EP4572730A1 - Compositions dentaires et leurs procédés de fabrication et d'utilisation - Google Patents

Compositions dentaires et leurs procédés de fabrication et d'utilisation

Info

Publication number
EP4572730A1
EP4572730A1 EP23761587.7A EP23761587A EP4572730A1 EP 4572730 A1 EP4572730 A1 EP 4572730A1 EP 23761587 A EP23761587 A EP 23761587A EP 4572730 A1 EP4572730 A1 EP 4572730A1
Authority
EP
European Patent Office
Prior art keywords
dental composition
previous
hardenable dental
water
acid
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.)
Pending
Application number
EP23761587.7A
Other languages
German (de)
English (en)
Inventor
Yizhong Wang
Joel D. Oxman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solventum Intellectual Properties Co
Original Assignee
Solventum Intellectual Properties Co
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 Solventum Intellectual Properties Co filed Critical Solventum Intellectual Properties Co
Publication of EP4572730A1 publication Critical patent/EP4572730A1/fr
Pending legal-status Critical Current

Links

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
    • A61K6/884—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
    • A61K6/889—Polycarboxylate cements; Glass ionomer cements
    • 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
    • A61K6/61—Cationic, anionic or redox initiators
    • 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
    • A61K6/77—Glass

Definitions

  • Two-part glass ionomer cements have been in dental use for some time. Such materials are comprised of an ionic polymer component and a reactive glass component, which when mixed together in the presence of water undergo a cement setting reaction. These dental materials provide several desirable attributes including prolonged fluoride release, tolerance to moisture and saliva, good mechanical properties and excellent adhesion to dental hard tissues without pretreatments such as conditioners or adhesives. Powder-liquid, powder-paste, paste-paste, pasteliquid, and liquid-liquid two-part cements have been reported.
  • the present disclosure is directed to such alternative methods and compositions.
  • the multi-part system of the present disclosure utilize a minimal (or no) amount of water in the first part to stabilize the water soluble metal persulfate salts in such part with no concern of water loss (i.e., the paste drying out).
  • a dispersion of 1-Benzyl -5- phenyl barbituric acid (BPBA) in an aqueous based second part that does not include a polymerizable monomer provides stability to the second part and preserves the reactivity of BPBA during storage.
  • BPBA based redox curing system produces no color change in the cured cement (in contrast to the above-discussed amine/peroxide based curing composition.
  • the range of viscosity ratios 1:0.06 to 1: 13 includes 1:0.06 to 1: 13, 1:0.1 to 1: 13, 1:0.25 to 1: 13, 1:0.5 to 1: 13, 1:0.6 to 1: 13, 1: 1 to 1: 13, 1:0.06 to 1: 10, 1:0.06 to 1:7.5, 1:0.06 to 1:5, 1:0.06 to 1:3.5, 1:0.06 to 1: 1, 1:0.1 to 1: 10, 1:0.25 to 1:7.5, 1:0.5 to 1:5, 1:0.6 to 1:3.5, 1:0.75 to 1:2, 1:0.9 to 1: 1.1, etc.).
  • the present disclosure is directed to a multi-part (e.g., two-part) hardenable dental composition (e.g., glass ionomer cement), the first part (sometimes referenced as paste A) including (i) liquid monofunctional and/or multifunctional monomers, oligomers, or polymers, (ii) an oxidizing agent; and (iii) acid-reactive glass, and the first part being free or substantially free of water; and the second part (sometimes referenced as paste B) including (i) a reducing agent; and (ii) a polyacid without a polymerizable sidechain group, (iii) water; and (iv) optionally, filler with no polymerizable groups attached to the surface.
  • a multi-part e.g., two-part
  • hardenable dental composition e.g., glass ionomer cement
  • the first part sometimes referenced as paste A
  • the second part including (i) a reducing agent; and (ii) a polyacid without
  • a first part of the multi-part hardenable composition may include (i) liquid mono- and/or multi-functional components having ethylenically unsaturated group(s) (sometimes referred to herein as a “resin system”), (ii) an oxidizing agent; and (iii) acid-reactive glass.
  • the first part may include no more than a small amount of water.
  • the first part may be in the form of a paste. That is, not a powder or a liquid, but a mixture of liquid and non-dissolvable powder/solid components having a generally uniform composition.
  • the first part may include either or both of liquid mono- and multifunctional (e.g., di-functional) components having ethylenically unsaturated group(s).
  • the liquid mono- or multi-functional components may include monomers, oligomers, or polymers.
  • the liquid mono- or multi-functional components may be water soluble.
  • the liquid mono- or multi-functional components may also be selected such that they are miscible with the other components of the hardenable composition. That is, these components may be at least sufficiently miscible that they do not undergo substantial sedimentation when combined with the other parts of the composition.
  • the first part may include both liquid mono- and multi-functional (e.g., di-functional) components having ethylenically unsaturated group(s).
  • the water soluble liquid monomer may be selected from the group consisting of 2-hydroxyethyl (meth)acrylate, glycerol mono(meth)acrylate, sugar methacrylates, and a combination thereof.
  • the multi-part hardenable compositions described herein may also include a component having at least two ethylenically unsaturated groups per monomer molecule which provides some cross linking in the composition when hardened.
  • this monomer may have a viscosity less than bisphenol A- glycidyl methacrylate (Bis-GMA), or not more than 50 percent of Bis-GMA.
  • suitable difunctional monomers may include glycerol dimethacrylate.
  • a water soluble monomer is used.
  • Suitable water soluble dimethacrylates include various molecular weights of polyethylenglycol (dimeth)acrylates ranging from approximately 400 to 1000 weight average molecular weight.
  • the components of the resin system are selected such that they are miscible with the other components of the hardenable composition. That is, preferably, the components of the resin system are at least sufficiently miscible that they do not undergo substantial sedimentation when combined with the other ingredients of the composition (e.g., reducing agent and oxidizing agent). Preferably, the components of the resin system are miscible with water.
  • the components of the resin system can be monomers, oligomers, polymers, or combinations thereof.
  • suitable oxidizing agents may include persulfates such as sodium, potassium, ammonium and alkyl ammonium persulfates, benzoyl peroxide, hydroperoxides such as cumene hydroperoxide, tert-butyl hydroperoxide, tert-amyl hydroperoxide and 2,5- dihydroperoxy-2,5-dimethylhexane, salts of cobalt (III) and iron (III), hydroxylamine, perboric acid and its salts, salts of a permanganate anion, and combinations thereof. Hydrogen peroxide can also be used, although it may, in some instances, interfere with the photoinitiator, if one is present.
  • persulfates such as sodium, potassium, ammonium and alkyl ammonium persulfates
  • benzoyl peroxide such as cumene hydroperoxide, tert-butyl hydroperoxide, tert-amyl hydroperoxide and 2,5- dihydr
  • the oxidizing agent may be present in the first part in an amount of between 0.01 and 10 wt. %, between 0.1 and 4.0 wt. %, or between 0.5 and 2.0 wt. %, based on the total weight the first part.
  • the average particle size (average longest dimension - typically, diameter) for the FAS glass is no greater than 10 micrometers or no greater than 5 micrometers as measured using, for example, a sedimentation analyzer.
  • Suitable FAS glasses will be familiar to those skilled in the art, and are available from a wide variety of commercial sources, and many are found in currently available glass ionomer cements such as those commercially available under the trade designations VITREMER, VITREBOND, RELY X LUTING CEMENT and KETAC-FIL (3M ESPE Dental Products, St.
  • the acid-reactive glass may be present in the first part in an amount of between 1 and 80 wt. %, between 3 and 60 wt. %, or between 5 and 40 wt. %, or based on the total weight the first part.
  • the first part may not include water or be substantially devoid of water.
  • the first part may include water in an amount of less than 5 wt. %, less than 1 wt. %, or less than 0.5 wt. %, based on the total weight of the first part.
  • the first part may include no water other than that which is unintentionally introduced by the various components that comprise the first part (i.e., the first part may not include any added water).
  • a second part of a multi-part hardenable composition may include (i) a polyacid (e.g., a polyacid without a polymerizable sidechain group); (ii) a reducing agent that includes 1-Benzyl -5- phenyl barbituric acid (BPBA); and (iii) water, and (iv) optionally filler with no polymerizable group attached to the filler surface.
  • a polyacid e.g., a polyacid without a polymerizable sidechain group
  • BPBA 1-Benzyl -5- phenyl barbituric acid
  • water e.g., 1, 2-Benzyl -5- phenyl barbituric acid
  • the second part may include a polyacid.
  • the polyacid may be water miscible. Suitable water miscible polyacids may include homo- or copolymers of unsaturated mono-, di-, and tricarboxylic acids, for example, homo- or copolymers of acrylic acid, itaconic acid or maleic acid.
  • the water miscible polyacids may include a polymer having sufficient pendent ionic groups to undergo a setting reaction in the presence of a reactive glass and water, and sufficient pendent non-ionically polymerizable groups to enable the resulting mixture to be cured by a redox curing mechanism and/or by exposure to radiant energy.
  • the polyacid may be a (co)polymer (the reaction product of a polyacid with a coupling agent).
  • the polyacid may be the reaction product of a polymer selected from the group consisting of polyacrylic acids, copolymers of acrylic and itaconic acids, copolymers of acrylic and maleic acids, copolymers of methyl vinyl ether and maleic anhydride or maleic acid, copolymers of ethylene and maleic anhydride or maleic acid, copolymers of styrene and maleic anhydride or maleic acid, and a combination thereof.
  • the polyacid may have Formula I:
  • B is an organic backbone
  • each X independently is an ionic group which can undergo a setting reaction in the presence of water and the acid-reactive glass particles
  • each Y independently is a non-ionically polymerizable group
  • m is at least 2
  • n is at least 1.
  • X is -COOH and Y is a copolymer group that does not include an ethylenically unsaturated group.
  • the backbone B is an oligomeric or polymeric backbone of carbon-carbon bonds, optionally containing non-interfering substituents such as oxygen, nitrogen or sulfur heteroatoms.
  • non-interfering refers to substituents or linking groups that do not unduly interfere with either the ionic or the non-ionic polymerization reaction.
  • B is a hydrocarbon backbone.
  • X and Y groups can be linked to the backbone B directly or by means of any non-interfering linking group, such as substituted or unsubstituted alkylene, alkyleneoxyalkylene, arylene, aryleneoxyalkylene, alkyleneoxyarylene, arylenealkylene, or alkylenearylene groups.
  • Alkylene and arylene refer to the divalent forms of alkyl and aryl, respectively.
  • Y is attached to B via an amide linkage.
  • the polyacid of Formula I can be prepared according to a variety of synthetic routes, including, but not limited to, (1) reacting n X groups of a polymer of the formula B(X) m +n with a suitable compound in order to form n pendent Y groups, (2) reacting a polymer of the formula B(X) m at positions other than the X groups with a suitable compound in order to form n pendent Y groups, (3) reacting a polymer of the formula B(Y) m +n or B(Y) n , either through Y groups or at other positions, with a suitable compound in order to form m pendent X groups and (4) copolymerizing appropriate monomers, e.g., a monomer containing one pendent X groups and a monomer containing one pendent Y groups.
  • the synthetic route (1) above is preferred.
  • Such groups can be reacted by the use of a "coupling compound", i.e., a compound containing both a Y group and a reactive group capable of reacting with the polymer through an X group, thereby covalently linking the Y group to the backbone B in a pendent fashion.
  • Suitable coupling compounds are organic compounds, optionally containing non-interfering substituents and/or noninterfering linking groups between the Y group and the reactive group.
  • polyacid may be present in the second part in an amount of between 2 and 50 wt. %, between 5 and 35 wt. %, or between 10 and 15 wt. %, based on the total weight the second part.
  • the reducing agent may include a water insoluble organic reducing agent such as 1 -Benzyl -5- phenyl barbituric acid (BPBA) or ascorbyl palmitate.
  • BPBA 1 -Benzyl -5- phenyl barbituric acid
  • Ascorbyl palmitate a water insoluble organic reducing agent
  • BPBA 1 -Benzyl -5- phenyl barbituric acid
  • Ascorbyl palmitate ascorbyl palmitate.
  • water insoluble organic reducing agents in contrast, will lose their redox curing reactivity overtime when they are dissolved in water.
  • the water insoluble organic reducing agents of the present disclosure may be dispersed as particles in water to achieve such storage stability.
  • these water insoluble reducing agents may dissolve by interaction with the resin system (e.g., methacrylate resins) after mixing of the two parts. The redox pair from the first part and the second part may then produce free radicals to cure the resin system.
  • the resin system
  • the reducing agent may be present in the second part in an amount of between 0.1 and 8.0 wt. %, between 0.25 and 5.0 wt. %, or between 0.5, and 3.0 wt. %, based on the total weight the second part.
  • the second part may include water. Water may be present in the second part in an amount of between 1 and 70 wt. %, between 2 and 60 wt. %, between 2 and 50 wt. %, between 5 and 40 wt. %, between 5 and 30 wt. %, or between 7 and 20 wt. %, based on the total weight the second part.
  • nonreactive fillers may also be included in the compositions described herein to control viscosity as well as for other reasons, such as to achieve a desired appearance, impart desired strength properties, impart radiopacity, and the like.
  • the first part, the second part, or both may further include a non-reactive filler in an amount of between 5 and 60 wt. %, between 10 and 50 wt. %, or between 15 and 40 wt. %, based on the total weight the respective part.
  • non-reactive fillers may be selected from one or more materials suitable for incorporation in compositions used for medical applications, such as fillers currently used in dental restorative compositions and the like.
  • the filler may have a maximum particle diameter less than 50 micrometers and an average particle diameter less than about 10 micrometers.
  • the filler can have a unimodal or polymodal (e.g., bimodal) particle size distribution.
  • the nonreactive filler is selected from the group consisting of inorganic material, crosslinked organic material, and a combination thereof. Suitable crosslinked organic materials are insoluble in the composition, and are optionally filled with inorganic filler.
  • the filler should be non-toxic and suitable for use in the mouth.
  • the filler can be radiopaque, radiolucent or non-radiopaque.
  • non-reactive inorganic fillers are naturally-occurring or synthetic materials such as quartz, nitrides (e.g., silicon nitride), glasses derived from, for example, Ce, Sb, Sn, Zr, Sr, Ba and Al, colloidal silica, colloidal zirconia, feldspar, borosilicate glass, kaolin, talc, titania, and zinc glass; low Mohs hardness fillers such as those described in U.S. Pat. No.
  • silica particles e.g., pyrogenic silicas such as the "Aerosil” Series “OX 50", “ 130", “ 150” and “200” silicas sold by Degussa and "Cab-O-Sil M5" silica sold by Cabot Corp.); metallic powders such as those disclosed in U.S. Pat. No. 5,084,491, especially those disclosed at column 2, lines 52-65; and combinations thereof.
  • non-reactive organic filler particles examples include filled or unfilled pulverized polycarbonates, polyepoxides, and the like.
  • Preferred non-reactive filler particles are quartz, submicron silica and zirconia, and non-vitreous microparticles of the type described in U.S. Pat. No. 4,503,169. Mixtures of these non-reactive fillers are also contemplated, as well as combination fillers made from organic and inorganic materials.
  • the nonreactive filler is selected from the group consisting of fumed silica, zirconia-silica, quartz, nonpyrogenic silica, and combinations thereof.
  • the surface of the non-reactive filler particles may be treated with a coupling agent in order to enhance the bond between the filler and polymerizable components when the composition is hardened.
  • suitable coupling agents include gamma- methacryloxypropyltrimethoysilane, gamma-mercaptopropyltriethoxysilane, gammaaminopropyltrimethoxysilane, SILQUEST A-1230 (Momentive Performance Chemicals), and the like.
  • Additional components which are suitable for use in the oral environment, may optionally be used in (either or both parts of) the multi-part hardenable compositions described herein.

Landscapes

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

Abstract

Une composition dentaire durcissable en plusieurs parties comprend une première partie et une seconde partie. La première partie comprend un composant mono-et/ou multifonctionnel ayant un ou plusieurs groupes éthyléniquement insaturés, des particules de verre réactif à l'acide ; et un agent oxydant. La seconde partie comprend un polyacide miscible à l'eau, un agent réducteur qui comprend un composé organique insoluble dans l'eau, et de l'eau.
EP23761587.7A 2022-08-16 2023-08-11 Compositions dentaires et leurs procédés de fabrication et d'utilisation Pending EP4572730A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263371525P 2022-08-16 2022-08-16
PCT/IB2023/058145 WO2024038364A1 (fr) 2022-08-16 2023-08-11 Compositions dentaires et leurs procédés de fabrication et d'utilisation

Publications (1)

Publication Number Publication Date
EP4572730A1 true EP4572730A1 (fr) 2025-06-25

Family

ID=87845836

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23761587.7A Pending EP4572730A1 (fr) 2022-08-16 2023-08-11 Compositions dentaires et leurs procédés de fabrication et d'utilisation

Country Status (3)

Country Link
EP (1) EP4572730A1 (fr)
JP (1) JP2025526843A (fr)
WO (1) WO2024038364A1 (fr)

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1139430A (en) 1966-12-30 1969-01-08 Nat Res Dev Improvements relating to surgical cements
US3814717A (en) 1970-12-04 1974-06-04 Dental Materials Section Labor Poly(carboxylic acid)-fluoroalumino-silicate glass surgical cement
US4209434A (en) 1972-04-18 1980-06-24 National Research Development Corporation Dental cement containing poly(carboxylic acid), chelating agent and glass cement powder
GB1532954A (en) 1974-10-24 1978-11-22 Nat Res Dev Poly-(carboxylate)cements
DE2929121A1 (de) 1979-07-18 1981-02-12 Espe Pharm Praep Calciumaluminiumfluorosilikatglas- pulver und seine verwendung
DE2932823A1 (de) 1979-08-13 1981-03-12 Espe Pharm Praep Anmischkomponente fuer glasionomerzemente
US4695251A (en) 1980-04-07 1987-09-22 Minnesota Mining And Manufacturing Company Orthodontic bracket adhesive and abrasive for removal thereof
US4503169A (en) 1984-04-19 1985-03-05 Minnesota Mining And Manufacturing Company Radiopaque, low visual opacity dental composites containing non-vitreous microparticles
CA1323949C (fr) 1987-04-02 1993-11-02 Michael C. Palazzotto Systeme ternaire de photoinitiateur pour la polymerisation additive
US5084491A (en) 1989-03-16 1992-01-28 The Ohio University Reinforcing glass ionomer dental filling material with stainless steel, or metals thereof
US5154762A (en) 1991-05-31 1992-10-13 Minnesota Mining And Manufacturing Company Universal water-based medical and dental cement
US5332429A (en) 1991-05-31 1994-07-26 Minnesota Mining And Manufacturing Company Method for treating fluoroaluminosilicate glass
US5501727A (en) 1994-02-28 1996-03-26 Minnesota Mining And Manufacturing Company Color stability of dental compositions containing metal complexed ascorbic acid
US6982288B2 (en) * 2002-04-12 2006-01-03 3M Innovative Properties Company Medical compositions containing an ionic salt, kits, and methods
WO2011081975A1 (fr) 2009-12-29 2011-07-07 3M Innovative Properties Company Procédés, dispositifs, et compositions d'auto-mélange dentaire
CN112789263A (zh) 2018-10-09 2021-05-11 3M创新有限公司 具有悬挂式胺基团的加成-断裂剂

Also Published As

Publication number Publication date
WO2024038364A1 (fr) 2024-02-22
JP2025526843A (ja) 2025-08-15

Similar Documents

Publication Publication Date Title
JP4828796B2 (ja) イオン塩を含有する医用組成物
US6818682B2 (en) Multi-part dental compositions and kits
JP4851454B2 (ja) ナノジルコニアフィラーを含有する歯科用組成物
US9351908B2 (en) Orthodontic composition with polymeric fillers
JP5952194B2 (ja) 歯科用自動混合方法、装置、及び組成物
US9408781B2 (en) Dental resin modified glass-ionomer composition
JP5833568B2 (ja) 仮着用セメントのための歯科用自動混合方法、用具、及び組成物
CN116350518A (zh) 具有良好透明度的自粘合牙科复合粘固剂
KR20230101728A (ko) 양호한 투명도를 갖는, 설페이트 함유 또는 포스페이트 함유, 자가 접착식 치과용 복합 시멘트
CN116350520A (zh) 基于酸处理的填料的具有良好透明度的自粘合牙科复合粘固剂
JP5670022B2 (ja) 表面修飾充填剤を含有する歯科組成物
US20020082317A1 (en) Dental adhesive compositions with desensitizing agents
EP4572730A1 (fr) Compositions dentaires et leurs procédés de fabrication et d'utilisation
JP7712116B2 (ja) ２ペースト型歯科用硬化性組成物
WO2023228049A1 (fr) Compositions dentaires et leurs procédés de fabrication et d'utilisation

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20250211

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)