Patent JPS6269656A successfully refreshed from Google Patents.
US4293687A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Tetraalkylated biscyclohexylamine derivatives
Assignee: Bayer AG
•
Filing: 1980-05-05
•
Granted: 1981-10-06
•
Expires: 2000-05-05
Abstract
Abstract New biscyclohexylamine derivatives represented by the following formula ##STR1## wherein R 1 to R 4 represent identical or different alkyl groups having 1 to 6 carbon atoms; X is a single bond, a divalent aliphatic straight-chain or branched-chain group having from 2 to 10 carbon atoms, a methylene group, when at least one of the substituents R 1 to R 4 has more than 1 carbon atom, a divalent cycloaliphatic group having from 6 to 12 carbon atoms, a divalent aliphatic straight-chain or branched-chain group with cycloaliphatic substituents having from 6 to 8 carbon atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 carbon atoms.
Inventors
- 👤 Oskar Weissel
- 👤 Volker Serini
- 👤 Hans-Josef Buysch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:15
CPC Classifications
C; C08; C08F; C08F12/00; C08F12/02; C08G; C08G71/00; C08G71/04
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
125 words
A biscyclohexylamine having the formula ##STR7## wherein: R 1 to R 4 each represents identical or different alkyl groups having 1 to 6 carbon atoms; X represents a single bond, a divalent straight-chain or branched-chain aliphatic group having from 2 to 10 carbon atoms, a methylene group, when at least one of said substituents R 1 to R 4 has more than 1 carbon atom, a divalent cycloaliphatic group having from 6 to 12 carbon atoms, a divalent aliphatic straight or branched chain group with cycloaliphatic substituents having from 6 to 8 carbon atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 carbon atoms.
Claim 2
Dependent Claim
125 words
A biscyclohexylamine having the formula ##STR7## wherein: R 1 to R 4 each represents identical or different alkyl groups having 1 to 6 carbon atoms; X represents a single bond, a divalent straight-chain or branched-chain aliphatic group having from 2 to 10 carbon atoms, a methylene group, when at least one of said substituents R 1 to R 4 has more than 1 carbon atom, a divalent cycloaliphatic group having from 6 to 12 carbon atoms, a divalent aliphatic straight or branched chain group with cycloaliphatic substituents having from 6 to 8 carbon atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 carbon atoms.
Claim 3
Dependent Claim
107 words
A biscyclohexylamine according to claim 1 wherein R 1 to R 4 are identical or different alkyl groups having from 1 to 3 carbon atoms, X is a single bond, a divalent aliphatic straight-chain or branched-chain group having from 2 to 4 carbon atoms, when R 1 to R 4 is a methyl group, a methylene group, when at least one of the substituents R 1 to R 4 having more than 1 carbon atom, a cyclohexylidene group, a divalent aliphatic group with cycloaliphatic substituents having 7 or 8 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 10 to 12 carbon atoms.
Claim 4
Dependent Claim
35 words
A biscyclohexylamine selected from the group consisting of bis(3,5-dimethyl-4-aminocyclohexyl); 1-(3,5)-dimethyl-4-aminocyclohexyl-1-(3'5'-diethyl-4'-aminocyclohexyl)propane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-ethane; 1,1-bis-(3,5-diethyl-4-amino-cyclohexyl)-ethane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-propane; 2,2-bis-(3,5-dimethyl-4-aminocyclohexyl)-propane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-butane; 2,2-bis-(3,5-dimethyl-4-aminocyclohexyl)-butane; 1,3-bis-(3,5-dimethyl-4-aminocyclohexyl)-3-methyl butane; 1,3-bis-(3,5-dimethyl-4-aminocyclohexyl)-butane; 1,3-bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclopentane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclohexane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclododecane; bis-(3,5-dimethyl-4-aminocyclohexyl)-phenyl methane; bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclohexyl methane; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-p-xylene; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-m-xylene; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-p-diisopropyl benzene; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-m-diisopropyl benzene; bis-(3,5-diethyl-4-aminocyclohexyl)-methane and bis-(3,5-diisopropyl-4-aminocyclohexyl)-methane.
Claim 5
Dependent Claim
35 words
A biscyclohexylamine selected from the group consisting of bis(3,5-dimethyl-4-aminocyclohexyl); 1-(3,5)-dimethyl-4-aminocyclohexyl-1-(3'5'-diethyl-4'-aminocyclohexyl)propane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-ethane; 1,1-bis-(3,5-diethyl-4-amino-cyclohexyl)-ethane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-propane; 2,2-bis-(3,5-dimethyl-4-aminocyclohexyl)-propane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-butane; 2,2-bis-(3,5-dimethyl-4-aminocyclohexyl)-butane; 1,3-bis-(3,5-dimethyl-4-aminocyclohexyl)-3-methyl butane; 1,3-bis-(3,5-dimethyl-4-aminocyclohexyl)-butane; 1,3-bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclopentane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclohexane; 1,1-bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclododecane; bis-(3,5-dimethyl-4-aminocyclohexyl)-phenyl methane; bis-(3,5-dimethyl-4-aminocyclohexyl)-cyclohexyl methane; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-p-xylene; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-m-xylene; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-p-diisopropyl benzene; α,α'-bis-(3,5-dimethyl-4-aminocyclohexyl)-m-diisopropyl benzene; bis-(3,5-diethyl-4-aminocyclohexyl)-methane and bis-(3,5-diisopropyl-4-aminocyclohexyl)-methane.
Claim 6
Dependent Claim
9 words
A biscyclohexylamine according to claim 1 which is 2,2-bis-(3,5-dimethyl-4-aminocyclohexyl)-propane.
Claim 7
Dependent Claim
9 words
A biscyclohexylamine according to claim 1 which is 1,1-bis-(3,5-dimethyl-4-amino-cyclohexyl)-n-butane.
Claim 8
Dependent Claim
148 words
A process for the preparation of a biscyclohexylamine of the formula ##STR8## wherein: R 1 to R 4 are identical or different alkyl substituents having from 1 to 6 C-atoms and X is a single bond, a divalent straight-chain or branched-chain aliphatic group having from 1 to 10 C-atoms, a divalent cycloaliphatic group having from 6 to 12 C-atoms, a divalent aliphatic straight-chain or branched-chain group with cycloaliphatic substituents having from 6 to 8 C-atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 C-atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 C-atoms, which comprises contacting a biscyclohexanol of the formula ##STR9## wherein R 1 to R 4 and X have the previously assigned significance, with ammonia at an elevated temperature and at an elevated pressure in the presence of hydrogen and a nickelchromium based hydrogenation catalyst.
Claim 9
Dependent Claim
148 words
A process for the preparation of a biscyclohexylamine of the formula ##STR8## wherein: R 1 to R 4 are identical or different alkyl substituents having from 1 to 6 C-atoms and X is a single bond, a divalent straight-chain or branched-chain aliphatic group having from 1 to 10 C-atoms, a divalent cycloaliphatic group having from 6 to 12 C-atoms, a divalent aliphatic straight-chain or branched-chain group with cycloaliphatic substituents having from 6 to 8 C-atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 C-atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 C-atoms, which comprises contacting a biscyclohexanol of the formula ##STR9## wherein R 1 to R 4 and X have the previously assigned significance, with ammonia at an elevated temperature and at an elevated pressure in the presence of hydrogen and a nickelchromium based hydrogenation catalyst.
Claim 10
Dependent Claim
15 words
A process according to claim 6 wherein the temperature is from 180° to 300° C.
Claim 11
Dependent Claim
35 words
A process according to claim 7 wherein the reaction is carried out at a hydrogen partial pressure of from 5 to 50 bar and at an ammonia partial pressure of from 150 to 500 bar.
Claim 12
Dependent Claim
23 words
A process according to claim 8 wherein the ammonia and the biscyclohexanol are used in a molar ratio of from 3:1 to 30:1.
Claim 13
Dependent Claim
55 words
A process according to claim 6 wherein the biscyclohexanol derivative is one which has been obtained by hydrogenation of a bisphenol represented by the formula ##STR10## wherein R 1 to R 4 and X have the previously assigned significance in the presence of a nickel/chromium hydrogenation catalyst without the bisphenol having been isolated or purified.
Claim 14
Dependent Claim
103 words
A process for producing 4,4'-diamino-3,3',5,5'-tetraalkyldicyclomethane of the formula ##STR11## wherein R 5 and R 6 may be the same or different and represent alkyl radicals of 1 to 6 carbon atoms which comprises: (a) condensing at least 1.8 mols of 2,6-dialkylphenol with 1 mol formaldehyde in the presence of oxalic acid and water and thereafter removing water so formed; (b) hydrogenating the condensation product from step (a) without isolating or purifying the same in the presence of a nickel-chromium catalyst, and (c) contacting the hydrogenation product of step (b) with ammonia, without isolating or purifying the same, at an elevated temperature and pressure.
Claim 15
Dependent Claim
103 words
A process for producing 4,4'-diamino-3,3',5,5'-tetraalkyldicyclomethane of the formula ##STR11## wherein R 5 and R 6 may be the same or different and represent alkyl radicals of 1 to 6 carbon atoms which comprises: (a) condensing at least 1.8 mols of 2,6-dialkylphenol with 1 mol formaldehyde in the presence of oxalic acid and water and thereafter removing water so formed; (b) hydrogenating the condensation product from step (a) without isolating or purifying the same in the presence of a nickel-chromium catalyst, and (c) contacting the hydrogenation product of step (b) with ammonia, without isolating or purifying the same, at an elevated temperature and pressure.
Claim 16
Dependent Claim
18 words
A process according to claim 11 wherein water formed during the reaction is removed as it is formed.
Claim 17
Dependent Claim
141 words
A polyamide obtained by reacting a biscyclohexylamine of the Formula ##STR12## wherein: R 1 to R 4 each represent identical or different alkyl groups having 1 to 6 carbon atoms; X represents a single bond, a divalent straight-chain or branched-chain aliphatic group having from 2 to 10 carbon atoms, a methylene group, when at least one of said substituents R 1 to R 4 has more than 1 carbon atom, a divalent cycloaliphatic group having from 6 to 12 carbon atoms, a divalent aliphatic straight or branched-chain group with cycloaliphatic substituents having from 6 to 8 carbon atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 carbon atoms with an aliphatic and/or aromatic dicarboxylic acid with up to 16 C-atoms.
Claim 18
Dependent Claim
141 words
A polyamide obtained by reacting a biscyclohexylamine of the Formula ##STR12## wherein: R 1 to R 4 each represent identical or different alkyl groups having 1 to 6 carbon atoms; X represents a single bond, a divalent straight-chain or branched-chain aliphatic group having from 2 to 10 carbon atoms, a methylene group, when at least one of said substituents R 1 to R 4 has more than 1 carbon atom, a divalent cycloaliphatic group having from 6 to 12 carbon atoms, a divalent aliphatic straight or branched-chain group with cycloaliphatic substituents having from 6 to 8 carbon atoms, a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 carbon atoms with an aliphatic and/or aromatic dicarboxylic acid with up to 16 C-atoms.
Claim 19
Dependent Claim
12 words
A biscyclohexylamine according to claim 1 wherein X is a single bond.
Claim 20
Dependent Claim
12 words
A biscyclohexylamine according to claim 1 wherein X is a methylene group.
Claim 21
Dependent Claim
14 words
A biscyclohexylamine according to claim 1 wherein X is a divalent branched aliphatic group.
Claim 22
Dependent Claim
12 words
A biscyclohexylamine according to claim 1 wherein X is an isopropyl group.
Claim 23
Dependent Claim
12 words
A polyamide according to claim 13 wherein X is a single bond.
Claim 24
Dependent Claim
12 words
A polyamide according to claim 13 wherein X is a methylene group.
Claim 25
Dependent Claim
14 words
A polyamide according to claim 13 wherein X is a divalent branched aliphatic group.
Claim 26
Dependent Claim
12 words
A polyamide according to claim 13 wherein X is an isopropyl group.
Claim 27
Dependent Claim
28 words
A polyamide according to claim 13 wherein said dicarboxylic acid is adipic acid, sebacic acid, decane dicarboxylic acid, dodecane dicarboxylic acid, azelaic acid, terephthalic acid and isophthalic acid.
References Cited (Backward Citations)
US2606928A
Cited
US2516585A
Cited
US3283002A
Cited
US3634512A
Cited
US3564834A
Cited
US3743677A
Cited
US3840501A
Cited
US4161492A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-05 | 1985-04-06 | 1985-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-05 | 1989-04-06 | 1989-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-05 | 1993-04-06 | 1993-10-06 | $7700.00 | Window Closed / Lapsed |