GB980069A - Bis(bicycloheptylmethylamines),process for their preparation and their use - Google Patents
Bis(bicycloheptylmethylamines),process for their preparation and their useInfo
- Publication number
- GB980069A GB980069A GB23887/63A GB2388763A GB980069A GB 980069 A GB980069 A GB 980069A GB 23887/63 A GB23887/63 A GB 23887/63A GB 2388763 A GB2388763 A GB 2388763A GB 980069 A GB980069 A GB 980069A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- bicyclo
- compounds
- prepared
- heptyl
- 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 abstract 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- NUUNDIOOYFEMQN-UHFFFAOYSA-N cyclopenta-1,3-diene;sodium Chemical compound [Na].C1C=CC=C1 NUUNDIOOYFEMQN-UHFFFAOYSA-N 0.000 abstract 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- -1 oxydiethyl Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 abstract 1
- XXJQYHLUBYNLQX-UHFFFAOYSA-N 1-[(2-amino-2-methyl-1-bicyclo[2.2.1]heptanyl)-dimethylsilyl]-2-methylbicyclo[2.2.1]heptan-2-amine Chemical compound NC1(C2(CCC(C1)C2)[Si](C)(C)C21C(CC(CC2)C1)(N)C)C XXJQYHLUBYNLQX-UHFFFAOYSA-N 0.000 abstract 1
- BLYCTGOIYUUNHH-UHFFFAOYSA-N 5-(3-cyclopenta-2,4-dien-1-ylcyclopent-3-en-1-yl)cyclopenta-1,3-diene Chemical compound C1(C=CC=C1)C1=CCC(C1)C1C=CC=C1 BLYCTGOIYUUNHH-UHFFFAOYSA-N 0.000 abstract 1
- HSXYQLQJMCYWEO-UHFFFAOYSA-N 5-(4-cyclopenta-2,4-dien-1-ylbut-1-enyl)cyclopenta-1,3-diene Chemical compound C1(C=CC=C1)C=CCCC1C=CC=C1 HSXYQLQJMCYWEO-UHFFFAOYSA-N 0.000 abstract 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 abstract 1
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical class C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- FPWYHHNBOYUKSS-UHFFFAOYSA-N di(cyclopenta-1,3-dien-1-yl)-dimethylsilane Chemical compound C=1C=CCC=1[Si](C)(C)C1=CC=CC1 FPWYHHNBOYUKSS-UHFFFAOYSA-N 0.000 abstract 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 abstract 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003961 organosilicon compounds Chemical class 0.000 abstract 1
- 150000002924 oxiranes Chemical class 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 239000008096 xylene Substances 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/5026—Amines cycloaliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0980069/C2/1> wherein R is Si(alkyl)2, Si(aryl)2 (see Division C3), or a divalent aliphatic, cycloaliphatic or araliphatic hydrocarbon residue which may be interrupted by oxygen atoms, or may be substituted by hydroxyl groups or halogen atoms, and R1, R11, R2 and R21 are each H or CH3. Such compounds are prepared by reacting a starting material of formula <FORM:0980069/C2/2> with acrylonitrile, acrolein or methylvinylketone and hydrogenating the intermediate bis(bi-cycloheptenyl) dinitrile, dialdehyde or di-(methylketone) adduct in presence of ammonia. The examples describe the preparation of the following compounds from the corresponding bis(bicycloheptenyl) dinitriles:-(1)b ,b 1-bis-(21 -aminomethyl - bicyclo[2,2,1]heptyl) - diethyl ether; (2) 1,4 - bis(21 - aminomethyl - bicyclo-[2,2,1] heptyl)butane; (4) the homologue of (1) (R1 and R11 are CH3); (6) 1,4-bis (21-amino-methyl - bicyclo [2,2,1] heptyl) cyclopentane; (7)-(9) bis(21 - aminomethyl - bicyclo[2,2,1]-heptylmethyl) - xylene(1,3) -mesitylene and -durene. In Example (3), the homologue of (2) (R2 and R21 are CH3) is prepared from the appropriate bis(bicycloheptenyl-methylketone). The starting materials (II) wherein R is oxydiethyl are prepared from the cyclopentadiene sodium and b ,b 1-dichlorodiethyl ether.ALSO:Epoxy compounds having an epoxide equivalence greater than 1 are cured with agents of formula <FORM:0980069/C3/1> wherein R is Si(alkyl)2, Si(aryl)2 or a divalent aliphatic, cycloaliphatic or araliphatic hydrocarbon residue which may be interrupted by oxygen atoms, or may be substituted by hydroxyl groups or halogen atoms and R1, R11, R2 and R21 are each H or CH3. In examples, agents of the above formula are used to cure an epoxy resin prepared from 1 mol of Bisphenol A and at least 2 mols of epichlorohydrin in presence of aqueous NaOH, but the Specification lists a large number of other suitable epoxy compounds. Organosilicon compounds of the above formula are prepared by reacting a di-(cyclopentadienyl)dialkyl or diarylsilane with acrylonitrile, acrolein or methylvinylketone and hydrogenating the resulting adduct in presence of ammonia. Using acrylonitrile according to this method in Example (5), di-(cyclopentadienyl) dimethylsilane (from cyclopentadiene sodium and dichlorodinethysilane) gives bis-(2 - cyano - bicyclo -[2,2,1] - heptenyl - 5)di -methylsilane and subsequently bis-(2-amino-methyl - bicyclo - [2,2,1] - heptyl) dimethylsilane.ALSO:The following bis-cyclopentadiene compounds are obtained by reacting cyclopentadiene sodium with the corresponding dichloro- or dibromocompounds: 1,4-dicyclopentadienylbutene - 2; 1,4 - dicyclopentadienylcyclopentene - 2; bis - (cyclopentadienylmethyl) - xylene-1,3; -mesithylene and -durene.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH746462A CH433262A (en) | 1962-06-21 | 1962-06-21 | Process for the production of new polyamines |
| CH1449162 | 1962-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB980069A true GB980069A (en) | 1965-01-13 |
Family
ID=25701398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23887/63A Expired GB980069A (en) | 1962-06-21 | 1963-06-14 | Bis(bicycloheptylmethylamines),process for their preparation and their use |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT241432B (en) |
| ES (1) | ES289226A1 (en) |
| GB (1) | GB980069A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2515486C2 (en) * | 1975-04-09 | 1984-05-24 | Bayer Ag, 5090 Leverkusen | Bicyclo [2.2.1] heptane triamines and process for their preparation |
-
1963
- 1963-06-14 GB GB23887/63A patent/GB980069A/en not_active Expired
- 1963-06-20 AT AT494563A patent/AT241432B/en active
- 1963-06-20 ES ES289226A patent/ES289226A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES289226A1 (en) | 1963-12-16 |
| AT241432B (en) | 1965-07-26 |
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