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US4026914A Expired / Lapsed US ⏱️ 0.0 years remaining

Styryl dyes

Assignee: Sandoz AG
•
Filing: 1975-09-29
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Granted: 1977-05-31
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Expires: 1995-09-29
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Abstract

Abstract Disclosed are compounds of formula I, <IMAGE> I in which R1 is C2-8alkylene or C5-8cycloalkylene, R2 is C5-8cycloalkyl, unsubstituted or substituted by up to 3 methyl groups; or C1-8alkyl, unsubstituted or substituted by a C1-4alkoxy, C1-4alkylthio, C1-4alkylcarbonyloxy, C1-4alkoxycarbonyloxy or C1-4alkoxycarbonyl, EITHER R3 is hydrogen, halogen, C1-4alkyl, C1-4alkoxy or C1-4alkoxycarbonyl, AND R4 is halogen, cyano, trifluoromethyl, C5-8cycloalkyl, C1-4alkoxy, C5-8cycloalkoxy, C1-4alkylthio, C5-8cycloalkylthio, phenyl, phenoxy, phenylthio, phenylthio-C1-4alkyl, phenyl-C1-4alkyl, phenoxy-C1-4alkyl, phenylazo, C1-4alkoxycarbonyl, C5-8-cycloalkoxycarbonyl, phenoxycarbonyl, benzoyl, benzoyloxy, phenoxycarbonyloxy, phenylsulphonyloxy or phenyl-C1-4alkylthio, OR R3 and R4 are located on adjacent carbon atoms and, together with such atoms, form a 5- or 6-membered, otherwise saturated, unsaturated or aromatic, carbo- or heterocyclic ring, optionally having a benzene ring fused thereto, and R5 is hydrogen, chlorine, bromine, methyl or methoxy; ANY ALKYL OR ALKOXY RADICAL AS R3 or R4 being optionally substituted by C1-4alkoxy, phenyl or C1-4alkoxycarbonyl; ANY CYCLOALKYL RADICAL OR MOIETY AS OR CONTAINED IN R3 or R4 being optionally substituted by up to 3 methyls or by C1-4alkoxy, phenyl or C1-4alkoxycarbonyl; ANY PHENYL RADICAL OR MOIETY AS OR CONTAINED IN R4 being optionally substituted by up to two substituents selected from halogen, methyl, C1-4alkoxy and C1-4alkoxycarbonyl, with the proviso that any alkoxy radical substituted by alkoxy is of at least two carbon atoms, their production and use as disperse dyes, particularly for polyester, cellulose acetate and synthetic polyamide substrates.

Inventors

  • 👤 Ulrich Zirngibl

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 19:20
CPC Classifications
D; D06; D06P; D06P1/00; D06P1/16; C; C09; C09B; C09B23/00; C09B23/14; C09B23/143; C09B57/00; Y; Y10; Y10S; Y10S8/00; Y10S8/92; Y10S8/921; Y10S8/922; Y10S8/924

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 296 words
A compound of formula I, ##STR29## in which R 1 is C 2 -8 alkylene or C 5 -8 cycloalkylene, R 2 is C 5 -8 cycloalkyl, unsubstituted or substituted by up to 3 methyl groups; or C 1 -8 alkyl, unsubstituted or substituted by a C 1 -4 alkoxy, C 1 -4 alkylthio, C 1 -4 alkylcarbonyloxy, C 1 -4 alkoxycarbonyloxy or C 1 -4 alkoxycarbonyl, either R 3 is hydrogen, halogen, C 1 -4 alkyl, C 1 -4 alkoxy or C 1 -4 alkoxycarbonyl, and R 4 is halogen, cyano, trifluoromethyl, C 5 -8 cycloalkyl, C 1 -4 alkoxy, C 5 -8 cycloalkoxy, C 1 -4 alkylthio, C 5 -8 cycloalkylthio, phenyl, phenoxy, phenylthio, phenylthio-C 1 -4 alkyl, phenyl-C 1 -4 alkyl, phenoxy-C 1 -4 alkyl, C 1 -4 alkoxycarbonyl, C 5 -8 -cycloalkoxycarbonyl, phenoxycarbonyl, benzoyl, benzoyloxy, phenoxycarbonyloxy, or phenyl-C 1 -4 alkylthio, or R 3 and R 4 are located on adjacent carbon atoms and, together with such atoms, form a 5- or 6-membered, otherwise saturated, unsaturated or aromatic, carbocyclic ring, optionally having a benzene ring fused thereto, and R 5 is hydrogen, chlorine, bromine, methyl or methoxy; any alkyl or alkoxy radical as R 3 or R 4 being optionally substituted by C 1 -4 alkoxy, phenyl or C 1 -4 alkoxycarbonyl; any cycloalkyl radical or moiety as or contained in R 4 being optionally substituted by up to 3 methyls or by C 1 -4 alkoxy, phenyl or C 1 -4 alkoxycarbonyl; any phenyl radical or moiety as or contained in R 4 being optionally substituted by up to two substituents selected from halogen, methyl, C 1 -4 alkoxy and C 1 -4 alkoxycarbonyl, with the proviso that any alkoxy radical substituted by alkoxy is of at least two carbon atoms.
Claim 2
Dependent Claim 296 words
A compound of formula I, ##STR29## in which R 1 is C 2 -8 alkylene or C 5 -8 cycloalkylene, R 2 is C 5 -8 cycloalkyl, unsubstituted or substituted by up to 3 methyl groups; or C 1 -8 alkyl, unsubstituted or substituted by a C 1 -4 alkoxy, C 1 -4 alkylthio, C 1 -4 alkylcarbonyloxy, C 1 -4 alkoxycarbonyloxy or C 1 -4 alkoxycarbonyl, either R 3 is hydrogen, halogen, C 1 -4 alkyl, C 1 -4 alkoxy or C 1 -4 alkoxycarbonyl, and R 4 is halogen, cyano, trifluoromethyl, C 5 -8 cycloalkyl, C 1 -4 alkoxy, C 5 -8 cycloalkoxy, C 1 -4 alkylthio, C 5 -8 cycloalkylthio, phenyl, phenoxy, phenylthio, phenylthio-C 1 -4 alkyl, phenyl-C 1 -4 alkyl, phenoxy-C 1 -4 alkyl, C 1 -4 alkoxycarbonyl, C 5 -8 -cycloalkoxycarbonyl, phenoxycarbonyl, benzoyl, benzoyloxy, phenoxycarbonyloxy, or phenyl-C 1 -4 alkylthio, or R 3 and R 4 are located on adjacent carbon atoms and, together with such atoms, form a 5- or 6-membered, otherwise saturated, unsaturated or aromatic, carbocyclic ring, optionally having a benzene ring fused thereto, and R 5 is hydrogen, chlorine, bromine, methyl or methoxy; any alkyl or alkoxy radical as R 3 or R 4 being optionally substituted by C 1 -4 alkoxy, phenyl or C 1 -4 alkoxycarbonyl; any cycloalkyl radical or moiety as or contained in R 4 being optionally substituted by up to 3 methyls or by C 1 -4 alkoxy, phenyl or C 1 -4 alkoxycarbonyl; any phenyl radical or moiety as or contained in R 4 being optionally substituted by up to two substituents selected from halogen, methyl, C 1 -4 alkoxy and C 1 -4 alkoxycarbonyl, with the proviso that any alkoxy radical substituted by alkoxy is of at least two carbon atoms.
Claim 3
Dependent Claim 92 words
A compound of claim 1, wherein R 1 is C 2 -4 alkylene, there being two carbon atoms between the N and O atoms, R 2 is C 2 -8 alkyl, unsubstituted or substituted by C 1 -4 alkoxy, C 1 -4 alkylthio, C 1 -4 alkylcarbonyloxy, C 1 -4 alkoxycarbonyloxy or C 1 -4 alkoxycarbonyl, R 3 is hydrogen, chlorine, bromine, C 1 -4 alkyl, C 1 -4 alkoxy or C 1 -4 alkoxycarbonyl, R 4 is as defined in claim 1 and R 5 is hydrogen, chlorine, methyl or methoxy.
Claim 4
Dependent Claim 60 words
A compound of claim 2, wherein R 2 is C 2 -8 alkyl, unsubstituted or substituted by a C 1 -4 alkoxy, and R 4 is chlorine, bromine, cyano, trifluoromethyl, cyclohexyl, C 1 -4 alkoxy, C 1 -4 alkylthio, phenyl, phenoxy, phenylthio, phenyl-C 1 -4 alkyl, phenyl-C 1 -4 alkoxy, phenoxy-C 1 -4 alkyl, C 1 -4 alkoxycarbonyl, or phenoxycarbonyl.
Claim 5
Dependent Claim 39 words
A compound of claim 2, wherein R 1 is 1,2-ethylene, 1,2-propylene or 1,2-butylene, the 1-C-atom being bound to the nitrogen, and R 2 is alkyl of 2 to 8 carbon atoms, unsubstituted or substituted by C 1 -4 alkoxy.
Claim 6
Dependent Claim 56 words
A compound of claim 3, wherein R 1 is 1,2-ethylene, 1,2-propylene or 1,2-butylene, the 1-C-atom being bound to the nitrogen, R 2 is unsubstituted C 2 -8 alkyl, R 3 is hydrogen, chlorine, bromine, C 1 -4 alkyl, C 1 -4 alkoxy or C 1 -4 alkoxycarbonyl and R 5 is hydrogen, chlorine, methyl or methoxy.
Claim 7
Dependent Claim 26 words
A compound of claim 5, wherein R 1 is 1,2-ethylene, R 4 is chlorine, bromine, cyano or C 1 -4 alkoxycarbonyl and R 5 is hydrogen.
Claim 8
Dependent Claim 17 words
A compound of claim 6, wherein at least one of R 3 and R 4 is chlorine.
Claim 9
Dependent Claim 14 words
A compound of claim 7, wherein both R 3 and R 4 are chlorine.
Claim 10
Dependent Claim 14 words
A compound of claim 6, wherein R 2 is unsubstituted C 2 -4 alkyl.
Claim 11
Dependent Claim 12 words
A compound of claim 9, wherein R 2 is ethyl or n-butyl.
Claim 12
Dependent Claim 8 words
A compound of claim 5, of formula ##STR30##

References Cited (Backward Citations)

US2850520A Cited
US3808256A Cited
US3808255A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-05-30 1980-11-29 1981-05-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-05-30 1984-11-29 1985-05-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-05-30 1988-11-29 1989-05-31 $7700.00 Window Closed / Lapsed

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