Patent US4038268A successfully refreshed from Google Patents.
US4038268A
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Process for preparing azo dyestuffs containing 2,4,6-tri-amino-3-(cyano ester or carbonamide)pyridine
Assignee: Bayer AG
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Filing: 1974-08-12
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Granted: 1977-07-26
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Expires: 1994-08-12
Abstract
Abstract Azo dyestuffs free of sulphonic acid groups and carboxylic acid groups are prepared by coupling a diazo compound with a coupler which is prepared by reacting an organic amine with a pyridinium salt having the formula ##STR1## IN WHICH R is substituted or unsubstituted alkyl, cycloalkyl, aralkyl or aryl; and R 1 is substituted or unsubstituted alkyl or aralkyl. The dyestuffs are suitable for dyeing and printing synthetic materials such as polyolefines, polyvinyl compounds, cellulose acetate and triacetate and polyesters to give yellow to blue dyeings and prints with good fastness properties especially to light and sublimation.
Inventors
- 👤 Karl Ludwig Moritz
- 👤 Karl Heinz Schundehutte
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 22:40
CPC Classifications
C; C09; C09B; C09B43/00; C09B43/11; C09B29/00; C09B29/34; C09B29/36; C09B29/3604; C09B29/3617; C09B29/3621; C09B29/3639; C09B31/00; C09B31/02; C09B31/12; C09B31/14; C09B31/153
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
272 words
A process for preparing an azo dyestuff comprising a. reacting ##STR21## with at least two equivalents of R 3 NH 2 at a temperature of 110° to 130° C. to form ##STR22## b. and then coupling IV, V or VI with diazotized DNH 2 wherein V and VI are prepared by converting IV to ##STR23## by reaction at the cyano group; in which D is the radical of a diazo component; R is C 1 -C 6 -alkyl; C 1 -C 6 -alkyl substituted by halogen, CN, OH, C 1 -C 4 -alkoxy or C 2 -C 5 -alkoxycarbonyl; cyclohexyl; methyl-cyclohexyl; phenyl; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or cyano; benzyl; phenethyl; or benzyl or phenethyl substituted with chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; R 1 and Q 3 are independently C 1 -C 6 -alkyl; C 1 -C 6 -alkyl substituted with halogen, cyano, hydroxyl, C 1 -C 4 -alkoxy or C 2 -C 5 -alkoxycarbonyl; benzyl; phenethyl; benzyl or phenethyl substituted by chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; Q 1 and Q 2 are independently of one another hydrogen, R or conjointly with the nitrogen atom form a morpholine, piperidine or pyrrolidine ring; and R 3 is C 1 -C 4 -alkyl; C 1 -C 4 -alkyl substituted by hydroxy, methoxy or ethoxy; benzyl; phenethyl; benzyl or phenethyl substituted by chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; phenyl; or phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or cyano.
Claim 2
Dependent Claim
272 words
A process for preparing an azo dyestuff comprising a. reacting ##STR21## with at least two equivalents of R 3 NH 2 at a temperature of 110° to 130° C. to form ##STR22## b. and then coupling IV, V or VI with diazotized DNH 2 wherein V and VI are prepared by converting IV to ##STR23## by reaction at the cyano group; in which D is the radical of a diazo component; R is C 1 -C 6 -alkyl; C 1 -C 6 -alkyl substituted by halogen, CN, OH, C 1 -C 4 -alkoxy or C 2 -C 5 -alkoxycarbonyl; cyclohexyl; methyl-cyclohexyl; phenyl; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or cyano; benzyl; phenethyl; or benzyl or phenethyl substituted with chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; R 1 and Q 3 are independently C 1 -C 6 -alkyl; C 1 -C 6 -alkyl substituted with halogen, cyano, hydroxyl, C 1 -C 4 -alkoxy or C 2 -C 5 -alkoxycarbonyl; benzyl; phenethyl; benzyl or phenethyl substituted by chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; Q 1 and Q 2 are independently of one another hydrogen, R or conjointly with the nitrogen atom form a morpholine, piperidine or pyrrolidine ring; and R 3 is C 1 -C 4 -alkyl; C 1 -C 4 -alkyl substituted by hydroxy, methoxy or ethoxy; benzyl; phenethyl; benzyl or phenethyl substituted by chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; phenyl; or phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or cyano.
Claim 3
Dependent Claim
25 words
Process of claim 1 in which R 3 NH 2 is a C 1 -C 4 -alkylamine; aniline; benzylamine; phenethylamine; γ-hydroxypropylamine, γ-ethoxypropylamine, β-methoxyethylamine or γ-methoxypropylamine.
Claim 4
Dependent Claim
12 words
Process of claim 1 in which R 3 NH 2 is benzylamine.
Claim 5
Dependent Claim
10 words
Process of claim 1 in which R 3 is benzyl.
Claim 6
Dependent Claim
13 words
Process of claim 1 in which said azo dyestuff has the formula ##STR24##
Claim 7
Dependent Claim
120 words
The process of claim 1 in which ##STR25## Y is halogen, nitro, cyano, CF 3 , C 2 -C 5 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonyl, C 2 -C 5 -alkoxycarbonyl, phenyl, ##STR26## Z is hydrogen, methyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitrile or halogen; V 1 and V 2 independently of one another are hydrogen or C 1 -C 4 -alkyl; n is the number 1 or 2; R and R 1 are C 1 -C 6 -alkyl, or C 1 -C 6 -alkyl substituted by OH, CN, halogen, C 1 -C 4 -alkoxy or C 2 -C 5 -alkylcarbonyl; and Q 1 and Q 2 are hydrogen or C 1 -C 4 -alkyl.
Claim 8
Dependent Claim
31 words
Process of claim 1 in which the cyano group is not converted; D is 4-methylsulphonylphenyl; R is CH 3 ; R 1 is CH 3 ; and R 3 is benzyl.
Claim 9
Dependent Claim
25 words
Process of claim 1 in which the cyano group is not converted; D is 6-methoxybenzthiazolyl-2; R is CH 3 ; and R 3 is benzyl.
Claim 10
Dependent Claim
37 words
Process of claim 1 in which the cyano group is not converted; D is 2,5-dichloro-4-sulphonamidophenyl; R is CH 3 ; R 1 is CH 3 ; and R 3 is --CH 2 --CH 2 --CH 2 OH.
Claim 11
Dependent Claim
41 words
Process of claim 1 in which the cyano group is not converted: D is 2-cyano-4-nitrophenyl; R is --CH 3 ; R 1 is --CH 3 ; and R 3 is --CH 2 --CH 2 --CH 2 --O--C 2 H 5 .
Claim 12
Dependent Claim
35 words
Process of claim 1 in which the cyano group is not converted; D is 3-phenyl-1,2,4-thiadiazolyl-5; R is CH 3 ; R 1 is CH 3 ; and R 3 is --CH 2 --CH 2 --OH.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |