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US4668775A Expired / Lapsed US ⏱️ 0.0 years remaining

α-methine substituted thiophene monoazo dye

Assignee: BASF SE
•
Filing: 1985-07-24
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Granted: 1987-05-26
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Expires: 2005-07-24
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Abstract

Abstract A compound of the formula: ##STR1## wherein K is a radical of a coupling component, R is a radical of a methylene-active compound, X is hydrogen or unsubstituted or substituted alkyl, aryl, or hetaryl and Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl. The present compound is useful for the dyeing of polyesters, nylons, cellulose esters and blends of polyesters and cellulose fibers.

Inventors

  • 👤 Udo Bergmann
  • 👤 Erwin Hahn
  • 👤 Guenter Hansen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 17:25
CPC Classifications
C; C09; C09B; C09B56/00; C09B56/16; Y; Y10; Y10S; Y10S534/00; Y10S534/02

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 904 words
A compound of formula I: ##STR146## wherein X 2 is cyano and Y 2 is CN, NO 2 , CH 3 CO, C 2 H 5 CO, C 3 H 7 CO, C 4 H 9 CO, C 5 H 11 CO, C 7 H 15 CO, (C 4 H 9 )(C 2 H 5 )CHCO, C 6 H 5 CO, CH 3 C 6 H 4 CO, ClC 6 H 4 CO, (CH 3 ) 2 C 6 H 3 CO, CH 3 OC 6 H 4 CO, Cl 2 C 6 H 2 CO, CH 3 SO 2 , C 2 H 5 SO 2 , C 4 H 9 SO 2 , C 6 H 5 SO 2 , CH 3 C 6 H 4 SO 2 , ClC 6 H 4 SO 2 , carboxyl, COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 , COOC 6 H 13 , COOC 8 H 17 , (C 4 H 9 )(C 2 H 5 )CHCH 2 OOC, CH 3 OC 2 H 4 OOC, C 2 H 5 OC 2 H 4 OOC, C 4 H 9 OC 2 H 4 OOC, C 6 H 5 OOC, CH 3 C 6 H 4 OOC, CONH 2 , CONHCH 3 , CONHC 2 H 5 , CONHC 4 H 9 , CONHC 6 H 5 , CONHC 6 H 13 , CONH(C 6 H 4 --CH 3 --p), CONHC 8 H 17 , CON(CH 3 ) 2 , CON(C 2 H 5 ) 2 , CON(C 4 H 9 ) 2 , (CH 3 )(C 2 H 5 )NOC, CONH(C 6 H 4 --OCH 3 --p), CONH(C 6 H 3 --OCH 3 --m, --OCH 3 --p), CONH(C 6 H 4 --Cl--p), C 6 H 5 , C 6 H 4 --NO 2 --p, C 6 H 4 --Cl--p, C 6 H 4 --OCH 3 --p, ##STR147## or group ##STR148## is a member selected from the group consisting of ##STR149## X is hydrogen C 1 -C 8 -alkyl, C 1 -C 8 -alkyl substituted by chlorine, bromine or phenyl, thienyl, furyl, phenyl or phenyl substituted by chlorine, bromine, methyl, ethyl, methoxy, ethoxy or nitro; Y is cyano, nitro, CH 3 CO, C 2 H 5 CO, C 3 H 7 CO, C 4 H 9 CO, C 5 H 11 CO, C 7 H 15 CO, ##STR150## C 6 H 5 CO, CH 3 C 6 H 4 CO, ClC 6 H 4 CO, (CH 3 ) 2 C 6 H 3 CO, H 3 COC 6 H 4 CO, Cl 2 C 6 H 3 CO, CH 3 SO 2 , C 2 H 5 SO 2 , C 4 H 9 SO 2 , C 6 H 5 SO 2 , CH 3 C 6 H 4 SO 2 , ClC 6 H 4 SO 2 , carboxyl, COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 , COOC 6 H 13 , COOC 8 H 17 , COOCH 2 CH(C 4 H 9 )(C 2 H 5 ), COOC 2 H 4 OCH 3 , COOC 2 H 4 OC 2 H 5 , COOC 2 H 4 OC 4 H 9 , COOC 6 H 5 , COOC 6 H 4 CH 3 , CONH 2 , CONHCH 3 , CONHC 2 H 5 , CONHC 4 H 9 , CONHC 6 H 13 , CONHC 8 H 17 , CON(CH 3 ) 2 , CON(C 2 H 5 ) 2 , CON(C.sub. 4 H 9 ) 2 , CON(CH 3 )(C 2 H 5 ), ##STR151## and K is derived from HK which is a compound selected from the group consisting of: ##STR152## where R 1 is hydrogen, C 1 -C 8 -alkyl, phenyl, o-, m- or p-tolyl, o-, m- or p-chlorophenyl, benzyl or phenethyl; R 2 is hydrogen or R 3 ; R 3 is C 1 -C 6 -alkyl, allyl, methallyl, cyclohexyl, phenethyl, benzyl, phenyl, or C 1 -C 6 -alkyl substituted by chlorine, bromine, hydroxyl, C 1 -C 8 -alkoxy, phenoxy, cyano, carboxyl, C 1 -C 8 -alkanoyloxy, C 1 -C 8 -alkoxy-C 1 -C 4 -alkoxy, benzyoloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C 1 -C 8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkoxy-alkoxycarbonyloxy, benzyloxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C 1 -C 8 -alkylaminocarbonyloxy, cyclohexylaminocarbonyloxy, phenylaminocarbonyloxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C 1 -C 4 -alkoxy or phenethoxycarbonyl; R 2 and R 3 together with the nitrogen form pyrrolidino, piperidino or morpholino; R 4 and R 5 independently of one another are each hydrogen, methyl, ethyl, propyl, methoxy, ethoxy, phenoxy, halogen, C 1 -C 4 -alkylsulfonylamino, C 1 -C 4 -dialkylaminosulfonylamino, C.sub. 1 -C 6 -alkanoylamino; R 6 is cyano, carbamyl, nitro, methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl, n-, iso- or sec-butoxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, n- or isopropoxyethoxycarbonyl or n-, iso- or sec-butoxyethoxycarbonyl, and R 7 is phenyl, C 1 -C 4 -alkyl, benzyl or phenyl mono- or polysubstituted by C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, phenoxy, benzoyloxy, phenyl, chlorine, bromine, nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -monoalkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkoxyethoxy, C 1 -C 4 -alkylmercapto, phenylmercapto or C 1 -C 5 -alkanoylamino.
Claim 2
Dependent Claim 904 words
A compound of formula I: ##STR146## wherein X 2 is cyano and Y 2 is CN, NO 2 , CH 3 CO, C 2 H 5 CO, C 3 H 7 CO, C 4 H 9 CO, C 5 H 11 CO, C 7 H 15 CO, (C 4 H 9 )(C 2 H 5 )CHCO, C 6 H 5 CO, CH 3 C 6 H 4 CO, ClC 6 H 4 CO, (CH 3 ) 2 C 6 H 3 CO, CH 3 OC 6 H 4 CO, Cl 2 C 6 H 2 CO, CH 3 SO 2 , C 2 H 5 SO 2 , C 4 H 9 SO 2 , C 6 H 5 SO 2 , CH 3 C 6 H 4 SO 2 , ClC 6 H 4 SO 2 , carboxyl, COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 , COOC 6 H 13 , COOC 8 H 17 , (C 4 H 9 )(C 2 H 5 )CHCH 2 OOC, CH 3 OC 2 H 4 OOC, C 2 H 5 OC 2 H 4 OOC, C 4 H 9 OC 2 H 4 OOC, C 6 H 5 OOC, CH 3 C 6 H 4 OOC, CONH 2 , CONHCH 3 , CONHC 2 H 5 , CONHC 4 H 9 , CONHC 6 H 5 , CONHC 6 H 13 , CONH(C 6 H 4 --CH 3 --p), CONHC 8 H 17 , CON(CH 3 ) 2 , CON(C 2 H 5 ) 2 , CON(C 4 H 9 ) 2 , (CH 3 )(C 2 H 5 )NOC, CONH(C 6 H 4 --OCH 3 --p), CONH(C 6 H 3 --OCH 3 --m, --OCH 3 --p), CONH(C 6 H 4 --Cl--p), C 6 H 5 , C 6 H 4 --NO 2 --p, C 6 H 4 --Cl--p, C 6 H 4 --OCH 3 --p, ##STR147## or group ##STR148## is a member selected from the group consisting of ##STR149## X is hydrogen C 1 -C 8 -alkyl, C 1 -C 8 -alkyl substituted by chlorine, bromine or phenyl, thienyl, furyl, phenyl or phenyl substituted by chlorine, bromine, methyl, ethyl, methoxy, ethoxy or nitro; Y is cyano, nitro, CH 3 CO, C 2 H 5 CO, C 3 H 7 CO, C 4 H 9 CO, C 5 H 11 CO, C 7 H 15 CO, ##STR150## C 6 H 5 CO, CH 3 C 6 H 4 CO, ClC 6 H 4 CO, (CH 3 ) 2 C 6 H 3 CO, H 3 COC 6 H 4 CO, Cl 2 C 6 H 3 CO, CH 3 SO 2 , C 2 H 5 SO 2 , C 4 H 9 SO 2 , C 6 H 5 SO 2 , CH 3 C 6 H 4 SO 2 , ClC 6 H 4 SO 2 , carboxyl, COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 , COOC 6 H 13 , COOC 8 H 17 , COOCH 2 CH(C 4 H 9 )(C 2 H 5 ), COOC 2 H 4 OCH 3 , COOC 2 H 4 OC 2 H 5 , COOC 2 H 4 OC 4 H 9 , COOC 6 H 5 , COOC 6 H 4 CH 3 , CONH 2 , CONHCH 3 , CONHC 2 H 5 , CONHC 4 H 9 , CONHC 6 H 13 , CONHC 8 H 17 , CON(CH 3 ) 2 , CON(C 2 H 5 ) 2 , CON(C.sub. 4 H 9 ) 2 , CON(CH 3 )(C 2 H 5 ), ##STR151## and K is derived from HK which is a compound selected from the group consisting of: ##STR152## where R 1 is hydrogen, C 1 -C 8 -alkyl, phenyl, o-, m- or p-tolyl, o-, m- or p-chlorophenyl, benzyl or phenethyl; R 2 is hydrogen or R 3 ; R 3 is C 1 -C 6 -alkyl, allyl, methallyl, cyclohexyl, phenethyl, benzyl, phenyl, or C 1 -C 6 -alkyl substituted by chlorine, bromine, hydroxyl, C 1 -C 8 -alkoxy, phenoxy, cyano, carboxyl, C 1 -C 8 -alkanoyloxy, C 1 -C 8 -alkoxy-C 1 -C 4 -alkoxy, benzyoloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C 1 -C 8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkoxy-alkoxycarbonyloxy, benzyloxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C 1 -C 8 -alkylaminocarbonyloxy, cyclohexylaminocarbonyloxy, phenylaminocarbonyloxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C 1 -C 4 -alkoxy or phenethoxycarbonyl; R 2 and R 3 together with the nitrogen form pyrrolidino, piperidino or morpholino; R 4 and R 5 independently of one another are each hydrogen, methyl, ethyl, propyl, methoxy, ethoxy, phenoxy, halogen, C 1 -C 4 -alkylsulfonylamino, C 1 -C 4 -dialkylaminosulfonylamino, C.sub. 1 -C 6 -alkanoylamino; R 6 is cyano, carbamyl, nitro, methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl, n-, iso- or sec-butoxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, n- or isopropoxyethoxycarbonyl or n-, iso- or sec-butoxyethoxycarbonyl, and R 7 is phenyl, C 1 -C 4 -alkyl, benzyl or phenyl mono- or polysubstituted by C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, phenoxy, benzoyloxy, phenyl, chlorine, bromine, nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -monoalkylamino, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkoxyethoxy, C 1 -C 4 -alkylmercapto, phenylmercapto or C 1 -C 5 -alkanoylamino.
Claim 3
Dependent Claim 418 words
The compound as claimed in claim 1, of the formula: ##STR153## wherein K' is derived from HK' which is an aniline compound of the formula: ##STR154## or a thiazole compound of the formula: ##STR155## wherein R 2 is hydrogen or R 3 , R 3 is C 1 -C 6 -alkyl, cyclohexyl, allyl, methallyl, phenethyl, benzyl, phenyl or C 1 -C 6 -alkyl substituted by chlorine, bromine, hydroxyl, C 1 -C 8 -alkoxy, phenoxy, cyano, carboxyl, C 1 -C 8 -alkanoyloxy, C 1 -C 8 -alkoxy-C 1 -C 4 -alkoxy, benzoyloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C 1 -C 8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkoxyalkoxycarbonyloxy, benzyloxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C 1 -C 8 -alkylaminocarbonyloxy, cyclohexylaminocarbonyloxy, phenylaminocarbonyloxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C 1 -C 4 -alkoxy or phenethyloxycarbonyl; R 2 and R 3 together with the nitrogen form pyrrolidino, piperidino or morpholino; R 4 and R 5 independently of one another are each hydrogen, methyl, ethyl, propyl, methoxy, ethoxy, phenoxy, halogen, C 1 -C 4 -alkylsulfonylamino, C 1 -C 4 -dialkylaminosulfonylamino, or C 1 -C 6 -alkanoylamino; and R 7 is phenyl, mono- or polysubstituted by C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, phenoxy, benzoyloxy, phenyl, chlorine, bromine, nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -monoalkylamino, C 1 - C 4 -dialkylamino, C 1 -C 4 -alkoxyethoxy, C 1 -C 4 -alkylmercapto, phenylmercapto or C 1 -C 5 -alkanoylamino, C 1-4 alkyl, C 1 -C 4 -alkoxycarbonylmethyl, cyanomethyl or benzyl; X is hydrogen, C 1-8 -alkyl, benzyl, phenethyl, or thienyl, furyl or phenyl which is unsubstituted or substituted by chlorine, bromine, methyl, ethyl, methoxy or ethoxy, and Y' is cyano, COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 , COOC 6 H 13 , COOC 8 H 17 , COOCH 2 CH(C 4 H 9 (C 2 H 5 ), COOC 2 H 4 OCH 3 , COOC 2 H 4 OC 2 H 5 , COOC 2 H 4 OC 4 H 9 , COOC 6 H 5 , COOC 6 H 4 CH 3 , CONHCH 3 , CONHC 2 H 5 , CONHC 4 H 9 , CONHC 6 H 13 , CONHC 8 H 17 , CON(CH 3 ) 2 , CON(C 2 H 5 ) 2 , CON(C 4 H 9 ) 2 , CON(CH 3 )(C 2 H 5 ), ##STR156##
Claim 4
Dependent Claim 53 words
The compound as claimed in claim 2, wherein said radical K is derived from a compound selected from the group consisting of ##STR157## wherein R is hydrogen, alkyl, aralkyl or aryl; R 2 -R 5 and R 7 are as defined in claim 2 and R 6 is cyano, carbamyl, nitro or carbalkoxy.
Claim 5
Dependent Claim 22 words
The compound as claimed in claim 2, wherein said radicals R 2 and R 3 together form a pyrrolidino, piperidino or morpholino.
Claim 6
Dependent Claim 22 words
The compound as claimed in claim 3, wherein said radicals R 2 and R 3 together form a pyrrolidino, piperidino or morpholino.
Claim 7
Dependent Claim 41 words
The compound of claim 2, wherein said R 4 and R 5 radicals are selected from the group consisting of hydrogen, methyl, ethyl, propyl, bromine, chlorine, methoxy, ethoxy, phenoxy, benzyloxy, C 1-6 alkanoylamino, benzylamino, C 1-4 alkylsulfonylamino and C 1-4 dialkylaminosulfonylamino.
Claim 8
Dependent Claim 41 words
The compound of claim 3, wherein said R 4 and R 5 radicals are selected from the group consisting of hydrogen, methyl, ethyl, propyl, bromine, chlorine, methoxy, ethoxy, phenoxy, benzyloxy, C 1-6 alkanoylamino, benzylamino, C 1-4 alkylsulfonylamino and C 1-4 dialkylaminosulfonylamino.
Claim 9
Dependent Claim 37 words
The compound as claimed in claim 3, wherein said R 6 radical is aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, diethylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, n- and isopropoxycarbonyl, n-, iso- and sec-butoxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, n- and isopropoxyethoxycarbonyl or n-, iso- or sec-butoxyethoxycarbonyl.
Claim 10
Dependent Claim 113 words
The compound claimed in claim 2, wherein said substituted alkyl is C 1-6 alkyl substituted by chlorine, bromine, hydroxyl, C 1 -C 8 -alkoxy, phenoxy, cyano, carboxyl, C 1 -C 8 -alkanoyloxy, C 1 -C 8 -alkoxy-C 1 -C 4 -alkoxy, benzoyloxy o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C 1 -C 8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkoxyalkoxycarbonyloxy, benzyloxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C 1 -C 8 -alkylaminocarbonyloxy, cyclohexylaminocarbonyloxy, phenylaminocarbonyloxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C 1 -C 4 -alkoxy or phenethyloxycarbonyl, said aryl radical is phenyl, said aralkyl radical is benzyl or phenethyl and said cycloalkyl radical is cyclohexyl.

References Cited (Backward Citations)

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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) 1990-05-25 1990-11-24 1991-05-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-05-25 1994-11-24 1995-05-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-05-25 1998-11-24 1999-05-26 $7700.00 Window Closed / Lapsed

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