US5118737A
Expired / Lapsed
US
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Water-soluble dye
Assignee: Canon Inc
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Filing: 1990-06-22
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Granted: 1992-06-02
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Expires: 2010-06-22
Abstract
Abstract A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## 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 1 and R 2 together with the nitrogen atom form a morpholine ring a and b are different and from 1 to 8 m is from 1 to 10; n is from 0 to 9; M is H, ammonium, or a monovalent metal; X (i) NR 1 R 2 , (ii) NR 3 R 4 , in which R 3 and R 4 are each independently selected from H, alkyl and aryl, or (iii) 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 an amino linking group; and Y is (i) the residue of a benzene, naphthalene or mono or bi-cyclic heteroaryl diazo component or (ii) the residue of a mono- or bis-azo chromophore carrying a diazotisable amino group and comprising benzene, naphthalene or mono-or bi-cyclic heteroaryl diazo and coupling components; provided that the dye contains one or at least three azo groups and an ink derived from the dye which is suitable for use in printing, especially ink jet printing.
Inventors
- 👤 Anthony G. W. Baxter
- 👤 Stephen B. Bostock
- 👤 David Greenwood
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 05:09
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/30; C09D11/32; C09D11/328; C09B; C09B29/00; C09B29/24; C09B29/28; C09B29/30; C09B43/00; C09B43/12; C09B43/136; C09B43/16; Y; Y10; Y10S; Y10S260/00; Y10S260/38
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
255 words
An ink for ink jet recording comprising a water soluble dye, of the formula: ##STR3## 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 1 and R 2 together with the nitrogen atom form a morpholine ring a and b are different and are from 2 to 6 m is from 1 to 10; n is from 0 to 9; M is H, ammonium, or a monovalent metal; X is (i) NR 1 R 2 , (ii) NR 3 R 4 , in which R 3 and R 4 are each independently selected from H, alkyl and aryl, or (iii) a monoazo chromophore derived from a benzene or naphthalene diazo component and a benzene, naphthalene or mono-heterocyclic coupling component or a bisazo chromophore derived from benzene or naphthalene diazo components and benzene or naphthalene coupling components, in which the monazo or bisazo chromophore is linked to the triazine group through a group --NR 5 -- in which R 5 is selected form H, C 1-4 -alkyl and phenyl; and Y is (i) a phenyl or naphthyl nucleus carrying at least one SO 3 M group or (ii) a monoazo chromophore derived from a benzene, naphthalene or monoheterocyclic diazo component and a benzene or naphthalene coupling component carrying at least one SO 3 M group; provided that the dye contains one or from three to five azo groups.
Claim 2
Dependent Claim
255 words
An ink for ink jet recording comprising a water soluble dye, of the formula: ##STR3## 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 1 and R 2 together with the nitrogen atom form a morpholine ring a and b are different and are from 2 to 6 m is from 1 to 10; n is from 0 to 9; M is H, ammonium, or a monovalent metal; X is (i) NR 1 R 2 , (ii) NR 3 R 4 , in which R 3 and R 4 are each independently selected from H, alkyl and aryl, or (iii) a monoazo chromophore derived from a benzene or naphthalene diazo component and a benzene, naphthalene or mono-heterocyclic coupling component or a bisazo chromophore derived from benzene or naphthalene diazo components and benzene or naphthalene coupling components, in which the monazo or bisazo chromophore is linked to the triazine group through a group --NR 5 -- in which R 5 is selected form H, C 1-4 -alkyl and phenyl; and Y is (i) a phenyl or naphthyl nucleus carrying at least one SO 3 M group or (ii) a monoazo chromophore derived from a benzene, naphthalene or monoheterocyclic diazo component and a benzene or naphthalene coupling component carrying at least one SO 3 M group; provided that the dye contains one or from three to five azo groups.
Claim 3
Dependent Claim
208 words
An ink for ink jet recording comprising a water soluble black dye, of the formula: ##STR4## 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 1 and R 2 together with the nitrogen atom form a morpholine ring a and b are different and are from 2 to 6 m is from 1 to 10; n is from 0 to 9; M is H, ammonium, or a monovalent metal; X is a monoazo chromophore derived from a benzene or naphthalene diazo component and a benzene, naphthalene or monoheterocyclic coupling component or a bisazo chromophore derived from benzene or naphthalene diazo components and benzene or naphthalene coupling components, in which the monoazo or bisazo chromophore is linked to the triazine group through a group --NR 5 -- in which R 5 is selected from H, C 1-4 -alkyl and phenyl; and Y is a monoazo chromophore derived from a benzene, naphthalene or monoheterocyclic diazo component and a benzene or naphthalene coupling component carrying at least one SO 3 M group; provided that the dye contains from three to five azo groups.
Claim 4
Dependent Claim
208 words
An ink for ink jet recording comprising a water soluble black dye, of the formula: ##STR4## 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 1 and R 2 together with the nitrogen atom form a morpholine ring a and b are different and are from 2 to 6 m is from 1 to 10; n is from 0 to 9; M is H, ammonium, or a monovalent metal; X is a monoazo chromophore derived from a benzene or naphthalene diazo component and a benzene, naphthalene or monoheterocyclic coupling component or a bisazo chromophore derived from benzene or naphthalene diazo components and benzene or naphthalene coupling components, in which the monoazo or bisazo chromophore is linked to the triazine group through a group --NR 5 -- in which R 5 is selected from H, C 1-4 -alkyl and phenyl; and Y is a monoazo chromophore derived from a benzene, naphthalene or monoheterocyclic diazo component and a benzene or naphthalene coupling component carrying at least one SO 3 M group; provided that the dye contains from three to five azo groups.
Claim 5
Dependent Claim
18 words
An ink according to claim 1 wherein NR 1 R 2 is selected from hydroxyethyamino, di(hydroxyethyl)amino and morpholino.
Claim 6
Dependent Claim
56 words
An ink according to claim 1 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, ureido, C 1-4 -alkylcarbonylamino, mono- and di-C 1-4 -alkylamino, phenylamino, nitro, halogen, carboxylate, sulphonate and, hydroxy.
Claim 7
Dependent Claim
58 words
An ink according to claim 1 wherein Y is the residue of a benzene or naphthalene diazo component carrying at least one sulphonate group, SO 3 M, and optionally carrying one or more groups selected from C 1-4 -alkyl, C 1-4 alkoxy, C 1-4 alkylcarbonylamino, ureido, mono- and di-C 1-4 -alkylamino, phenylamino, nitro, halogen, carboxylate, sulphonate and hydroxy.
Claim 8
Dependent Claim
67 words
An ink according to claim 1 wherein Y is the residue of a mono- or dis-azo chromophore comprising benzene or naphthalene diazo and coupling components and carrying at least one sulphonate group, SO 3 M and optionally carrying one or more other substituents selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, mono- and di-C 1-4 -alkylamino, phenylamino, nitro, ureido, halogen, carboxylate, sulphonate and hydroxy.
Claim 9
Dependent Claim
12 words
An ink according to claim 1 carrying at least five sulphonate groups.
Claim 10
Dependent Claim
29 words
The ink according to claim 1 wherein M is potassium, Y is 2-methoxy-4-(2,5-disulphophenylazo)-5-methylphenyl (K salt), X is 5-hydroxy-6-(2-sulphophenylazo)-7-sulphonaphth-2-ylimino (K salt), R 1 is hydroxyethyl and R 2 is H.
Claim 11
Dependent Claim
29 words
The ink according to claim 1 wherein M is potassium, Y is 2-methoxy-4-(2,5-disulphophenylazo)-5-methylphenyl (K salt), X is 3-ureido-4-(4-[2,5-disulphophen-1-ylazo]-2,5-dimethylphen-1-ylazo)-phenylimino (K salt), R 1 is hydroxyethyl and R 2 is H.
Claim 12
Dependent Claim
31 words
The ink according to claim 1 wherein R 1 is hydroxyethyl, R 2 is H, X is NR 1 R 2 , M is sodium and Y is 3,6,8-trisulphonaphth-2-yl, (Na salt).
Claim 13
Dependent Claim
31 words
The ink according to claim 1 wherein R 1 is hydroxyethyl, R 2 is H, X is NR 1 R 2 , M is sodium and Y is 2-methyl-4-sulphophenyl, (Na salt).
Claim 14
Dependent Claim
45 words
An ink comprising a dye in accordance with claim 1 suitable for a recording system of the type in which an ink is ejected from a small orifice in the form of droplets directed towards a substrate on which an image is to be formed.
Claim 15
Dependent Claim
23 words
An ink according to claim 1 wherein the dye is dissolved in water of a mixture of water and a water-soluble organic solvent.
Claim 16
Dependent Claim
15 words
An ink according to claim 13 wherein the water-soluble organic solvent is a polyhydric alcohol.
Claim 17
Dependent Claim
16 words
An ink according to claim 1 containing from 0.5% to 20% by weight of the dye.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-06-02 | 1995-12-02 | 1996-06-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-06-02 | 1999-12-02 | 2000-06-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-06-02 | 2003-12-02 | 2004-06-02 | $7700.00 | Window Closed / Lapsed |