DE3510962C2 - - Google Patents
Info
- Publication number
- DE3510962C2 DE3510962C2 DE3510962A DE3510962A DE3510962C2 DE 3510962 C2 DE3510962 C2 DE 3510962C2 DE 3510962 A DE3510962 A DE 3510962A DE 3510962 A DE3510962 A DE 3510962A DE 3510962 C2 DE3510962 C2 DE 3510962C2
- Authority
- DE
- Germany
- Prior art keywords
- anhydride
- group
- methacryloxyethylnaphthalene
- tooth
- 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
Links
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- IDVDAZFXGGNIDQ-UHFFFAOYSA-N benzo[e][2]benzofuran-1,3-dione Chemical class C1=CC2=CC=CC=C2C2=C1C(=O)OC2=O IDVDAZFXGGNIDQ-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- -1 vinyl compound Chemical class 0.000 description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 210000004268 dentin Anatomy 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- 241000283690 Bos taurus Species 0.000 description 14
- 230000009102 absorption Effects 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 14
- 210000003298 dental enamel Anatomy 0.000 description 13
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 13
- 239000004926 polymethyl methacrylate Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 235000015278 beef Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 229920000298 Cellophane Polymers 0.000 description 3
- 229910001651 emery Inorganic materials 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 3
- HSTRFIAEOJFYLI-UHFFFAOYSA-N 94040-23-0 Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3C(=O)CCC(=O)O HSTRFIAEOJFYLI-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000178 monomer Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- UGRAJKVJLIUYIH-UHFFFAOYSA-N 2-naphthalen-2-ylethyl 2-methylprop-2-enoate Chemical compound C1=CC=CC2=CC(CCOC(=O)C(=C)C)=CC=C21 UGRAJKVJLIUYIH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- YDTOECZZFODICB-UHFFFAOYSA-N butylborane Chemical compound BCCCC YDTOECZZFODICB-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 210000004283 incisor Anatomy 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- POXJIJAKRASZGS-UHFFFAOYSA-N naphthalene-1,2,6-tricarbonyl chloride Chemical compound ClC(=O)C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 POXJIJAKRASZGS-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/40—Primers
-
- 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
- C08F20/00—Homopolymers 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Dental Preparations (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59058783A JPS60202873A (ja) | 1984-03-27 | 1984-03-27 | （メタ）アクリロキシアルキルナフタレントリカルボン酸無水物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3510962A1 DE3510962A1 (de) | 1985-10-10 |
| DE3510962C2 true DE3510962C2 (enExample) | 1987-09-10 |
Family
ID=13094165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853510962 Granted DE3510962A1 (de) | 1984-03-27 | 1985-03-26 | Mit zahnunterlagen verbindbare massen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4591649A (enExample) |
| JP (1) | JPS60202873A (enExample) |
| CH (1) | CH662115A5 (enExample) |
| DE (1) | DE3510962A1 (enExample) |
| FR (1) | FR2561913B1 (enExample) |
| GB (1) | GB2156347B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423430A3 (en) * | 1989-10-19 | 1991-07-24 | Heraeus Kulzer Gmbh | Dental adhesive |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4719149A (en) * | 1986-02-28 | 1988-01-12 | Minnesota Mining And Manufacturing Company | Method for priming hard tissue |
| JPH02212455A (ja) * | 1989-02-14 | 1990-08-23 | Ube Ind Ltd | イタコン酸モノエステル化合物及びそれらを含有してなる接着剤 |
| DE4039440A1 (de) * | 1990-08-15 | 1992-02-27 | Bayer Ag | N-alkyl-n-(meth)acryloyloxyalkylcarboxamide aromatischer carbonsaeuren und aromatischer carbonsaeureanhydride sowie adhaesive enthaltend diese verbindungen |
| DE4137076A1 (de) * | 1991-11-12 | 1993-05-13 | Ivoclar Ag | Dentalklebstoff |
| US5525648A (en) | 1991-12-31 | 1996-06-11 | Minnesota Mining And Manufacturing Company | Method for adhering to hard tissue |
| US5338773A (en) * | 1993-04-19 | 1994-08-16 | 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 |
| US6500879B1 (en) | 1993-04-19 | 2002-12-31 | Dentsply Research & Development Corp. | Dental composition and method |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU362006A1 (ru) * | 1970-12-22 | 1972-12-13 | Способ получения 4-фенилового эфира нафталевого ангидрида | |
| SU571485A1 (ru) * | 1974-07-17 | 1977-09-05 | Рубежанский филиал Ворошиловградского машиностроительного института | 4-(3-Карбоксипропионил)-нафталевый ангидрид как полупродукт в синтезе 1,4,8-нафталинтрикарбоновой кислоты и способ его получени |
| US4148988A (en) * | 1977-06-28 | 1979-04-10 | Mitsui Petrochemical Industries Ltd. | Curable composition |
| JPS5827781B2 (ja) * | 1977-06-28 | 1983-06-11 | 三井化学株式会社 | ４−メタクリロキシエチルトリメリット酸、その酸無水物およびそれらの製造方法 |
| JPS55149277A (en) * | 1980-04-07 | 1980-11-20 | Rikagaku Kenkyusho | Sesquiterpene derivative compound |
| JPS58173175A (ja) * | 1982-04-05 | 1983-10-12 | Kuraray Co Ltd | 歯科用接着剤 |
-
1984
- 1984-03-27 JP JP59058783A patent/JPS60202873A/ja active Granted
-
1985
- 1985-03-15 GB GB08506774A patent/GB2156347B/en not_active Expired
- 1985-03-18 US US06/712,429 patent/US4591649A/en not_active Expired - Fee Related
- 1985-03-26 DE DE19853510962 patent/DE3510962A1/de active Granted
- 1985-03-27 FR FR858504533A patent/FR2561913B1/fr not_active Expired
- 1985-03-27 CH CH1330/85A patent/CH662115A5/fr not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423430A3 (en) * | 1989-10-19 | 1991-07-24 | Heraeus Kulzer Gmbh | Dental adhesive |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2156347A (en) | 1985-10-09 |
| US4591649A (en) | 1986-05-27 |
| FR2561913A1 (fr) | 1985-10-04 |
| JPH026753B2 (enExample) | 1990-02-13 |
| JPS60202873A (ja) | 1985-10-14 |
| CH662115A5 (fr) | 1987-09-15 |
| DE3510962A1 (de) | 1985-10-10 |
| GB8506774D0 (en) | 1985-04-17 |
| GB2156347B (en) | 1987-08-26 |
| FR2561913B1 (fr) | 1989-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |