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US4525583A Expired / Lapsed US ⏱️ 0.0 years remaining

Quaternary ammonium substituted benzothiazolylphenyl azo pyrimidine dyes

Assignee: BASF Corp
•
Filing: 1983-01-13
•
Granted: 1985-06-25
•
Expires: 2003-01-13
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Abstract

Abstract Benzthiazole compounds of the formula ##STR1## or a tautomeric form thereof, in which KK is the radical of a pyrimidine coupling compound as defined, W is a radical of the formula --CH 2 --NH--CO--C 1 --C 4 -alkyl-Q.sup.⊕ An.sup.⊖ in which An is an anion and Q is a quaternary radical of the formula ##STR2## in which R 1 to R 6 independently of one another are a substituted or unsubstituted C 1 -C 4 -alkyl radical, or the radicals R 1 and R 2 , or R 3 and R 4 , or R 3 and R 4 and R 5 , together with the N atom, form a heterocyclic ring, m is the number 1, 2 or 3 and n is the number 0 or 1, and in which the benzene radicals A, B and/or C may be further substituted are particularly suitable as dyes for paper, brilliant yellow to orange dyeings which have, in particular, good wet-fastness and light-fastness, being obtained.

Inventors

  • 👤 Jean-Marie Adam

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 10:18
CPC Classifications
C; C09; C09B; C09B44/00; C09B44/02; C09B44/08

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 338 words
A benzthiazole compound of the formula ##STR36## in which KK is the radical of a pyrimidine coupling component of the formula ##STR37## in which X and Z independently of one another are O or NH, Y is the group O, NH, S or N--CN, U and V independently of one another are hydrogen, C 1 -C 4 -alkyl which is unsubstituted or substituted by hydroxy or phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, halogen or C 1 -C 4 alkoxy, or one of the radicals U or V is CN and the other is hydrogen, X 1 is C 1 -C 4 -alkyl, Y 1 is hydrogen, NH--C 1 -C 4 -alkyl, NH-phenyl, N--(C 1 -C 4 -alkyl) 2 , phenyl or C 1 -C 4 -alkyl and V 1 is hydrogen, C 1 -C 4 -alkyl which is unsubstituted or substituted by hydroxy or phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, halogen or C 1 -C 4 alkoxy, W is a radical of the formula --CH 2 --NH--CO--C 1 -C 4 -alkyl-Q.sup.⊕ An.sup.⊖ in which An is an anion and Q is a quaternary radial of the formula ##STR38## in which R 1 to R 6 independently of one another are C 1 -C 4 -alkyl which is unsubstituted or substituted by hydroxy, or the radicals R 1 and R 2 , or R 3 and R 4 together with the N atom to which they are attached form a heterocyclic ring selected from morpholine, pyrrolidine, piperidine or piperazine, or R 3 and R 4 and R 5 , together with the N atom to which they are attached, form a heterocyclic ring selected from pyridinium which is unsubstituted or substituted by C 1 -C 4 alkyl or ##STR39## m is the number 1, 2 or 3 and n is the number 0 or 1, and in which the benzene radicals A, B and C independently are unsubstituted or are substituted by C 1 -C 4 alkyl.
Claim 2
Dependent Claim 338 words
A benzthiazole compound of the formula ##STR36## in which KK is the radical of a pyrimidine coupling component of the formula ##STR37## in which X and Z independently of one another are O or NH, Y is the group O, NH, S or N--CN, U and V independently of one another are hydrogen, C 1 -C 4 -alkyl which is unsubstituted or substituted by hydroxy or phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, halogen or C 1 -C 4 alkoxy, or one of the radicals U or V is CN and the other is hydrogen, X 1 is C 1 -C 4 -alkyl, Y 1 is hydrogen, NH--C 1 -C 4 -alkyl, NH-phenyl, N--(C 1 -C 4 -alkyl) 2 , phenyl or C 1 -C 4 -alkyl and V 1 is hydrogen, C 1 -C 4 -alkyl which is unsubstituted or substituted by hydroxy or phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, halogen or C 1 -C 4 alkoxy, W is a radical of the formula --CH 2 --NH--CO--C 1 -C 4 -alkyl-Q.sup.⊕ An.sup.⊖ in which An is an anion and Q is a quaternary radial of the formula ##STR38## in which R 1 to R 6 independently of one another are C 1 -C 4 -alkyl which is unsubstituted or substituted by hydroxy, or the radicals R 1 and R 2 , or R 3 and R 4 together with the N atom to which they are attached form a heterocyclic ring selected from morpholine, pyrrolidine, piperidine or piperazine, or R 3 and R 4 and R 5 , together with the N atom to which they are attached, form a heterocyclic ring selected from pyridinium which is unsubstituted or substituted by C 1 -C 4 alkyl or ##STR39## m is the number 1, 2 or 3 and n is the number 0 or 1, and in which the benzene radicals A, B and C independently are unsubstituted or are substituted by C 1 -C 4 alkyl.
Claim 3
Dependent Claim 26 words
A benzthiazole compound according to claim 1 wherein the benzene radials A, B and C are not further substituted except, where relevant, by the substitutent W.
Claim 4
Dependent Claim 11 words
A benzthiazole compound according to claim 1 wherein n is 0.
Claim 5
Dependent Claim 11 words
A benzthiazole compound according to claim 1 wherein m is 1.
Claim 6
Dependent Claim 20 words
A benzthiazole compound according to claim 1 wherein KK is ##STR40## in which X, Y and Z are each 0.
Claim 7
Dependent Claim 23 words
A benzthiazole compound according to claim 1 wherein KK is ##STR41## in which X and Z are each 0 and Y is NH.
Claim 8
Dependent Claim 43 words
A benzthiazole compound according to claim 1 wherein KK is ##STR42## in which U and V independently of one another are hydrogen, CH 3 or chlorophenyl or in which one of the radicals U and V is hydrogen and the other is CN.
Claim 9
Dependent Claim 11 words
A benzthiazole compound according to claim 1 wherein W is ##STR43##
Claim 10
Dependent Claim 11 words
A benzthiazole compound according to claim 1 wherein W is ##STR44##

References Cited (Backward Citations)

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US3609136A Cited
US3577404A Cited
US4071312A Cited
US4071312B1 Cited
US3933787A Cited
US4211697A Cited
EP0034725A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-06-24 1988-12-24 1989-06-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-06-24 1992-12-24 1993-06-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-06-24 1996-12-24 1997-06-25 $7700.00 Window Closed / Lapsed

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