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US4283540A
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Process for the preparation of cationic naphtholactam dyestuffs
Assignee: Bayer AG
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Filing: 1978-09-18
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Granted: 1981-08-11
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Expires: 1998-09-18
Abstract
Abstract Water-soluble cationic dyestuffs are prepared by the reaction of dyestuffs of the formula ##STR1## wherein R and R 1 represent alkyl, R 2 represents alkyl, aralkyl, cycloalkyl or aryl or represents alkylene which is bonded to the ring A in the o-position relative to the nitrogen atom, and An - represents an anion, and wherein the said radicals, the ring A and the naphthalene ring can contain nonionic substituents customary in dyestuff chemistry, and wherein at least one of the radicals R and R 1 contains a hydroxyl group or a halogen atom or another group which can be split off as an anion, with polyhydric alcohols in the presence of a catalyst.
Inventors
- 👤 Alfred Brack
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:14
CPC Classifications
C; C09; C09B; C09B57/00; C09B57/06
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
436 words
A process for the preparation of a dyestuff of the formula ##STR23## wherein R 3 ' and R 4 ' independently of one another represent C 1 -C 6 -alkyl, which can be substituted by a C 1 -C 4 -alkoxy, cyano, aminocarboxyl or C 1 -C 4 -alkoxycarbonyl group, and at least one of the radicals R 3 ' or R 4 ' is the radical ##STR24## n and n 1 independently of one another denote 0, 1 or 2, R 5 and R 5 ' independently of one another denote hydrogen, methyl, ethyl or hydroxyl, R 6 and R 6 ' independently of one another denote hydrogen, methyl or ethyl, or R 5 and R 6 conjointly denote methylene or ethylidene, D denotes a direct bond, vinylene, ethinylene, sulphur or --O--(CH 2 --CH 2 O) x , x=0, 1 or 2, R 2 ' represents C 1 -C 6 -alkyl, which can be substituted by a C 1- C 4 -alkoxy, cyano, aminocarbonyl or C 1 -C 4 -alkoxycarbonyl group; or represents phenyl, cyclopentyl, cyclohexyl, benzyl or phenylethyl, which, in the rings, can be substituted by 1-5 halogen or C 1 -C 4 -alkyl groups or by 1 or 2 hydroxyl, C 1 -C 4 -alkoxy or nitro groups, R 7 represents C 1 -C 6 -alkyl, halogen, hydroxyl, C 1 -C 4 -alkoxy, cyano, aminocarbonyl, C 1 -C 4 -alkoxycarbonyl, amino, acetylamino, mono- and di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulphonylamino, C 1 -C 4 -alkylmercapto, cyanoethylmercapto, phenylmercapto, phenylmercapto substituted by chlorine or methyl, or aminosulphonyl or C 1 -C 4 -alkylsulphonyl, R 8 represents hydrogen, methyl, ethyl or C 1 -C 4 -alkoxy or a R 8 which is in the o-position relative to the nitrogen represents, conjointly with R 2 , propylene-(1,2) ethylene, methyl-substituted propylene-(1,3) or methyl-substituted ethylene, m represents 0, 1 or 2 and An - represents an anion, consisting essentially reacting a dyestuff of the formula ##STR25## wherein R' and R 1 ' independently of one another represent C 1 -C 6 -alkyl, which can be substituted by a C 1 -C 4 -alkoxy, cyano, aminocarbonyl or C 1 -C 4 -alkoxycarbonyl group, and at least one of the radicals R' and R 1 ' is ethyl substituted by chlorine, bromine or hydroxyl, with a polyhyric alcohol of the formula ##STR26## at 80° to 160° C. in the presence of a catalyst selected from the group consisting of an aluminium oxide, active alumina, silica, active zeolite finely divided platinum, phosphorus pentoxide, polyphosphoric acid, phosphoric acid, sulfuric acid, titanium oxide, zirconium oxide, thorium oxide and polystyrene-sulphonic acids.
Claim 2
Dependent Claim
436 words
A process for the preparation of a dyestuff of the formula ##STR23## wherein R 3 ' and R 4 ' independently of one another represent C 1 -C 6 -alkyl, which can be substituted by a C 1 -C 4 -alkoxy, cyano, aminocarboxyl or C 1 -C 4 -alkoxycarbonyl group, and at least one of the radicals R 3 ' or R 4 ' is the radical ##STR24## n and n 1 independently of one another denote 0, 1 or 2, R 5 and R 5 ' independently of one another denote hydrogen, methyl, ethyl or hydroxyl, R 6 and R 6 ' independently of one another denote hydrogen, methyl or ethyl, or R 5 and R 6 conjointly denote methylene or ethylidene, D denotes a direct bond, vinylene, ethinylene, sulphur or --O--(CH 2 --CH 2 O) x , x=0, 1 or 2, R 2 ' represents C 1 -C 6 -alkyl, which can be substituted by a C 1- C 4 -alkoxy, cyano, aminocarbonyl or C 1 -C 4 -alkoxycarbonyl group; or represents phenyl, cyclopentyl, cyclohexyl, benzyl or phenylethyl, which, in the rings, can be substituted by 1-5 halogen or C 1 -C 4 -alkyl groups or by 1 or 2 hydroxyl, C 1 -C 4 -alkoxy or nitro groups, R 7 represents C 1 -C 6 -alkyl, halogen, hydroxyl, C 1 -C 4 -alkoxy, cyano, aminocarbonyl, C 1 -C 4 -alkoxycarbonyl, amino, acetylamino, mono- and di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulphonylamino, C 1 -C 4 -alkylmercapto, cyanoethylmercapto, phenylmercapto, phenylmercapto substituted by chlorine or methyl, or aminosulphonyl or C 1 -C 4 -alkylsulphonyl, R 8 represents hydrogen, methyl, ethyl or C 1 -C 4 -alkoxy or a R 8 which is in the o-position relative to the nitrogen represents, conjointly with R 2 , propylene-(1,2) ethylene, methyl-substituted propylene-(1,3) or methyl-substituted ethylene, m represents 0, 1 or 2 and An - represents an anion, consisting essentially reacting a dyestuff of the formula ##STR25## wherein R' and R 1 ' independently of one another represent C 1 -C 6 -alkyl, which can be substituted by a C 1 -C 4 -alkoxy, cyano, aminocarbonyl or C 1 -C 4 -alkoxycarbonyl group, and at least one of the radicals R' and R 1 ' is ethyl substituted by chlorine, bromine or hydroxyl, with a polyhyric alcohol of the formula ##STR26## at 80° to 160° C. in the presence of a catalyst selected from the group consisting of an aluminium oxide, active alumina, silica, active zeolite finely divided platinum, phosphorus pentoxide, polyphosphoric acid, phosphoric acid, sulfuric acid, titanium oxide, zirconium oxide, thorium oxide and polystyrene-sulphonic acids.
Claim 3
Dependent Claim
21 words
A process according to claim 1, wherein aluminium oxide, silica, active alumina (bleaching earth) or platinum is used as the catalyst.
Claim 4
Dependent Claim
100 words
A process according to claim 1 in which the polyhyric alcohol has the formula HO--CH.sub.2 --D'--CH.sub.2 --OH in which D' is a direct bond, methylene, ethylene or a radical of the formula --CH.sub.2 --O--(CH.sub.2 --CH.sub.2 --O).sub.x' --CH.sub.2 --, and x' is 0, 1 or 2, and the starting dyestuff has the formula ##STR27## in which R" 2 and R" 3 independently of one another represent methyl, ethyl, β-cyanoethyl, n- or iso-propyl or n-butyl, R 7 ' represents hydrogen, chlorine or bromine and Z' represents chlorine or hydroxyl, Z' being replaced in the end product by --O--CH 2 --D'--CH 2 --OH.
Claim 5
Dependent Claim
16 words
A process according to claim 3, in which the polyhydric alcohol is ethylene glycol or 1,3-dihydroxypropane.
Claim 6
Dependent Claim
16 words
A process according to claim 4, in which the polyhydric alcohol is ethylene glycol or 1,3-dihydroxypropane.
Claim 7
Dependent Claim
94 words
A process according to claim 1 in which the polyhydric alcohol has the formula HO--CH.sub.2 --D'--CH.sub.2 --OH in which D' is a direct bond, methylene, ethylene or a radical of the formula --CH.sub.2 --O--(CH.sub.2 --CH.sub.2 --O).sub.x' --CH.sub.2 --, and and the starting dyestuff has the formula ##STR28## in which R" 2 and R" 3 independently of one another represent methyl, ethyl, β-cyanoethyl, n- or iso-propyl or n-butyl, R 7 ' represents hydrogen, chlorine or bromine and Z' represents chlorine or hydroxyl, Z' being replaced in the end product by --O--CH 2 --D'--CH 2 --OH.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-10 | 1985-02-09 | 1985-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-10 | 1989-02-09 | 1989-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-10 | 1993-02-09 | 1993-08-11 | $7700.00 | Window Closed / Lapsed |