GB816923A - Process for the production of basic n,n-diepoxides - Google Patents
Process for the production of basic n,n-diepoxidesInfo
- Publication number
- GB816923A GB816923A GB34987/55A GB3498755A GB816923A GB 816923 A GB816923 A GB 816923A GB 34987/55 A GB34987/55 A GB 34987/55A GB 3498755 A GB3498755 A GB 3498755A GB 816923 A GB816923 A GB 816923A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diepoxides
- basic
- benzene
- epichlorhydrin
- reacting
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 4
- 150000001412 amines Chemical class 0.000 abstract 3
- -1 amino compound Chemical class 0.000 abstract 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 abstract 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 150000001555 benzenes Chemical class 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 235000011187 glycerol Nutrition 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- AIMXDOGPMWDCDF-UHFFFAOYSA-N 1-n,4-n-dicyclohexylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1CCCCC1 AIMXDOGPMWDCDF-UHFFFAOYSA-N 0.000 abstract 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- 229920003986 novolac Polymers 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000005011 phenolic resin Substances 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012262 resinous product Substances 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3227—Compounds containing acyclic nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Color Printing (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Basic diepoxides having terminal nitrogen atoms each carrying one epoxy propane group are prepared by reacting a secondary 4,41-di-(monalkylamino) derivative of a diphenyl methane or a secondary 1,4-di-(monoalkylamino) derivative of benzene with more than 1 mol. of epichlorhydrin or of a glycerine dichlorhydrin per mol. of amino compound, and converting the resulting di-(hydroxychloropropyl) amine into the basic diepoxide by reacting with aqueous alkali at a temperature not exceeding 30 DEG C. A solvent such as benzene or toluene may be present. High molecular resinous products are obtained if less than 1 mol. of chlorhydrin is reacted with each secondary amino group. The diepoxides may be hardened with the usual agents, e.g. polyvalent alcohols, carboxylic acids, amines, amides of carboxylic or sulphonic acids, and melamine-, urea- and phenolic resins; and other diepoxides may be present. Diluents may be present, including reactive diluents such as phenoxypropane oxide glycide ethers or basic propane oxides. Novolaks may be used as hardeners and the action may be accelerated by more strongly basic mono- or di-epoxides. The examples describe the preparation of diepoxides from 4,41 - di - (monomethylamino) diphenyl methane and epichlorhydrin in varying proportions, and from 1,4-di-(monocyclohexylamino benzene. Specifications 518,057, [Group IV], and 664,271 are referred to.ALSO:Basic diepoxides having terminal nitrogen atoms each carrying one epoxy propane group are prepared by reacting a secondary 4,41-di-(monoalkylamino) derivative of a diphenyl methane or a secondary 1,4-di-(monoalkylamino) derivative of benzene with more than 1 mol. of epichlorhydrin or of a glycerine dichlorhydrin per mol. of amino compound, and converting the resulting di-(hydroxychloropropyl) amine into the basic diepoxide by reacting with aqueous alkali at a temperature not exceeding 30 DEG C. A solvent such as benzene or toluene may be present. Examples give the preparation of diepoxides from 4,41-di-(monomethylamino)diphenylmethane and epichlorhydrin, and from 1,4-di-(monocyclohexylamino) benzene. The former have the formula <FORM:0816923/IV (b)/1> where n is O or an integer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE816923X | 1954-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816923A true GB816923A (en) | 1959-07-22 |
Family
ID=6735103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34987/55A Expired GB816923A (en) | 1954-12-06 | 1955-12-06 | Process for the production of basic n,n-diepoxides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB816923A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6768010B1 (en) | 2003-09-16 | 2004-07-27 | Samsung Electronics Co., Ltd. | Organophotoreceptor with an epoxy-modified charge transport compound having an azine group |
| US6960418B2 (en) | 2003-10-23 | 2005-11-01 | Samsung Electronics Co., Ltd. | Organophotoreceptor with charge transport material with two N,N,N-trisubstituted-amino groups |
| US7008743B2 (en) | 2003-10-31 | 2006-03-07 | Samsung Electronics Co., Ltd. | Organophotoreceptor with charge transport material having a vinyl ether group |
| US7320849B2 (en) | 2003-12-31 | 2008-01-22 | Samsung Electronics Co., Ltd. | Organophotoreceptor with a charge transport material having two epoxidated-hydrazone groups |
| WO2009076090A3 (en) * | 2007-12-12 | 2010-03-11 | Chemtura Corporation | Cycloalkyl phenylenediamines as deposit control agents for lubricants |
| WO2012080185A1 (en) | 2010-12-15 | 2012-06-21 | Bayer Materialscience Ag | Foams of high thermal stability |
| WO2012150201A2 (en) | 2011-05-02 | 2012-11-08 | Bayer Intellectual Property Gmbh | High-temperature-resistant foams having low thermal conductivity |
| EP3059270A1 (en) | 2015-02-20 | 2016-08-24 | Basf Se | Temperature-resistant isocyanate-based foams having a high flame resistance |
| CN110494468A (en) * | 2017-10-17 | 2019-11-22 | 阿迪蒂亚·比拉化工(泰国)有限公司 | Glycidylamine epoxy resin based on AMES negative amine |
| US10526463B2 (en) | 2015-02-20 | 2020-01-07 | Covestro Deutschland Ag | Foam materials resistant to high temperatures |
| US11142608B2 (en) | 2017-03-17 | 2021-10-12 | Basf Se | Method for producing compounds having oxazolidinone groups |
| WO2022136046A1 (en) | 2020-12-21 | 2022-06-30 | Basf Se | Thermoplastic polyoxazolidinone having a high temperature stability |
| WO2022136048A1 (en) | 2020-12-21 | 2022-06-30 | Basf Se | Stabilized epoxy-isocyanate mixtures and oxazolidinone containing polymers obtained therefrom |
| WO2023001686A1 (en) | 2021-07-22 | 2023-01-26 | Basf Se | Isocyanate-epoxy hybrid foams having low brittleness and improved adhesion |
-
1955
- 1955-12-06 GB GB34987/55A patent/GB816923A/en not_active Expired
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6768010B1 (en) | 2003-09-16 | 2004-07-27 | Samsung Electronics Co., Ltd. | Organophotoreceptor with an epoxy-modified charge transport compound having an azine group |
| US6960418B2 (en) | 2003-10-23 | 2005-11-01 | Samsung Electronics Co., Ltd. | Organophotoreceptor with charge transport material with two N,N,N-trisubstituted-amino groups |
| US7008743B2 (en) | 2003-10-31 | 2006-03-07 | Samsung Electronics Co., Ltd. | Organophotoreceptor with charge transport material having a vinyl ether group |
| US7320849B2 (en) | 2003-12-31 | 2008-01-22 | Samsung Electronics Co., Ltd. | Organophotoreceptor with a charge transport material having two epoxidated-hydrazone groups |
| WO2009076090A3 (en) * | 2007-12-12 | 2010-03-11 | Chemtura Corporation | Cycloalkyl phenylenediamines as deposit control agents for lubricants |
| US9481776B2 (en) | 2010-12-15 | 2016-11-01 | Covestro Deutschland Ag | Foams of high thermal stability |
| WO2012080185A1 (en) | 2010-12-15 | 2012-06-21 | Bayer Materialscience Ag | Foams of high thermal stability |
| WO2012150201A2 (en) | 2011-05-02 | 2012-11-08 | Bayer Intellectual Property Gmbh | High-temperature-resistant foams having low thermal conductivity |
| EP3059270A1 (en) | 2015-02-20 | 2016-08-24 | Basf Se | Temperature-resistant isocyanate-based foams having a high flame resistance |
| US10526463B2 (en) | 2015-02-20 | 2020-01-07 | Covestro Deutschland Ag | Foam materials resistant to high temperatures |
| US11142608B2 (en) | 2017-03-17 | 2021-10-12 | Basf Se | Method for producing compounds having oxazolidinone groups |
| CN110494468A (en) * | 2017-10-17 | 2019-11-22 | 阿迪蒂亚·比拉化工(泰国)有限公司 | Glycidylamine epoxy resin based on AMES negative amine |
| CN110494468B (en) * | 2017-10-17 | 2022-08-23 | 阿迪蒂亚·比拉化工(泰国)有限公司 | Glycidylamine epoxy resins based on AMES negative amines |
| US11548976B2 (en) * | 2017-10-17 | 2023-01-10 | Aditya Birla Chemicals (Thailand) Limited | Glycidyl amine epoxy resins based on AMES negative amines |
| WO2022136046A1 (en) | 2020-12-21 | 2022-06-30 | Basf Se | Thermoplastic polyoxazolidinone having a high temperature stability |
| WO2022136048A1 (en) | 2020-12-21 | 2022-06-30 | Basf Se | Stabilized epoxy-isocyanate mixtures and oxazolidinone containing polymers obtained therefrom |
| WO2023001686A1 (en) | 2021-07-22 | 2023-01-26 | Basf Se | Isocyanate-epoxy hybrid foams having low brittleness and improved adhesion |
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