← Back to Patent Explorer
US5268459A Expired / Lapsed US ⏱️ 0.0 years remaining

Azo dyes suitable for ink jet printing

Assignee: Syngenta Ltd
•
Filing: 1991-06-28
•
Granted: 1993-12-07
•
Expires: 2011-06-28
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## wherein: Ar and Ar 1 are each independently aryl or substituted aryl providing at least one of Ar and Ar 1 has at least one substituent selected from COOH and COSH; J and J 1 are each independently of formula (2), (3) or (4): ##STR2## each R 5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR 6 ; R 6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl; each T is independently alkyl; each W is independently selected from H, CN, CONR 10 R 11 , pyridinium and COOH; each m is an alkylene chain having 2 to 8 carbon atoms; B is H, alkyl or COOH; R 1 , R 2 , R 3 , R 4 , R 10 and R 11 are each independently H, alkyl or substituted alkyl; L is a divalent organic linking group; n is 0 or 1; each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR3## Z is OR 7 , SR 7 or NR 8 R 9 ; Y is H, Cl, CN or Z; E is Cl or CN; R 7 , R 8 and R 9 are independently H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring; provided (i) if the compound of Formula (1) has no --SO 3 H groups then it has at least two groups selected from --COOH and --COSH; and (ii) the compound of Formula (1) has at least as many groups selected from --COOH and --COSH as --SO 3 H groups. The compounds are useful for the preparation of inks for use in ink-jet printing.

Inventors

  • 👤 Peter Gregory
  • 👤 Ronald W. Kenyon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 08:42
CPC Classifications
C; C09; C09B; C09B31/00; C09D; C09D11/00; C09D11/30; C09D11/32; C09D11/328; C09B43/00; C09B43/12; C09B43/136; C09B43/16; C09B62/00; C09B62/02; C09B62/022; C09B62/026; C09B62/03

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 291 words
An anionic azo compound which, in the free acid form, has the formula (1): ##STR19## wherein: Ar and Ar 1 are each independently aryl or substituted aryl providing at least one of Ar and Ar 1 has at least one substituent selected from COOH and COSH; J and J 1 are each independently of formula (2), (3), or (4): ##STR20## each R 5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR 6 ; R 6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl; each T is independently alkyl; each W is independently selected from H, CN, CONR 10 R 11 , pyridinium and COOH; each m is an alkylene chain having 2 to 8 carbon atoms; B is H, alkyl or COOH; R 1 , R 2 , R 3 , R 4 , R 10 , and R 11 , are each independently H, alkyl or substituted alkyl; each L is a divalent organic linking group; n is 0 or 1; each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR21## each Z is OR 7 , SR 7 or NR 8 R 9 ; Y is H, Cl, CN or Z; E is Cl or CN; R 7 , R 8 , R 9 are independently H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring; provided (i); the compound of Formula (1) has at least three and (ii) the compound of Formula (1) has at least as many --COOH groups as --SO 3 H groups.
Claim 2
Dependent Claim 291 words
An anionic azo compound which, in the free acid form, has the formula (1): ##STR19## wherein: Ar and Ar 1 are each independently aryl or substituted aryl providing at least one of Ar and Ar 1 has at least one substituent selected from COOH and COSH; J and J 1 are each independently of formula (2), (3), or (4): ##STR20## each R 5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR 6 ; R 6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl; each T is independently alkyl; each W is independently selected from H, CN, CONR 10 R 11 , pyridinium and COOH; each m is an alkylene chain having 2 to 8 carbon atoms; B is H, alkyl or COOH; R 1 , R 2 , R 3 , R 4 , R 10 , and R 11 , are each independently H, alkyl or substituted alkyl; each L is a divalent organic linking group; n is 0 or 1; each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR21## each Z is OR 7 , SR 7 or NR 8 R 9 ; Y is H, Cl, CN or Z; E is Cl or CN; R 7 , R 8 , R 9 are independently H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring; provided (i); the compound of Formula (1) has at least three and (ii) the compound of Formula (1) has at least as many --COOH groups as --SO 3 H groups.
Claim 3
Dependent Claim 17 words
A compound according to claim 1 having at least as many --COOH as --SO 3 H groups.
Claim 4
Dependent Claim 18 words
A compound according to claim 1 having no --SO 3 H groups and at least two --COOH groups.
Claim 5
Dependent Claim 12 words
A compound according to claim 3 having at least three --COOH groups.
Claim 6
Dependent Claim 23 words
A compound according to any preceding claim wherein at least one of the Ar and Ar 1 has at least one --COOH substituent.
Claim 7
Dependent Claim 19 words
A compound according to claim 5 wherein each of Ar and Ar 1 has at least one --COOH substituent.
Claim 8
Dependent Claim 20 words
A compound according to claim 6 wherein each of Ar and and Ar 1 has at least two --COOH substituents.
Claim 9
Dependent Claim 15 words
A compound according to claim 7 wherein each of Ar and Ar 1 is dicarboxyphenyl.
Claim 10
Dependent Claim 40 words
A compound according to claim 1, 2, 3, or 4 wherein X is a group of Formula (5) and Z is selected from --NHC 2 H 4 OH, --N(C 2 H 4 OH) 2 , --NH(C 1-6 -alkyl) and morpholino.
Claim 11
Dependent Claim 303 words
An anionic azo compound which, in the free acid form, has the Formula (1): ##STR22## wherein: Ar and Ar 1 are each independently aryl or substituted aryl providing at least one of Ar and Ar 1 has at least one substituent selected from COOH and COSH: J and J 1 are each independently of formula (2), (3) or (4): ##STR23## each R 5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR 6 ; R 6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl; each T is independently alkyl; each W is independently selected from H, CN, CONR 10 R 11 , pyridinium and COOH; each m is an alkylene chain having 2 to 8 carbon atoms; B is H, alkyl or COOH; R 1 , R 2 , R 3 , R 4 , R 10 and R 11 are each independently H, alkyl or substituted alkyl; L is a divalent organic linking group; n is 1; each x is independently carbonyl or a group of the Formula (5), (6) or (7: ##STR24## Z is OR 7 , SR 7 or NR 8 R 9 ; Y is N, Cl, CN or Z; E is Cl or CN; R 7 , R 8 and R 9 are independently H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, phenyl, substituted phenyl, aralkyl or substituted aralkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring; provided (i) if the compound of Formula (1) has no --SO 3 H groups then it has at least two groups selected --COOH and --COSH; and (ii) the compound of Formula (I) has at least as many groups selected from --COOH and --COSH as --SO 3 H groups.
Claim 12
Dependent Claim 303 words
An anionic azo compound which, in the free acid form, has the Formula (1): ##STR22## wherein: Ar and Ar 1 are each independently aryl or substituted aryl providing at least one of Ar and Ar 1 has at least one substituent selected from COOH and COSH: J and J 1 are each independently of formula (2), (3) or (4): ##STR23## each R 5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR 6 ; R 6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl; each T is independently alkyl; each W is independently selected from H, CN, CONR 10 R 11 , pyridinium and COOH; each m is an alkylene chain having 2 to 8 carbon atoms; B is H, alkyl or COOH; R 1 , R 2 , R 3 , R 4 , R 10 and R 11 are each independently H, alkyl or substituted alkyl; L is a divalent organic linking group; n is 1; each x is independently carbonyl or a group of the Formula (5), (6) or (7: ##STR24## Z is OR 7 , SR 7 or NR 8 R 9 ; Y is N, Cl, CN or Z; E is Cl or CN; R 7 , R 8 and R 9 are independently H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, phenyl, substituted phenyl, aralkyl or substituted aralkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring; provided (i) if the compound of Formula (1) has no --SO 3 H groups then it has at least two groups selected --COOH and --COSH; and (ii) the compound of Formula (I) has at least as many groups selected from --COOH and --COSH as --SO 3 H groups.
Claim 13
Dependent Claim 23 words
A compound according to claim 10 wherein R 8 and R 9 are independently H, C 1-6 -alkyl or substituted C 1-6 -alkyl.
Claim 14
Dependent Claim 12 words
A compound according to claim 10 having at least three --COOH groups.
Claim 15
Dependent Claim 19 words
A compound according to claim 10 wherein each of Ar and Ar 1 has at least two --COOH substituents.
Claim 16
Dependent Claim 36 words
A compound according to claim 10 wherein X is a group of Formula (5) and Z is selected from --NHC 2 H 4 OH, --N(C 2 H 4 OH) 2 , --NH(C 1-6 -alkyl) and morpholino.

References Cited (Backward Citations)

US1594828A Cited
US1808849A Cited
US1845426A Cited
US2696486A Cited
US2777840A Cited
US3945990A Cited
DE2555533A1 Cited
US4474696A Cited
US4661158A Cited
US4605442A Cited
US4843150A Cited
US4997919A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-12-06 1997-06-07 1997-12-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-12-06 2001-06-07 2001-12-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-12-06 2005-06-07 2005-12-07 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag