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WO2018038227A1 - Ciment dentaire - Google Patents

Ciment dentaire Download PDF

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Publication number
WO2018038227A1
WO2018038227A1 PCT/JP2017/030405 JP2017030405W WO2018038227A1 WO 2018038227 A1 WO2018038227 A1 WO 2018038227A1 JP 2017030405 W JP2017030405 W JP 2017030405W WO 2018038227 A1 WO2018038227 A1 WO 2018038227A1
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WO
WIPO (PCT)
Prior art keywords
paste
phosphorylated
meth
acrylate
dental cement
Prior art date
Application number
PCT/JP2017/030405
Other languages
English (en)
Japanese (ja)
Inventor
靖弘 吉田
英彦 佐野
健哉 松尾
紗綾子 堀田
Original Assignee
国立大学法人北海道大学
ダイヤ工業株式会社
株式会社ジーシー
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 国立大学法人北海道大学, ダイヤ工業株式会社, 株式会社ジーシー filed Critical 国立大学法人北海道大学
Priority to JP2018535767A priority Critical patent/JP6944158B2/ja
Publication of WO2018038227A1 publication Critical patent/WO2018038227A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/849—Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements

Definitions

  • the present invention relates to a dental cement used in the dental field.
  • cement containing calcium silicate as a main component for example, see Patent Documents 1 and 2) and Portland cement (for example, patents) Reference 3) is used.
  • These cements are usually composed of a powder component and a liquid component, and are hardened by mixing and kneading both components to form a hardened cement body.
  • the dental cement composed of such a powder component and a liquid component has a problem that kneading is difficult and the mixing and kneading operation of both components depends on the skill level of the user at the time of use.
  • an object of the present invention is to provide a dental cement that can be used more easily and has high adhesion to a tooth surface.
  • the present inventors made dental cement composed of a first paste containing (meth) acrylate and a second paste containing water and / or (meth) acrylate. If the paste powder and phosphorylated polysaccharide are contained in the first paste or the second paste, respectively, two types of paste are mixed as compared with dental cement composed of a powder component and a liquid component. Mixing the two pastes is easy if it is easy to knead and very easy to handle, and one of the oxidizing agent and reducing agent for initiating polymerization is contained in the first paste and the other in the second paste. Until then, the polymerization does not proceed, and it is easy to handle. By adding phosphorylated polysaccharide, the phosphate group of phosphorylated polysaccharide is chelated to the tooth. In is the high adhesion to the tooth surface and completed the present invention by investigating in that it is obtained.
  • the present invention comprises a first paste containing (meth) acrylate and a second paste containing water and / or (meth) acrylate, wherein one of the oxidizing agent or reducing agent is the first paste, and the other is the second paste.
  • a dental cement characterized in that it is contained in each paste, and Portland cement powder and phosphorylated polysaccharide are contained in the first paste and / or the second paste, respectively.
  • the phosphorylated polysaccharide is comprised from the 1st paste containing (meth) acrylate and Portland cement powder, and the 2nd paste containing phosphorylated polysaccharide and water, and one of an oxidizing agent or a reducing agent is a 1st paste, and the other is a 2nd paste. If one of the pastes is composed of phosphorylated polysaccharide and water, the phosphorylated polysaccharide has the effect of producing viscosity, so that it has an appropriate viscosity even for pastes containing water.
  • phosphorylated pullulan is used as a phosphorylated polysaccharide, which is harmless to the human body and ensures high safety, and is less susceptible to metabolism by amylase or the like in the oral cavity. It was also found that it is preferable because it is difficult to become a nutrient for bacteria.
  • the dental cement according to the present invention comprises a first paste containing (meth) acrylate and a second paste containing water and / or (meth) acrylate, and each of Portland cement powder and phosphorylated polysaccharide is the first paste. And / or because it is contained in the second paste, it is easy to knead and very easy to handle by mixing two types of paste compared to dental cement consisting of a powder component and a liquid component. In addition, since one of the oxidizing agent and the reducing agent for initiating the polymerization is contained in the first paste and the other is contained in the second paste, the polymerization does not proceed until the two types of paste are mixed. By blending the oxidized polysaccharide, the phosphoric acid group of the phosphorylated polysaccharide can be chelated to the tooth and high adhesion to the tooth surface can be obtained.
  • one paste is composed of phosphorylated polysaccharide and water, and the phosphorylated polysaccharide has an effect of causing viscosity.
  • phosphorylated pullulan as the phosphorylated polysaccharide, it is possible to ensure high safety without harming the human body, and is difficult to be metabolized by amylase or the like in the oral cavity. It is preferable because it is difficult to become nutrition.
  • Portland cement powder used in the present invention is primarily tricalcium silicate (alite, 3CaO ⁇ SiO 2), dicalcium silicate (belite, 2CaO ⁇ SiO 2), calcium aluminate (aluminate, 3CaO ⁇ Al 2 O 3 ) and calcium aluminoferrite (ferrite, 4CaO.Al 2 O 3 .Fe 2 O 3 ).
  • These main components are calcium oxide (CaO), silicon dioxide (SiO 2 ), aluminum oxide (Al 2 O 3 ), and iron oxide (Fe 2 O 3 ).
  • 2 The curing speed and strength of the cured product differ when two pastes are mixed.
  • the Portland cement powder used in the present invention can be used without any particular limitation to the conventional Portland cement powder, but when the kneaded product is hardened, particularly if the composition is as follows, In use under conditions of high moisture content such as capping, it is more preferable because it can be cured in a stable state and an appropriate strength can be obtained.
  • Other components such as magnesium oxide and sodium carbonate may be included.
  • the content of Portland cement powder in dental cement is preferably 5% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 40% by mass or less.
  • the content of the Portland cement powder in the dental cement is 5% by mass or more, the strength of the cement cured body can be increased, and when the content is 50% by mass or less, pasting becomes easy.
  • the phosphorylated polysaccharide used in the present invention has low irritation and high affinity for living tissue. Phosphorylated polysaccharides exhibit high adhesion to the tooth surface due to chelate bonding of their phosphate groups to the tooth.
  • phosphorylated polysaccharide used in the present invention those in which a part or all of the hydroxyl groups of the polysaccharide are phosphorylated can be used.
  • phosphorylated lactose, phosphorylated sucrose, phosphorylated sucralose, phosphorylated cellobiose, phosphorylated Trehalose, phosphorylated maltose, phosphorylated palatinose (registered trademark), phosphorylated maltotriose, phosphorylated maltodextrin, phosphorylated cyclodextrin, phosphorylated glycosyl sucrose, phosphorylated amylose, phosphorylated amylopectin, phosphorylated cycloamylose, phosphorylated Glycogen, phosphorylated cellulose, phosphorylated agarose, phosphorylated cluster dextrin, phosphorylated mannan, phosphorylated pullulan and the like can be preferably used, and these can be used alone or in combination
  • phosphorylated polysaccharides phosphorylated maltodextrin, phosphorylated cyclodextrin, phosphorylated glycosyl sucrose, phosphorylated amylose, phosphorylated amylopectin, phosphorylated cycloamylose, phosphorylated glycogen, phosphorylated cellulose, phosphorylated agarose, phosphorylated
  • One or more selected from the group consisting of cluster dextrin, phosphorylated mannan, and phosphorylated pullulan can be preferably used from the viewpoints of adhesion to a living hard tissue, strength of a cured product, production cost, and the like.
  • phosphorylated pullulan is preferable because it is harmless to the human body and can ensure high safety, and is not easily metabolized by amylase or the like in the oral cavity and hardly becomes a nutrient for bacteria.
  • Such a phosphorylated polysaccharide can be produced by a known method of phosphorylating the hydroxyl group of the polysaccharide. For example, the method of making it react with sodium metaphosphate, the method of making it react with sodium phosphate, etc. are mentioned. A method of obtaining phosphorylated pullulan by reacting phosphorus pentoxide and pullulan is also used. The structure of the obtained phosphorylated polysaccharide can be confirmed by a known analysis method. The degree of phosphorylation of the phosphorylated polysaccharide can be adjusted by changing the amount of raw material used and the reaction conditions.
  • the phosphorylated polysaccharide may be partially or wholly salted, such as sodium salt, potassium salt, calcium salt, magnesium salt, ammonium salt, and the like. Can be prepared according to known methods.
  • the phosphorylated polysaccharide is preferably one in which, among all the hydroxyl groups contained in one molecule, several (number%) or more and tens (number%) or less hydroxyl groups are phosphorylated.
  • the number ratio of phosphorylated hydroxyl groups in the phosphorylated polysaccharide can be calculated from the phosphorus content by performing elemental analysis of the phosphorylated polysaccharide.
  • the content of phosphorylated polysaccharide in dental cement is preferably 0.1% by mass or more and 40% by mass or less, and more preferably 1% by mass or more and 30% by mass or less.
  • the content of the phosphorylated polysaccharide in the dental cement is 0.1% by mass or more, the blending effect is obtained, and when it is 40% by mass or less, the viscosity of the paste can be prevented from becoming too high.
  • (meth) acrylate means various monomers, oligomers or prepolymers of acrylate or methacrylate, and has one or more (meth) acryloyloxy groups.
  • the (meth) acryloyloxy group means a methacryloyloxy group and / or an acryloyloxy group.
  • the (meth) acrylate is not particularly limited, but methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, hydroxypropyl (meth) acrylate , Tetrahydrofurfuryl (meth) acrylate, glycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate 2-ethoxyethyl (meth) acrylate, 2-methylhexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxy-1,3- (Meth) acryloyloxypropane
  • the content of (meth) acrylate in the dental cement is preferably 1% by mass or more and 50% by mass or less, and more preferably 5% by mass or more and 25% by mass or less.
  • the content of (meth) acrylate in the dental cement is 1% by mass or more, the adhesive strength of the dental cement is improved, and when it is 50% by mass or less, the tooth surface adhesion of the dental cement is improved. It is to do.
  • a chemical polymerization initiator (oxidizing agent, reducing agent) can be used.
  • a combination of an oxidizing agent and a reducing agent can be used.
  • the mass ratio of one paste to the other paste in the two-paste type dental cement is preferably in the range of 1: 1 to 1:15.
  • the oxidizing agent in the chemical polymerization initiator is not particularly limited, but cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, benzoyl peroxide, t-butylperoxyisopropyl carbonate, t-butylperoxy-2 -Peroxides such as ethylhexanoate, azobisisobutyronitrile, 1,1'-azobis (cyclohexanecarbonitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), dimethyl 2,2 Examples include azo compounds such as' -azobis (2-methylpropionate), persulfates such as hydrogen peroxide, potassium persulfate, and sodium persulfate, and two or more of them may be used in combination.
  • the content of the oxidizing agent in the chemical polymerization initiator in the dental cement is preferably 0.01% by mass or more and 20% by mass or less, and more preferably 0.05% by mass or more and 10% by mass or less.
  • the content of the oxidizing agent in the chemical polymerization initiator in the dental cement is 0.01% by mass or more, the adhesiveness of the dental cement is improved, and when the content is 20% by mass or less, Storage stability is improved.
  • the reducing agent in the chemical polymerization initiator is not particularly limited, but is a thiourea derivative, vanadium compound, copper compound, 4-aminobenzoic acid, N, N-dimethyl-p-toluidine, triethanolamine, 4-dimethylaminobenzoic acid.
  • tertiary amines such as methyl acid, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and sulfinates such as N-phenylglycine, sodium p-toluenesulfinate, sodium benzenesulfinate, and the like.
  • Examples of the thiourea derivative include ethylenethiourea, diethylthiourea, tetramethylthiourea, N-acetylthiourea, N-benzoylthiourea, diphenylthiourea, dicyclohexylthiourea and the like.
  • Examples of the vanadium compound include vanadium acetylacetonate, vanadyl acetylacetonate, vanadyl stearate, vanadium naphthenate, and vanadium benzoylacetonate.
  • the content of the reducing agent in the chemical polymerization initiator in the dental cement is preferably 0.5% by mass or more and 20% by mass or less, and more preferably 1% by mass or more and 10% by mass or less.
  • the content of the reducing agent in the chemical polymerization initiator in the dental cement is 0.5% by mass or more, the adhesiveness of the dental cement is improved, and when it is 20% by mass or less, Storage stability is improved.
  • the dental polymerizable composition can replace with a chemical polymerization initiator or can use a photoinitiator with a chemical polymerization initiator.
  • the dental polymerizable composition contains a photopolymerization initiator, the dental polymerizable composition can be given a property of being cured when irradiated with light.
  • the photopolymerization initiator is not particularly limited, and examples thereof include ketone compounds, ⁇ -diketone compounds, ketal compounds, anthraquinone compounds, thioxanthone compounds, benzoin alkyl ether compounds, and acylphosphine oxide compounds.
  • Examples of the ketone compound include benzophenone, bis (4-dimethylaminophenyl) ketone, 4,4′-bis (diethylamino) benzophenone, and the like.
  • Examples of the ⁇ -diketone compound include camphorquinone, benzyl, diacetyl, acenaphthenequinone, 9,10-phenanthraquinone, and the like.
  • ketal compounds include benzyl ketal, diacetyl ketal, benzyl dimethyl ketal, benzyl diethyl ketal, benzyl bis ( ⁇ -phenylethyl) ketal, benzyl bis (2-methoxyethyl) ketal, 4,4′-dimethyl (benzyl dimethyl ketal). ) And the like.
  • anthraquinone compound examples include anthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 1,2-benzanthraquinone, 1-hydroxyanthraquinone, 1-methylanthraquinone, 2-ethylanthraquinone, 1-bromoanthraquinone, and the like.
  • thioxanthone compounds include thioxanthone, 2-isopropylthioxanthone, 2-nitrothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chloro- 7-trifluoromethylthioxanthone, thioxanthone-10,10-dioxide, thioxanthone-10-oxide, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-hydroxy-3- (3,4-dimethyl-9-oxo-9H- And thioxanthen-2-yloxy) -N, N, N-trimethyl-1-propaneaminium chloride.
  • benzoin alkyl ether compounds include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether.
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethoxybenzoyldiphenylphosphine oxide, 2,6-dimethylbenzoyldiphenylphosphine oxide, and 2,6-dimethoxy. Examples include benzoyldiphenylphosphine oxide.
  • a photopolymerization accelerator may be used in combination.
  • the photopolymerization accelerator is not particularly limited, but 4-aminobenzoic acid, N, N-dimethyl-p-toluidine, triethanolamine, tolyldiethanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate Tertiary amines such as isoamyl 4-dimethylaminobenzoate, barbituric acid, 1,3-dimethylbarbituric acid, 1,3,5-trimethylbarbituric acid, 1,3,5-triethylbarbituric acid, 5 -Barbituric acid derivatives such as butyl barbituric acid, 1-benzyl-5-phenylbarbituric acid, 1-cyclohexyl-5-ethylbarbituric acid and the like may be mentioned, and two or more may be used in combination.
  • the dental cement according to the present invention may contain water for making a paste.
  • the water content in the dental cement is preferably 0.1% by mass or more and 40% by mass or less, and more preferably 3% by mass or more and 35% by mass or less.
  • the water content of the dental cement is 0.1% by mass or more, the curability of the cement can be improved, and when it is 35% by mass or less, a decrease in strength of the cement cement is suppressed. .
  • the dental cement according to the present invention may further contain a polymerization inhibitor.
  • the polymerization inhibitor is not particularly limited, and examples thereof include dibutylhydroxytoluene, ethylenediaminetetraacetic acid disodium, 2,6-t-butyl-2,4-xylenol, and two or more of them may be used in combination.
  • the dental cement according to the present invention may further contain an X-ray contrast material in order to impart X-ray contrast properties.
  • the X-ray contrast material is not particularly limited, but known bismuth oxide, barium sulfate, tantalum oxide, cerium oxide, tin oxide, zirconium oxide, zinc oxide, ytterbium oxide, ytterbium fluoride powder, barium, tantalum, A radiopaque glass powder containing lanthanum or strontium can be used, and these can be used alone or in combination.
  • the content of the X-ray contrast medium is preferably not more than the content of Portland cement powder.
  • the dental cement according to the present invention may further contain a filler.
  • the filler may be either an organic filler or an inorganic filler, but is preferably an inorganic filler. Although it does not specifically limit as an inorganic filler, A silica powder, a fumed silica, an alumina powder, a glass powder (For example, barium glass powder, fluoroaluminosilicate glass powder) etc. are mentioned, You may use 2 or more types together.
  • the inorganic filler may be treated with a surface treatment agent such as a silane coupling agent as necessary.
  • a colorant, a stabilizer, an antibacterial agent, an antiseptic, a thickener and the like can be appropriately blended as long as the properties are not affected.
  • dental cement according to the present invention will be described in detail using examples, but the dental cement according to the present invention is not limited to the following examples.
  • Table 2 shows the blending ratio of dental cement used in each example and each comparative example.
  • HEMA 2-hydroxyethyl methacrylate
  • GDMA 2-hydroxy-1,3-dimethacryloyloxypropane
  • Bis-EMA ethoxylated bisphenol A dimethacrylate (BPE-1300N manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • BHT Dibutylhydroxytoluene EDTA ⁇ 2Na: Disodium ethylenediaminetetraacetate Fumed silica: Aerosil (registered trademark) (manufactured by Nippon Aerosil Co., Ltd.)
  • CMC-Na Carboxymethylcellulose sodium
  • the obtained dental cement kneaded material was applied to the through-holes of the seals, thinned and cured by light irradiation. Further, a composite resin was irradiated with light on each cured dental cement and cured. After the composite resin is cured, it is immersed in water one hour later, taken out from the water 24 hours later, and using an autograph, the bovine tooth crown and the cured composite resin are relatively displaced to cross-speed 1 mm. Shear test was performed at / min.
  • the dental cement of Examples 1 to 4 is a dental cement having 60% or more remaining on the dentin surface after the shear test and having high adhesion to the tooth surface. It was done.
  • the dental cements of Comparative Examples 1 and 2 remained less than 20% on the dentin surface after the shear test, and were confirmed to be dental cements having low adhesion to the tooth surface.
  • the dental cement according to the present invention has high adhesion to the tooth surface, beneficial effects such as prevention of bacteria and the like from entering the gap between the dental cement and the tooth surface can be obtained.

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dental Preparations (AREA)

Abstract

La présente invention concerne un ciment dentaire qui peut être utilisé facilement et qui a une adhésivité élevée à une surface de dent. Ce ciment dentaire est formé d'une première pâte contenant un (méth)acrylate et d'une seconde pâte contenant de l'eau et/ou un (méth)acrylate, dans lequel : l'un d'un agent d'oxydation ou d'un agent réducteur est inclus dans la première pâte, tandis que l'autre est inclus dans la seconde pâte; et de la poudre de ciment Portland et un polysaccharide phosphorylé sont chacun inclus dans la première pâte ou la seconde pâte. De préférence, le ciment dentaire est formé d'une première pâte contenant un (méth)acrylate et une poudre de ciment Portland et d'une seconde pâte contenant un polysaccharide phosphorylé et de l'eau, l'un d'un agent d'oxydation ou d'un agent réducteur étant inclus dans la première pâte et l'autre étant inclus dans la seconde pâte, et un pullulane phosphorylé étant utilisé en tant que polysaccharide phosphorylé.
PCT/JP2017/030405 2016-08-26 2017-08-24 Ciment dentaire WO2018038227A1 (fr)

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JP2018535767A JP6944158B2 (ja) 2016-08-26 2017-08-24 歯科用セメント

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JP2016-165754 2016-08-26
JP2016165754 2016-08-26

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WO2018038227A1 true WO2018038227A1 (fr) 2018-03-01

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002015848A2 (fr) * 2000-08-22 2002-02-28 Jeneric/Pentron Incorporated Compositions dentaires restauratrices et leur procedes d'utilisation
JP2011016776A (ja) * 2009-07-10 2011-01-27 Kuraray Medical Inc 歯科用組成物
JP2012020983A (ja) * 2010-07-16 2012-02-02 Sun Medical Co Ltd 歯科用組成物
WO2014156138A1 (fr) * 2013-03-26 2014-10-02 クラレノリタケデンタル株式会社 Composition durcissable à usage dentaire
WO2016208457A1 (fr) * 2015-06-26 2016-12-29 国立大学法人北海道大学 Poudre pour utilisation dentaire

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002015848A2 (fr) * 2000-08-22 2002-02-28 Jeneric/Pentron Incorporated Compositions dentaires restauratrices et leur procedes d'utilisation
JP2011016776A (ja) * 2009-07-10 2011-01-27 Kuraray Medical Inc 歯科用組成物
JP2012020983A (ja) * 2010-07-16 2012-02-02 Sun Medical Co Ltd 歯科用組成物
WO2014156138A1 (fr) * 2013-03-26 2014-10-02 クラレノリタケデンタル株式会社 Composition durcissable à usage dentaire
WO2016208457A1 (fr) * 2015-06-26 2016-12-29 国立大学法人北海道大学 Poudre pour utilisation dentaire

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JP6944158B2 (ja) 2021-10-06

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