US3742033A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of mono-and polyimines with electrophilic double-bond systems
Assignee: Bayer AG
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Filing: 1969-11-20
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Granted: 1973-06-26
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Expires: 1989-11-20
Abstract
Abstract Imines substituted in the Alpha -position are obtained by reacting mono- or polyimines (ket- and aldimines) with an electrophilic olefin (i.e., acrylic and metacrylic acid derivatives) at a temperature between 10* and 150* C, optionally under pressure and optionally in the presence of an inert solvent. The imines modified by the process of the invention have many possible uses and represent valuable intermediates for many organic syntheses. The new compounds obtainable according to the process can be used in the preparation of elastic moulding masses.
Inventors
- 👤 M Hajek
- 👤 K Wagner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 08:36
CPC Classifications
C; C08; C08G; C08G18/00
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
23 words
an alkyl, aralkyl or aryl primary mono- and polyamines, said reaction being carried out at a temperature of between 10* and 150* C.
Claim 2
Dependent Claim
86 words
Alpha-substituted imines according to claim 1 wherein said electrophilic olefin is selected from the group of acrylic acid, acrylic acid methyl ester, acrylic acid ethyl ester, acrylic acid propyl ester, acrylic acid butyl ester, methacrylic acid, methacrylic acid methyl ester, methacrylic acid ethyl ester, methacrylic acid propyl ester, methacrylic acid butyl ester, maleic acid, fumaric acid, and the half and diesters of maleic and fumaric acids derived from methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, ethylene glycol, diethylene glycol, triethylene glycol, 2,2-dimethylpropanediol-(1,3), glycerine and trimethylol propane.
Claim 3
Dependent Claim
17 words
an alkyl, araalkyl or aryl primary mono- and polyamines, at a temperature between 10* and 150* C.
Claim 4
Dependent Claim
26 words
Alpha-substituted imines according to claim 1 wherein said cycloaliphatic ketone is selected from the group of cyclopentanone, cyclohexanone, 1-methyl-cyclohexanone-(2), 1-cyclohexyl cyclohexanone-(2), cyclohexadione-(1,4), acetyl cyclohexanone, and cyclododecanone.
Claim 5
Dependent Claim
35 words
Alpha-substituted imines according to claim 1 wherein said amine is a monoamine selected from the group of methylamine, ethylamine, propylamine, isopropylamine, butylamine, isobutylamine, t-butylamine, amylamine, allylamine, isoamylamine, dodecylamine, tetradecylamine, benzylamine, aniline, and o-, m-and p-toluidine.
Claim 6
Dependent Claim
45 words
Alpha-substituted imines according to claim 1 wherein said amine is a polyamine selected from the group of ethylene diamine, propylene diamine, 1,4-diaminobutane, hexamethylene diamine, trimethyl hexamethylene diamine, m- and p-xylylenediamine, isophorone diamine, 2,4-diamino-toluene, 2,6-diaminotoluene, 4-amino-2-acetylamino toluene, dimethyl-(4-aminobenzyl)-amine, 1,3-bis-aminomethyl-4,6-di-methyl benzene, 2,4-diamino-3,5-diethyl toluene, 2,4-diamino-1,3,5-triisopropylbenzene, and 4,4''-diaminodiphenyl methane.
Claim 7
Dependent Claim
14 words
Alpha-substituted imines according to claim 1 consisting principally of a compound having the formula:
Claim 8
Dependent Claim
14 words
Alpha-substituted imine according to claim 1 consisting primarily of a compound having the formula
Claim 9
Dependent Claim
61 words
Alpha-substituted imines according to claim 1 comprising the reaction product of a. an electrophilic olefin selected from the group of acrylic acid methyl ester, acrylic acid butyl ester, maleic acid methyl ester, and maleic dimethyl ester; and b. a ketimine consisting of the reaction product of cyclohexanone with an amine selected from the group of benzylamine, hexamethylenediamine, 1,3-xylylenediamine, and 4, 4''-diamino-diphenylmethane.
Claim 10
Dependent Claim
17 words
Process for the preparation of alpha-substituted imines which comprises reacting a. an electrophilic olefin having the formula
Claim 11
Dependent Claim
14 words
Process of claim 9 wherein the electrophilic olefin is added dropwise to the ketimine.
Claim 12
Dependent Claim
12 words
Process of claim 9 wherein the reaction is carried out under pressure.
Claim 13
Dependent Claim
14 words
Process of claim 9 wherein the reaction is carried out in an inert solvent.
Claim 14
Dependent Claim
19 words
Process of claim 9 wherein the reaction is carried out at a temperature of from 20* to 80* C.
Claim 15
Dependent Claim
17 words
Process of claim 9 wherein the reaction is carried out in the presence of a basic catalyst.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1976-06-25 | 1976-12-25 | 1977-06-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-06-25 | 1980-12-25 | 1981-06-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-06-25 | 1984-12-25 | 1985-06-26 | $7700.00 | Window Closed / Lapsed |