US4264495A
Expired / Lapsed
US
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2-Thienyl azo dyestuff compounds
Assignee: Novartis Corp
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Filing: 1972-05-15
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Granted: 1981-04-28
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Expires: 1992-05-15
Abstract
Abstract Azo compounds having the formula ##STR1## in which R 1 is cyano, aryl, an acyl radical or a carbamoyl radical, R 2 is hydrogen, alkyl, alkoxy, aralkyl or aryl, R 3 is alkyl, halogen, thiocyanato, arylazo or one of the substituents which R 1 can represent, and A is an aniline, tetrahydroquinoline, benzomorpholine or α-naphthylamine disperse azo dye coupling component. The azo compounds produce red to blue shades on polyamide, polyester and cellulose acetate fibers and exhibit improved fastness and dyeability properties on synthetic polyamide fibers.
Inventors
- 👤 Ronald J. Maher
- 👤 John G. Fisher
- 👤 Max A. Weaver
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 02:19
CPC Classifications
C; C09; C09B; C09B31/00; C09B31/02; C09B29/00; C09B29/0025; C09B29/0059; C09B29/06; C09B29/34; C09B29/36; C09B29/3604; C09B29/3617; C09B29/3643; C09B29/3686
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
305 words
A compound having the formula ##STR14## wherein R 1 is cyano; lower alkanoyl; benzoyl and benzoyl substituted with lower alkyl or lower alkoxy of 1-6 carbons, chlorine and bromine; lower alkoxycarbonyl; lower hydroxyalkoxycarbonyl; lower alkoxy-lower-alkoxycarbonyl; or the group --CONR 4 R 5 in which R 4 individually is hydrogen, lower alkyl, cyclohexyl, lower alkylcyclohexyl, cyclohexylmethylene, lower alkylcyclohexylmethylene, lower hydroxyalkylcyclohexylmethylene, or phenyl-lower-alkylene; R 5 individually is hydrogen or lower alkyl; and R 4 and R 5 in combination are pentamethylene; R 2 is hydrogen, lower alkyl, lower alkoxy, aryl-lower-alkylene or aryl; R 3 is aryl or a group which R 1 can represent; A is a disperse azo dye coupling component selected from an aniline having the formula ##STR15## wherein R 6 is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine, lower alkanoylamino, lower alkoxycarbonylamino, or ##STR16## R 7 is hydrogen, lower alkoxy, or when R 9 is hydrogen, R 7 is lower alkyl; R 8 individually is lower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, cyano, carbamoyl, lower alkylcarbamoyl, lower dialkylcarbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, lower alkanoyloxy, or lower alkoxycarbonyl; or cyclohexyl; R 9 individually is hydrogen; lower alkyl; or lower alkyl substituted with hydroxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyl; and R 8 and R 9 in combination are pentamethylene or ethyleneoxyethylene; a 1,2,3,4-tetrahydroquinoline having the formula ##STR17## wherein R 6 is as defined above; R 8 is as defined above; and R 11 and R 12 are hydrogen or methyl; a benzomorpholine having the formula ##STR18## in which R 6 and R 8 are as defined above and R 10 is hydrogen or lower alkyl; or an α-naphthylamine having the formula ##STR19## wherein R 8 is as defined above; in which each aryl moiety is phenyl or phenyl substituted with lower alkyl, lower alkoxy, chlorine, bromine, lower alkanoylamino, cyano or lower alkoxycarbonyl.
Claim 2
Dependent Claim
305 words
A compound having the formula ##STR14## wherein R 1 is cyano; lower alkanoyl; benzoyl and benzoyl substituted with lower alkyl or lower alkoxy of 1-6 carbons, chlorine and bromine; lower alkoxycarbonyl; lower hydroxyalkoxycarbonyl; lower alkoxy-lower-alkoxycarbonyl; or the group --CONR 4 R 5 in which R 4 individually is hydrogen, lower alkyl, cyclohexyl, lower alkylcyclohexyl, cyclohexylmethylene, lower alkylcyclohexylmethylene, lower hydroxyalkylcyclohexylmethylene, or phenyl-lower-alkylene; R 5 individually is hydrogen or lower alkyl; and R 4 and R 5 in combination are pentamethylene; R 2 is hydrogen, lower alkyl, lower alkoxy, aryl-lower-alkylene or aryl; R 3 is aryl or a group which R 1 can represent; A is a disperse azo dye coupling component selected from an aniline having the formula ##STR15## wherein R 6 is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine, lower alkanoylamino, lower alkoxycarbonylamino, or ##STR16## R 7 is hydrogen, lower alkoxy, or when R 9 is hydrogen, R 7 is lower alkyl; R 8 individually is lower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, cyano, carbamoyl, lower alkylcarbamoyl, lower dialkylcarbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, lower alkanoyloxy, or lower alkoxycarbonyl; or cyclohexyl; R 9 individually is hydrogen; lower alkyl; or lower alkyl substituted with hydroxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyl; and R 8 and R 9 in combination are pentamethylene or ethyleneoxyethylene; a 1,2,3,4-tetrahydroquinoline having the formula ##STR17## wherein R 6 is as defined above; R 8 is as defined above; and R 11 and R 12 are hydrogen or methyl; a benzomorpholine having the formula ##STR18## in which R 6 and R 8 are as defined above and R 10 is hydrogen or lower alkyl; or an α-naphthylamine having the formula ##STR19## wherein R 8 is as defined above; in which each aryl moiety is phenyl or phenyl substituted with lower alkyl, lower alkoxy, chlorine, bromine, lower alkanoylamino, cyano or lower alkoxycarbonyl.
Claim 3
Dependent Claim
148 words
A compound according to claim 1 having the formula ##STR20## wherein R 1 is lower alkoxycarbonyl, carbamoyl, or lower alkylcarbamoyl; R 2 is hydrogen, lower alkyl or aryl; R 3 is aryl, lower alkanoyl, benzoyl and benzoyl substituted with lower alkyl or lower alkoxy of 1-6 carbons, chlorine and bromine, or lower alkoxycarbonyl; R 6 is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine, lower alkanoylamino, lower alkoxycarbonylamino, or ##STR21## R 7 is hydrogen, lower alkoxy, or when R 9 is hydrogen, R 7 is lower alkyl; R 8 individually is lower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, cyano, carbamoyl, lower alkylcarbamoyl, lower dialkylcarbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, lower alkanoyloxy, or lower alkoxycarbonyl; or cyclohexyl; R 9 individually is hydrogen, lower alkyl, or lower alkyl substituted with hydroxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyl; and R 8 and R 9 in combination are pentamethylene or ethyleneoxyethylene.
Claim 4
Dependent Claim
81 words
A compound according to claim 1 having the formula ##STR22## wherein R 1 is lower alkoxycarbonyl, carbamoyl or lower alkylcarbamoyl; R 6 is hydrogen, methyl, lower alkanoylamino or lower alkoxycarbonylamino; R 7 is hydrogen or, when R 9 is hydrogen, R 7 is methyl; R 8 is lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl, lower alkanoyloxypropyl, carbamoylethyl, lower alkylcarbamoylethyl, lower alkanoylaminoethyl, lower alkanoylaminopropyl, lower alkoxycarbonylaminoethyl or lower alkoxycarbonylaminopropyl; and R 9 is hydrogen, lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl or lower alkanoyloxypropyl.
Claim 5
Dependent Claim
88 words
A compound according to claim 1 having the formula ##STR23## wherein R 1 and R 3 each is lower alkoxycarbonyl; R 2 is hydrogen, methyl or aryl; R 6 is hydrogen, methyl, lower alkanoylamino or lower alkoxycarbonylamino; R 7 is hydrogen, or, when R 9 is hydrogen, R 7 is methyl; R 8 is lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl, lower alkanoyloxypropyl, carbamoylethyl, lower alkylcarbamoylethyl, lower alkanoylaminoethyl, lower alkanoylaminopropyl, lower alkoxycarbonylaminoethyl or lower alkoxycarbonylaminopropyl; and R 9 is hydrogen, lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl or lower alkanoyloxypropyl.
Claim 6
Dependent Claim
81 words
A compound according to claim 1 having the formula ##STR24## wherein R 1 is lower alkoxycarbonyl, carbamoyl or lower alkylcarbamoyl; R 6 is hydrogen, methyl, lower alkanoylamino or lower alkoxycarbonylamino; R 7 is hydrogen or, when R 9 is hydrogen, R 7 is methyl; R 8 is lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl, lower alkanoyloxypropyl, carbamoylethyl, lower alkylcarbamoylethyl, lower alkanoylaminoethyl, lower alkanoylaminopropyl, lower alkoxycarbonylaminoethyl or lower alkoxycarbonylaminopropyl; and R 9 is hydrogen, lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl or lower alkanoyloxypropyl.
Claim 7
Dependent Claim
200 words
A compound of the formula ##STR25## wherein X is --CN; --COR; --CO-phenyl or --CO-phenyl substituted by --R, --OR, Cl or Br; --COOR--OH; --COOR; --COOR--OR; or --CONR 5 R 6 in which R 5 is individually H, --R, --C 6 H 11 --R, --R--C 6 H 11 , --C 6 H 11 , --R--C 6 H 11 --R, --R--C 6 H 11 --R--OH or --R-phenyl; R 6 is individually H or --R; and, R 5 and R 6 in combination are pentamethylene; Y is H, --R; --OR; phenyl or phenyl substituted by --R, --OR, Cl, Br, --NHCOR, --CN or --COOR; --R-phenyl or --R-phenyl substituted by --R, --OR, Cl, Br, --CN, --NHCOR or --COOR; Z is X, phenyl or phenyl substituted by --R, --OR, Cl, Br, --NHCOR, --CN or --COOR; R 1 is H, --R, --OR, Cl, Br, --NHCOR, --NHCOOR or --NHCO-phenyl; R 2 is H; --OR; or when R 4 is H, R 2 is --R; R 3 is --R, --R--OH, --R--OR, --R--CN, --R--CONH 2 , --R--CONHR, --R--CON(R) 2 , --R--NHCOR, --R--NHCOOR, --R--OCOR, --RCOOR or --R--C 6 H 11 ; R 4 is H, --R, --R--OH, --R--OR, --R--OCOR or --R--COOR; and R is alkyl or alkylene as the case may be.
Claim 8
Dependent Claim
200 words
A compound of the formula ##STR25## wherein X is --CN; --COR; --CO-phenyl or --CO-phenyl substituted by --R, --OR, Cl or Br; --COOR--OH; --COOR; --COOR--OR; or --CONR 5 R 6 in which R 5 is individually H, --R, --C 6 H 11 --R, --R--C 6 H 11 , --C 6 H 11 , --R--C 6 H 11 --R, --R--C 6 H 11 --R--OH or --R-phenyl; R 6 is individually H or --R; and, R 5 and R 6 in combination are pentamethylene; Y is H, --R; --OR; phenyl or phenyl substituted by --R, --OR, Cl, Br, --NHCOR, --CN or --COOR; --R-phenyl or --R-phenyl substituted by --R, --OR, Cl, Br, --CN, --NHCOR or --COOR; Z is X, phenyl or phenyl substituted by --R, --OR, Cl, Br, --NHCOR, --CN or --COOR; R 1 is H, --R, --OR, Cl, Br, --NHCOR, --NHCOOR or --NHCO-phenyl; R 2 is H; --OR; or when R 4 is H, R 2 is --R; R 3 is --R, --R--OH, --R--OR, --R--CN, --R--CONH 2 , --R--CONHR, --R--CON(R) 2 , --R--NHCOR, --R--NHCOOR, --R--OCOR, --RCOOR or --R--C 6 H 11 ; R 4 is H, --R, --R--OH, --R--OR, --R--OCOR or --R--COOR; and R is alkyl or alkylene as the case may be.
Claim 9
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR26##
Claim 10
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR27##
Claim 11
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR28##
Claim 12
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR29##
Claim 13
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR30##
Claim 14
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR31##
Claim 15
Dependent Claim
93 words
A compound according to claim 1 having the formula ##STR32## wherein R 1 is lower alkoxycarbonyl, carbamoyl, or lower alkylcarbamoyl; R 2 is hydrogen, lower alkyl or aryl; R 3 is aryl, lower alkanoyl, aroyl, or lower alkoxycarbonyl; R 6 is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine, lower alkanoylamino, lower alkoxycarbonylamino, or ##STR33## R 8 is lower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, cyano, carbamoyl, lower alkylcarbamoyl, lower dialkylcarbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, lower alkanoyloxy, or lower alkoxycarbonyl; or cyclohexyl; and R 11 and R 12 are hydrogen or methyl.
Claim 16
Dependent Claim
41 words
A compound according to claim 13 wherein R 6 is hydrogen, methyl, lower alkanoylamino or lower alkoxycarbonylamino; and R 8 is lower alkyl, hydroxyethyl, hydroxypropyl, lower alkanoyloxyethyl, lower alkanoyloxypropyl, carbamoylethyl, lower alkylcarbamoylethyl, lower alkanoylaminoethyl, lower alkanoylaminopropyl, lower alkoxycarbonylaminoethyl or lower alkoxycarbonylaminopropyl.
Claim 17
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR34##
Claim 18
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR35##
Claim 19
Dependent Claim
10 words
A compound according to claim 1 having the formula ##STR36##
Claim 20
Dependent Claim
83 words
A compound according to claim 1 having the formula ##STR37## wherein R 1 is lower alkoxycarbonyl, carbamoyl, or lower alkylcarbamoyl; R 2 is hydrogen, lower alkyl, or aryl; R 3 is aryl; lower alkanoyl; benzoyl and benzoyl substituted with lower alkyl or lower alkoxy of 1-6 carbons, chlorine and bromine; or lower alkoxycarbonyl; and R 8 is lower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, cyano, carbamoyl, lower alkylcarbamoyl, lower dialkylcarbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, lower alkanoyloxy, or lower alkoxycarbonyl; or cyclohexyl.
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) | 1984-04-27 | 1984-10-27 | 1985-04-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-27 | 1988-10-27 | 1989-04-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-27 | 1992-10-27 | 1993-04-28 | $7700.00 | Window Closed / Lapsed |