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US 5,189,154 AGranted
Anionic phthalocyanine compounds
AssigneeImperial Chemical Industries PLC
InventorsPeter Gregory, Ronald W. Kenyon, Christine Millard
Life of this patent
Estimating the term…
Abstract
Anionic phthalocyanine compounds which, in the free acid form, have the Formula (1): Pc(SO.sub.3 H).sub.t (SO.sub.2 --NR.sup.1 --L--NR.sup.2 --X--NR.sup.3 --G).sub.q (1) The compounds are useful as the colored component of inks, particularly those used in ink jet printing.
Claims17
An anionic phthalocyanine compound which, in the free acid form, has the Formula (1):
- Pc(SO.sub.3 H).sub.t (SO.sub.2 --NR.sup.1 --L--NR.sup.2 --X--NR.sup.3 --G).sub.q ( 1)
- wherein:
- Pc is a Li, Na, K, Mg, Ca, Ba, Al, Si, Sn, Pb, Rh, Sc, Ti, V, Cr, Mn, Fe, Co, Zn, Ni or Cu-containing phthalocyanine nucleus;
- R.sup.1, R.sup.2 and R.sup.3 are each independently H, C.sub.1-4 -alkyl or hydroxy-C.sub.1-4 -alkyl;
- L is a divalent aliphatic radical containing from 2 to 6 carbon atoms, benzylene, xylylene or a monocyclic radical of the benzene series;
- each X independently is carbonyl or a group of formula (2), (3) or (4):
- ##STR3## each Z independently is NR.sup.4 R.sup.5, SR.sup.6 or OR.sup.6 ;
- each Y independently is H, Cl or Z;
- each E independently is Cl or CN;
- R.sup.4 and R.sup.5 are each independently H, C.sub.1-4 -alkyl or substituted C.sub.1-4 -alkyl in which the substituents are selected from --COOH, --SO.sub.3 H and --OH or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholine or piperidine ring;
- R.sup.6 is selected from C.sub.1-4 -alkyl and hydroxy-C.sub.1-4 -alkyl
- G is a colourless C.sub.1-4 -substituted alkyl, (C.sub.1-3 -alkyl)substituted phenyl, substituted phenyl or substituted naphthyl radical wherein the substituent is selected from B, --(CH.sub.2).sub.n --B, --O--(CH.sub.2).sub.n --B, --S--(CH.sub.2).sub.n --B, and --NR.sup.8 (CH.sub.2).sub.n --B in which B is CO.sub.2 H or COSH, n is an integer from 1 to 6 and R.sup.8 is H or C.sub.1-4 -alkyl;
- and
- (t+q) is from 3 to 4 inclusive.
11 more elements
An anionic phthalocyanine compound which, in the free acid form, has the Formula (1):
- Pc(SO.sub.3 H).sub.t (SO.sub.2 --NR.sup.1 --L--NR.sup.2 --X--NR.sup.3 --G).sub.q ( 1)
- wherein:
- Pc is a nickel- or copper-containing phthalocyanine nucleus;
- R.sup.1, R.sup.2 and R.sup.3 are each independently H, C.sub.1-4 -alkyl or hydroxy C.sub.1-4 -alkyl;
- L is a divalent aliphatic containing from 2 to 6 carbon atoms or a group selected from:
- ______________________________________ 1,3- or 1,4-phenylene 2-nitro-1,4-phenylene 3-sulpho-1,4-phenylene 4-methoxy-1,3-phenylene 4-sulpho-1,3-phenylene 4-nitro-1,3-phenylene 2-carboxy-1,4-phenylene 2-chloro-1,4-phenylene 4-carboxy-1,3-phenylene 3,7-disulpho-1,5-naphthylene 2-methoxy-1,4-phenylene diphenyl azobenzene diphenyloxide diphenyloxadiazole diphenylamine benzanilide diphenylsulphide diphenylurea diphenylsulphone 1,2-bis(phenylcarbamyl)ethylene diphenylmethane 1,4-bis-(phenylcarbamyl)butadiene diphenylketone 1,2-bis-(phenylcarbamyl)ethane diphenylethane 1,3-bis-(phenylcarbamyl)propane diphenylethylene 2,4-dianilino-s-triazine 3,3'-dichlorobenzidine and 3,3'-dicarboxybenzidine;
- ______________________________________
- each X independently is carbonyl or a group of formula (2), (3) or (4):
- ##STR4## each Z independently is NR.sup.4 R.sup.5, SR.sup.6 or OR.sup.6 ;
- each Y independently is H, Cl or Z;
- each E independently is Cl or CN;
- R.sup.4 and R.sup.5 are each independently H or C.sub.1-4 -alkyl or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholine or piperidine ring;
- R.sup.6 is C.sub.1-4 alkyl;
- the group --NR.sup.3 G is derived from an amino acid of Formula GNR.sup.3 H selected from:
- ______________________________________ 2-aminoisophthalic acid 3-amino-4-fluorobenzoic acid 4-aminoisophthalic acid 3-amino-5-hydroxybenzoic acid 5-aminoisophthalic acid 3-amino-4-hydroxybenzoic acid 3-aminophthalic acid 3-amino-2-hydroxybenzoic acid 4-aminophthalic acid 2-amino-6-hydroxybenzoic acid 2-aminoterephthalic acid 2-amino-4-nitrobenzoic acid 3-aminobenzoic acid 3-amino-5-nitrobenzoic acid 4-aminobenzoic acid 2-nitro-3-aminobenzoic acid 4-(methylamino)benzoic acid 2-nitro-5-aminobenzoic acid anthranilic acid 3-nitro-4-aminobenzoic acid 4-sulphoanthranilic acid 3-acetylamino-5-aminobenzoic acid 5-sulphoanthranilic acid 3-amino-4-methylbenzoic acid 2-amino-4-chlorobenzoic acid 2-amino-3-methylbenzoic acid 2-amino-5-chlorobenzoic acid 3-amino-4-methoxybenzoic acid 3-amino-4-chlorobenzoic acid 3-amino-4-hydroxybenzoic acid 5-amino-2-chlorobenzoic acid 4-aminosalicylic acid 2-amino-5-methylbenzoic acid 5-aminosalicylic acid 2-amino-6-methylbenzoic acid 3-amino-2-naphthoic acid 2-amino-5-bromobenzoic acid 5-amino-2-naphthoic acid Beta-alanine 8-amino-2-naphthoic acid Alanine 2-n-butoxy-4-aminobenzoic acid Asparagine Arginine Cystein Aspartic acid Glutamic acid Cystine Glycine Glutamine Hydroxylysine Glycyl glycine Isoleucine Hydroxyproline Lysine Leucine Phenylalanine Methionine Serine Proline Tryptophane Threonine Valine and Tyrosine;
- and ______________________________________
- (t+q) is from 3 to 4 inclusive.
14 more elements
An anionic phthalocyanine compound which, in the free acid form, has the Formula (1):
- Pc(SO.sub.3 H).sub.t (SO.sub.2 --NR.sup.1 --L--NR.sup.2 --X--NR.sup.3 --G).sub.q ( 1)
- wherein:
- Pc is a nickel- or copper-containing phthalocyanine nucleus;
- R.sup.1, R.sup.2 and R.sup.3 are each independently H or C.sub.1-4 -alkyl;
- L is a divalent aliphatic radical containing from 2 to 6 carbon atoms;
- each X independently is carbonyl or a group of formula (2), (3) or (4):
- ##STR5## each Z independently is NR.sup.4 R.sup.5, SR.sup.6 or OR.sup.6 ;
- each Y independently is H, Cl or Z;
- each E independently is Cl or CN;
- R.sup.4 and R.sup.5 are each independently H, C.sub.1-4 -alkyl, -HO(C.sub.1-4 -alkylene) or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholine or piperidine ring;
- R.sup.6 is C.sub.1-4 alkyl or hydroxy-C.sub.1-4 -alkyl
- G is carboxyphenyl or dicarboxyphenyl;
- and
- (t+q) is from 3 to 4 inclusive.
11 more elements
Dependencies are inferred from the claim text.