WO2004098541A1 - 歯科用セメント組成物 - Google Patents
歯科用セメント組成物 Download PDFInfo
- Publication number
- WO2004098541A1 WO2004098541A1 PCT/JP2004/005331 JP2004005331W WO2004098541A1 WO 2004098541 A1 WO2004098541 A1 WO 2004098541A1 JP 2004005331 W JP2004005331 W JP 2004005331W WO 2004098541 A1 WO2004098541 A1 WO 2004098541A1
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- WO
- WIPO (PCT)
- Prior art keywords
- meth
- group
- unit
- acrylate
- cement composition
- Prior art date
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Classifications
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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
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
- A61K6/836—Glass
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- 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
-
- 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
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Definitions
- the present invention relates to a dental cement composition.
- a glass ionomer cement utilizing a reaction between glass such as fluoroaluminosilicate glass powder and a polycarboxylic acid.
- the metal ion in the glass is released from the glass by the action of an acid in the presence of water, and the metal ion and the carboxylic acid group of the polycarboxylic acid undergo an ionic reaction, which hardens. is there.
- This glass ionomer cement has many features, such as excellent biocompatibility, adhesiveness to teeth, durability in the oral cavity, and a cured product that is translucent and excellent in aesthetics. ing. For this reason, it is widely used for coalescence of inlays and crowns, filling in caries cavities, lining, and preventive filling of pit cavities.
- the biggest disadvantage of the glass ionomer cement is that when it comes into contact with moisture such as saliva immediately after kneading, the curing reaction is inhibited, and the physical properties eventually deteriorate.
- Glass ionomer cements undergo a hardening reaction in the presence of water by a chelate-forming reaction between a polycarboxylic acid and a polyvalent metal generated from an inorganic compound such as fluoroaluminosilicate glass. Therefore, the reaction requires water to release metal ions.
- water present in the hardening system or in the hardening material has a negative effect on increasing the hardening speed and initial strength.
- the glass ionomer cement has low initial adhesion to the tooth material, and other physical properties are further deteriorated over time.
- glass ionomer cement is particularly inferior in toughness compared to composite resin and resin cement.
- a cement has been developed that forms a hybrid layer on the dentin surface, such as an adhesive resin cement, and shows stable adhesion (for example, see JP-A-9-25). No. 5,515).
- This resin-reinforced glass ionomer cement is composed of fluoroaluminosilicate glass powder, polycarboxylic acid, water, 2-hydroxyethyl methacrylate (HE MA), a cross-linking agent, etc., and is made up of fluoroaluminosilicate glass and polycarboxylic acid.
- HE MA 2-hydroxyethyl methacrylate
- the HEMA polymer and the polycarboxylate formed by the redox catalyst or photopolymerization catalyst form a hardened product entangled with hydrogen bonds, giving the toughness unique to high molecular substances.
- this resin-reinforced glass ionomer cement has a lower ionic reactivity to the tooth substance than conventional glass ionomer cement. For this reason, it is hard to say that it has sufficient adhesive strength. In addition, the operation is complicated, and performance differences due to the skills of the dentist are likely to occur.
- the dental cement composition of the present invention is a dental cement composition containing the following organic polymer and an inorganic powder containing a polyvalent metal compound.
- the organic polymer contains a (substituted) carboxylic acid group-containing unit (A) represented by the following formula (I) and a (substituted) carbamoyl group-containing unit (B) represented by the following formula (II); ;), (B) the total of both units accounts for at least 20 mol% of the total units forming the organic polymer, and the unit (A) and the unit (B) are 0.6 Z 1.0 to 1.0.
- n 0 or 1
- X represents a hydrogen atom, —NH 4 , or 1 / mM (M is selected from alkali metals, alkaline earth metals, transition metals, Zn, and C d Represents a metal atom, m represents the valence of the metal), and R 1 represents a hydrogen atom or a methyl group.
- n 0 or 1
- R 2 represents a hydrogen atom or a methyl group
- R 3 represents hydrogen, an alkyl group having 1 to 18 carbon atoms, an alkenyl group or an aralkyl group.
- the (substituted) hapoxyl group is a hapoxyl group Z or a metal whose hydrogen atom is selected from —NH 4 , an alkali metal, an alkaline earth metal, a transition metal, Zn, and Cd.
- a (substituted) carpamoyl group is a carbamoyl group or a carbamoyl group in which one hydrogen is substituted with an alkyl, alkenyl, or aralkyl group having 1 to 18 carbon atoms.
- the method for preparing a dental cement composition of the present invention includes a step of preparing an inorganic powder containing a polyvalent metal compound, a step of preparing an organic polymer, and a step of obtaining a dental cement composition by mixing these.
- the organic polymer comprises a (substituted) dexamethasyl group-containing unit (A) represented by the following formula (I) and a (substituted) dexamethasyl group-containing unit (B) represented by the following formula (II) , (A) and (B) together account for at least 20 mol% of all units forming the organic polymer, with unit (A) unit (B) being 0.6 1.0 to 1.0. When the amount of the unit present in the polymer, which is the smaller of the two units, is 100 mol%, the unit is present in at least 70 mol% of the unit.
- the carbon bonded to the (substituted) carbonyl group of the unit (A) and the carbon bonded to the (substituted) carbamoyl group of the unit (B) are adjacent to each other directly or via a methylene group or an ethylene group.
- n 0 or 1
- X represents a hydrogen atom, —NH 4 , or 1 mM
- M is a metal selected from alkali metals, alkaline earth metals, transition metals, Zn, and Cd
- m represents the valence of the metal
- R 1 represents a hydrogen atom or a methyl group.
- n 0 or 1
- R 2 represents a hydrogen atom or a methyl group
- R 3 represents hydrogen, an alkyl group having 1 to 18 carbon atoms, an alkenyl group or an aralkyl group.
- the above method may further include the step of providing water and mixing the same.
- the present invention relates to a dental cement composition.
- An object of the present invention is to improve the disadvantages of conventional glass ionomer cements and to provide a dental cement composition that is excellent in adhesion to teeth, hardening speed, and initial strength, and that does not deteriorate with time.
- the dental cement composition of the present invention comprises, as an adhesive component to the tooth substance, a (substituted) carboxyl group-containing unit (A) and a (substituted) carbamoyl group-containing unit (B) instead of the conventional polycarboxylic acid.
- A substituted carboxyl group-containing unit
- B carbamoyl group-containing unit
- the organic polymer used in the dental cement composition of the present invention is preferably such that the sum of both units (A) and (B) is at least 20 mol%, preferably at least 40 mol%, of all the units forming the polymer. %, More preferably at least 60 mol%, and most preferably a polymer consisting of both units (A) and (B), that is, 100 mol%.
- the unit that may be contained in the organic polymer is not particularly limited. As appropriate, any unit may be included alone or in combination of two or more. Examples of such a unit include an alkylene unit, an aromatic group, an alkylene unit which may have an alkyloxy group in a side chain, a cycloalkylene unit, a unit having an amide bond, and the like. it can.
- the unit (A) and the unit (B) are such that (A) :( B) is present in the organic polymer in a ratio of 0.6: 1.0 to 1.0: 0.6. is necessary.
- the ratio of the total of the unit (A) and the unit (B) to the polymer is 20 mol% or more, and (A) :( B) is within the above-mentioned necessary range, the following formula ( As shown in III), the carbon bonded to the (substituted) carbonyl group of the unit (A) and the carbon bonded to the (substituted) carbamoyl group of the unit (B) are directly, or a methylene group, or an ethylene group.
- the adjacent structure (C) can be efficiently formed through the structure.
- this structure (C) When this structure (C) is formed, the bond between the organic polymer and the inorganic compound becomes strong, so that the dental cement composition containing this polymer has a strong bond with the tooth.
- the presence of both units in the polymer It is preferred that the amounts are of the same level.
- (A): (B) is preferably 0.7: 1.0 to 1.0: 0.7, more preferably 0.8: 1.0 to 1.0: 0.8. It is also preferred that the abundances are the same.
- p 0, 1 or 2
- X represents a hydrogen atom, —NH 4 , or 1 / mM (M is selected from alkali metals, alkaline earth metals, transition metals, Zn, and Cd.
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents a hydrogen atom or a methyl group
- R 3 represents a carbon atom having 1 to 18 carbon atoms. Represents an alkyl group, an alkenyl group or an aralkyl group.
- the abundance of the lower unit in the polymer of the unit (A) and the unit (B) is defined as 100 mol%, 70 mol% or more, preferably 80% or more, more preferably Is 90% or more, and most preferably 100%, of the carbon bonded to the olepoxyl group of unit (A) and the carbon conjugated to the rubamoyl group of unit (B), either directly or via a methylene or ethylene group. It must form a combined structure (C).
- the unit (A) occupies 40 mol% and the unit (B) occupies 30 mol% of all 100 mol% of the unit constituting the polymer, if the unit (A) has a small amount, Based on the abundance of B), at least 70 mol% of these (ie, at least 21 mol% in all constituent units) exist adjacent to unit (A) to form structure (C). That is, it must be
- the organic polymer used in the present invention adopts an irregular existence form in which the structure (C) is present in one part in the polymer and not present at all in the other part.
- the structure (C) is changed to a polymer molecule by adopting the manufacturing method described later. Preferably, it is relatively evenly distributed in the chain.
- the structure (C) is uniformly distributed in this way, it is considered that the dental cement composition using this organic polymer adheres more firmly to the tooth material.
- this organic polymer is produced by the method described later, the structure (C) is relatively uniformly dispersed in the polymer molecule.
- benzoic acid in which there is no bilamoyl group near the lipoxyl group examples include the following.
- the pKa of 2,2-dimethylpropanoylaminobenzoic acid is 5.4
- the pKa of sterically hindered 2,4,6-trimethylbenzoic acid is 4.8.
- R 3 is preferably an alkyl group, an alkenyl group, or an aralkyl group from the viewpoint of promoting hydrogen bonding and increasing acid strength.
- the carbon bonded to the (substituted) carbonyl group and the carbon bonded to the (substituted) valmoyl group of the unit (B) are preferably adjacent to each other via a methylene group.
- the polymerization degree of the organic polymer is preferably 5 or more, more preferably 10 or more, further preferably 50 or more, and most preferably 100 or more.
- the degree of polymerization of the organic polymer is preferably 1000 or less from the viewpoint of ease of preparation of dental cement and application properties.
- the degree of polymerization means a number average degree of polymerization.
- the organic polymer used in the dental cement composition of the present invention can be produced, for example, by the following method.
- a monomer containing a carboxyl group for example, (meth) acrylic acid
- a polymer having a lipoxyl group in which at least 20 mol% of all the units constituting the polymer are (meth) acrylic acid units.
- the obtained polymer containing a carbonyl group is treated with a dehydrating agent to convert two adjacent carboxyl groups into an acid anhydride to obtain a polymer having an acid anhydride group introduced therein.
- the acid anhydride group is subjected to ring-opening addition under known conditions using an amidating agent such as ammonia or an alkylamine to form a monoamidated compound.
- an organic polymer having a structure (C) in which the carbon bonded to the (substituted) carboxyl group and the carbon bonded to the (substituted) rubamoyl group are bonded directly or via a methylene group or an ethylene group is obtained.
- (III) is to form a so-called head-to-tail bond at the time of polymerization, when forming a structure (C) after polymerizing a monomer containing a lipoxyl group such as (meth) acrylic acid. It takes into account that there may be both cases where head-to-tail coupling is performed. When p is 0 or 2, head-to-tail (tail-to-tail) coupling is performed, and when p is 1, head-to-tail coupling is performed.
- a polymer is formed by a known method using maleic anhydride, and then the acid anhydride group in the obtained polymer is converted to a known acid using an amidating agent such as ammonia or amine.
- an organic polymer used in the dental cement composition of the present invention can also be obtained.
- This organic polymer is mainly composed of monomers having an acid anhydride group such as maleic anhydride.
- p is 0, that is, the carbon atom bonded to the (substituted) carboxyl group and the carbon atom bonded to the (substituted) carbamoyl group are always directly in the polymer main chain. It becomes a combined form.
- the maleic anhydride unit is the unit (C) itself. Therefore, the polymer may be a random copolymer as long as maleic anhydride in the polymer is 70% or more. However, when the maleic anhydride content is less than 40 to 70%, it is preferable to form an alternating copolymer in which maleic anhydride moieties are uniformly dispersed in order to uniformly disperse the structure (C).
- the alternating copolymer is obtained by radical polymerization of maleic anhydride and an electron donating monomer.
- the electron-donating monomer is a monomer having a negative e-value, which is a characteristic value of the monomer.
- examples thereof include aryl monomers such as aryl alcohol, vinyl ether monomers such as methyl vinyl ether and ethyl vinyl ether, and P-dioxene. And the like, vinyl ester monomers such as vinyl acetate, ⁇ -olefins such as propylene, and styrenes.
- the dental cement composition of the present invention contains an inorganic powder containing a polyvalent metal compound in addition to the above organic polymer.
- a polyvalent metal compound any compound can be selected as necessary. Examples thereof include oxides, hydroxides, carbonates, sulfates, phosphates, and silicates of the polyvalent metal. Can be.
- oxide of the polyvalent metal zinc oxide, magnesium oxide, calcium oxide, aluminum oxide, strontium oxide, or the like can be used.
- the polyvalent metal hydroxide include zinc hydroxide, calcium hydroxide, and aluminum hydroxide.
- the polyvalent metal carbonate include zinc carbonate, calcium carbonate, aluminum carbonate, and strontium carbonate.
- polyvalent metal sulfate examples include gypsum and palladium sulfate.
- polyvalent metal phosphates include phosphoric acid
- calcium, zinc phosphate, aluminum phosphate, and silicates examples include aluminum silicate, calcium silicate, and aluminum borosilicate.
- polyvalent metal ion leaching glasses belonging to silicates examples include aluminosilicate glass and fluoroaluminosilicate glass, but are not limited thereto. is not.
- metals such as aluminum and calcium in the powder are coordinated to lipoxyl groups in an organic polymer having an acid strength enhanced by intramolecular hydrogen bonds. To form a strong bond.
- the mass average particle diameter of the inorganic powder containing the polyvalent metal compound is preferably 10 ⁇ or less.
- the inorganic powder may contain a substance other than the polyvalent metal compound.
- a substance other than the polyvalent metal compound for example, metal oxides, hydroxides, carbonates, sulfates, phosphates, silicates and transition metal oxides, hydroxides, carbonates, sulfates, phosphates, silicates, etc. May be included.
- the adhesive component is composed of only the above organic polymer, it can be used as a solution in which the organic polymer is dissolved in water or a mixed solvent of water and an organic solvent.
- the dental cement composition of the present invention may further contain a (meth) acrylate polymerizable monomer and a polymerization catalyst.
- a (meth) acrylate-based polymerizable monomer for example, an organic polymer, a polymerization catalyst, or the like can be used as a solution in which the (meth) acrylate-based polymerizable monomer is dissolved.
- organic solvent examples include, but are not limited to, ethyl alcohol, propyl alcohol, and acetone.
- methacrylate polymerizable monomer examples include (meth) acrylic acid, hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, and hydroxymethacrylate.
- Hexyl (meth) acrylate or (meth) acrylic acid mono-, di-glycerin ester, (meth) acrylic acid mono-, di-, tri-pentaerythritol ester, (meth) acryloyloxetyl phosphate, (Meth) acryloyloxypropyl phosphate, (meth) acryloyloxybutyl phosphate, tetra (meth) Evening) acryloyloxyshethyl pyrophosphate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, 2-ethylhexyl ( Meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, decyl (meth) acrylate, lau
- a photopolymerization catalyst As the polymerization catalyst, a photopolymerization catalyst, a redox polymerization catalyst, or the like can be used, and both of them can be used in combination. Other catalysts may be used as needed.
- the photopolymerization catalyst include camphorquinone, naphthoquinone, benzyl, piercetyl and the like.
- Redox polymerization catalysts include known radical polymerizations such as benzoyl peroxide, cumenehydride peroxide, t-butylhydroxide peroxide, potassium persulfate, ammonium persulfate, azobisisobutyronitrile, and azovispaleronitrile.
- a combination system of an initiator and a reducing agent can be mentioned.
- the reducing agent include amine-based reducing agents such as N, N-dimethylamino-P-toluidine, butylethylenolamine, N, N-dimethylaminoethyl methacrylate, morpholinoethyl methacrylate, and dimethylaminobenzoic acid. .
- These catalysts may be used alone or in combination of two or more as necessary.
- the dental cement composition of the present invention contains the above-mentioned organic polymer and a polyvalent metal compound. It can contain inorganic powder and water. Polyvalent metal ions elute from the inorganic powder containing the polyvalent metal compound to the surface in the presence of water. Since the organic polymer has a strong acid strength of the hydroxyl group, it strongly binds to the polyvalent metal ion. The organic polymer is firmly bound to the inorganic powder via this bond, and the organic polymer is further bound to the calories in the dentin. Strongly bonds with shims. Therefore, the dental cement composition of the present invention firmly adheres to the tooth surface without performing a pretreatment for bonding the surface of the tooth surface, so that the number of operation steps at the time of filling and bonding is reduced.
- the method for adjusting the cement composition can also be selected as needed.
- an organic polymer and water are mixed first, and this mixture and an inorganic powder containing a polyvalent metal compound are uniformly mixed at the time of use.
- the ratio of the amount of the inorganic powder containing the polyvalent metal compound to water is arbitrarily selected as necessary.
- the preferred ratio range is 1: 2 to 20: 1 (weight ratio).
- the preferred concentration of the organic polymer in the mixture of the organic polymer and water is from about 10 to about 90% by weight.
- the polymerizable monomer is polymerized in a state in which it is entangled with the organic polymer. It is preferable because toughness is imparted to the cured product.
- the dental cement composition of the present invention can be used for bonding dental prostheses such as inlays, crowns, and bridges with dental materials, bonding orthodontic appliances with dental materials, filling carious cavity grooves, lining, and pit cavities. It is suitably used for preventive filling of grooves.
- the mixed dental cement composition was filled into a predetermined mold made of polytetrafluoroethylene and cured as it was at room temperature for 30 minutes to prepare a test specimen for compression test having a diameter of 6 mm and a length of 12 mm. After immersing this test piece in water at 37 ° C for 48 hours, a compression test was performed at an autograph crosshead speed of 2 mm / min.
- a 40% by mass aqueous solution of the organic polymer A obtained in the same manner as in Example 1 was prepared and used as a cement liquid.
- Table 1 shows that the dental cement of the present invention using a specific organic polymer as compared with a conventional glass ionomer cement using a noacryloyloxyshethyl phosphate acrylate copolymer as an organic polymer. It can be seen that the composition shows high adhesiveness to tooth material. In addition, as can be seen from the results of the compressive strength test, the toughness is excellent, and the water resistance and durability are also excellent. Industrial potential
- the present invention contains a metal oxide or glass powder and a specific organic polymer. It is a dental cement composition. According to the present invention, there is provided a dental cement composition which is excellent in adhesion to teeth, hardening speed and initial strength, and does not deteriorate with time. According to the present invention, compared to a conventional glass ionomer cement using acrylic acid and an acryloyloxy group-containing monomer or polyacrylic acid, the adhesiveness to the tooth material and the curing speed are improved. The present invention provides a dental cement composition which has excellent initial strength and does not deteriorate with time.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/555,610 US20070293599A1 (en) | 2003-05-07 | 2004-04-14 | Dental Cement Composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003128982A JP2004331558A (ja) | 2003-05-07 | 2003-05-07 | 歯科用セメント組成物 |
JP2003-128982 | 2003-05-07 |
Publications (2)
Publication Number | Publication Date |
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WO2004098541A1 true WO2004098541A1 (ja) | 2004-11-18 |
WO2004098541A8 WO2004098541A8 (ja) | 2007-02-08 |
Family
ID=33432063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2004/005331 WO2004098541A1 (ja) | 2003-05-07 | 2004-04-14 | 歯科用セメント組成物 |
Country Status (3)
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US (1) | US20070293599A1 (ja) |
JP (1) | JP2004331558A (ja) |
WO (1) | WO2004098541A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8642679B2 (en) * | 2008-09-12 | 2014-02-04 | Gc Corporation | Dental cement composition |
CN112545900A (zh) * | 2019-09-26 | 2021-03-26 | 株式会社松风 | 配合过渡金属吸附体的牙科用固化性组合物 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2123246B1 (en) * | 2007-02-19 | 2021-06-23 | Tokuyama Dental Corporation | Adhesive composition for dental use |
Citations (3)
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JPS5661471A (en) * | 1979-10-24 | 1981-05-26 | Lion Corp | Adhesive composition for dental use |
JPH09255515A (ja) * | 1996-03-25 | 1997-09-30 | Sankin Kogyo Kk | 歯科用セメント組成物 |
JP2000204124A (ja) * | 1998-11-12 | 2000-07-25 | Nippon Shokubai Co Ltd | 有機重合体およびその製造方法並びに該有機重合体と無機化合物との複合体および該複合体の製造方法 |
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JPS59135272A (ja) * | 1983-01-21 | 1984-08-03 | Kuraray Co Ltd | 接着剤 |
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US5055046A (en) * | 1990-09-20 | 1991-10-08 | Isp Investments Inc. | Bioadhesive composition |
US5270351A (en) * | 1992-06-15 | 1993-12-14 | American Dental Association Health Foundation | Adhesion-promoting agents incorporating polyvalent cations |
US5369145A (en) * | 1993-06-14 | 1994-11-29 | Block Drug Company | Denture adhesive |
US5442038A (en) * | 1993-10-06 | 1995-08-15 | Srchem, Inc. | Polymers of maleic acid with amines |
BR9713405A (pt) * | 1996-11-22 | 2000-01-25 | Clariant Gmbh | Aditivos para inibir a formação de hidratos gasosos. |
DE19704293A1 (de) * | 1997-02-05 | 1998-08-06 | Basf Ag | Zahnprothesenhaftmittel |
JP2000086421A (ja) * | 1998-09-08 | 2000-03-28 | Gc Corp | 歯科用接着剤セット |
JP4305594B2 (ja) * | 2000-11-28 | 2009-07-29 | 株式会社トクヤマ | 歯科用接着キット |
US7101942B2 (en) * | 2001-01-19 | 2006-09-05 | Ivoclar Vivadent Ag | Dental materials based on metal oxide clusters |
DE10124029B4 (de) * | 2001-05-16 | 2004-08-26 | 3M Espe Ag | Initiatorsystem für saure Dentalformulierungen |
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- 2003-05-07 JP JP2003128982A patent/JP2004331558A/ja active Pending
-
2004
- 2004-04-14 WO PCT/JP2004/005331 patent/WO2004098541A1/ja active Application Filing
- 2004-04-14 US US10/555,610 patent/US20070293599A1/en not_active Abandoned
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JPS5661471A (en) * | 1979-10-24 | 1981-05-26 | Lion Corp | Adhesive composition for dental use |
JPH09255515A (ja) * | 1996-03-25 | 1997-09-30 | Sankin Kogyo Kk | 歯科用セメント組成物 |
JP2000204124A (ja) * | 1998-11-12 | 2000-07-25 | Nippon Shokubai Co Ltd | 有機重合体およびその製造方法並びに該有機重合体と無機化合物との複合体および該複合体の製造方法 |
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Title |
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NORIKAZU, U. ET AL.: "Secure Binding of Alternately Amidated Poly(acrylate) to Cry stalline Calcium Carbonate by NH ... O Hydrogen Bond", MACROMOLECULES, vol. 34, no. 8, 2001, pages 2607 - 2614, XP002983593 * |
ONODA, A. ET AL.: "Haii Sanso Genshi eno NH...O Suiso o Motsu Karubokirato Polymer to Phosphoric Acid Calcium Kessho no Ketsugo", POLYMER PREPRINTS, vol. 49, no. 5, 2000, pages 892, XP002983592 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8642679B2 (en) * | 2008-09-12 | 2014-02-04 | Gc Corporation | Dental cement composition |
CN112545900A (zh) * | 2019-09-26 | 2021-03-26 | 株式会社松风 | 配合过渡金属吸附体的牙科用固化性组合物 |
CN112545900B (zh) * | 2019-09-26 | 2024-02-13 | 株式会社松风 | 配合过渡金属吸附体的牙科用固化性组合物 |
Also Published As
Publication number | Publication date |
---|---|
US20070293599A1 (en) | 2007-12-20 |
JP2004331558A (ja) | 2004-11-25 |
WO2004098541A8 (ja) | 2007-02-08 |
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