JP2019512526A - 歯科用接着剤組成物 - Google Patents
歯科用接着剤組成物 Download PDFInfo
- Publication number
- JP2019512526A JP2019512526A JP2018549880A JP2018549880A JP2019512526A JP 2019512526 A JP2019512526 A JP 2019512526A JP 2018549880 A JP2018549880 A JP 2018549880A JP 2018549880 A JP2018549880 A JP 2018549880A JP 2019512526 A JP2019512526 A JP 2019512526A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- water
- adhesive composition
- dental adhesive
- composition according
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 239000003479 dental cement Substances 0.000 title claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000002904 solvent Substances 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000009835 boiling Methods 0.000 claims abstract description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000853 adhesive Substances 0.000 claims description 18
- 230000001070 adhesive effect Effects 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000009472 formulation Methods 0.000 description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- 210000004268 dentin Anatomy 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 238000007664 blowing Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241001481665 Protophormia terraenovae Species 0.000 description 2
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 2
- 229930006711 bornane-2,3-dione Natural products 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- CFKBCVIYTWDYRP-UHFFFAOYSA-N 10-phosphonooxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOP(O)(O)=O CFKBCVIYTWDYRP-UHFFFAOYSA-N 0.000 description 1
- QCUCAQZMPVIYAJ-UHFFFAOYSA-N 2-(4-methyl-1h-indol-3-yl)ethanamine Chemical compound CC1=CC=CC2=C1C(CCN)=CN2 QCUCAQZMPVIYAJ-UHFFFAOYSA-N 0.000 description 1
- GOGCLLMDQOJKHB-UHFFFAOYSA-N 4-[2-(2-methylprop-2-enoyloxy)ethoxycarbonyl]phthalic acid Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GOGCLLMDQOJKHB-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical group 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003178 glass ionomer cement Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical group 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dental Preparations (AREA)
Abstract
Description
a)15重量%から60重量%の全有機溶媒、
b)0.5重量%から20重量%の水、
c)40重量%から90重量%の光硬化性接着剤モノマー混合物
を含有する。
本発明で使用される溶媒系の例は、以下のとおりである。
上述の接着剤配合物の1滴を、室温で、はかり上に静かに置かれた平らなスライドガラスの表面に塗布した。蒸発乾燥は、5分間、30秒毎に重量を記録することによって評価した。初期と比較した失われた質量の百分率の計算を行った。
上述の各接着剤配合物の1滴を、室温で静かに置かれた平らなスライドガラスの表面に塗布した。
より良好な貯蔵安定性を有する2成分系のエタノール/水溶媒系に対する3成分系の溶媒系の利点を評価するために、ヒトの象牙質への剪断接着強さを、初期と、脱イオン水に1か月間貯蔵した後に評価した。
Claims (7)
- メチルエチルケトンと水の共沸物である溶媒を含むことを特徴とする歯科用接着剤組成物。
- 前記溶媒がメチルエチルケトンと水を含む2成分共沸系である請求項1に記載の歯科用接着剤組成物。
- 前記溶媒が有機アルコールとともにメチルエチルケトンと水を含む3成分共沸溶媒系であることを特徴とする請求項1に記載の歯科用接着剤組成物。
- 前記有機アルコールがエタノールまたはイソプロパノールであることを特徴とする請求項3に記載の歯科用接着剤組成物。
- 前記溶媒が75℃未満の沸点を有することを特徴とする請求項1〜4のいずれかに記載の歯科用接着剤組成物。
- 前記溶媒が70〜74℃の範囲の沸点を有することを特徴とする請求項5に記載の歯科用接着剤組成物。
- 前記組成物が15〜60重量%の有機溶媒、0.5〜20重量%の水および40〜90重量%の光硬化性接着性モノマーを含むことを特徴とする請求項1〜6のいずれかに記載の歯科用接着剤組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2016901119 | 2016-03-24 | ||
AU2016901119A AU2016901119A0 (en) | 2016-03-24 | Dental adhesive compositions | |
PCT/AU2017/000069 WO2017161408A1 (en) | 2016-03-24 | 2017-03-22 | Dental adhesive compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019512526A true JP2019512526A (ja) | 2019-05-16 |
JP6888760B2 JP6888760B2 (ja) | 2021-06-16 |
Family
ID=59900896
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018549880A Active JP6888760B2 (ja) | 2016-03-24 | 2017-03-22 | 歯科用接着剤組成物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11213462B2 (ja) |
EP (1) | EP3432853A4 (ja) |
JP (1) | JP6888760B2 (ja) |
CN (1) | CN109069351B (ja) |
AU (1) | AU2017239150B2 (ja) |
WO (1) | WO2017161408A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2017239150B2 (en) * | 2016-03-24 | 2022-12-22 | Sdi Limited | Dental adhesive compositions |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4588756A (en) | 1983-01-10 | 1986-05-13 | American Dental Association Health Foundation | Multi-step method for obtaining strong adhesive bonding of composites to dentin, enamel and other substrates |
EP0367058A3 (en) | 1988-11-04 | 1991-03-27 | Giovanni Pasini | New composition for dynamicofunctional impressions |
DE60216951T2 (de) | 2001-10-26 | 2007-06-14 | Dentsply Detrey Gmbh | Hydrolysestabile selbstätzende und selbstgrundierende dental-einkomponenten-kleberzusammensetzung |
DE102004049740B4 (de) | 2004-10-13 | 2009-08-27 | Lts Lohmann Therapie-Systeme Ag | Selbstklebende Zahnfolie und Verfahren zur Herstellung der Zahnfolie |
CA2624228A1 (en) * | 2005-09-30 | 2007-04-12 | Danville Materials, Inc. | Biomedical bond enhancer |
US7963769B2 (en) * | 2007-10-08 | 2011-06-21 | Kerr Corporation | Dental adhesive and method of use |
CN101239024B (zh) | 2008-03-20 | 2010-06-23 | 吉林省登泰克牙科材料有限公司 | 纳米银含氟自酸蚀单瓶牙科粘接剂 |
US9527931B2 (en) * | 2012-02-16 | 2016-12-27 | Bisco, Inc. | Hydrophobic self-etch dental adhesive compositions |
US10365189B2 (en) * | 2015-05-07 | 2019-07-30 | Steven Wheeler | Histological specimen treatment |
AU2017239150B2 (en) * | 2016-03-24 | 2022-12-22 | Sdi Limited | Dental adhesive compositions |
-
2017
- 2017-03-22 AU AU2017239150A patent/AU2017239150B2/en active Active
- 2017-03-22 WO PCT/AU2017/000069 patent/WO2017161408A1/en active Application Filing
- 2017-03-22 US US16/088,073 patent/US11213462B2/en active Active
- 2017-03-22 CN CN201780018710.9A patent/CN109069351B/zh active Active
- 2017-03-22 EP EP17769177.1A patent/EP3432853A4/en active Pending
- 2017-03-22 JP JP2018549880A patent/JP6888760B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP6888760B2 (ja) | 2021-06-16 |
WO2017161408A1 (en) | 2017-09-28 |
EP3432853A1 (en) | 2019-01-30 |
US20200405584A1 (en) | 2020-12-31 |
US11213462B2 (en) | 2022-01-04 |
EP3432853A4 (en) | 2019-11-27 |
AU2017239150A1 (en) | 2018-11-08 |
AU2017239150B2 (en) | 2022-12-22 |
CN109069351B (zh) | 2021-12-07 |
CN109069351A (zh) | 2018-12-21 |
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