US20060287459A1 - Radical polymerizable macrocyclic resin compositions with low polymerization stress - Google Patents

Radical polymerizable macrocyclic resin compositions with low polymerization stress Download PDF

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Publication number
US20060287459A1
US20060287459A1 US11/153,090 US15309005A US2006287459A1 US 20060287459 A1 US20060287459 A1 US 20060287459A1 US 15309005 A US15309005 A US 15309005A US 2006287459 A1 US2006287459 A1 US 2006287459A1
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United States
Prior art keywords
polymerizable
radical polymerizable
precursor
resin compositions
polymerization
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Abandoned
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US11/153,090
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English (en)
Inventor
Xiaoming Jin
Paul Hammesfahr
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Dentsply Research and Development Corp
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Dentsply Research and Development Corp
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Publication date
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Priority to US11/153,090 priority Critical patent/US20060287459A1/en
Assigned to DENTSPLY RESEARCH & DEVELOPMENT CORP. reassignment DENTSPLY RESEARCH & DEVELOPMENT CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HAMMESFAHR, PAUL D., JIN, XIAOMING
Publication of US20060287459A1 publication Critical patent/US20060287459A1/en
Priority to US12/079,525 priority patent/US20080182997A1/en
Priority to US12/381,781 priority patent/US20090182109A1/en
Priority to US12/655,028 priority patent/US20100234549A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1691—Aliphatic-aromatic or araliphatic polycarbonates unsaturated
    • 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
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/34—Oligomeric, e.g. cyclic oligomeric

Definitions

  • This invention relates to free radical polymerizable macrocyclic compounds and composition, which feature by their low shrinkage and low contraction stress upon polymerization.
  • Such low shrinkage and low stress resin could find their wide range of applications, especially in microelectronic, special coating and restorative dentistry where the dimensional stability and contraction stress within cured materials are critical to the total performance.
  • the polymerization shrinkage of curable material is referred to the dimensional contraction during polymerization or curing, because the formation of covalent bonding during polymerization bring the molecules closer each other than that while they are free in van der Walls distance.
  • the origin of polymerization stress comes from a restrained polymerization or shrinking during curing. Therefore, it is not only related to polymerization shrinkage, but also is dependent on the polymerization kinetics.
  • the objective is to present a general method to produce a macrocyclic oligomer which would be converted into 3D network via free radical polymerization.
  • U.S. Pat. No. 4,644,053 disclosed a method to synthesize single macrocyclic compounds. Then various macrocyclics oligomers, including carbonates, esters, amides, ethers, imides, sulfides, et al, have been prepared. However, high temperature ring-opening reaction has to be involved to convert these macrocyclics into high molecular weight polymers.
  • U.S. Pat. No. 5,047,261 disclosed a composition containing a five-member carbonate cyclic group for fast copolymerization with mathacrylate.
  • U.S. Pat. No. 5,962,703 disclosed functionalized bicyclic methacrylate with norboneyl or norbonadienl group.
  • U.S. Pat. No. 6,043,361 disclosed polymerizable cyclic allylic sufides is used for low shrinkage materials.
  • the macrocyclic oligomers are prepared under pseudo-high-dilution condition via a condensation between a reactive and free radical polymerizable precursor and various coupling agents to afford carbonate, ester, siloxane, phosphonate, et al linkages to result in macrocyclic oligomers.
  • the condensation groups usually have to be activated to assure a mild reaction for cyclization with the coupling monomers.
  • BisGMA is one of widely used dental resin and it contains two free radical polymerizable group, methacrylate and two hydroxyl groups. This turns BisGMA an ideal candidate for polymerizable macrocyclic oligomer, although the presence of BisGMA isomer would make more complicated to this approach.
  • carbonyldiimidazol (CDI, 1), was used to selectively reacted with the secondary alcohol in BisGMA (2) to give an activated BisGMA, DIZ-BisGMA(3). It was isolated and the chemical structure of DIZ-BisGMA was fully characterized with FITR and NMR.
  • CDI and its intermediates could exhibit surprisingly specificity towards primary, secondary, tertiary functional groups, of the same type, during the controlled formation of various well-defined molecular sequence [1-5] .
  • Our idea is to adopt same chemistry of CDI and to activate the two secondary hydroxyl group.
  • an activated precursor, DIZ-BisGMA was made to react with various primary diols 1,10-decanediol, under a pseudo high-dilution condition, as shown in Scheme II. Both reactants were simultaneously charged into the system in a high-dilution condition via slowly, precisely controlled addition to ensure a favorable formation of cyclic product.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Dental Preparations (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Polymerisation Methods In General (AREA)
US11/153,090 2004-06-15 2005-06-15 Radical polymerizable macrocyclic resin compositions with low polymerization stress Abandoned US20060287459A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US11/153,090 US20060287459A1 (en) 2004-06-15 2005-06-15 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/079,525 US20080182997A1 (en) 2004-06-15 2008-03-27 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/381,781 US20090182109A1 (en) 2004-06-15 2009-03-16 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/655,028 US20100234549A1 (en) 2004-06-15 2009-12-22 Radical polymerizable macrocyclic resin compositions with low polymerization stress

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57983604P 2004-06-15 2004-06-15
US11/153,090 US20060287459A1 (en) 2004-06-15 2005-06-15 Radical polymerizable macrocyclic resin compositions with low polymerization stress

Related Child Applications (1)

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US12/079,525 Continuation US20080182997A1 (en) 2004-06-15 2008-03-27 Radical polymerizable macrocyclic resin compositions with low polymerization stress

Publications (1)

Publication Number Publication Date
US20060287459A1 true US20060287459A1 (en) 2006-12-21

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ID=34972726

Family Applications (6)

Application Number Title Priority Date Filing Date
US11/153,090 Abandoned US20060287459A1 (en) 2004-06-15 2005-06-15 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/079,525 Abandoned US20080182997A1 (en) 2004-06-15 2008-03-27 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/381,781 Abandoned US20090182109A1 (en) 2004-06-15 2009-03-16 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/655,028 Abandoned US20100234549A1 (en) 2004-06-15 2009-12-22 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/912,951 Expired - Fee Related US8129446B2 (en) 2004-06-15 2010-10-27 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US13/300,908 Abandoned US20120108837A1 (en) 2004-06-15 2011-11-21 Radical polymerizable macrocyclic resin compositions with low polymerization stress

Family Applications After (5)

Application Number Title Priority Date Filing Date
US12/079,525 Abandoned US20080182997A1 (en) 2004-06-15 2008-03-27 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/381,781 Abandoned US20090182109A1 (en) 2004-06-15 2009-03-16 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/655,028 Abandoned US20100234549A1 (en) 2004-06-15 2009-12-22 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US12/912,951 Expired - Fee Related US8129446B2 (en) 2004-06-15 2010-10-27 Radical polymerizable macrocyclic resin compositions with low polymerization stress
US13/300,908 Abandoned US20120108837A1 (en) 2004-06-15 2011-11-21 Radical polymerizable macrocyclic resin compositions with low polymerization stress

Country Status (7)

Country Link
US (6) US20060287459A1 (de)
EP (1) EP1778164B1 (de)
JP (2) JP2008502781A (de)
AT (1) ATE464875T1 (de)
CA (1) CA2570341C (de)
DE (1) DE602005020806D1 (de)
WO (1) WO2005123008A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060063854A1 (en) * 2004-06-15 2006-03-23 Xiaoming Jin Low shrinkage and low stress dental compositions

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE464875T1 (de) 2004-06-15 2010-05-15 Dentsply Int Inc Radikale polymerisierbare makrozyklische harzzusammensetzungen mit geringer polymerisationsspannung
US8747831B2 (en) 2011-06-22 2014-06-10 Dentsply International Inc. Method and antibacterial/antimicrobial compositions in dental compositions
US8779024B2 (en) * 2012-02-28 2014-07-15 Dentsply International Inc. Acid-neutralizing resins and hardenable dental compositions thereof
JP6058482B2 (ja) * 2013-06-26 2017-01-11 積水化成品工業株式会社 環状マクロモノマー、高分子架橋体、高分子ゲル、及びそれらの製造方法
CN105125415B (zh) * 2015-06-30 2018-01-16 吉林省登泰克牙科材料有限公司 低聚合收缩率的牙科复合树脂材料的制备方法
CN110249118B (zh) * 2017-02-14 2022-01-25 卡明斯公司 压缩机旁路流布置
JP7493534B2 (ja) 2019-12-10 2024-05-31 クラレノリタケデンタル株式会社 歯科用組成物
WO2022138973A1 (ja) 2020-12-25 2022-06-30 クラレノリタケデンタル株式会社 歯科用組成物
JPWO2022138972A1 (de) 2020-12-25 2022-06-30

Citations (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4131729A (en) * 1978-04-21 1978-12-26 Espe Fabrik Pharmazeutischer Praparate Gmbh Dental compositions comprising acrylic esters of tricyclo [5.2.1.02,6 ] decane polymers
US4323696A (en) * 1979-08-07 1982-04-06 Bayer Aktiengesellschaft (Meth)acrylic acid esters of tricyclic decanediols containing ether groups
US4323348A (en) * 1979-08-07 1982-04-06 Bayer Aktiengesellschaft Dental compositions
US4379695A (en) * 1980-06-02 1983-04-12 Scientific Pharmaceuticals, Inc. Dental material comprising dimethyacrylate adducts of glycidyl methacrylate with diesters of bis(hydroxymethyl) tricyclo[5.2.1.02,6 ]decane and dicarboxylic acids
US4407984A (en) * 1980-12-03 1983-10-04 Imperial Chemical Industries Plc Dental compositions
US4459193A (en) * 1981-03-04 1984-07-10 Imperial Chemical Industries Plc Dental compositions containing camphorquinone and organic peroxide as catalyst
US4644053A (en) * 1984-05-11 1987-02-17 General Electric Company Cyclic polycarbonate oligomers and methods for their preparation and use
US4722947A (en) * 1985-08-05 1988-02-02 Pony Industries, Inc. Production of radiation curable partial esters of anhydride-containing copolymers
US4744827A (en) * 1985-06-20 1988-05-17 Bayer Aktiengesellschaft (Meth)-acrylic acid derivatives of tricyclodecanes and their use
US5047261A (en) * 1989-06-29 1991-09-10 Societe Nationale Des Pourdres Et Explosifs Process for the manufacture of coatings by radiocrosslinking
US5444104A (en) * 1985-03-29 1995-08-22 Jeneric/Pentron, Inc. Dental resin materials
US5609675A (en) * 1994-07-04 1997-03-11 Tokuyama Corporation Inorganic composition
US5621119A (en) * 1994-07-22 1997-04-15 Heraeus Kulzer Gmbh & Co., Kg Di(meth)acrylates having cyclic carbonate groups
US5760142A (en) * 1996-12-04 1998-06-02 Dentsply Detrey G.M.B.H. Epoxide-amine dendrimers and the preparation and use thereof
US5792821A (en) * 1997-01-06 1998-08-11 American Dental Association Health Foundation Polymerizable cyclodextrin derivatives
US5846075A (en) * 1997-02-28 1998-12-08 Bisco, Inc. One package, shelf-stable photo-curable band cement
US5856374A (en) * 1996-11-01 1999-01-05 Tokuyama Corporation Curable composition
US5886064A (en) * 1994-12-08 1999-03-23 Ivoclar Ag Fine-grained polymerizable compositions flowable under pressure or shear stress
US5944527A (en) * 1994-10-06 1999-08-31 Hasel; Robert W. Method of restoring a tooth
US5962703A (en) * 1996-02-22 1999-10-05 Ivoclar Ag Functionalized bicyclic (meth)acrylate, a method of making a bicyclic (meth)acrylate, and its uses
US5998499A (en) * 1994-03-25 1999-12-07 Dentsply G.M.B.H. Liquid crystalline (meth)acrylate compounds, composition and method
US6022940A (en) * 1993-07-01 2000-02-08 The Curators Of The University Of Missouri Polymeric compositions and composites prepared from spiroorthocarbonates and epoxy monomers
US6031015A (en) * 1995-07-18 2000-02-29 Ivoclar Ag Dental materials based on liquid crystalline monomers
US6037444A (en) * 1995-12-22 2000-03-14 Courtaulds Coatings (Holdings) Limited Selective chemical reactions and polymers of controlled architecture produced thereby
US6043361A (en) * 1994-12-22 2000-03-28 Commonwealth Scientific And Industrial Research Organisation Polymerisable monomers and polymers
US6057460A (en) * 1996-02-22 2000-05-02 Ivoclar Ag Polymerizable hybrid monomers
US6096903A (en) * 1997-03-25 2000-08-01 Ivoclar Ag Hydrolysable and polymerizable oxetane silanes
US6121344A (en) * 1998-06-19 2000-09-19 Kerr Corporation Optimum particle sized hybrid composite
US6127450A (en) * 1998-06-09 2000-10-03 Kerr Corporation Dental restorative composite
US6147136A (en) * 1997-09-29 2000-11-14 Espe Dental Ag Dental compositions based on ROMP oligomers and polymers
US6177534B1 (en) * 1997-12-23 2001-01-23 The United States Of America As Represented By The Secretary Of Commerce Silylated resins and the synthesis thereof
US6184339B1 (en) * 1996-11-14 2001-02-06 The United States Of America As Represented By The Secretary Of The Commerce High strength polymeric networks derived from (meth) acrylate resins with organofluorine content and process for preparing same
US6187836B1 (en) * 1998-06-05 2001-02-13 3M Innovative Properties Company Compositions featuring cationically active and free radically active functional groups, and methods for polymerizing such compositions
US6204302B1 (en) * 1998-11-20 2001-03-20 Bisco, Inc. Photosensitizers for free radical polymerization initiation resins and method of making the same
US6232367B1 (en) * 1999-10-07 2001-05-15 Kerr Corporation Opalescent fillers for dental restorative composites
US6262142B1 (en) * 1997-04-02 2001-07-17 Dentsply Research & Development Translucent wear resistant dental enamel material and method
US20020025993A1 (en) * 1998-12-11 2002-02-28 Dr. Joachim E. Klee Dental composition
US6353040B1 (en) * 1997-04-02 2002-03-05 Dentsply Research & Development Corp. Dental composite restorative material and method of restoring a tooth
US6353061B1 (en) * 1993-05-26 2002-03-05 Dentsply Gmbh α, ω-methacrylate terminated macromonomer compounds
US6380347B1 (en) * 1999-04-09 2002-04-30 Honeywell International Inc. Nanoporous polymers comprising macrocycles
US6391940B1 (en) * 1993-04-19 2002-05-21 Dentsply Research & Development Corp. Method and composition for adhering to metal dental structure
US6399037B1 (en) * 1997-10-03 2002-06-04 Dentsply Detrey Gmbh Dental materials having a nanoscale filler
US20020068771A1 (en) * 1997-02-21 2002-06-06 Dentsply Detrey Gmbh. Low shrinking polymerizable dental material
US6448301B1 (en) * 2000-09-08 2002-09-10 3M Innovative Properties Company Crosslinkable polymeric compositions and use thereof
US20020128347A1 (en) * 1999-04-12 2002-09-12 Blackwell Grodon B. Dental composite restorative material and method of restoring a tooth
US20030060535A1 (en) * 1999-09-08 2003-03-27 Norbert Moszner Hydrolyzable and polymerizable silanes based on methylene dithiepane
US6566413B1 (en) * 1998-12-24 2003-05-20 3M Espe Ag Polymerisable materials which are based on hardenable siloxane compounds
US20030125435A1 (en) * 2001-03-07 2003-07-03 Norling Barry K. Ultra-low shrinkage composite resins based on blended nematic liquid crystal monomers
US20040077882A1 (en) * 2002-10-22 2004-04-22 Norbert Moszner Polymerizable bicyclic cyclopropane derivatives and their use for the preparation of dental materials
US20040106741A1 (en) * 2002-09-17 2004-06-03 Kriesel Joshua W. Nanofilm compositions with polymeric components
US20050154199A1 (en) * 2003-08-06 2005-07-14 Whiteford Jeffery A. Bridged macrocyclic module compositions
US20060063854A1 (en) * 2004-06-15 2006-03-23 Xiaoming Jin Low shrinkage and low stress dental compositions

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58179801A (ja) * 1982-04-15 1983-10-21 Tokuyama Soda Co Ltd 有機光学ガラス
JPS60231712A (ja) * 1984-05-02 1985-11-18 Tokuyama Soda Co Ltd 高屈折率樹脂の製造方法
CA1238914A (en) * 1984-05-11 1988-07-05 Daniel J. Brunelle Cyclic polycarbonate of thiol analog oligomers
US4727134A (en) * 1985-02-22 1988-02-23 General Electric Company Method for preparing cyclic polycarbonate oligomer mixtures
US5110893A (en) * 1988-01-20 1992-05-05 General Electric Company Preparation and polymerization of cyclic aromatic ketones
US5321117A (en) * 1992-11-19 1994-06-14 General Electric Company Macrocyclic polyester oligomer preparation with Lewis acid as catalyst
US5906490A (en) 1994-06-09 1999-05-25 Ceramco Inc. Dental product, shading kit and method
WO1997002787A1 (en) 1995-07-11 1997-01-30 Dentsply International Inc. Fluoride releasing dental pit and fissure sealant dispensing system and method
EP1017354B1 (de) 1998-07-20 2005-07-06 Dentsply International, Inc. Lichtdurchlässiges verschleissfestes zahnschmelzmaterial
JP3785874B2 (ja) * 1999-10-01 2006-06-14 富士ゼロックス株式会社 変性ポリビニルアルコール及びその製造方法、並びに、それを用いた電子デバイス及び電子写真感光体
US6376026B1 (en) * 1999-12-20 2002-04-23 Rohm And Haas Company Method of coating with powders comprising macrocyclic oligomers
CA2411464A1 (en) 2000-06-13 2001-12-20 Dentsply International Inc. Low shrinking polymerizable dental material
ATE464875T1 (de) 2004-06-15 2010-05-15 Dentsply Int Inc Radikale polymerisierbare makrozyklische harzzusammensetzungen mit geringer polymerisationsspannung

Patent Citations (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4131729A (en) * 1978-04-21 1978-12-26 Espe Fabrik Pharmazeutischer Praparate Gmbh Dental compositions comprising acrylic esters of tricyclo [5.2.1.02,6 ] decane polymers
US4323696A (en) * 1979-08-07 1982-04-06 Bayer Aktiengesellschaft (Meth)acrylic acid esters of tricyclic decanediols containing ether groups
US4323348A (en) * 1979-08-07 1982-04-06 Bayer Aktiengesellschaft Dental compositions
US4379695A (en) * 1980-06-02 1983-04-12 Scientific Pharmaceuticals, Inc. Dental material comprising dimethyacrylate adducts of glycidyl methacrylate with diesters of bis(hydroxymethyl) tricyclo[5.2.1.02,6 ]decane and dicarboxylic acids
US4407984A (en) * 1980-12-03 1983-10-04 Imperial Chemical Industries Plc Dental compositions
US4459193A (en) * 1981-03-04 1984-07-10 Imperial Chemical Industries Plc Dental compositions containing camphorquinone and organic peroxide as catalyst
US4644053A (en) * 1984-05-11 1987-02-17 General Electric Company Cyclic polycarbonate oligomers and methods for their preparation and use
US5444104A (en) * 1985-03-29 1995-08-22 Jeneric/Pentron, Inc. Dental resin materials
US4744827A (en) * 1985-06-20 1988-05-17 Bayer Aktiengesellschaft (Meth)-acrylic acid derivatives of tricyclodecanes and their use
US4722947A (en) * 1985-08-05 1988-02-02 Pony Industries, Inc. Production of radiation curable partial esters of anhydride-containing copolymers
US5047261A (en) * 1989-06-29 1991-09-10 Societe Nationale Des Pourdres Et Explosifs Process for the manufacture of coatings by radiocrosslinking
US6391940B1 (en) * 1993-04-19 2002-05-21 Dentsply Research & Development Corp. Method and composition for adhering to metal dental structure
US6353061B1 (en) * 1993-05-26 2002-03-05 Dentsply Gmbh α, ω-methacrylate terminated macromonomer compounds
US6022940A (en) * 1993-07-01 2000-02-08 The Curators Of The University Of Missouri Polymeric compositions and composites prepared from spiroorthocarbonates and epoxy monomers
US5998499A (en) * 1994-03-25 1999-12-07 Dentsply G.M.B.H. Liquid crystalline (meth)acrylate compounds, composition and method
US5609675A (en) * 1994-07-04 1997-03-11 Tokuyama Corporation Inorganic composition
US5621119A (en) * 1994-07-22 1997-04-15 Heraeus Kulzer Gmbh & Co., Kg Di(meth)acrylates having cyclic carbonate groups
US5944527A (en) * 1994-10-06 1999-08-31 Hasel; Robert W. Method of restoring a tooth
US5886064A (en) * 1994-12-08 1999-03-23 Ivoclar Ag Fine-grained polymerizable compositions flowable under pressure or shear stress
US6043361A (en) * 1994-12-22 2000-03-28 Commonwealth Scientific And Industrial Research Organisation Polymerisable monomers and polymers
US6344556B1 (en) * 1994-12-22 2002-02-05 Commonwealth Scientific And Industrial Research Organisation Polymerisable monomers and polymers
US6495643B1 (en) * 1994-12-22 2002-12-17 Commonwealth Scientific And Industrial Research Organization Polymerizable monomers and polymers
US6031015A (en) * 1995-07-18 2000-02-29 Ivoclar Ag Dental materials based on liquid crystalline monomers
US6037444A (en) * 1995-12-22 2000-03-14 Courtaulds Coatings (Holdings) Limited Selective chemical reactions and polymers of controlled architecture produced thereby
US5962703A (en) * 1996-02-22 1999-10-05 Ivoclar Ag Functionalized bicyclic (meth)acrylate, a method of making a bicyclic (meth)acrylate, and its uses
US6057460A (en) * 1996-02-22 2000-05-02 Ivoclar Ag Polymerizable hybrid monomers
US5856374A (en) * 1996-11-01 1999-01-05 Tokuyama Corporation Curable composition
US6184339B1 (en) * 1996-11-14 2001-02-06 The United States Of America As Represented By The Secretary Of The Commerce High strength polymeric networks derived from (meth) acrylate resins with organofluorine content and process for preparing same
US5760142A (en) * 1996-12-04 1998-06-02 Dentsply Detrey G.M.B.H. Epoxide-amine dendrimers and the preparation and use thereof
US5792821A (en) * 1997-01-06 1998-08-11 American Dental Association Health Foundation Polymerizable cyclodextrin derivatives
US20020068771A1 (en) * 1997-02-21 2002-06-06 Dentsply Detrey Gmbh. Low shrinking polymerizable dental material
US5846075A (en) * 1997-02-28 1998-12-08 Bisco, Inc. One package, shelf-stable photo-curable band cement
US6096903A (en) * 1997-03-25 2000-08-01 Ivoclar Ag Hydrolysable and polymerizable oxetane silanes
US6262142B1 (en) * 1997-04-02 2001-07-17 Dentsply Research & Development Translucent wear resistant dental enamel material and method
US6353040B1 (en) * 1997-04-02 2002-03-05 Dentsply Research & Development Corp. Dental composite restorative material and method of restoring a tooth
US6147136A (en) * 1997-09-29 2000-11-14 Espe Dental Ag Dental compositions based on ROMP oligomers and polymers
US6399037B1 (en) * 1997-10-03 2002-06-04 Dentsply Detrey Gmbh Dental materials having a nanoscale filler
US6177534B1 (en) * 1997-12-23 2001-01-23 The United States Of America As Represented By The Secretary Of Commerce Silylated resins and the synthesis thereof
US6187836B1 (en) * 1998-06-05 2001-02-13 3M Innovative Properties Company Compositions featuring cationically active and free radically active functional groups, and methods for polymerizing such compositions
US6127450A (en) * 1998-06-09 2000-10-03 Kerr Corporation Dental restorative composite
US6384106B1 (en) * 1998-06-09 2002-05-07 Kerr Corporation Dental restorative composite
US6395803B1 (en) * 1998-06-09 2002-05-28 Kerr Corporation Dental restorative composite
US6121344A (en) * 1998-06-19 2000-09-19 Kerr Corporation Optimum particle sized hybrid composite
US6204302B1 (en) * 1998-11-20 2001-03-20 Bisco, Inc. Photosensitizers for free radical polymerization initiation resins and method of making the same
US20020025993A1 (en) * 1998-12-11 2002-02-28 Dr. Joachim E. Klee Dental composition
US6566413B1 (en) * 1998-12-24 2003-05-20 3M Espe Ag Polymerisable materials which are based on hardenable siloxane compounds
US6380347B1 (en) * 1999-04-09 2002-04-30 Honeywell International Inc. Nanoporous polymers comprising macrocycles
US20020128347A1 (en) * 1999-04-12 2002-09-12 Blackwell Grodon B. Dental composite restorative material and method of restoring a tooth
US20030060535A1 (en) * 1999-09-08 2003-03-27 Norbert Moszner Hydrolyzable and polymerizable silanes based on methylene dithiepane
US6232367B1 (en) * 1999-10-07 2001-05-15 Kerr Corporation Opalescent fillers for dental restorative composites
US6448301B1 (en) * 2000-09-08 2002-09-10 3M Innovative Properties Company Crosslinkable polymeric compositions and use thereof
US20030125435A1 (en) * 2001-03-07 2003-07-03 Norling Barry K. Ultra-low shrinkage composite resins based on blended nematic liquid crystal monomers
US20040106741A1 (en) * 2002-09-17 2004-06-03 Kriesel Joshua W. Nanofilm compositions with polymeric components
US20040077882A1 (en) * 2002-10-22 2004-04-22 Norbert Moszner Polymerizable bicyclic cyclopropane derivatives and their use for the preparation of dental materials
US20050154199A1 (en) * 2003-08-06 2005-07-14 Whiteford Jeffery A. Bridged macrocyclic module compositions
US20060063854A1 (en) * 2004-06-15 2006-03-23 Xiaoming Jin Low shrinkage and low stress dental compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060063854A1 (en) * 2004-06-15 2006-03-23 Xiaoming Jin Low shrinkage and low stress dental compositions
US20080182948A1 (en) * 2004-06-15 2008-07-31 Xiaoming Jin Low shrinkage and low stress dental compositions
US8461227B2 (en) 2004-06-15 2013-06-11 Dentsply International Inc. Radical polymerizable macrocyclic resin compositions with low polymerization stress

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US20100234549A1 (en) 2010-09-16
CA2570341A1 (en) 2005-12-29
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JP5647176B2 (ja) 2014-12-24
DE602005020806D1 (de) 2010-06-02
US20080182997A1 (en) 2008-07-31
ATE464875T1 (de) 2010-05-15
US20110152569A1 (en) 2011-06-23
EP1778164B1 (de) 2010-04-21
US8129446B2 (en) 2012-03-06
JP2012188672A (ja) 2012-10-04
US20090182109A1 (en) 2009-07-16

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