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US4083840A Expired / Lapsed US ⏱️ 0.0 years remaining

Disazo dyes having a 6-amino or substituted triazinylamino-1-hydroxynaphthalene-3-sulfonic acid coupling component radical

Assignee: Sandoz AG
•
Filing: 1976-04-19
•
Granted: 1978-04-11
•
Expires: 1996-04-19
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Abstract

Abstract Disclosed are compounds of the formula, <IMAGE> or WHEREIN D is, <IMAGE> X is -COOM or -SO3M, R1 and R2, independently, are hydrogen, halogen, C1-3alkyl or C1-3alkoxy, M IS 1, 2 OR 3, AND, WHEN 3, THE TWO SULPHO GROUPS ARE OTHER THAN ON ADJACENT CARBON ATOMS, N IS 1 OR 2, WITH THE PROVISO THAT THE SUM OF N + M IS 3 OR 4, R3 is hydrogen, C1-3alkyl or C1-3alkoxy, R4 is hydrogen or C1-3alkyl, R3 and R4, when both other than hydrogen, being in para position relative to each other, R is hydrogen or, <IMAGE> it being hydrogen only when D is, <IMAGE> in which the -COOM group is m- or p- to the azo linkage, R5 is -CHR6-CHR6-O-CHR7CH2O-pH, either both R6's are hydrogen, or one of the R6's is hydrogen, the other methyl or ethyl, R7 is hydrogen, methyl or ethyl, R8 is hydrogen, C1-6alkyl or -CHR6-CHR6-O-CHR7CH2O-qH, Y is -NR9R10 or -N(R11)-CHR6</=CHR6-O-CHR7CH2O-rH, R9 and R10, independently, are hydrogen or C1-6alkyl, preferably both not being simultaneously tertiary alkyl, R11 is hydrogen, C1-6alkyl or -CHR6-CHR6O-CHR7CH2-tH, p, q, r and t, independently, are 0, 1, 2 or 3, and M is hydrogen or a non-chromophoric cation, their production and use in the dyeing of paper and leather, particularly the Former, optionally in the form of concentrated liquid or powder or granulate dyeing preparations. The compounds have good solubility in cold water, substantivity and pH stability and produce dyeings having notable fastness to light and resistance to bleeding.

Inventors

  • 👤 Georg Schoefberger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 01:31
CPC Classifications
C; C09; C09B; C09B62/00; C09B62/44; C09B62/78; C09B62/82; C09B62/83; C09B31/00; C09B31/02; C09B31/08; C09B43/00; C09B43/12; C09B43/124; C09B43/1242; C09B43/136; C09B43/16

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 190 words
A compound of the formula ##STR92## wherein R 1 ' is hydrogen, chloro, methyl, methoxy or ethoxy, R 2 ' is hydrogen, chloro or methyl, R 3 ' is hydrogen, methyl, methoxy or ethoxy, R 4 ' is hydrogen or methyl, R 5 ' is --CHR 6 'CHR 6 'O--CHR 7 'CH 2 O-- p' H, wherein p' is 0 or 1, R 8 ' is hydrogen or --CHR 6 'CHR 6 'OH, with the proviso that R 8 ' must be hydrogen when p' is 1, Y' is --NR 9 'R 10 ', --NR 11 'CHR 6 'CHR 6 'OH or --NHCHR 6 'CHR 6 'OCHR 7 'CH 2 OH, wherein each R 6 ' is hydrogen or methyl, with the proviso that at least one R 6 ' on each R 6 '-containing group is hydrogen, each R 7 ' is hydrogen or methyl, each of R 9 ' and R 10 ' is independently hydrogen, methyl or ethyl, and R 11 ' is hydrogen or --CHR 6 'CHR 6 'OH, wherein R 6 ' is as defined above, and each M is hydrogen or a non-chromophoric cation.
Claim 2
Dependent Claim 190 words
A compound of the formula ##STR92## wherein R 1 ' is hydrogen, chloro, methyl, methoxy or ethoxy, R 2 ' is hydrogen, chloro or methyl, R 3 ' is hydrogen, methyl, methoxy or ethoxy, R 4 ' is hydrogen or methyl, R 5 ' is --CHR 6 'CHR 6 'O--CHR 7 'CH 2 O-- p' H, wherein p' is 0 or 1, R 8 ' is hydrogen or --CHR 6 'CHR 6 'OH, with the proviso that R 8 ' must be hydrogen when p' is 1, Y' is --NR 9 'R 10 ', --NR 11 'CHR 6 'CHR 6 'OH or --NHCHR 6 'CHR 6 'OCHR 7 'CH 2 OH, wherein each R 6 ' is hydrogen or methyl, with the proviso that at least one R 6 ' on each R 6 '-containing group is hydrogen, each R 7 ' is hydrogen or methyl, each of R 9 ' and R 10 ' is independently hydrogen, methyl or ethyl, and R 11 ' is hydrogen or --CHR 6 'CHR 6 'OH, wherein R 6 ' is as defined above, and each M is hydrogen or a non-chromophoric cation.
Claim 3
Dependent Claim 53 words
A compound according to claim 1 wherein each M is hydrogen, lithium, sodium, potassium or N.sup.⊕ (R x ) 4 , wherein each R x is independently hydrogen, C 1-4 alkyl or C 2-4 hydroxyalkyl, with the proviso that at least one R x is hydrogen when the others are C 2-4 hydroxyalkyl.
Claim 4
Dependent Claim 14 words
A compound according to claim 2 wherein each M is lithium, sodium or potassium.
Claim 5
Dependent Claim 11 words
A compound according to claim 3 wherein each M is sodium.
Claim 6
Dependent Claim 12 words
A compound according to claim 1 wherein Y' and ##STR93## are identical.
Claim 7
Dependent Claim 59 words
A compound according to claim 1 wherein R 5 ' is --CH 2 CH 2 O--CH 2 CH 2 O-- p' H, wherein p' is 0 or 1, R 8 ' is hydrogen or --CH 2 CH 2 OH, with the proviso that R 8 ' must be hydrogen when p' is 1, and Y' is --NH 2 .
Claim 8
Dependent Claim 97 words
A compound according to claim 1 having the formula ##STR94## wherein R 1 '" is hydrogen or methyl, R 5 " is --CH 2 CH 2 O--CH 2 CH 2 O-- p' H, wherein p' is 0 or 1, R 8 " is hydrogen or --CH 2 CH 2 OH, with the proviso that R 8 " must be hydrogen when p' is 1, Y" is --NH 2 or --NR 11 "--CH 2 CH 2 OH, wherein R 11 " is hydrogen or --CH 2 CH 2 OH, and each M is hydrogen or a non-chromophoric cation.
Claim 9
Dependent Claim 12 words
A compound according to claim 7 wherein Y" and ##STR95## are identical.
Claim 10
Dependent Claim 12 words
A compound according to claim 7 wherein Y" is --NH 2 .
Claim 11
Dependent Claim 10 words
The compound according to claim 1 having the formula ##STR96##
Claim 12
Dependent Claim 10 words
A compound according to claim 8 having the formula ##STR97##
Claim 13
Dependent Claim 10 words
The compound according to claim 11 having the formula ##STR98##
Claim 14
Dependent Claim 10 words
A compound according to claim 8 having the formula ##STR99##
Claim 15
Dependent Claim 10 words
The compound according to claim 13 having the formula ##STR100##
Claim 16
Dependent Claim 10 words
A compound according to claim 5 having the formula ##STR101##
Claim 17
Dependent Claim 10 words
A compound according to claim 9 having the formula ##STR102##
Claim 18
Dependent Claim 10 words
A compound according to claim 8 having the formula ##STR103##

References Cited (Backward Citations)

US2722527A Cited
US3072454A Cited
US3165506A Cited
US3169953A Cited
US3340247A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-04-10 1981-10-10 1982-04-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-04-10 1985-10-10 1986-04-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-04-10 1989-10-10 1990-04-11 $7700.00 Window Closed / Lapsed

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