US6737517B2
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Metal chelated azo dyestuff for inkjet recording and recording liquid for inkjet and inkjet recording method using same
Assignee: Mitsubishi Chemical Corp
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Filing: 2002-08-12
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Granted: 2004-05-18
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Expires: 2022-08-12
Abstract
Abstract A metal chelated azo dyestuff containing at least one hydrophilic group and having formula (1):wherein M is a metal; A, B and C are each independently a substituted or unsubstituted aromatic ring; D is an aromatic ring optionally substituted by a group other than an azo group; m is 0 or 1; n is an integer from 0 to 3; p is an integer from 0 to 2; q is an integer from 1 to 3; with the proviso that in the event of a plurality of B's, they are the same or different; R1 and R2 are each independently hydrogen or a substituent group; M is tridentate or of higher coordination; and optionally a metal ion coordinated to A and B, B and B in the event of plural B's separated by azo or B and C, in the form of the structure: -O-M-O-.
Inventors
- 👤 Wataru Shimizu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 07:44
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/30; C09D11/32; C09D11/328; C09B; C09B45/00; C09B45/02; C09B45/24
Claims Analysis
Total Claims: 62
Claim 1
Independent Claim
298 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1): (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1) or with arbitrary ligands; and a metal ion may be further coordinated to A and B, B and B which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B's or B and C in the form of —O—M—O—), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted; and when D is a naphthalene ring, m is 0, and n and p are each 1, (NR 1 R 2 )is not acylamino.
Claim 2
Dependent Claim
298 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1): (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1) or with arbitrary ligands; and a metal ion may be further coordinated to A and B, B and B which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B's or B and C in the form of —O—M—O—), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted; and when D is a naphthalene ring, m is 0, and n and p are each 1, (NR 1 R 2 )is not acylamino.
Claim 3
Dependent Claim
257 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1′): (wherein the general formula (1′) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; and M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1′) or with arbitrary ligands), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted; and when D is a naphthalene ring, m is 0, and n and p are each 1, (NR 1 R 2 ) is not acylamino.
Claim 4
Dependent Claim
257 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1′): (wherein the general formula (1′) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; and M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1′) or with arbitrary ligands), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted; and when D is a naphthalene ring, m is 0, and n and p are each 1, (NR 1 R 2 ) is not acylamino.
Claim 5
Dependent Claim
26 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), p is 1 or 2.
Claim 6
Dependent Claim
26 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), D is a naphthalene ring.
Claim 7
Dependent Claim
200 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), A represents phenyl group which may be substituted or naphthyl group which may be substituted; and B and C each independently represents phenylene group which may be substituted or naphthylene group which may be substituted, with the proviso that if A, B or C has substituents, the substituents for A are at least one substituent selected from the group consisting of halogen atom, phosphono group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted, sulfonylamino group which may be substituted, phenylazo group which may be substituted and naphthylazo group which may be substituted and the substituents for B and C are at least one substituent selected from the group consisting of halogen atom, phosphono group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 8
Dependent Claim
86 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), D has at least one substituent selected from the group consisting of halogen atom, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted, sulfonylamino group which may be substituted, alkoxycarbonyl group and aminocarbonyl group in addition to those defined in the general formula (1).
Claim 9
Dependent Claim
68 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), R 1 and R 2 each independently is selected from the group consisting of hydrogen atom, alkyl group which may be substituted, phenyl group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted and triazinyl group which may be substituted.
Claim 10
Dependent Claim
104 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), R 1 is selected from the group consisting of hydrogen atom, alkyl group which may be substituted, phenyl group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted and triazinyl group which may be substituted and R 2 is selected from the group consisting of alkyl group which may be substituted, phenyl group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted and triazinyl group which may be substituted.
Claim 11
Dependent Claim
24 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), m is 0.
Claim 12
Dependent Claim
26 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), n is 1 or 2.
Claim 13
Dependent Claim
24 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), p is 1.
Claim 14
Dependent Claim
28 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein in the aforementioned general formula (1), M is copper, nickel, iron or cobalt.
Claim 15
Dependent Claim
29 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein the aforementioned general formula (1) is a compound having three azo groups per molecule.
Claim 16
Dependent Claim
30 words
A metal chelated azo dyestuff for inkjet recording as defined in claim 1 , wherein the aforementioned general formula (1) is a compound containing from 2 to 6 hydrophilic groups.
Claim 17
Dependent Claim
277 words
A recording liquid comprising a metal chelated azo dyestuff the free acid form of which is represented by the general formula (1) and an aqueous medium, (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1) or with arbitrary ligands; and a metal ion may be further coordinated to A and B, B and B which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B's or B and C in the form of —O—M—O—), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl gioup, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 18
Dependent Claim
277 words
A recording liquid comprising a metal chelated azo dyestuff the free acid form of which is represented by the general formula (1) and an aqueous medium, (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1) or with arbitrary ligands; and a metal ion may be further coordinated to A and B, B and B which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B's or B and C in the form of —O—M—O—), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl gioup, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 19
Dependent Claim
235 words
A recording liquid comprising a metal chelated azo dyestuff the free acid form of which is represented by the general formula (1′) and an aqueous medium, (wherein the general formula (1′) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; and M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1′) or with arbitrary ligands), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 20
Dependent Claim
235 words
A recording liquid comprising a metal chelated azo dyestuff the free acid form of which is represented by the general formula (1′) and an aqueous medium, (wherein the general formula (1′) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; and M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1′) or with arbitrary ligands), wherein when B is phenylene, the phenylene is substituted by at least one substituent selected from the group consisting of halogen atom, phosphono group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 21
Dependent Claim
21 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), p is 1 or 2.
Claim 22
Dependent Claim
21 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), D is a naphthalene ring.
Claim 23
Dependent Claim
195 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), A represents phenyl group which may be substituted or naphthyl group which may be substituted; and B and C each independently represents phenylene group which may be substituted or naphthylene group which may be substituted, with the proviso that if A, B or C has substituents, the substituents for A are at least one substituent selected from the group consisting of halogen atom, phosphono group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted, sulfonylamino group which may be substituted, phenylazo group which may be substituted and naphthylazo group which may be substituted and the substituents for B and C are at least one substituent selected from the group consisting of halogen atom, phosphono group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 24
Dependent Claim
81 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), D has at least one substituent selected from the group consisting of halogen atom, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted, sulfonylamino group which may be substituted, alkoxycarbonyl group and aminocarbonyl group in addition to those defined in the general formula (1).
Claim 25
Dependent Claim
63 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), R 1 and R 2 each independently is selected from the group consisting of hydrogen atom, alkyl group which may be substituted, phenyl group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted and triazinyl group which may be substituted.
Claim 26
Dependent Claim
99 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), R 1 is selected from the group consisting of hydrogen atom, alkyl group which may be substituted, phenyl group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted and triazinyl group which may be substituted and R 2 is selected from the group consisting of alkyl group which may be substituted, phenyl group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted and triazinyl group which may be substituted.
Claim 27
Dependent Claim
19 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), m is 0.
Claim 28
Dependent Claim
21 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), n is 1 or 2.
Claim 29
Dependent Claim
19 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), p is 1.
Claim 30
Dependent Claim
23 words
A recording liquid as defined in claim 15 , wherein in the aforementioned general formula (1), M is copper, nickel, iron or cobalt.
Claim 31
Dependent Claim
24 words
A recording liquid as defined in claim 15 , wherein the aforementioned general formula (1) is a compound having three azo groups per molecule.
Claim 32
Dependent Claim
27 words
A recording liquid as defined in claim 15 , wherein the aforementioned general formula (1) is a compound containing from 2 to 6 hydrophilic groups per molecule.
Claim 33
Dependent Claim
37 words
A recording liquid as defined in claim 15 , wherein there is incorporated a dyestuff represented by the general formula (1) in an amount of from 0.5% to 10% by weight based on the total amount thereof.
Claim 34
Dependent Claim
69 words
A recording liquid as defined in claim 15 , comprising water and a water soluble organic solvent incorporated therein wherein water is incorporated in an amount of from 45% to 95% by weight based on the total amount of the recording liquid and the water soluble organic solvent is incorporated in an amount of from 1% to 50% by weight based on the total amount of the recording liquid.
Claim 35
Dependent Claim
254 words
A recording liquid comprising an aqueous medium, i) at least one black metal chelated azo dyestuff the free acid form of which is represented by the following general formula (8) and ii) at least one or more other water soluble dyestuff: (wherein the general formula (8) represents a compound having at least one or more hydrophilic group per molecule; M 1 represents an arbitrary metal; A 1 , B 1 and C 1 each independently represents an aromatic ring which may have arbitrary substituents; D 1 represents an aromatic ring which may have arbitrary substituents other than azo group; m 1 represents an integer of 0 to 1; n 1 represents an integer of from 0 to 3; p 1 represents an integer of from 0 to 2; q 1 represents an integer of from 0 to 3, with the proviso that if there are a plurality of B 1 's, they may be the same or different; R 13 and R 14 each independently represents hydrogen atom or arbitrary substituent; M 1 can take tridentate or higher coordination in which M 1 may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (8) or with arbitrary ligands; and a metal ion may be further coordinated to A 1 and B 1 , B 1 and B 1 which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B 1 's or B 1 and C 1 in the form of —O—M—O—).
Claim 36
Dependent Claim
254 words
A recording liquid comprising an aqueous medium, i) at least one black metal chelated azo dyestuff the free acid form of which is represented by the following general formula (8) and ii) at least one or more other water soluble dyestuff: (wherein the general formula (8) represents a compound having at least one or more hydrophilic group per molecule; M 1 represents an arbitrary metal; A 1 , B 1 and C 1 each independently represents an aromatic ring which may have arbitrary substituents; D 1 represents an aromatic ring which may have arbitrary substituents other than azo group; m 1 represents an integer of 0 to 1; n 1 represents an integer of from 0 to 3; p 1 represents an integer of from 0 to 2; q 1 represents an integer of from 0 to 3, with the proviso that if there are a plurality of B 1 's, they may be the same or different; R 13 and R 14 each independently represents hydrogen atom or arbitrary substituent; M 1 can take tridentate or higher coordination in which M 1 may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (8) or with arbitrary ligands; and a metal ion may be further coordinated to A 1 and B 1 , B 1 and B 1 which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B 1 's or B 1 and C 1 in the form of —O—M—O—).
Claim 37
Dependent Claim
202 words
A recording liquid comprising an aqueous medium, i) at least one black metal chelated azo dyestuff the free acid form of which is represented by the following formula (8′) and ii) at least one or more other water soluble dyestuff: (wherein the general formula (8′) represents a compound having at least one or more hydrophilic group per molecule; M 1 represents an arbitrary metal; A 1 , B 1 or C 1 each independently represents an aromatic ring which may have arbitrary substituents; D 1 represents an aromatic ring which may have arbitrary substituents other than azo group; m 1 represents an integer of 0 to 1; n 1 represents an integer of from 0 to 3; p 1 represents an integer of from 0 to 2; q 1 represents an integer of from 0 to 3, with the proviso that if there are a plurality of B 1 's, they may be the same or different; R 13 and R 14 each independently represents hydrogen atom or arbitrary substituent; and M 1 can take tridentate or higher coordination in which M 1 may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (8′) or with arbitrary ligands).
Claim 38
Dependent Claim
202 words
A recording liquid comprising an aqueous medium, i) at least one black metal chelated azo dyestuff the free acid form of which is represented by the following formula (8′) and ii) at least one or more other water soluble dyestuff: (wherein the general formula (8′) represents a compound having at least one or more hydrophilic group per molecule; M 1 represents an arbitrary metal; A 1 , B 1 or C 1 each independently represents an aromatic ring which may have arbitrary substituents; D 1 represents an aromatic ring which may have arbitrary substituents other than azo group; m 1 represents an integer of 0 to 1; n 1 represents an integer of from 0 to 3; p 1 represents an integer of from 0 to 2; q 1 represents an integer of from 0 to 3, with the proviso that if there are a plurality of B 1 's, they may be the same or different; R 13 and R 14 each independently represents hydrogen atom or arbitrary substituent; and M 1 can take tridentate or higher coordination in which M 1 may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (8′) or with arbitrary ligands).
Claim 39
Dependent Claim
22 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), D 1 is a naphthalene ring.
Claim 40
Dependent Claim
126 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), A 1 represents phenyl group which may be substituted or naphthyl group which may be substituted; and B 1 and C 1 each independently represents phenylene group which may be substituted or naphthylene group which may be substituted, with the proviso that if A 1 , B 1 or C 1 has substituents, the substituents are at least one substituent selected from the group consisting of halogen atom, phosphono group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, alkyl group which may be substituted, alkoxyl group which may be substituted, amino group which may be substituted, acylamino group which may be substituted and sulfonylamino group which may be substituted.
Claim 41
Dependent Claim
32 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), wherein m 1 is 0, n 1 is 1 to 2 and p 1 is 1.
Claim 42
Dependent Claim
27 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), wherein q 1 is an integer of from 1 to 3.
Claim 43
Dependent Claim
21 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), wherein q 1 is 1.
Claim 44
Dependent Claim
39 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), wherein one of R 13 and R 14 is a hydrogen atom and the other is a phenyl group which may be substituted.
Claim 45
Dependent Claim
27 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), wherein both R 13 and R 14 each is hydrogen atom.
Claim 46
Dependent Claim
25 words
A recording liquid as defined in claim 31 , wherein in the aforementioned general formula (8), wherein M 1 is copper, nickel, iron or cobalt.
Claim 47
Dependent Claim
21 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is an azo-based water soluble dyestuff.
Claim 48
Dependent Claim
132 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is a water soluble dyestuff the free acid form of which is represented by the following general formula (2): (wherein E represents phenyl group which may be substituted or naphthyl group which may be substituted; R 3 represents hydrogen atom, halogen atom, alkyl group having from 1 to 4 carbon atoms, alkoxy group having from 1 to 4 carbon atoms, carboxyl group or sulfonic acid group; R 4 represents carbonyl group or triazinyl group which may be substituted; L represents an arbitrary connecting group; and r represents 0 or 1, with the proviso that a plurality of E's, R 3 's and R 4 's which are present in the molecule each maybe the same or different).
Claim 49
Dependent Claim
78 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is a water soluble dyestuff the free acid form of which is represented by the following general formula (3): (wherein in the formula (3) R 5 represents hydrogen atom, alkyl group having from 1 to 4 carbon atoms, acyl group or triazinyl group which may be substituted; and E represents phenyl group which may be substituted or naphthyl group which may be substituted).
Claim 50
Dependent Claim
73 words
A recording liquid as defined in claim 43 , wherein the other water soluble dyestuff is a water soluble dyestuff the free acid form of which is represented by the following general formula (4): (wherein in the formula (4) E represents phenyl group which may be substituted or naphthyl group which may be substituted; R 4 represents carbonyl group or triazinyl group which may be substituted; and L represents an arbitrary connecting group).
Claim 51
Dependent Claim
80 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is a water soluble dyestuff the free acid form of which is represented by the following general formula (5): (wherein in the formula (5) R 6 represents triazinyl group which may be substituted; and R 7 represents hydrogen atom, halogen atom, alkyl group having from 1 to 4 carbon atoms, alkoxy group having from 1 to 4 carbon atoms, carboxyl group or sulfonic acid group).
Claim 52
Dependent Claim
137 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is an anthrapyridone-based water soluble dyestuff the free acid form of which is represented by the following general formula (6): (wherein in the formula (6) R 8 represents hydrogen atom, halogen atom, cyano group, alkyl group which may be substituted, alkoxy group which may be substituted, alkoxycarbonyl group which may be substituted or acyl group which may be substituted; R 9 represents hydrogen atom, alkyl group which may be substituted or alkoxy group which may be substituted; R 10 represents hydrogen atom, alkyl group which may be substituted, alkoxy group which may be substituted or phenoxy group which may be substituted; and R 11 represents hydrogen atom, halogen atom, amino group which may be substituted or anilino group which may be substituted).
Claim 53
Dependent Claim
170 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is a metal chelated azo dyestuff formed by an azo compound the free acid form of which is represented by the following general formula (7) and a metal element: (wherein in the formula (7) X 1 and X 2 each independently represents a plurality of atoms required to form at least one 5- to 7-membered aromatic ring, with the proviso that the aromatic rings containing X 1 or X 2 each may have substituents, the substituents on the aromatic rings may be further condensed to form condensed rings and the aromatic rings containing X 1 or X 2 each may contain heteroatoms; R 12 represents hydroxyl group, carboxyl group, sulfonic acid group, phosphono group, alkyl group, alkoxy group or amino group which may be substituted; and s represents an integer of from 1 to 5, with the proviso that if there are a plurality of R 12 's, they may be the same or different).
Claim 54
Dependent Claim
20 words
A recording liquid as defined in claim 31 , wherein the other water soluble dyestuff is a metal phthalocyanine dyestuff.
Claim 55
Dependent Claim
15 words
A recording liquid for inkjet comprising a recording liquid as defined in claim 31 .
Claim 56
Dependent Claim
17 words
An inkjet recording method comprising using a recording liquid as defined in claim 15 or 31 .
Claim 57
Dependent Claim
246 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1): (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1) or with arbitrary ligands; and a metal ion may be further coordinated to A and B, B and B which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B's or B and C in the form of —O—M—O—) wherein B is a naphthalene ring which may be substituted when q is 1, or at least one B is a naphthalene ring which may be substituted when q is 2 or 3.
Claim 58
Dependent Claim
246 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1): (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A, B and C each independently represents an aromatic ring which may have arbitrary substituents; D represents an aromatic ring which may have arbitrary substituents other than azo group; m represents an integer of 0 to 1; n represents an integer of from 0 to 3; p represents an integer of from 0 to 2; q represents an integer of from 1 to 3, with the proviso that if there are a plurality of B's, they may be the same or different; R 1 and R 2 each independently represents hydrogen atom or arbitrary substituent; M can take tridentate or higher coordination in which M may take arbitrary ligand-to-metal coordination at arbitrary substituent or bond in the general formula (1) or with arbitrary ligands; and a metal ion may be further coordinated to A and B, B and B which are adjacent to each other with an azo group interposed therebetween if there are a plurality of B's or B and C in the form of —O—M—O—) wherein B is a naphthalene ring which may be substituted when q is 1, or at least one B is a naphthalene ring which may be substituted when q is 2 or 3.
Claim 59
Dependent Claim
22 words
A metal chelated azo dyestuff selected from the group consisting of compound nos. 1 through 53 in Table 1 of the specification.
Claim 60
Dependent Claim
22 words
A metal chelated azo dyestuff selected from the group consisting of compound nos. 1 through 53 in Table 1 of the specification.
Claim 61
Dependent Claim
105 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1): (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A is selected from the group consisting of(A-1) through (A-12); B is selected from the group consisting of (B-1) through (B-10); C is selected from the group consisting of (C-1) through (C-4); and D(O)(OH) m (SO 3 H) n (NR 1 R 2 ) p is selected from the group consisting of (D-1) through (D-14), all of the specification.
Claim 62
Dependent Claim
105 words
A metal chelated azo dyestuff for inkjet recording characterized in that its free acid form is represented by the following general formula (1): (wherein the general formula (1) represents a compound having at least one or more hydrophilic group per molecule; M represents an arbitrary metal; A is selected from the group consisting of(A-1) through (A-12); B is selected from the group consisting of (B-1) through (B-10); C is selected from the group consisting of (C-1) through (C-4); and D(O)(OH) m (SO 3 H) n (NR 1 R 2 ) p is selected from the group consisting of (D-1) through (D-14), all of the specification.
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) | 2007-05-18 | 2007-11-17 | 2008-05-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2011-05-18 | 2011-11-17 | 2012-05-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2015-05-18 | 2015-11-17 | 2016-05-18 | $7700.00 | Window Closed / Lapsed |