EP0179549A2
Expired / Lapsed
EP
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Water-soluble dye
Assignee: Syngenta Ltd
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Filing: 1985-08-02
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Granted: —
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Expires: 2005-08-02
Abstract
Abstract A water-soluble dye, free from cellulose reactive groups, of the formula: wherein R 1 is -(C a H 2a O) m (C b H 2b O) n H, R 2 is H or -(C a H 2a O) m (C b H 2b O) n H, or R' & R 2 together with the nitrogen atom form a morpholine ring a & b are different and from 1 to 8 m is from 1 to 10; n is from 0 to 9; q is ½ or 1 p is 1 or 2 L is a transition metal capable of complexing with a dye M is H, ammonium, or a monovalent metal; Q is H or SO 3 M T is H or C 1-4 -alkyl; D is a substituted azo group; B, E & F are H or substituents; X is NR'R 2 , NR 3 R 4 , -NR 3 -Z-NR 4 -, OR 3 , or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R 3 & R 4 each independently are H, alkyl or aryl; and Z is a divalent linking group; a mixture of this dye with an unmetallised orange dye of similar structure and an ink derived from the dye or dye mixture which is suitable for use in printing, especially ink jet printing.
Inventors
- 👤 Anthony Gerard William Baxter
- 👤 Stephen Bernard Bostock
- 👤 David Greenwood
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 19:31
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/30; C09D11/32; C09D11/328; C09B; C09B43/00; C09B43/12; C09B43/136; C09B43/16; C09B45/00; C09B45/02; C09B45/04; Y; Y10; Y10S; Y10S534/00; Y10S534/01; Y10S534/02
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
211 words
A water-soluble dye, free from cellulose reactive groups, of the formula: wherein R1is -(C a H 2a O) m (C b H 2b O) n H, R 2 is H or -(C a H 2a O) m (C b H 2b ) n H, or R 1 & R together with the nitrogen atom form a morpholine ring a & b are different and from 1 to 8 m is from 1 to 10; n is from 0 to 9; q is ½ or 1 p is 1 or 2 L is a transition metal capable of complexing with a dye M is H, ammonium, or a monovalent metal; Q is H or SO 3 M T is H or C 1-4 -alkyl; D is a substituted azo group; B, E & F are H or substituents; X is NR 1 R 2 , NR 3 R 4 , -NR 3 -Z-NR 4 -, OR 3 , or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group; Z is a divalent linking group; and R 3 & R 4 each independently are H, alkyl or aryl.
Claim 2
Dependent Claim
211 words
A water-soluble dye, free from cellulose reactive groups, of the formula: wherein R1is -(C a H 2a O) m (C b H 2b O) n H, R 2 is H or -(C a H 2a O) m (C b H 2b ) n H, or R 1 & R together with the nitrogen atom form a morpholine ring a & b are different and from 1 to 8 m is from 1 to 10; n is from 0 to 9; q is ½ or 1 p is 1 or 2 L is a transition metal capable of complexing with a dye M is H, ammonium, or a monovalent metal; Q is H or SO 3 M T is H or C 1-4 -alkyl; D is a substituted azo group; B, E & F are H or substituents; X is NR 1 R 2 , NR 3 R 4 , -NR 3 -Z-NR 4 -, OR 3 , or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group; Z is a divalent linking group; and R 3 & R 4 each independently are H, alkyl or aryl.
Claim 3
Dependent Claim
18 words
A dye according to Claim 1 wherein NR 1 R 2 is selected from hydroxyethyamino, di(hydroxyethyl)amino and morpholino.
Claim 4
Dependent Claim
12 words
A dye according to Claim 2 wherein X is NR R .
Claim 5
Dependent Claim
86 words
A dye according to Claim 1 or Claim 2 wherein X is NR 3 R 4 or O R 3 and R3is selected from H and C 1-4 -alkyl and R 4 is selected from H, C 1-4 -alkyl, phenyl or naphthyl in which the phenyl and naphthyl are unsubstituted or substituted by a group selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, unsubstituted and mono- & di-alkyl-amino-sulphonyl & carbonyl, nitro, halogen, and hydroxy, mono & di-C 1-4 -alkylamino, phenylamino, carboxylate and sulphonate.
Claim 6
Dependent Claim
65 words
A dye according to Claim 1 or Claim 2 wherein X is the residue of a mono- or dis-azo chromophore comprising benzene or naphthalene diazo and coupling components optionally substituted by one or more groups selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, mono- & di-C 1-4 -alkylamino, unsubstituted and mono- & di-alkyl-amino-sulphonyl & carbonyl, phenylamino, nitro, halogen, carboxylate, sulphonate and hydroxy.
Claim 7
Dependent Claim
66 words
A dye according to any one of Claims 1 to 5 wherein D is a phenylazo or naphthylazo group carrying at least one sulphonate group, S0 3 M, and optionally carrying one or more groups selected from C 1-4 -alkyl, C 1-4 alkoxy, C 1-4 alkylcarbonylamino, unsubstituted and mono- & di-alkyl-amino-sulphonyl & carbonyl, mono- & di-C 1-4 -alkyl- amino, phenylamino, nitro, halogen, carboxylate, sulphonate and hydroxy.
Claim 8
Dependent Claim
14 words
A dye according to any one of Claims 1 to 6 wherein X is
Claim 9
Dependent Claim
88 words
-NR -Z-NR - wherein Rand R are selected from H, C 1-4 -alkyl, phenyl and phenyl substituted by one or more substituents defined for R 4 in Claim 5 and Z is selected from optionally substituted or optionally interrupted C 1-6 -alkylene, phenylene, biphenylene, C 1-4 -alkylene- phen-4-ylene, in which the substituents are selected from those defined for R 4 in Claim 5 and interrupting atoms are selected from oxygen, nitrogen and sulphur or Z is a divalent residue of a mono or bisazo or a stilbene chromophore.
Claim 10
Dependent Claim
17 words
A dye according to any one of Claims 1 to 7 carrying at least five sulphonate groups.
Claim 11
Dependent Claim
53 words
The dye according to Claim 1 wherein R is hydroxyethyl; R 2 , B, F and T are H; Q is SO 3 Na; p = 1; L is copper; q = 1; E is CH 3 ; D is 2,5-disulphophenylazo (Na salt); X is 2-methyl-5-sulphophenyl- amino (Na salt) and M is Na.
Claim 12
Dependent Claim
51 words
The dye according to Claim 1 wherein R is hydroxyethyl, R , T, B & F are H, E is CH 3 , M is K, L is copper, Q is SO 3 K, q = 1, p = 1, D is 2,5-disulphophenylazo (K salt) and X is 5-hydroxy-6-(2-sulphophenyl-azo)-7-sulpho-naphth-2-ylimino (K salt).
Claim 13
Dependent Claim
49 words
The dye according to Claim 1 wherein R is hydroxyethyl; R 2 , B, F, Q and T are H; E is CH 3 ; D is 2,5-disulphophenylazo (K salt); M is K; L is copper; q = 1; p = 1 and X is 5-hydroxy-6-(2-sulphophenyl- azo)-7-sulpho-naphth-2-ylamino (K salt).
Claim 14
Dependent Claim
104 words
A mixture of a dye according to any one of Claims 1 to 11 and a dye of the formula: wherein R 1 , R 2 , P, Q, M, and X are as defined in Claim 1; B 1 , D 1 , E 1 , F & G 1 , are H or substituents or B and D form a second benzene ring fused to ring A which is optionally substituted, provided that neither F nor G 1 is hydroxy; and J is selected from: wherein T is H, alkyl or phenyl; W is an acyl group; V is alkyl or alkoxy.
Claim 15
Dependent Claim
83 words
A mixture of the dye of Claim 9 and the dye according to Claim 12 wherein J is 1-hydroxy-3-sulpho-6-imino-naphth-2-yl (Na salt); B & D 1 form a second benzene ring fused to Ring A' and carrying an SO 3 Na group in the position adjacent to the point where D is attached to Ring A; E 1 , F 1 & R 2 are H; R is hydroxyethyl; p = 1; X is 4,4'-dimino-2,2'-disulphodiphenyl (Na salt) and G 1 is SO 3 Na.
Claim 16
Dependent Claim
16 words
An ink comprising a dye or mixture according to any one of Claims 1 to 13.
Claim 17
Dependent Claim
52 words
An ink comprising a dye or mixture according to any one of Claims 1 to 13 suitable for a recording system of the type in which the ink is ejected from a small orifice in the form of a droplet directed towards a substrate on which an image is to be formed.
Claim 18
Dependent Claim
26 words
An ink according to Claim 14 or Claim 15 wherein the dye is dissolved in water or a mixture of water and a water-soluble organic solvent.
Claim 19
Dependent Claim
15 words
An ink according to Claim 16 wherein the water soluble solvent is a polyhydric alcohol.
Claim 20
Dependent Claim
25 words
An ink according to any one of Claims 14 to 17 containing from 0.5% to 20% by weight of the dye or mixture of dyes.
Claim 21
Independent Claim
40 words
A method of printing which comprises ejecting an ink in accordance with any one of Claims 14 to 18 from a small orifice in the form of droplets directed towards a substrate on which an image is to be formed.
References Cited (Backward Citations)
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