← Back to Patent Explorer
US3935182A Expired / Lapsed US ⏱️ 0.0 years remaining

Water-soluble quaternary ammonium heterocyclic azo dyestuffs

Assignee: HD ACQUISITION CORP A CORP OF DE
•
Filing: 1973-02-14
•
Granted: 1976-01-27
•
Expires: 1993-02-14
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Water-soluble cationic dyestuffs of the formulae ##SPC1## Wherein R 0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R 1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NRO Y or R 1 and R 2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##EQU1## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge. k is a small integer whose value is dependent on the nature or A such that it has a range from one to two; R 8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 9 is lower-alkyl, hydroxy-lower-alkyl or NH 2 ; R 10 is lower-alkyl or lower-alkenyl; A 1 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; g is a small integer whose value is dependent on the nature of A 1 such that it has a range from one to two; R 8 ' is lower-alkyl; R 9 ' is lower-alkyl, lower alkenyl or hydroxy-lower-alkyl; R 10 ' is lower-alkyl, lower -alkenyl or hydroxy-lower-alkyl or R 9 ' and R 10 ' together with the nitrogen atom are morpholino; A 2 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; h is a small integer whose value is dependent on the nature of A 2 such that it has a range from one to two; and An is an anion Are particularly useful for coloring natural fibers, synthetic fiber-forming materials and cellulosic materials.

Inventors

  • 👤 Patrick J. Jefferies
  • 👤 Nathan N. Crounse

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 11:45
CPC Classifications
C; C09; C09B; C09B44/00; C09B44/02; Y; Y10; Y10S; Y10S8/00; Y10S8/916; Y10S8/919

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 129 words
A compound of the formula ##SPC46## wherein: R 0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R 1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR o Y; or R 1 and R 2 together with the nitrogen atom are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##EQU17## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; An is an anion; Y 1 is a divalent radical of the formula ##SPC47## in which Q 1 is hydrogen, lower-alkyl, lower-alkoxy or halogen; and Z is an azoic coupling radical of the formula ##SPC48## in which Q 2 , q 3 and Q 4 are each hydrogen, lower-alkyl, lower-alkoxy, hydroxy, nitro, amino, carbo-lower-alkoxy, carboxamido, sulphamyl or halogen; and R 4 is lower-alkyl, lower-alkoxy, carboxamido or carbo-lower-alkoxy.
Claim 2
Dependent Claim 129 words
A compound of the formula ##SPC46## wherein: R 0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R 1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR o Y; or R 1 and R 2 together with the nitrogen atom are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##EQU17## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; An is an anion; Y 1 is a divalent radical of the formula ##SPC47## in which Q 1 is hydrogen, lower-alkyl, lower-alkoxy or halogen; and Z is an azoic coupling radical of the formula ##SPC48## in which Q 2 , q 3 and Q 4 are each hydrogen, lower-alkyl, lower-alkoxy, hydroxy, nitro, amino, carbo-lower-alkoxy, carboxamido, sulphamyl or halogen; and R 4 is lower-alkyl, lower-alkoxy, carboxamido or carbo-lower-alkoxy.
Claim 3
Dependent Claim 55 words
A compound according to claim 1 wherein, (lower-alkylene) 1 is methylene, said dyestuff having the formula ##SPC49## in which Q 1 , Q 2 , Q 3 , Q 4 , R 0 , R 1 , R 2 , R 4 , Y and An have the same respective meanings indicated in claim 1.
Claim 4
Dependent Claim 41 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 , R 2 and R 4 are each methyl; Q 1 is methoxy, Q 3 is 4-methyl, and Q 2 , Q 4 and R 0 are each hydrogen.
Claim 5
Dependent Claim 44 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 and R 2 are each methyl; R 4 is carbamyl; Q 1 is methoxy; Y is formyl; and Q 2 , Q 3 , Q 4 and R 0 are each hydrogen.
Claim 6
Dependent Claim 45 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 , R 2 and R 4 are each methyl; Q 1 is methoxy; Q 3 is 4-sulfamyl; Y is formyl; and Q 2 , Q 4 , and R 0 are each hydrogen.
Claim 7
Dependent Claim 44 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 , R 2 and R 4 are each methyl; Q 1 is methoxy; Q 3 is 4-carbamyl; Y is formyl; and Q 2 , Q 4 and R 0 are each hydrogen.
Claim 8
Dependent Claim 43 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 , R 2 and R 4 are each methyl; Q 1 is methoxy; Q 2 and Q 4 are 2,5-dichloro; and Q 3 , R 0 and Y are each hydrogen.
Claim 9
Dependent Claim 45 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 and R 4 are each methyl; R 2 is 3-(YR 0 N-)propyl; Q 3 is 4-methyl; Q 1 is methoxy; and Q 3 , Q 4 R 0 and Y are each hydrogen.
Claim 10
Dependent Claim 43 words
The compound according to claim 2 wherein (lower-alkylene) is 1,3-propylene; R 1 , R 2 and R 4 are each methyl; Q 1 is methoxy, Q 3 is 4-methyl, and Q 2 , Q 4 , R 0 and Y are each hydrogen.
Claim 11
Dependent Claim 58 words
A compound according to claim 196 wherein c is one, (lower-alkylene) 1 is methylene, said dyestuff having the formula ##SPC50## in which Q 1 ; Q 2 , Q 3 , Q 4 , R 0 , R 1 , R 2 , R 4 , Y and An have the same respective meanings indicated in claim 196.
Claim 12
Dependent Claim 44 words
The compound according to claim 10 wherein (lower-alkylene) is 1,3-propylene; R 1 and R 4 are each methyl; R 2 is 3-(YR 0 N-)propyl; Q 3 is 4-methyl; Q 1 , Q 2 , Q 4 , R 0 and Y are each hydrogen.
Claim 13
Dependent Claim 46 words
A compound according to claim 1 wherein c is one, (lower-alkylene) 1 is methylene, said dyestuff having the formula ##SPC51## in which Q 1 , R 0 , R 1 , R 2 , Y and An have the same respective meanings indicated in claim 1.
Claim 14
Dependent Claim 30 words
The compound according to claim 12 wherein (lower-alkylene) is 1,3-propylene; R 0 is hydrogen; R 1 and R 2 are each methyl; Y is formyl; and Q 1 is methoxy.
Claim 15
Dependent Claim 90 words
A compound of the formula ##SPC52## wherein: Q 5 , q 5 ' and Q 6 are each hydrogen, lower-alkyl, lower-alkoxy or halogen; R 0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R 1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR 0 Y; or R 1 and R 2 together with the nitrogen atom are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; R 7 is hydrogen, lower-alkyl or cyano-lower-alkyl; Y is hydrogen or ##EQU18## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; and An is an anion.
Claim 16
Dependent Claim 90 words
A compound of the formula ##SPC52## wherein: Q 5 , q 5 ' and Q 6 are each hydrogen, lower-alkyl, lower-alkoxy or halogen; R 0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R 1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR 0 Y; or R 1 and R 2 together with the nitrogen atom are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; R 7 is hydrogen, lower-alkyl or cyano-lower-alkyl; Y is hydrogen or ##EQU18## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; and An is an anion.
Claim 17
Dependent Claim 40 words
A compound according to claim 14 wherein (lower-alkylene) is 1,3-propylene; Q 5 , Q 5 ' , Q 6 , R 0 and Y are each hydrogen; R 1 and R 2 are each methyl; and R 7 is ethyl.
Claim 18
Dependent Claim 71 words
A compound of the formula ##SPC53## wherein: Q 1 is hydrogen, lower-alkyl, lower-alkoxy or halogen; Q 2 , q 3 and Q 4 are each hydrogen, lower-alkyl, lower-alkoxy, hydroxy, nitro, amino, carbo-lower-alkoxy, carboxamido, sulphamyl or halogen; R 4 is lower-alkyl, lower-alkoxy, carboxamido or carbo-lower-alkoxy; R 8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 9 is lower-alkyl, hydroxy-lower-alkyl or NH 2 ; R 10 is lower-alkyl or lower-alkenyl; and An is an anion.
Claim 19
Dependent Claim 71 words
A compound of the formula ##SPC53## wherein: Q 1 is hydrogen, lower-alkyl, lower-alkoxy or halogen; Q 2 , q 3 and Q 4 are each hydrogen, lower-alkyl, lower-alkoxy, hydroxy, nitro, amino, carbo-lower-alkoxy, carboxamido, sulphamyl or halogen; R 4 is lower-alkyl, lower-alkoxy, carboxamido or carbo-lower-alkoxy; R 8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R 9 is lower-alkyl, hydroxy-lower-alkyl or NH 2 ; R 10 is lower-alkyl or lower-alkenyl; and An is an anion.
Claim 20
Dependent Claim 24 words
The compound according to claim 16 wherein Q 1 is lower-alkoxy; R 9 is hydroxy-lower-alkyl; and R 8 and R 10 are each lower-alkyl.
Claim 21
Dependent Claim 39 words
The compound according to claim 17 wherein Q 1 is methoxy; Q 2 and Q 4 are each hydrogen; Q 3 is 4-methyl; R 4 , R 8 and R 10 are each methyl; and R 9 is 2-hydroxyethyl.

References Cited (Backward Citations)

US2151518A Cited
US2972508A Cited
US3119810A Cited
US3117960A Cited
US3271383A Cited
US3541076A Cited
US3635940A Cited
US3524842A Cited
US3577404A Cited
US3549612A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-26 1979-07-28 1980-01-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-26 1983-07-28 1984-01-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-26 1987-07-28 1988-01-27 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag