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US4097476A Expired / Lapsed US ⏱️ 0.0 years remaining

Trisazo dyes having a 2,7-(1-amino-3,6-or 4,6-disulfo-8-hydroxynaphthylene) radical

Assignee: Sandoz AG
•
Filing: 1975-06-10
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Granted: 1978-06-27
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Expires: 1995-06-10
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Abstract

Abstract Disclosed are compounds of the formula, <IMAGE> in which X is hydrogen, chlorine, C1-4alkyl or alkoxy, -SO3M or -CO2M, one of the Y's is hydrogen, the other -SO3M, A is a mono- or di-sulphonaphthyl radical which is optionally further substituted, or <IMAGE> in which R is hydrogen, hydroxy or C1-4alkyl or alkoxy, B is a radical or a coupling component (b1) to (b10), <IMAGE> (b1) WHERE R1 is -NH2, anilino or toluidino, R2 is -NH2 or -OH, and EITHER R3 is hydrogen, or WHEN R1 and R2 both are -NH2, R3 is hydrogen, -SO3M or C1-4alkyl; <IMAGE> (b2) WHERE R4 is hydrogen or C1-4alkyl; <IMAGE> (b3) WHERE R5 is hydrogen or -CO2M; <IMAGE> (b4) <IMAGE> (b5) <IMAGE> (b6) WHERE ONE OF THE Y1's is hydrogen, the other -SO3M; <IMAGE> (b7) <IMAGE> (b8) <IMAGE> (b9) WHERE R6 is phenyl or C1-4alkylphenyl; <IMAGE> (b10) where R7 is -OH or -NH2, R8 is hydrogen, phenyl or sulphophenyl, and R9 is C1-4alkyl or -CO2M, and the M's independently, signify hydrogen or a non-chromophoric cation, their production and use for dyeing and printing anionic dyeable substrates, e.g., natural and regenerated cellulose, natural and synthetic polyamides, polyurethanes and basically modified polypropylene and particularly leather, paper and anodized aluminum. The obtained dyeings have shades ranging from deep green or blue to black. The dyeings on paper exhibit notable fastness to water and water-spotting while the dyeings on leather are level and exhibit good fastness to perspiration, dry cleaning, water, water-spotting and buffing and resistance to migration onto polyvinyl chloride.

Inventors

  • 👤 Heinz Wicki

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 01:59
CPC Classifications
C; C09; C09B; C09B35/00; C09B35/38; C09B35/44; C09B35/46; C09B35/461

Claims Analysis

Total Claims: 46
Claim 1
Independent Claim 96 words
A compound of the formula ##STR100## or a mixture thereof, wherein A is sulfonaphthyl, substituted sulfonaphthyl, disulfonaphthyl, substituted disulfonaphthyl or ##STR101## wherein R is hydrogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy, and each substituent of substituted sulfonaphthyl and substituted disulfonaphthyl is independently hydroxy or C 1-4 alkoxy, X is hydrogen, chloro, C 1-4 alkyl, C 1-4 alkoxy, --SO 3 M or --CO 2 M, one Y is --SO 3 M and the other is hydrogen, R 6 ' is hydrogen or C 1-4 alkyl, and each M is independently hydrogen or a non-chromophoric cation.
Claim 2
Dependent Claim 96 words
A compound of the formula ##STR100## or a mixture thereof, wherein A is sulfonaphthyl, substituted sulfonaphthyl, disulfonaphthyl, substituted disulfonaphthyl or ##STR101## wherein R is hydrogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy, and each substituent of substituted sulfonaphthyl and substituted disulfonaphthyl is independently hydroxy or C 1-4 alkoxy, X is hydrogen, chloro, C 1-4 alkyl, C 1-4 alkoxy, --SO 3 M or --CO 2 M, one Y is --SO 3 M and the other is hydrogen, R 6 ' is hydrogen or C 1-4 alkyl, and each M is independently hydrogen or a non-chromophoric cation.
Claim 3
Dependent Claim 8 words
A mixture of compounds according to claim 1.
Claim 4
Dependent Claim 6 words
A compound according to claim 1.
Claim 5
Dependent Claim 103 words
A compound according to claim 3 wherein each M is independently hydrogen, lithium, sodium, potassium or ##STR102## wherein each of R 10 , R 11 , R 12 and R 13 is independently hydrogen, C 1-3 alkyl or C 2-3 hydroxyalkyl, with the provisos that at least one of R 10 , R 11 , R 12 and R 13 is hydrogen when one or more of R 10 , R 11 , R 12 and R 13 is C 2-3 hydroxyalkyl, and the hydroxy group of each C 2-3 hydroxyalkyl is not attached to the carbon atom attached to the nitrogen atom.
Claim 6
Dependent Claim 14 words
A compound according to claim 4 wherein each M is independently hydrogen or sodium.
Claim 7
Dependent Claim 11 words
A compound according to claim 5 wherein each M is hydrogen.
Claim 8
Dependent Claim 11 words
A compound according to claim 5 wherein each M is sodium.
Claim 9
Dependent Claim 23 words
A compound according to claim 3 wherein the total number of --SO 3 M and --CO 3 M groups is 3 or 4.
Claim 10
Dependent Claim 21 words
A compound according to claim 3 wherein A is sulfonaphthyl, sulfonaphthyl monosubstituted by hydroxy or C 1-4 alkoxy, disulfonaphthyl or ##STR103##
Claim 11
Dependent Claim 48 words
A compound according to claim 9 wherein A is ##STR104## wherein one Y 2 is --SO 3 M and the other is hydrogen, and n is 1 or 2, with the proviso that when n is 2 the --SO 3 M groups are not ortho to each other.
Claim 12
Dependent Claim 10 words
A compound according to claim 10 wherein A is ##STR105##
Claim 13
Dependent Claim 10 words
A compound according to claim 11 wherein A is t,380
Claim 14
Dependent Claim 10 words
A compound according to claim 11 wherein A is ##STR106##
Claim 15
Dependent Claim 10 words
A compound according to claim 13 wherein A is ##STR107##
Claim 16
Dependent Claim 10 words
A compound according to claim 11 wherein A is ##STR108##
Claim 17
Dependent Claim 10 words
A compound according to claim 11 wherein A is ##STR109##
Claim 18
Dependent Claim 14 words
A compound according to claim 3 wherein R 6 ' is hydrogen or methyl.
Claim 19
Dependent Claim 12 words
A compound according to claim 17 wherein R 6 ' is hydrogen.
Claim 20
Dependent Claim 10 words
A compound according to claim 3 having the formula ##STR110##
Claim 21
Dependent Claim 15 words
A compound according to claim 19 wherein X is hydrogen, chloro or --SO 3 M.
Claim 22
Dependent Claim 14 words
A compound according to claim 20 wherein X is hydrogen or --SO 3 M.
Claim 23
Dependent Claim 147 words
A compound according to claim 3 wherein A is ##STR111## wherein one Y 2 is --SO 3 M and the other is hydrogen, and n is 1 or 2, with the proviso that when n is 2 the --SO 3 M groups are not ortho or peri to each other, and each M is independently hydrogen, lithium, sodium, potassium or ##STR112## wherein each of R 10 , R 11 , R 12 and R 13 is independently hydrogen, C 1-3 alkyl or C 2-3 hydroxyalkyl, with the provisos that at least one of R 10 , R 11 , R 12 and R 13 is hydrogen when one or more of R 10 , R 11 , R 12 and R 13 is C 2-3 hydroxyalkyl, and the hydroxy group of each C 2-3 hydroxyalkyl is not attached to the carbon atom attached to the nitrogen atom.
Claim 24
Dependent Claim 15 words
A compound according to claim 22 having the formula ##STR113## wherein A" is ##STR114## and
Claim 25
Dependent Claim 8 words
X' is hydrogen, chloro or --SO 3 M.
Claim 26
Dependent Claim 8 words
X' is hydrogen, chloro or --SO 3 M.
Claim 27
Dependent Claim 13 words
A compound according to claim 23 wherein each M is hydrogen or sodium.
Claim 28
Dependent Claim 11 words
A compound according to claim 24 wherein each M is sodium.
Claim 29
Dependent Claim 50 words
A compound according to claim 3 having the formula ##STR115## wherein A' is ##STR116## X' is hydrogen, chloro or --CO 3 M, one Y is --SO 3 M and the other is hydrogen, R 6 " is hydrogen or methyl, and each M is independently hydrogen or a non-chromophoric cation.
Claim 30
Dependent Claim 10 words
A compound according to claim 26 having the formula ##STR117##
Claim 31
Dependent Claim 13 words
A compound according to claim 27 wherein each M is hydrogen or sodium.
Claim 32
Dependent Claim 10 words
A compound according to claim 26 having the formula ##STR118##
Claim 33
Dependent Claim 13 words
A compound according to claim 29 wherein each M is hydrogen or sodium.
Claim 34
Dependent Claim 103 words
A compound according to claim 26 wherein each M is independently hydrogen, lithium, sodium, potassium or ##STR119## wherein each of R 10 , R 11 , R 12 and R 13 is independently hydrogen, C 1-3 alkyl or C 2-3 hydroxyalkyl, with the provisos that at least one of R 10 , R 11 , R 12 and R 13 is hydrogen when one or more of R 10 , R 11 , R 12 and R 13 is C 2-3 hydroxyalkyl, and the hydroxy group of each C 2-3 hydroxyalkyl is not attached to the carbon atom attached to the nitrogen atom.
Claim 35
Dependent Claim 14 words
A compound according to claim 31 wherein each M is independently hydrogen or sodium.
Claim 36
Dependent Claim 11 words
A compound according to claim 32 wherein each M is hydrogen.
Claim 37
Dependent Claim 11 words
A compound according to claim 32 wherein each M is sodium.
Claim 38
Dependent Claim 12 words
A compound according to claim 26 wherein R 6 " is hydrogen.
Claim 39
Dependent Claim 10 words
A compound according to claim 26 wherein A' is ##STR120##
Claim 40
Dependent Claim 14 words
A compound according to claim 26 wherein X' is hydrogen or --SO 3 M.
Claim 41
Dependent Claim 20 words
A compound according to claim 37 having the formula ##STR121## wherein each M is independently hydrogen or a non-chromophoric cation.
Claim 42
Dependent Claim 11 words
A compound according to claim 37 wherein each M is hydrogen.
Claim 43
Dependent Claim 20 words
A compound according to claim 37 having the formula ##STR122## wherein each M is independently hydrogen or a non-chromophoric cation.
Claim 44
Dependent Claim 13 words
A compound according to claim 40 wherein each M is hydrogen or sodium.
Claim 45
Dependent Claim 48 words
A compound according to claim 10 wherein A is ##STR123## wherein one Y 2 is --SO 3 M and the other is hydrogen, and n is 1 or 2, with the proviso that when n is 2 the --SO 3 M groups are not ortho to each other.
Claim 46
Dependent Claim 20 words
A compound according to claim 37 having the formula ##STR124## wherein each M is independently hydrogen or a non-chromophoric cation.

References Cited (Backward Citations)

US1716063A Cited
US1982332A Cited
US2024797A Cited
US2488076A Cited
US2676957A Cited
JPS4939619A Cited
FR2211510A1 Cited
US3917887A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-06-26 1981-12-26 1982-06-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-06-26 1985-12-26 1986-06-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-06-26 1989-12-26 1990-06-27 $7700.00 Window Closed / Lapsed

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