DE1418698A1 - Verfahren zur Herstellung mischpolymerisierbarer Epoxyester - Google Patents
Verfahren zur Herstellung mischpolymerisierbarer EpoxyesterInfo
- Publication number
- DE1418698A1 DE1418698A1 DE19601418698 DE1418698A DE1418698A1 DE 1418698 A1 DE1418698 A1 DE 1418698A1 DE 19601418698 DE19601418698 DE 19601418698 DE 1418698 A DE1418698 A DE 1418698A DE 1418698 A1 DE1418698 A1 DE 1418698A1
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- epoxy esters
- esters
- epoxy
- acid
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims description 12
- 239000004593 Epoxy Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 olefin alcohols Chemical class 0.000 claims description 8
- 150000004965 peroxy acids Chemical class 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 125000005396 acrylic acid ester group Chemical group 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940117958 vinyl acetate Drugs 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0021929 | 1960-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1418698A1 true DE1418698A1 (de) | 1968-10-10 |
Family
ID=7017102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19601418698 Pending DE1418698A1 (de) | 1960-07-16 | 1960-07-16 | Verfahren zur Herstellung mischpolymerisierbarer Epoxyester |
Country Status (3)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656809A (en) * | 1984-02-25 | 1987-04-14 | Wilson Double Deck Trailers Limited | Profiled sheet material |
| WO1998028286A3 (en) * | 1996-12-23 | 1998-08-13 | Sartomer Co Inc | Unsaturated (meth)acrylate esters containing at least one epoxidized cyclic group and process for preparing them |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63221123A (ja) * | 1987-03-09 | 1988-09-14 | Kansai Paint Co Ltd | 低温硬化性樹脂組成物 |
| US6211320B1 (en) | 1999-07-28 | 2001-04-03 | Dexter Corporation | Low viscosity acrylate monomers formulations containing same and uses therefor |
| JP2006151900A (ja) * | 2004-11-30 | 2006-06-15 | Daicel Chem Ind Ltd | 脂環式エポキシ（メタ）アクリレート及びその製造方法 |
-
0
- GB GB984827D patent/GB984827A/en active Active
-
1960
- 1960-07-16 DE DE19601418698 patent/DE1418698A1/de active Pending
-
1961
- 1961-07-12 CH CH818761A patent/CH410911A/de unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656809A (en) * | 1984-02-25 | 1987-04-14 | Wilson Double Deck Trailers Limited | Profiled sheet material |
| WO1998028286A3 (en) * | 1996-12-23 | 1998-08-13 | Sartomer Co Inc | Unsaturated (meth)acrylate esters containing at least one epoxidized cyclic group and process for preparing them |
Also Published As
| Publication number | Publication date |
|---|---|
| GB984827A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| CH410911A (de) | 1966-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1668500C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE1418698A1 (de) | Verfahren zur Herstellung mischpolymerisierbarer Epoxyester | |
| EP0286937B1 (de) | Verfahren zur Herstellung epoxidierter Fettalkohole | |
| DE2423405C3 (de) | Verfahren zur Herstellung von Glycidylmethacrylat | |
| DE1058987B (de) | Darstellung von Cyclododecadienmonoepoxyd aus Cyclododecatrienen | |
| DE1031786B (de) | Verfahren zur Herstellung Epoxygruppen enthaltender Weichmacher | |
| DE1161553C2 (de) | Verfahren zur Herstellung von Diepoxyestern | |
| DE844442C (de) | Verfahren zur Herstellung von 1, 1-Dihalogen-1, 3-alkadienen | |
| DE2110584A1 (de) | Verfahren zur Herstellung von Isopentanhydroperoxyd bzw. Isopren | |
| DE907774C (de) | Verfahren zur Herstellung von mehrwertigen Alkoholen | |
| DE1081462B (de) | Verfahren zur Herstellung von Epoxyden aus olefinisch ungesaettigten organischen Verbindungen | |
| DE912810C (de) | Verfahren zur Herstellung von monomeren Vinylestern | |
| DE2444389B2 (de) | Verfahren zur herstellung von hydroperoxiden aus terpentin-kohlenwasserstoffen | |
| DE868153C (de) | Verfahren zur Herstellung von Estern ª‡,ª‰-ungesaettigter Carbonsaeuren | |
| DE2136496C3 (de) | Verfahren zur Herstellung von Oxablcyclo-alkenen | |
| DE1161881B (de) | Verfahren zur Herstellung von 1, 2-Epoxycyclododecadien-(5, 9) | |
| DE1157598B (de) | Verfahren zur Herstellung von N-substituierten Carbaminsaeureestern | |
| DE2343974A1 (de) | Aroylessigester | |
| DE1124478C2 (de) | Verfahren zur Herstellung von ungesaettigten, gegebenenfalls veresterten Alkoholen | |
| DE1071694B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH410912A (de) | Verfahren zur Herstellung mischpolymerisierbarer Epoxyäther | |
| DE1054444B (de) | Verfahren zur Herstellung von esterartigen Anlagerungsprodukten von Formaldehyd an ungesaettigte Fettstoffe | |
| DE2115327B2 (de) | Verfahren zur herstellung von 3- chlorpropanol-(1) | |
| DE1016691B (de) | Verfahren zur Herstellung von mehrwertigen Alkoholen aus ungesaettigten Kohlenstoffverbindungen und Wasserstoffsuperoxyd | |
| DE1645647A1 (de) | Verfahren zur Emulsionspolymerisation ungesaettigter Verbindungen mittels Tallseifen |