Disazo dyes

Details Disazo dyes Disazo dyes

1998-11-18

2001-02-27

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S828000, C008S527000, C008S687000, C008S918000, C008S919000, C106S031520

Reexamination Certificate

active

06194554

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to new disazo dyes, a process for their preparation, their use for dyeing and printing polymeric materials, in particular cellulosic materials and leather, and liquid preparations containing these dyes and their use as recording liquids for ink jet recording apparatuses.
The new disazo dyes correspond to the formula (1)
wherein
R
1
represents hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkyl-carbonylamino, ureido, or amino;
R
2
represents hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, sulfo, or carboxyl;
R
3
represents hydrogen; unsubstituted C
1
-C
4
-alkyl or C
1
-C
4
-alkyl substituted by NH
2
, di(C
1
-C
4
-alkyl)amino, OH, or C
1
-C
4
-alkoxy; unsubstituted aryl or aryl substituted one to four times in an identical or different manner by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, NH
2
, OH, sulfo, or carboxyl; ureido; formyl; C
1
-C
4
-alkylcarbonyl; or unsubstituted benzoyl or benzoyl substituted one to four times in an identical or different manner by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, sulfo, or carboxyl;
R
4
represents hydrogen, unsubstituted C
1
-C
4
-alkyl, or C
1
-C
4
-alkyl substituted by hydroxyl or C
1
-C
4
-alkoxy;
the dotted lines represent an optional fused-on benzene ring; and
n and n′ independently of one another represent the number 0 or 1 with the provisos that
(i) in naphthyl ring A of formula (1) the OH group is in the 5-, 6-, or 8-position, the SO
3
H group is in the 6-, 7-, or 8-position, the (SO
3
H)
n
group is in the 1-, 3-, or 4-position, and the azo group is in the 1- or 2-position,
(ii) in naphthyl ring B of formula (1) the NR
3
R
4
group is in the 2- or 3-position and the (SO
3
H)
n
group is in the 1- or 2-position, and
(iii) the disazo dyes exclude the dye of the formula (2)
Disazo dye (2) is described in Japanese patent specification jp 1,172,907 and is claimed for use in polarizing sheets:
The dyes of the formula (1) according to the invention can each be present both as the free acid or partly or completely in the form of their salts. The dyes are generally employed as salts, particularly as lithium, sodium, potassium, ammonium, mono-, di- or tris(C
1
-C
4
-alkyl)ammonium, mono, di or tris(C
1
-C
4
-alkanol)ammonium, or mixed (C
1
-C
4
-alkyl) (C
1
-C
4
-alkanol)ammonium salts.
The expression di(C
1
-C
4
-alkyl)amino in the definition of R
3
denotes C
1
-C
4
-alkylamino and C
1
-C
4
-dialkylamino.
Preferred dyes of the formula (1) according to the invention are those which correspond to the formula (3)
wherein
R
3
, R
4
, n, and n′ have the meanings stated above for formula (1) and the substituents are bonded to the naphthyl rings in the same positions as stated above for formula (1), and
R
5
represents hydrogen, C
1
-C
4
-alkyl, or C
1
-C
4
-alkoxy.
Dyes that are particularly preferred because of their usually deep black desired shade have the formula (4)
wherein
R
3
, R
4
, n and n′ have the meanings stated above for formula (1) and the bonding of the substituents in naphthyl ring A is in the same positions as stated for these substituents under formula (1), and
R
5
represents hydrogen, C
1
-C
4
-alkyl, or C
1
-C
4
-alkoxy.
The dyes (1) according to the invention can be obtained by a process in which aminonaphtholsulfonic acids of the formula (5)
(wherein the OH group is in position 5, 6, or 8, the SO
3
H group is in position 6, 7, or 8, the (SO
3
H)
n
group is in position 1, 3, or 4, the amino group is in position 1 or 2, and n denotes the number 0 or 1) are diazotized and the resultant diazotization products are coupled to an aminobenzene or aminonaphthalene of the formula (6)
(wherein R
1
and R
2
and the dotted lines have the meanings stated above for formula (1)) and the aminoazo dyes formed in this reaction having the formula (7)
(wherein R
1
, R
2
, and n and the dotted lines have the meanings stated above under formula (1) and the bonding of the substituents in naphthyl ring A is as stated above for these substituents under formula (5)) are again diazotized and the resultant second diazotization products are coupled to aminonaphtholsulfonic acids of the formula (8)
(wherein R
3
, R
4
and n′ have the meanings stated under (1), the NR
3
R
4
group is in the 2- or 3-position, and the (SO
3
H)
n′
group is in 1- or 2-position).
Examples of suitable aminonaphtholsulfonic acids of the formula (5) include:
2-amino-5-naphthol-7-sulfonic acid,
2-amino-5-naphthol-1,7-disulfonic acid,
2-amino-8-naphthol-6-sulfonic acid,
2-amino-8-naphthol-3,6-disulfonic acid,
2-amino-6-naphthol-8-sulfonic acid,
1-amino-5-naphthol-6-sulfonic acid,
1-amino-5-naphthol-7-sulfonic acid,
1-amino-6-naphthol-3,8-disulfonic acid, and
1-amino-8-naphthol-4-sulfonic acid.
Suitable aminobenzenes and aminonaphthalenes of the formula (6) include:
1-amino-2- or -3-methoxybenzene,
1-amino-2- or -3-methylbenzene,
1-amino-3-ureidobenzene,
1-amino-3-acetylaminobenzene,
1-amino-2-methoxy-5-methylbenzene,
1-amino-2,5-dimethylbenzene,
1-amino-2,5-dimethoxybenzene,
1-amino-2-methyl-5-acetylaminobenzene,
1-amino-2- methoxy-5-acetylaminobenzene,
1-amino-2-methyl-5-ureidobenzene,
1-amino-2- methoxy-5-ureidobenzene,
1-amino-5-acetylamino-2-sulfonic acid,
1-aminonaphthalene-6- or -7-sulfonic acid,
1-aminonaphthalene-6- or -7-carbonic acid,
1-aminonaphthalene-2-methyl-6- or -7-sulfonic acid, and
1-aminonaphthalene-2-methoxy-6- or -7-sulfonic acid.
The following coupling components are examples of amino-naphtholsulfonic acids of the formula (8): 2-amino-, 2-methylamino-, 2-dimethylamino-, 2-(2-aminoethylamino)-, 2-(3-diethylaminopropyl-amino)-, 2-phenylamino-, 2-(4-sulfophenylamino)-, 2-(3-sulfophenyl-amino)-, 2-(4-carboxyphenylamino)-, 2-(3-carboxyphenylamino)-, 2-(4-methylphenylamino)-, 2-(2,4-dimethylphenylamino)-, 2-(4-methoxyphenyl-amino)-, 2-(4-aminophenylamino)-, 2-(4-amino-3-sulfophenylamino)-, 2-(4-benzoylamino-3-sulfophenylamino)-, 2-ureido, 2-acetamino-, 2-(N-ethyl-acetamino)-, 2-propionylamino-, 2-benzoylamino-, 2-(4-methylbenzoyl-amino)-5-hydroxynaphthalene-7-sulfonic acid; 2-amino-, 2-acetamino-, and 2-benzoylamino-5-hydroxynaphthalene-1,7-disulfonic acid; 2-amino-, 2-methylamino-, 2-dimethylamino-, 2-ethylamino-, 2-(2-hydroxyethyl-amino)-, 2-(bis-2-hydroxyethylamino)-2-(2-aminoethylamino)-, 2-(3-diethylaminopropylamino)-, 2-phenylamino-, 2-(4-sulfophenylamino)-, 2-(3-sulfophenylamino)-, 2-(4-carboxyphenylamino)-, 2-(3-carboxyphenyl-amino)-, 2-(2,4-dimethylphenylamino)-, 2-(4-methoxyphenylamino)-, 2-(4-aminophenylamino)-, 2-(4-amino-3-sulfophenylamino)-, 2-(4-benzoyl-amino-3-sulfophenylamino)-, 2-ureido, 2-acetamino-, 2-propionylamino-, 2-benzoylamino-, and 2-(4-methylbenzoylamino)-8-hydroxynaphthalene-6-sulfonic acid; and 2-amino-8-hydroxynaphthalene-6-sulfonic acid.
The diazotization of the aminonaphtholsulfonic acids of the formula (5) and of the aminoazo dyes of the formula (7) formed as intermediates is carried out in a known manner known, for example, with an alkali metal nitrite (such as sodium nitrite) in a mineral acid medium (preferably a hydrochloric acid medium) at temperatures of 0° C. to 30° C. (preferably 0° C. to 15° C.). The coupling of the diazotized aminonaphtholsulfonic acids of the formula (5) with an aminobenzene or aminonaphthalene of the formula (6) and the coupling of the diazotized aminoazo dyes of the formula (7) with an aminonaphtholsulfonic acid of the formula (8) are likewise carried out under customary known conditions. The coupling reaction is preferably carried out in an aqueous medium at a weakly acid, neutral, or alkaline pH and at temperatures of 0° C. to 30° C. (preferably 10° C. to 25° C.). A neutral to weakly acid pH (preferably in the range from 7 to 4) is advantageous for the coupling reaction with the aminobenzenes or aminonaphthalenes of the formula (6) and a neutral to weakly alkaline pH (preferably in the range from 7.5 to 9) is advantageous for the coupling reaction with the amino-naphtholsulfonic acids of the formula (8). The desired pH can be established and maintained by addition of bases, such as alkali metal hydroxide

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