JPH0791172B2 - 歯科材料を調製するための硬化性モノマー混合物 - Google Patents

歯科材料を調製するための硬化性モノマー混合物

Info

Publication number
JPH0791172B2
JPH0791172B2 JP1319070A JP31907089A JPH0791172B2 JP H0791172 B2 JPH0791172 B2 JP H0791172B2 JP 1319070 A JP1319070 A JP 1319070A JP 31907089 A JP31907089 A JP 31907089A JP H0791172 B2 JPH0791172 B2 JP H0791172B2
Authority
JP
Japan
Prior art keywords
curable monomer
monomer mixture
dental material
value
group
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.)
Expired - Lifetime
Application number
JP1319070A
Other languages
English (en)
Japanese (ja)
Other versions
JPH02202850A (ja
Inventor
ユルゲン・フオツク
ギユンター・ハーン
ギユンター・ヴアーゲンクネヒト
Original Assignee
ゲーデーエフ・ゲゼルシヤフト・フユア・デンターレ・フオルシユンク・ウント・イノフアチオーネン・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング
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 ゲーデーエフ・ゲゼルシヤフト・フユア・デンターレ・フオルシユンク・ウント・イノフアチオーネン・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング filed Critical ゲーデーエフ・ゲゼルシヤフト・フユア・デンターレ・フオルシユンク・ウント・イノフアチオーネン・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング
Publication of JPH02202850A publication Critical patent/JPH02202850A/ja
Publication of JPH0791172B2 publication Critical patent/JPH0791172B2/ja
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62Halogen-containing esters
    • C07C69/65Halogen-containing esters of unsaturated acids
    • C07C69/653Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/08Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/16Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10Esters
    • C08F20/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/28Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10Esters
    • C08F20/34Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805Compounds having only one group containing active hydrogen
    • C08G18/288Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/2885Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81Unsaturated isocyanates or isothiocyanates
    • C08G18/8108Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dental Preparations (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP1319070A 1988-12-10 1989-12-11 歯科材料を調製するための硬化性モノマー混合物 Expired - Lifetime JPH0791172B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3841617.4 1988-12-10
DE3844619A DE3844619A1 (de) 1988-12-10 1988-12-10 Verwendung von perfluoroalkylgruppen aufweisenden (meth-)acrylsaeureestern in der dentaltechnik
DE3841617A DE3841617C1 (enExample) 1988-12-10 1988-12-10

Publications (2)

Publication Number Publication Date
JPH02202850A JPH02202850A (ja) 1990-08-10
JPH0791172B2 true JPH0791172B2 (ja) 1995-10-04

Family

ID=25874996

Family Applications (2)

Application Number Title Priority Date Filing Date
JP1319070A Expired - Lifetime JPH0791172B2 (ja) 1988-12-10 1989-12-11 歯科材料を調製するための硬化性モノマー混合物
JP1319069A Expired - Lifetime JPH0739382B2 (ja) 1988-12-10 1989-12-11 マクロモノマーフルオルアルキル基を有する(メタ)アクリル酸エステルおよびその製法

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP1319069A Expired - Lifetime JPH0739382B2 (ja) 1988-12-10 1989-12-11 マクロモノマーフルオルアルキル基を有する(メタ)アクリル酸エステルおよびその製法

Country Status (5)

Country Link
EP (2) EP0373384B1 (enExample)
JP (2) JPH0791172B2 (enExample)
DE (3) DE3844619A1 (enExample)
ES (2) ES2053923T3 (enExample)
GR (2) GR3006881T3 (enExample)

Families Citing this family (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1270818B (it) * 1993-04-28 1997-05-13 Ausimont Spa Coatings a base di perfluoropolieteri contenenti gruppi acrilici
US5662887A (en) * 1994-12-01 1997-09-02 Minnesota Mining And Manufacturing Company Fluorocarbon containing coatings, compositions and methods of use
DE4445266A1 (de) * 1994-12-19 1996-06-20 Thera Ges Fuer Patente Fluoridabgebende Composite-Massen
FR2749170B1 (fr) * 1996-05-30 1998-08-21 Bellesort Stephane Protheses dentaires modifiees en surface et procede d'obtention
DE60018044T2 (de) * 1999-02-18 2005-12-29 Commonwealth Scientific And Industrial Research Organisation Neue biomaterialien
DE60005423T2 (de) 1999-03-03 2004-07-22 KURARAY CO., LTD, Kurashiki Unterfütterungsmaterial für Zahnprothesen
WO2000078830A1 (en) * 1999-06-22 2000-12-28 Novartis Ag Process for the manufacture of moldings
US6773261B2 (en) 2002-06-28 2004-08-10 3M Innovative Properties Company Processes for forming dental materials
US7134875B2 (en) 2002-06-28 2006-11-14 3M Innovative Properties Company Processes for forming dental materials and device
US20040206932A1 (en) 2002-12-30 2004-10-21 Abuelyaman Ahmed S. Compositions including polymerizable bisphosphonic acids and methods
US7632098B2 (en) 2003-08-12 2009-12-15 3M Innovative Properties Company Self-adhesive dental compositions and methods
US7026367B2 (en) 2003-09-26 2006-04-11 3M Innovative Properties Company Photoiniators having triarylsulfonium and arylsulfinate ions
US7250452B2 (en) 2003-09-26 2007-07-31 3M Innovative Properties Company Dental compositions and methods with arylsulfinate salts
US7030169B2 (en) 2003-09-26 2006-04-18 3M Innovative Properties Company Arylsulfinate salts in initiator systems for polymeric reactions
US7090721B2 (en) 2004-05-17 2006-08-15 3M Innovative Properties Company Use of nanoparticles to adjust refractive index of dental compositions
US7090722B2 (en) 2004-05-17 2006-08-15 3M Innovative Properties Company Acid-reactive dental fillers, compositions, and methods
US7649029B2 (en) 2004-05-17 2010-01-19 3M Innovative Properties Company Dental compositions containing nanozirconia fillers
US7156911B2 (en) 2004-05-17 2007-01-02 3M Innovative Properties Company Dental compositions containing nanofillers and related methods
US8465284B2 (en) 2004-07-08 2013-06-18 3M Innovative Properties Company Dental methods, compositions, and kits including acid-sensitive dyes
JP4879894B2 (ja) 2004-07-14 2012-02-22 スリーエム イノベイティブ プロパティズ カンパニー カルボシランポリマーを含有する歯科用組成物
AU2005275246B2 (en) 2004-07-14 2011-10-06 3M Deutschland Gmbh Dental compositions containing carbosilane monomers
EP1784155B1 (en) 2004-08-11 2011-09-28 3M Innovative Properties Company Self-adhesive compositions including a plurality of acidic compounds
EP1819313B1 (en) 2004-11-16 2010-12-29 3M Innovative Properties Company Dental fillers and compositions including phosphate salts
KR101240883B1 (ko) 2004-11-16 2013-03-07 쓰리엠 이노베이티브 프로퍼티즈 컴파니 카제이네이트를 포함하는 치과용 충전제, 방법, 조성물
US8957126B2 (en) 2004-11-16 2015-02-17 3M Innovative Properties Company Dental compositions with calcium phosphorus releasing glass
CA2587556A1 (en) 2004-11-16 2006-05-26 3M Innovative Properties Company Dental fillers including a phosphorus containing surface treatment, and compositions and methods thereof
CN102512329A (zh) 2005-05-09 2012-06-27 3M创新有限公司 含有杂化单体的牙科组合物
EP1909742B1 (en) 2005-08-05 2010-07-14 3M Espe AG Dental compositions containing a surface-modified filler
EP1787627A1 (en) 2005-11-17 2007-05-23 3M Innovative Properties Company Anti-microbial dental impression material
US7896650B2 (en) 2005-12-20 2011-03-01 3M Innovative Properties Company Dental compositions including radiation-to-heat converters, and the use thereof
US8026296B2 (en) 2005-12-20 2011-09-27 3M Innovative Properties Company Dental compositions including a thermally labile component, and the use thereof
US7776940B2 (en) 2005-12-20 2010-08-17 3M Innovative Properties Company Methods for reducing bond strengths, dental compositions, and the use thereof
US8071662B2 (en) 2005-12-29 2011-12-06 3M Innovative Properties Company Dental compositions with surface-treated filler for shelf stability
WO2007079070A1 (en) 2005-12-29 2007-07-12 3M Innovative Properties Company Dental compositions and initiator systems with polycyclic aromatic component
EP1881010B1 (en) 2006-05-31 2010-08-11 3M Innovative Properties Company Polymerizable compositions containing salts of barbituric acid derivatives
CN101516319B (zh) 2006-09-13 2015-11-25 3M创新有限公司 包含有机凝胶因子的牙科用组合物、产品及方法
US9539065B2 (en) 2006-10-23 2017-01-10 3M Innovative Properties Company Assemblies, methods, and kits including a compressible material
US20080096150A1 (en) 2006-10-23 2008-04-24 3M Innovative Properties Company Dental articles, methods, and kits including a compressible material
JP5507256B2 (ja) 2006-12-13 2014-05-28 スリーエム イノベイティブ プロパティズ カンパニー 酸性成分及び光退色性染料を有する歯科用組成物の使用方法
EP2114351B1 (en) 2006-12-28 2016-07-13 3M Innovative Properties Company Dental compositions with natural tooth fluorescence
WO2008082929A2 (en) 2006-12-28 2008-07-10 3M Innovative Properties Company Adhesive composition for hard tissue
JP5512280B2 (ja) 2006-12-28 2014-06-04 スリーエム イノベイティブ プロパティズ カンパニー 歯科充填剤及び方法
EP2203144A2 (en) 2007-10-01 2010-07-07 3M Innovative Properties Company Orthodontic composition with polymeric fillers
JP5461415B2 (ja) 2007-11-01 2014-04-02 スリーエム イノベイティブ プロパティズ カンパニー 歯科用組成物及び色安定アミン電子供与体を有する開始剤系
WO2009075977A1 (en) 2007-12-13 2009-06-18 3M Innovative Properties Company Orthodontic article having partially hardened composition and method of its use and manufacture
CN102224106A (zh) 2008-10-15 2011-10-19 3M创新有限公司 具有氧化锆和二氧化硅纳米粒子的填料和复合材料
BRPI0914427C8 (pt) 2008-10-15 2018-07-24 3M Innovative Properties Co composição dental endurecível
WO2010068359A1 (en) 2008-12-11 2010-06-17 3M Innovative Properties Company Surface-treated calcium phosphate particles suitable for oral care and dental compositions
WO2012021442A1 (en) 2010-08-11 2012-02-16 3M Innovative Properties Company Coated dental crows and method of making the same
US20130130203A1 (en) 2010-08-11 2013-05-23 3M Innovative Properties Company Polymer coated dental articles and method of making the same
EP2603159A1 (en) 2010-08-11 2013-06-19 3M Innovative Properties Company Aesthetic and abrasion resistant coated dental articles and methods of making the same
CN103281986B (zh) 2010-12-30 2016-08-17 3M创新有限公司 包括可压缩材料的可粘合牙科用组件和方法
EP2688508A1 (en) 2011-03-24 2014-01-29 3M Innovative Properties Company Dental adhesive comprising a coated polymeric component
KR102186225B1 (ko) 2013-03-19 2020-12-03 쓰리엠 이노베이티브 프로퍼티즈 컴파니 자유 라디칼 중합 방법 및 그에 의한 물품
EP3013868B1 (en) 2013-06-28 2017-10-18 3M Innovative Properties Company Acid-modified nanoparticles, dual part polymerizable compositions, and methods
CN105705112B (zh) 2013-10-04 2018-02-27 3M创新有限公司 牙科研磨坯料、牙科修复体以及形成牙科研磨坯料的方法
US20170190937A1 (en) 2014-06-24 2017-07-06 3M Innovative Properties Company Adhesive precursor composition, two-part adhesive kit, and method of making an adhesive composition
KR102407089B1 (ko) 2014-07-22 2022-06-10 쓰리엠 이노베이티브 프로퍼티즈 캄파니 자유 라디칼 중합 방법 및 그에 의한 물품
EP3194455B1 (en) 2014-09-16 2019-02-06 3M Innovative Properties Company Free-radical polymerization methods and articles thereby
WO2016053877A1 (en) 2014-09-30 2016-04-07 3M Innovative Properties Company Free-radical polymerization methods and articles thereby
CN107108571A (zh) 2014-12-22 2017-08-29 3M创新有限公司 立体受阻烷基和烷氧基胺光稳定剂
EP3237381A1 (en) 2014-12-22 2017-11-01 3M Innovative Properties Company Sterically hindered amine and oxyalkyl amine light stabilizers
JP6659716B2 (ja) 2015-03-05 2020-03-04 スリーエム イノベイティブ プロパティズ カンパニー セラミック繊維を有する複合材料
JP6497350B2 (ja) * 2016-04-15 2019-04-10 信越化学工業株式会社 含フッ素アクリル組成物及びその製造方法、含フッ素活性エネルギー線硬化性組成物並びに物品
WO2021191773A1 (en) 2020-03-25 2021-09-30 3M Innovative Properties Company Dental appliance with graphic image
WO2022064292A1 (en) 2020-09-25 2022-03-31 3M Innovative Properties Company Photopolymerizable compositions and reaction products thereof
EP4271322A1 (en) 2020-12-30 2023-11-08 3M Innovative Properties Company Bondable orthodontic assemblies and methods for bonding
WO2022162488A1 (en) 2021-01-29 2022-08-04 3M Innovative Properties Company Dental appliances from multilayer films having discrete structures covered by an ion permeable release layer
EP4308571A1 (en) 2021-03-17 2024-01-24 3M Innovative Properties Company Polymerizable 4,4'-spirobi[chromane]-2,2'-diones and curable compositions including the same
EP4355794A1 (en) 2021-06-16 2024-04-24 3M Innovative Properties Company Free-radically polymerizable copolymer, free-radically polymerizable composition containing the same, and polymerized reaction product therefrom
CN117836333A (zh) 2021-09-01 2024-04-05 3M创新有限公司 可自由基聚合的组合物、其聚合的方法以及聚合的组合物
WO2023073444A1 (en) 2021-10-28 2023-05-04 3M Innovative Properties Company Photopolymerizable composition, methods of bonding and sealing, and at least partially polymerized composition
CN118525068A (zh) 2021-12-14 2024-08-20 3M创新有限公司 粘合剂组合物的可固化前体

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL266570A (enExample) * 1960-07-09
CH1753669D (enExample) * 1968-11-25
US3660360A (en) * 1970-06-24 1972-05-02 Nat Starch Chem Corp Water- and oil repellency agents
US4508916A (en) * 1979-04-11 1985-04-02 Minnesota Mining And Manufacturing Company Curable substituted urethane acrylates
JPS60146810A (ja) * 1984-01-05 1985-08-02 Kureha Chem Ind Co Ltd 軟質義歯床裏装材料
US4616073A (en) * 1984-08-09 1986-10-07 The United States Of America As Represented By The Department Of Health And Human Services Hydrophobic dental composites based on a polyfluorinated dental resin
US4612356A (en) * 1984-10-01 1986-09-16 Ciba-Geigy Corporation Homo- and co- (addition) polymers of di-perfluoroalkyl carbamyl group containing (meth) acrylate monomers
JPS61111309A (ja) * 1984-11-02 1986-05-29 Daikin Ind Ltd α−フルオロアクリル酸誘導体ポリマ−
IT1185520B (it) * 1985-02-22 1987-11-12 Montefluos Spa Poliacrilati e poliacrilammidi fluorurati a grado di reticolazione controllato e loro procedimento di preparazione
JPH01305052A (ja) * 1988-06-01 1989-12-08 Nippon Oil & Fats Co Ltd ポリフルオロアルキルポリオキシアルキレン(メタ)アクリレート

Also Published As

Publication number Publication date
GR3006881T3 (enExample) 1993-06-30
JPH02202866A (ja) 1990-08-10
DE3841617C1 (enExample) 1990-05-10
ES2052867T3 (es) 1994-07-16
GR3007024T3 (enExample) 1993-07-30
EP0373385B1 (de) 1993-01-13
JPH0739382B2 (ja) 1995-05-01
EP0373384A1 (de) 1990-06-20
DE58903288D1 (de) 1993-02-25
JPH02202850A (ja) 1990-08-10
EP0373385A1 (de) 1990-06-20
ES2053923T3 (es) 1994-08-01
DE3844619A1 (de) 1990-07-12
EP0373384B1 (de) 1992-10-28

Similar Documents

Publication Publication Date Title
JPH0791172B2 (ja) 歯科材料を調製するための硬化性モノマー混合物
US5026902A (en) Dental compsition of perfluoroalkyl group-containing (meth-)acrylate esters
Moszner et al. A partially aromatic urethane dimethacrylate as a new substitute for Bis-GMA in restorative composites
US6057383A (en) Dental material based on polymerizable waxes
US5076844A (en) Perfluoroalkyl group-containing (meth-)acrylate esters, their synthesis and use in dental technology
JP2555365B2 (ja) トリシクロ〔5.2.1.0▲上2▼・▲上6▼〕デカン類のアクリル酸誘導体又はメタクリル酸誘導体
JP2880455B2 (ja) 液晶モノマーベースの歯科用材料
Ge et al. Synthesis and photopolymerization of low shrinkage methacrylate monomers containing bulky substituent groups
US3810938A (en) Novel diacrylic and dimethacrylic acid esters
JP2588534B2 (ja) アクリル酸エステルおよびメタクリル酸エステル
WO1989000170A1 (fr) Composition polymerisable
Tauscher et al. Evaluation of alternative monomers to HEMA for dental applications
JPS61293960A (ja) (メタ)アクリル酸エステル類
US20040229972A1 (en) Low shrinking polymerizable dental material
CA2207351C (en) Dental material based on polymerizable waxes
AU6170598A (en) Low shrinking polymerizable dental material
JPH10511354A (ja) 重合性化合物および組成物
EP1879544B1 (en) Materials and dental composites made therefrom
EP0943601B1 (de) Vinylcyclopropan-(Meth) acrylate und deren Verwendung
US5132335A (en) Acrylic and methacrylic esters of substituted 1,2-bis(phenoxy)-3,3,4,4,5,5-hexafluoro-1-cyclopentenes
JP2023135159A (ja) 歯科用接着性組成物
JP7851010B2 (ja) 歯科用接着性組成物
WO2026042014A1 (en) A photocurable acrylate resin monomer and the use thereof
JPH0674235B2 (ja) 含フッ素ビスフェノール基を骨格とするジアクリレートまたはジメタクリレートおよびこれらを成分とする高分子材料
JP2024045938A (ja) 歯科用接着性組成物及びポリマー