DE3736554C2 - - Google Patents
Info
- Publication number
- DE3736554C2 DE3736554C2 DE3736554A DE3736554A DE3736554C2 DE 3736554 C2 DE3736554 C2 DE 3736554C2 DE 3736554 A DE3736554 A DE 3736554A DE 3736554 A DE3736554 A DE 3736554A DE 3736554 C2 DE3736554 C2 DE 3736554C2
- Authority
- DE
- Germany
- Prior art keywords
- adhesive
- acid
- methacryloyloxybenzoic
- teeth
- methyl methacrylate
- 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 - Fee Related
Links
- 239000000853 adhesive Substances 0.000 claims description 20
- 230000001070 adhesive effect Effects 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 241000283690 Bos taurus Species 0.000 description 11
- QFPKSTNFHFEHJL-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)benzoic acid Chemical compound CC(=C)C(=O)OC1=CC=CC=C1C(O)=O QFPKSTNFHFEHJL-UHFFFAOYSA-N 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 210000003298 dental enamel Anatomy 0.000 description 8
- 210000004268 dentin Anatomy 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ROJHKBPPJIXIBJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)benzoic acid Chemical compound CC(=C)C(=O)OC1=CC=CC(C(O)=O)=C1 ROJHKBPPJIXIBJ-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- DNCFPDURLPJGKX-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)benzoic acid Chemical compound CC(=C)C(=O)OC1=CC=C(C(O)=O)C=C1 DNCFPDURLPJGKX-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003479 dental cement Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 2
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 241000252185 Cobitidae Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- DKOQGJHPHLTOJR-WHRDSVKCSA-N cefpirome Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 DKOQGJHPHLTOJR-WHRDSVKCSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- -1 o-substituted benzene Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 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
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Dental Preparations (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62103220A JPS63268780A (ja) | 1987-04-28 | 1987-04-28 | 歯質接着性化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3736554A1 DE3736554A1 (de) | 1988-11-10 |
| DE3736554C2 true DE3736554C2 (enExample) | 1993-03-25 |
Family
ID=14348411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873736554 Granted DE3736554A1 (de) | 1987-04-28 | 1987-10-28 | Zahnklebeverbindung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4985198A (enExample) |
| JP (1) | JPS63268780A (enExample) |
| DE (1) | DE3736554A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2027921C (en) * | 1989-10-19 | 1997-12-09 | Nobuo Nakabayashi | Bone cement composition, cured product thereof, implant material and process for the preparation of the same |
| JP2656417B2 (ja) * | 1991-12-18 | 1997-09-24 | 富士写真フイルム株式会社 | 重合性フェノ−ル誘導体 |
| US6500879B1 (en) | 1993-04-19 | 2002-12-31 | Dentsply Research & Development Corp. | Dental composition and method |
| US6391940B1 (en) | 1993-04-19 | 2002-05-21 | Dentsply Research & Development Corp. | Method and composition for adhering to metal dental structure |
| US5710194A (en) * | 1993-04-19 | 1998-01-20 | Dentsply Research & Development Corp. | Dental compounds, compositions, products and methods |
| US5338773A (en) * | 1993-04-19 | 1994-08-16 | Dentsply Research & Development Corp. | Dental composition and method |
| US6369164B1 (en) | 1993-05-26 | 2002-04-09 | Dentsply G.M.B.H. | Polymerizable compounds and compositions |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US6353061B1 (en) | 1993-05-26 | 2002-03-05 | Dentsply Gmbh | α, ω-methacrylate terminated macromonomer compounds |
| US20050043490A1 (en) * | 1993-05-26 | 2005-02-24 | Klee Joachim E. | Polymerizable compounds and compositions |
| CA2146816A1 (en) | 1994-04-22 | 1995-10-23 | Joachim E. Klee | Process and composition for preparing a dental polymer product |
| US5922785A (en) * | 1997-08-11 | 1999-07-13 | The Kerr Corporation | Dental resins |
| TW201029966A (en) * | 2008-11-17 | 2010-08-16 | Bayer Materialscience Llc | Biofilm-inhibitory coatings that release salicylic acid by hydrolisis |
| JP5923423B2 (ja) * | 2011-10-13 | 2016-05-24 | 住友化学株式会社 | 化合物、樹脂、レジスト組成物及びレジストパターンの製造方法 |
| ES2981890T3 (es) * | 2015-07-24 | 2024-10-11 | Trimph Ip Pty Ltd | Polímero antiséptico y síntesis del mismo |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1309149A (en) * | 1970-05-21 | 1973-03-07 | Aspro Nicholas Ltd | Substituted phenyl acrylates and fungicidal uses thereof |
| US4144283A (en) * | 1976-10-07 | 1979-03-13 | Toyo Ink Manufacturing Co., Ltd. | Curable coating compositions |
| JPS5817513B2 (ja) * | 1977-10-13 | 1983-04-07 | 三井化学株式会社 | 接着剤組成物 |
| JPS5466614A (en) * | 1977-11-01 | 1979-05-29 | Mitsubishi Gas Chem Co Inc | Preparation of carboxylic acid or its ester |
| DE3269173D1 (en) * | 1981-07-29 | 1986-03-27 | Kuraray Co | Adhesive composition |
| JPS59129278A (ja) * | 1983-01-14 | 1984-07-25 | Kuraray Co Ltd | 歯科・整形外科用接着剤 |
| JPS5915468A (ja) * | 1982-07-16 | 1984-01-26 | Kuraray Co Ltd | 接着剤 |
| JPS5970644A (ja) * | 1982-10-16 | 1984-04-21 | Teikoku Chem Ind Corp Ltd | （メタ）アクリロイルオキシアルキルオキシフエニル化合物 |
| JPS5970643A (ja) * | 1982-10-16 | 1984-04-21 | Teikoku Chem Ind Corp Ltd | （メタ）アクリロイルオキシアルキルオキシフエニルカルボン酸及びその製造方法 |
| JPS59223772A (ja) * | 1983-06-02 | 1984-12-15 | Tokuyama Soda Co Ltd | 重合用組成物 |
| JPS6128567A (ja) * | 1983-12-29 | 1986-02-08 | Tokuyama Soda Co Ltd | 分割包装された歯科用接着材 |
| JPH0970643A (ja) * | 1995-09-06 | 1997-03-18 | Sugitani Kinzoku Kogyo Kk | 中空中子の製造方法及びその製造装置 |
-
1987
- 1987-04-28 JP JP62103220A patent/JPS63268780A/ja active Pending
- 1987-10-28 DE DE19873736554 patent/DE3736554A1/de active Granted
-
1989
- 1989-03-07 US US07/319,889 patent/US4985198A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63268780A (ja) | 1988-11-07 |
| US4985198A (en) | 1991-01-15 |
| DE3736554A1 (de) | 1988-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: DEUFEL, P., DIPL.-WIRTSCH.-ING.DR.RER.NAT. HERTEL, |
|
| 8128 | New person/name/address of the agent |
Representative=s name: DEUFEL, P., DIPL.-WIRTSCH.-ING.DR.RER.NAT. HERTEL, |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: KIRSCHNER & PARTNER, 81479 MUENCHEN |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: DERZEIT KEIN VERTRETER BESTELLT |
|
| 8339 | Ceased/non-payment of the annual fee |