JPS6236513B2 - - Google Patents
Info
- Publication number
- JPS6236513B2 JPS6236513B2 JP11361080A JP11361080A JPS6236513B2 JP S6236513 B2 JPS6236513 B2 JP S6236513B2 JP 11361080 A JP11361080 A JP 11361080A JP 11361080 A JP11361080 A JP 11361080A JP S6236513 B2 JPS6236513 B2 JP S6236513B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- present
- absorption
- acid
- 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
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 trimellitic anhydride ester Chemical class 0.000 claims description 9
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004018 acid anhydride group Chemical group 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000009102 absorption Effects 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-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
- WXSYRUFELJWENS-UHFFFAOYSA-N 4-[2-(3,4-dicarboxybenzoyl)oxy-3-(2-methylprop-2-enoyloxy)propoxy]carbonylphthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(=O)OC(COC(=O)C(=C)C)COC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 WXSYRUFELJWENS-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CJPIDIRJSIUWRJ-UHFFFAOYSA-N benzene-1,2,4-tricarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C(C(Cl)=O)=C1 CJPIDIRJSIUWRJ-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11361080A JPS5738750A (en) | 1980-08-18 | 1980-08-18 | 2,3-bis 3,4-dicarboxybenzoyloxy propyl methacrylate and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11361080A JPS5738750A (en) | 1980-08-18 | 1980-08-18 | 2,3-bis 3,4-dicarboxybenzoyloxy propyl methacrylate and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5738750A JPS5738750A (en) | 1982-03-03 |
| JPS6236513B2 true JPS6236513B2 (US06521211-20030218-C00004.png) | 1987-08-07 |
Family
ID=14616574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11361080A Granted JPS5738750A (en) | 1980-08-18 | 1980-08-18 | 2,3-bis 3,4-dicarboxybenzoyloxy propyl methacrylate and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5738750A (US06521211-20030218-C00004.png) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6255913A (ja) * | 1985-09-05 | 1987-03-11 | Nippon Ferrite Ltd | ロ−タリ−トランス |
| JPS6244413U (US06521211-20030218-C00004.png) * | 1985-09-05 | 1987-03-17 | ||
| JPS6244414U (US06521211-20030218-C00004.png) * | 1985-09-05 | 1987-03-17 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58173175A (ja) * | 1982-04-05 | 1983-10-12 | Kuraray Co Ltd | 歯科用接着剤 |
| US5260476A (en) * | 1990-12-14 | 1993-11-09 | Tokuyama Soda Kabushiki Kaisha | Diacrylate compounds |
| DE19525031A1 (de) * | 1995-07-10 | 1997-01-16 | Heraeus Kulzer Gmbh | Derivate aromatischer Carbonsäuren, aromatische Carbonsäureanhydride und Hydroxy(meth)acrylaten sowie Adhäsive, enthaltend diese Verbindungen |
| WO2011054818A2 (de) * | 2009-11-03 | 2011-05-12 | Bayer Materialscience Ag | Neue, nicht kristallisierende methacrylate, deren herstellung und verwendung |
-
1980
- 1980-08-18 JP JP11361080A patent/JPS5738750A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6255913A (ja) * | 1985-09-05 | 1987-03-11 | Nippon Ferrite Ltd | ロ−タリ−トランス |
| JPS6244413U (US06521211-20030218-C00004.png) * | 1985-09-05 | 1987-03-17 | ||
| JPS6244414U (US06521211-20030218-C00004.png) * | 1985-09-05 | 1987-03-17 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5738750A (en) | 1982-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0206810B1 (en) | Acrylate compound and composition containing the same | |
| JPS61293960A (ja) | （メタ）アクリル酸エステル類 | |
| JPS6340406B2 (US06521211-20030218-C00004.png) | ||
| US6057460A (en) | Polymerizable hybrid monomers | |
| JPS6236513B2 (US06521211-20030218-C00004.png) | ||
| JP2887419B2 (ja) | バルプロ酸に類似の抗癲癇薬 | |
| JP3616346B2 (ja) | 加水分解安定性である重合可能なアクリロホスホン酸 | |
| JP6733908B2 (ja) | （メタ）アクリルアミド部位を有する（メタ）アクリル酸エステル誘導体の製造方法 | |
| JP3002152B2 (ja) | 多官能性ビニルシクロプロパン誘導体 | |
| JPS6313435B2 (US06521211-20030218-C00004.png) | ||
| JPH1192461A (ja) | ジスルフィド化合物および金属表面処理剤 | |
| US4243763A (en) | Tertiary aromatic amine accelerators in acrylic resin | |
| JPS6236512B2 (US06521211-20030218-C00004.png) | ||
| JPH101473A (ja) | チオウラシル誘導体 | |
| US5795497A (en) | Thiouracil derivatives and metal surface-treating agent comprising thereof | |
| JP3296476B2 (ja) | 金属表面処理剤 | |
| JP3180818B2 (ja) | １−置換エチルメタクリレート類の製造法 | |
| JP7090884B2 (ja) | 高誘電率を有する官能基を有する酸性基含有重合性単量体 | |
| JPS58192891A (ja) | 新重合性リン酸モノエステル | |
| JP5008852B2 (ja) | トリシクロデカン誘導体の異性体混合物 | |
| JP2001131138A (ja) | アダマンタン誘導体及びその製造法 | |
| JPS6251928B2 (US06521211-20030218-C00004.png) | ||
| JPS62153295A (ja) | 分子内に不飽和カルボン酸エステル基を含有するプロペニルジアルコキシシラン | |
| Tanaka et al. | Syntheses of O-methacryloyl-N-acyl tyrosines and their adhesiveness to un-etched human dentin | |
| JP4868104B2 (ja) | シクロブタンテトラカルボン酸の（メタ）アクリレート化合物及びその製造法 |
