorbide structure, as opposed to 3M ESPE ClinproTMThe bis-GMA and TEGDMA of Sealant show more excellent biological safety.
Drawings
FIG. 1 shows the isosorbide-bis { succinic acid mono [2- [ (2-methyl-acryloyl) oxy ] bis { isosorbide obtained in the examples of the present application]Ethyl radical]Of esters1H NMR nuclear magnetic spectrum;
FIG. 2 is an LR-MS (ESI +) mass spectrum of isosorbide-bis { succinic acid mono [2- [ (2-methyl-acryloyl) oxy ] ethyl ] ester } ester obtained in an example of the present application;
FIG. 3 is a drawing of isosorbide-bis-methacrylate as isosorbide-based diluent obtained in the examples of the present application1H NMR nuclear magnetic spectrum;
FIG. 4 is an LR-MS (ESI +) mass spectrum of isosorbide-dimethacrylate isosorbide diluent obtained in the examples of the present application;
FIG. 5 is an infrared spectrum of a silane coupling agent-modified dental glass powder obtained by an example of the present application;
FIG. 6 shows the results of viscosity measurements of HEMA-ISO-HEMA obtained in the examples of the present application and bis-GMA of the control example;
FIG. 7 shows isosorbide-based pit and fissure sealants of the present application and 3M ESPE Clinpro of the comparative exampleTMSealant viscosity test results.
Detailed Description
The present application is further illustrated by the following examples, which are not intended to limit the scope of the invention. Modifications and variations based on the technology of the present application are within the scope of the present application without departing from the basic idea of the present application. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
Example 1: isosorbide-based base preparation of isosorbide-bis { succinic acid mono [2- [ (2-methyl-acryloyl) oxy ] ethyl ] ester } ester (HEMA-ISO-HEMA)
To a 1000mL three-necked flask with a stirrer attached, 1-ethyl- (3-dimethyl) was addedAminopropyl) carbodiimide hydrochloride (EDC. HCl, 23.61g, 0.123mol), dichloromethane (DCM, 500mL), triethylamine (Et)3N, 24.92g,0.246mol) and Triethylamine succinic acid mono [2- [ (2-methyl-acryloyl) oxy ]]Ethyl radical]Ester 2(23.63g,0.102mol), stirred for 30min and added with isosorbide 1(5g,0.034mol) and 4-dimethylaminopyridine (DMAP, 0.84g,0.0068 mol).
The reaction bottle is connected with a reflux condenser tube, and the temperature is raised to about 45 ℃ for reflux reaction for 24 hours. The reaction was stopped, the reaction solution was washed with water, washed with a saturated sodium bicarbonate solution, the organic phase was separated, and dried over anhydrous sodium sulfate until the liquid was clear. Suction filtration was carried out, and the filtrate was concentrated and then separated by silica gel column chromatography (eluent: n-hexane/dichloromethane/methanol (v/v/v ═ 100/400/6-100/400/10)) to obtain 13.82g of a slightly yellow transparent liquid product HEMA-ISO-HEMA with a yield of 71%. Of the product HEMA-ISO-HEMA1The NMR spectrum is shown in FIG. 1, and the LR-MS (ESI +) mass spectrum is shown in FIG. 2.
1H NMR(400MHz,CDCl3):δ6.06(s,2H),5.53(d,2H),5.10(m,2H),4.75(t,1H),4.40(d,1H),4.28(s,8H),3.83(m,4H),2.62(m,8H),1.88(s,6H).
LR-MS(ESI+):m/zcalculated C26H34O14 for 570.54；found 593.2[M+Na]+,588.3[M+NH4]+.
Example 2: preparation of isosorbide-bis-methacrylate (IBM) as isosorbide-based diluent
Adding isosorbide (5.01g,0.034mol) and Et3N (14.56g,0.144mol) and DMAP (0.42g,3.4mmol) were added to a 250mL three-necked flask with a preset magneton, with 30mL anhydrous CH2Cl2Stirring to dissolve. The reaction flask was placed in an ice-water bath at 0 ℃ and methacryloyl chloride (11.92g,0.114mol) was slowly added dropwise. After the dropwise addition, the reaction temperature naturally returns to room temperature, and the reaction is carried out overnight.
Adding water to quench the reaction, separating the organic phase, CH2Cl2Extracting the aqueous phase once. The organic phases were combined with anhydrous Na2SO4After drying, spin drying and chromatography on silica gel column (eluent: n-hexane/dichloromethane/methanol (v/v/v. 100/300/5)) gave 5.14g of IBM as a clear, colorless liquid product in 53.55% yield. Of product IBM1The NMR spectrum is shown in FIG. 3, and the LR-MS (ESI +) mass spectrum is shown in FIG. 4.
1H NMR(400MHz,CDCl3):δ6.13(d,2H),5.60(d,2H),5.21(m,2H),4.90(t,1H),4.53(d,1H),3.94(m,4H),1.95(s,3H),1.91(s,3H).
LR-MS(ESI+):m/zcalculated C14H18O6 for 282.29；found 283.1[M+H]+,300.1[M+NH4]+,305.0[M+Na]+.
Example 3: dental glass powder silanization modification
Preparing 50mL of 60% ethanol-water solution, adjusting the pH value of the solution to 3-4 by acetic acid, adding 1g of gamma-MPS, stirring uniformly, adding 10g of glass powder, stirring at room temperature for 1h, and heating and stirring at 70 ℃ for 1 h. Evaporating the solvent at 65-70 deg.C under reduced pressure, reacting the rest powder mixture at 120 deg.C, and oven drying. Washing the dried powder with ethanol, centrifuging, and vacuum drying the lower precipitate at 40 deg.C. The infrared spectrum of the dental glass powder modified by the silane coupling agent is shown in figure 5.
FT-IR:ν(cm-1):2962(＝C-H),1726(C＝O).
Example 4: preparation of pit and furrow sealants based on isosorbide structure (group 1)
4.00g of HEMA-ISO-HEMA prepared according to example 1, 0.45g of IBM prepared according to example 2, 0.50g of the modified dental glass powder according to example 3, 0.01g of camphorquinone and 0.04g of dimethylaminoethyl methacrylate were weighed into a special weighing cup and mixed for 80s with a FlackTek SpeedMixer 2500 r/min.
Example 5: preparation of pit and furrow sealants based on isosorbide structure (group 2)
3.78g of HEMA-ISO-HEMA prepared according to example 1, 0.67g of IBM prepared according to example 2, 0.50g of the modified dental glass powder according to example 3, 0.01g of camphorquinone and 0.04g of dimethylaminoethyl methacrylate were weighed into a special weighing cup and mixed for 80s with a FlackTek SpeedMixer 2500 r/min.
Example 6: preparation of pit and furrow sealants based on isosorbide structure (group 3)
3.56g of HEMA-ISO-HEMA prepared according to example 1, 0.89g of IBM prepared according to example 2, 0.50g of the modified dental glass powder according to example 3, 0.01g of camphorquinone and 0.04g of dimethylaminoethyl methacrylate were weighed into a special weighing cup and mixed for 80s with a FlackTek SpeedMixer 2500 r/min.
Comparative example 1: commercially available bis-GMA monomers
Comparative example 2: commercial 3M ESPE Clinpro as pit and trench blocking agentTM Sealant
Commercial 3M ESPE Clinpro as pit and trench blocking agentTMSealant, the matrix is bis-GMA, the diluent is TEGDMA, and the proportion is 40-50 wt%.
Effect example 1: viscosity testing of matrix monomers
The product HEMA-ISO-HEMA obtained in example 1 and bis-GMA obtained in comparative example 1 were subjected to rheological viscosity test. The results are shown in table 1 and fig. 6.
TABLE 1 viscosity (Pa s) of different matrix monomers
The results show that the viscosity of the isosorbide-based matrix HEMA-ISO-HEMA is much lower than that of the traditional matrix monomer bis-GMA.
Effect example 2: viscosity test of pit and furrow sealer
The products obtained in examples 4, 5 and 6 were used as a litter sealer having an isosorbide structure, and the commercial litter sealer 3M ESPE Clinpro of comparative example 2TMSealant was subjected to rheological viscosity testing. The results are shown in FIG. 7. The results show that the viscosities of examples 4, 5, 6 are comparable or lower than comparative example 2, showing similar or better flow than the comparative example 2, with the diluent IBM addition ratio of 8 wt% to 18 wt%.
Effect example 3: calculation of double bond Density of pit and furrow sealants
The double bond densities of commercially available bis-GMA, TEGDMA, HEMA-ISO-HEMA prepared in example 1, IBM prepared in example 2, examples 4, 5, 6 and the pit-closing agent of comparative example 2 were calculated by dividing the number of molecular double bonds of the equivalent amount of material by the molecular molar mass, and the results shown in Table 2 were obtained.
TABLE 2 double bond Density (number of double bonds/g) of different matrix/pit-gap sealers
From the results given in Table 2, it can be seen that the isosorbide-based pit and fissure sealants provided herein compare 3M ESPE Clinpro while maintaining the same or better flowabilityTMSealant reduces the double bond density by at least 13-21%, indicating that the material has a relatively low degree of polymerization shrinkage upon cross-linking cure and improved microleakage after cure.
Effect example 4: monomer residue and conversion testing of pit and furrow sealer
The pit and groove sealing agents of examples 4, 5 and 6 and comparative example 2 were filled in a mold, light-cured for 1min to prepare a sample having a diameter of 6mm and a height of 3.3mm, fourier infrared tests before and after curing were performed after overnight, and the monomer residual rate and conversion rate of the pit and groove sealing agent were calculated from the change in the ratio of the vibration peak area of the carbon-carbon double bond to the carbonyl peak area before and after curing, to obtain the results shown in table 3.
TABLE 3 monomer residue and conversion (%)
As is clear from the results in Table 3, the monomer residue ratios of the 3 examples and the comparative example are all 30% or less, the corresponding conversion ratios are all 70% or more, and the curing process of the material is sufficient.
Effect example 5: vickers hardness test of pit and furrow sealer
The pit and groove sealants of examples 4, 5 and 6 and comparative example 2 were filled in a mold and cured by light for 1min to prepare a sample having a diameter of 6mm and a height of 3.3mm or so. The diamond indenter indents the surface of the sample with a test force (load) of 1kgf (1 kgf, 9.8N), a retention time of 15 seconds, and vickers hardness was calculated to obtain the results shown in table 4.
TABLE 4 Vickers hardness (mean + standard deviation) of pit and furrow sealer samples
As is apparent from Table 4, the samples of examples have Vickers hardnesses equivalent to those of the comparative examples, while maintaining a low double bond density, good fluidity and sufficient curing. This shows that although the interaction between isosorbide molecules is weaker than the π - π interaction between bisphenol A, the diluent selected in the examples, IBM, also has a rigid isosorbide core, compensating for the lack of mechanical strength of the monomer HEMA-ISO-HEMA compared to bis-GMA.
Effect example 6: monomer dissolution rate test of pit and furrow sealer
The pit and groove sealants of examples 4, 5 and 6 and comparative example 2 were filled in a mold and cured by light for 1min to prepare a sample having a diameter of 6mm and a height of 3.3mm or so. Soaking the samples in absolute ethyl alcohol according to the mass-volume ratio of 0.05g/mL, sampling 100 mu L of sample injection HPLC after 3 and 11 days, and calculating the monomer dissolution rate of the pit and trench sealing agent by using monomer HEMA-ISO-HEMA, IBM, bis-GMA and TEGDMA as reference fitting standard curves. The results are shown in tables 5 and 6.
TABLE 5 rate of dissolution of different monomers (%) -from pit and furrow sealer samples soaked in ethanol for 3 days
a.The matrix molecule of the example was HEMA-ISO-HEMA, and the matrix molecule of the control example was bis-GMA
b.The diluent molecule of the example was IBM and the diluent molecule of the control was TEGDMA
TABLE 6 dissolution rates (%)% of different monomers from pit and furrow sealer samples soaked in ethanol for 11 days
a.The matrix molecule of the example was HEMA-ISO-HEMA, and the matrix molecule of the control example was bis-GMA
b.The diluent molecule of the example was IBM and the diluent molecule of the control was TEGDMA
As can be seen from the results of tables 5 and 6, the leaching concentrations of the matrix molecules and the diluent after 3 and 11 days in the 3 groups of examples were less than those in the comparative example 2. The matrix HEMA-ISO-HEMA and the diluent IBM dissolved out in the embodiment 4 both take bio-based isosorbide as a parent nucleus and do not contain toxic bisphenol A structure, so the damage to body cells or tissues is reduced; in addition, the dissolution rate of the monomer is reduced, the degree of weakening the mechanical property of the material is reduced, and the service life of the material is prolonged.
Effect example 7: water contact Angle test of pit and furrow sealants
The pit and groove sealants of example 5 and comparative example 2 were filled in a mold, cured by light for 40 seconds to prepare a test piece having a diameter of 15mm and a height of 1mm, and subjected to a water contact angle test. The results are shown in Table 7.
TABLE 7 Water contact Angle (mean + standard deviation) of pit and furrow sealer samples
As can be seen from Table 7, the results for the water contact angles of the samples of example 5 and comparative example 2 differ by 1 degree, indicating that there is no significant difference in the hydrophilicity of the two materials.
The present application has been described in relation to the above embodiments, which are only examples for implementing the present application. It must be noted that the disclosed embodiments do not limit the scope of the application. Rather, modifications and equivalent arrangements included within the spirit and scope of the claims are included within the scope of the present application.
Claims (17)
1. An isosorbide derivative having a structure represented by general formula (I):
wherein the A group is
R is H or CH3。
2. The isosorbide derivative of claim 1, wherein the isosorbide derivative is a compound of formula (I-1), (I-2) or (I-3):
3. a pit closure agent based on an isosorbide structure, characterized in that it comprises an isosorbide derivative according to claim 1 or 2.
4. A socket and ditch sealer according to claim 3, wherein the socket and ditch sealer comprises an isosorbide-based base and an isosorbide-based diluent, wherein,
the isosorbide-based matrix is a compound with a structure shown in a formula (I-1);
the isosorbide-based diluent is at least one of a compound having a structure represented by formula (I-2) or a compound having a structure represented by formula (I-3).
5. A socket sealer according to claim 4, wherein the isosorbide-based base is present in an amount of 60 to 85% by weight, based on the total weight of the socket sealer.
6. A pit and channel sealer according to claim 4 wherein the isosorbide-based diluent is present in an amount of 4 to 27% by weight, based on the total weight of the pit and channel sealer.
7. The socket sealer according to any one of claims 4 to 6, further comprising at least one of a photoinitiator or an inorganic filler, wherein,
the photoinitiator is at least one of alpha-diketone photoinitiators, ketal photoinitiators, thioxanthone photoinitiators, acyl phosphine oxide photoinitiators or coumarin photoinitiators;
the inorganic filler is at least one of silicon dioxide, aluminum oxide, titanium oxide, zirconium oxide, ceramic, hydroxyapatite or calcium phosphate.
8. The socket sealer of claim 7, wherein the photoinitiator is at least one of camphorquinone, benzyl dimethyl aldehyde acetophenone, benzyl diethyl aldehyde acetophenone, or 2-chlorothioxanthone.
9. A socket sealer according to claim 7, wherein the photoinitiator is present in an amount of 0.2 to 2 wt% based on the total mass of the socket sealer.
10. The socket sealer according to claim 7, wherein the inorganic filler has an average particle diameter of 50nm to 900 nm.
11. A socket sealer according to claim 7, wherein the inorganic filler is contained in an amount of 5 to 20 wt% based on the total mass of the socket sealer.
12. A socket closure of claim 7, further comprising a fluoride ion releasing substance, said fluoride ion releasing substance being at least one of tetrabutylammonium tetrafluoroborate, potassium fluoride, sodium fluoride, calcium fluoride, or fluoroaluminosilicate glass.
13. A socket closure of claim 12, wherein said fluoride ion releasing material is present in an amount of 10 wt% or less based on the total mass of said socket closure.
14. The socket sealer according to claim 7, further comprising an antibacterial substance, wherein the antibacterial substance is at least one of organic antibacterial quaternary ammonium salt, antibacterial nanoparticles, antibacterial drug, acryloyloxyethyl phosphorylcholine, silicone, or organic fluoride.
15. A socket closure according to claim 14, wherein the antibacterial substance is present in an amount of 10 wt% or less, based on the total mass of the socket closure.
16. The socket sealer of claim 7, further comprising an adjuvant, wherein the adjuvant is at least one of a stabilizer, an accelerator, a colorant, or a color-masking agent.
17. A socket sealer according to claim 16, wherein the mass percentages of the stabilizer, the accelerator, the colorant or the color-masking agent are respectively less than or equal to 10 wt% based on the total mass of the socket sealer.
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Effective date of registration: 20231201 Address after: 201816 No. 461 Tanghang Village, Huating Town, Jiading District, Shanghai Patentee after: SHANGHAI NEW CENTURY DENTAL MATERIAL Co.,Ltd. Address before: 200011 No. 639, manufacturing Bureau Road, Shanghai, Huangpu District Patentee before: SHANGHAI NINTH PEOPLE'S HOSPITAL SHANGHAI JIAOTONG University SCHOOL OF MEDICINE |