JPS60202873A - （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 - Google Patents
（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Info
- Publication number
- JPS60202873A JPS60202873A JP59058783A JP5878384A JPS60202873A JP S60202873 A JPS60202873 A JP S60202873A JP 59058783 A JP59058783 A JP 59058783A JP 5878384 A JP5878384 A JP 5878384A JP S60202873 A JPS60202873 A JP S60202873A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- adhesive
- compound
- dentin
- 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
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 30
- 239000000853 adhesive Substances 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 210000004268 dentin Anatomy 0.000 title abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- -1 naphthalene- 1,2,6-tricarboxylic acid chloride anhydride Chemical class 0.000 abstract description 6
- 125000001165 hydrophobic group Chemical group 0.000 abstract description 5
- 229920001577 copolymer Polymers 0.000 abstract description 3
- 239000003479 dental cement Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000000945 filler Substances 0.000 abstract description 2
- 229920002554 vinyl polymer Polymers 0.000 abstract description 2
- 125000002579 carboxylato group Chemical group [O-]C(*)=O 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 18
- 230000009102 absorption Effects 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 150000008065 acid anhydrides Chemical class 0.000 description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 210000003298 dental enamel Anatomy 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 9
- 239000004926 polymethyl methacrylate Substances 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 230000001464 adherent effect Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- LKAPTZKZHMOIRE-KVTDHHQDSA-N (2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde Chemical compound OC[C@H]1O[C@H](C=O)[C@@H](O)[C@@H]1O LKAPTZKZHMOIRE-KVTDHHQDSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- LKAPTZKZHMOIRE-UHFFFAOYSA-N chitose Natural products OCC1OC(C=O)C(O)C1O LKAPTZKZHMOIRE-UHFFFAOYSA-N 0.000 description 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- 206010011732 Cyst Diseases 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 208000031513 cyst Diseases 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910001651 emery Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 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
- 210000000214 mouth Anatomy 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- RMCCONIRBZIDTH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 RMCCONIRBZIDTH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BYMMIQCVDHHYGG-UHFFFAOYSA-N Cl.OP(O)(O)=O Chemical compound Cl.OP(O)(O)=O BYMMIQCVDHHYGG-UHFFFAOYSA-N 0.000 description 1
- 229920002148 Gellan gum Polymers 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000002747 voluntary effect Effects 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)
Priority Applications (6)
| 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 |
| GB08506774A GB2156347B (en) | 1984-03-27 | 1985-03-15 | (meth)acrylic acid ester compounds boundable to tooth substrates |
| US06/712,429 US4591649A (en) | 1984-03-27 | 1985-03-18 | Compounds bondable to tooth substrates |
| DE19853510962 DE3510962A1 (de) | 1984-03-27 | 1985-03-26 | Mit zahnunterlagen verbindbare massen |
| CH1330/85A CH662115A5 (fr) | 1984-03-27 | 1985-03-27 | Composes aptes a se lier a des substrats dentaires. |
| FR858504533A FR2561913B1 (fr) | 1984-03-27 | 1985-03-27 | Composes aptes a etre lies a des substrats dentaires |
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 |
|---|---|
| JPS60202873A true JPS60202873A (ja) | 1985-10-14 |
| JPH026753B2 JPH026753B2 (enExample) | 1990-02-13 |
Family
ID=13094165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59058783A Granted 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 |
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 |
|---|---|---|---|---|
| US5234972A (en) * | 1989-02-14 | 1993-08-10 | Ube Industries, Ltd. | Dental adhesive comprising an itaconic acid monoester compound |
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 |
| EP0423430B1 (de) * | 1989-10-19 | 1993-04-21 | Heraeus Kulzer GmbH | Dentales Haftmittel |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5412338A (en) * | 1977-06-28 | 1979-01-30 | Mitsui Petrochem Ind Ltd | 4-methacryloxyethyl trimellitic acid, its anhydride, and their preparation |
| JPS58173175A (ja) * | 1982-04-05 | 1983-10-12 | Kuraray Co Ltd | 歯科用接着剤 |
Family Cites Families (4)
| 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 |
| JPS55149277A (en) * | 1980-04-07 | 1980-11-20 | Rikagaku Kenkyusho | Sesquiterpene derivative compound |
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5412338A (en) * | 1977-06-28 | 1979-01-30 | Mitsui Petrochem Ind Ltd | 4-methacryloxyethyl trimellitic acid, its anhydride, and their preparation |
| JPS58173175A (ja) * | 1982-04-05 | 1983-10-12 | Kuraray Co Ltd | 歯科用接着剤 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234972A (en) * | 1989-02-14 | 1993-08-10 | Ube Industries, Ltd. | Dental adhesive comprising an itaconic acid monoester compound |
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 |
| 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 |
| DE3510962C2 (enExample) | 1987-09-10 |
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