US4405329A
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US
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Stable concentrated fluid formulations of metal-free dyes, process for their preparation, and their use
Assignee: Novartis Corp
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Filing: 1981-06-01
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Granted: 1983-09-20
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Expires: 2001-06-01
Abstract
Abstract Concentrated fluid formulations of textile dyes, leather dyes or paper dyes, comprising (1) metal-free dyes, (2) non-ionic compounds having a hydrotropic action, at least one of components (3) or (4), component (3) being a reaction product of a fatty acid having 8 to 22 carbon atoms and 1 to 2 mols of diethanolamine, and component (4) being a compound of the formula ##STR1## in which R is an aliphatic hydrocarbon radical having 8 to 22 carbon atoms or a cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 10 to 22 carbon atoms, R 1 is hydrogen or methyl, A is --O-- or ##STR2## X is the acid radical of an inorganic, oxygen-containing acid, the acid radical of a polybasic carboxylic acid or a carboxyalkyl radical and m is a number from 1 to 50, (5) water, a water-soluble organic solvent having a boiling point of at least 80° C., or a mixture of the two, and, (6) optionally conventional formulating assistants, have excellent stability over a wide temperature range and, on dilution with water or solvents, do not form any undesired multi-phase systems or precipitates.
Inventors
- 👤 Heinz Abel
- 👤 Paul Hugelshofer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:51
CPC Classifications
C; C09; C09B; C09B67/00; C09B67/0071; C09B67/0092; C09B67/0072; C09B67/0073; C09B67/0096
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
203 words
A method of preparation of a spray solution for dyeing leather, which comprises diluting a stable concentrated fluid formation with water, organic solvents, or a mixture of water and organic solvents, the fluid formulation containing, in the absence of metallized dyes: (1) a metal-free leather dye consisting essentially of a monoazo or polyazo dye or an anthraquinone dye, (2) a non-ionic compound having a hydrotropic action, at least one of the components (3) or (4), the component (3) being a reaction product of a fatty acid having 8 to 22 carbon atoms and 1 to 2 mols of diethanolamine, and the component (4) being a compound of the formula ##STR13## in which R is an aliphatic hydrocarbon radical having 8 to 22 carbon atoms or a cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 10 to 22 carbon atoms, R 1 is hydrogen or methyl, A is --O-- or ##STR14## X is the acid radical of an inorganic oxygen containing acid, the acid radical of a polybasic carboxylic acid or a carboxyalkyl radical and m is a number from 1 to 50, and (5) water, a water-soluble organic solvent having a boiling point of at least 80° C., or a mixture of the two.
Claim 2
Independent Claim
203 words
A method of preparation of a spray solution for dyeing leather, which comprises diluting a stable concentrated fluid formation with water, organic solvents, or a mixture of water and organic solvents, the fluid formulation containing, in the absence of metallized dyes: (1) a metal-free leather dye consisting essentially of a monoazo or polyazo dye or an anthraquinone dye, (2) a non-ionic compound having a hydrotropic action, at least one of the components (3) or (4), the component (3) being a reaction product of a fatty acid having 8 to 22 carbon atoms and 1 to 2 mols of diethanolamine, and the component (4) being a compound of the formula ##STR13## in which R is an aliphatic hydrocarbon radical having 8 to 22 carbon atoms or a cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 10 to 22 carbon atoms, R 1 is hydrogen or methyl, A is --O-- or ##STR14## X is the acid radical of an inorganic oxygen containing acid, the acid radical of a polybasic carboxylic acid or a carboxyalkyl radical and m is a number from 1 to 50, and (5) water, a water-soluble organic solvent having a boiling point of at least 80° C., or a mixture of the two.
Claim 3
Dependent Claim
34 words
A method according to claim 1, which contains, as the formulation component (5), a water-soluble organic solvent having a boiling point of at least 80° C., or a mixture of water and this solvent.
Claim 4
Dependent Claim
27 words
A method according to claim 1, which contains, in the formulation, at least 10 percent by weight of the dye, relative to the weight of the formulation.
Claim 5
Dependent Claim
71 words
A method according to claim 3, wherein the formulation contains 10 to 60 percent by weight of component (1), 1 to 25 percent by weight of component (2), 1 to 20 percent by weight of at least one of components (3) and (4) and 20 to 88 percent by weight of component (5), the weight percentages relating to the total formulation an the sum of the constituents adding up to 100%.
Claim 6
Dependent Claim
71 words
A method according to claim 4, wherein the formulation contains 10 to 30 percent by weight of component (1) 1 to 20 percent by weight of component (2), 1 to 15 percent by weight of at least one of components (3) and (4) and 20 to 88 percent by weight of component (5), the weight percentages relating to the total formulation and the sum of the constituents adding up to 100%.
Claim 7
Dependent Claim
71 words
A method according to claim 5, wherein the formulation contains 10 to 30 percent by weight of component (1), 3 to 20 percent by weight of component (2), 3 to 20 percent by weight of at least one of components (3) and (4) and 30 to 84 percent by weight of component (5), the weight percentages relating to the total formulation and the sum of the constituents adding up to 100%.
Claim 8
Dependent Claim
70 words
A method according to claim 3, wherein the formulation contains 10 to 35 percent by weight of component (1), 1 to 40 percent by weight of component (2), 1 to 40 percent by weight of at least one of components (3) and (4) and at least 5 percent by weight of water, the weight percentages relating to the total formulation and the sum of the constituents adding up to 100%.
Claim 9
Dependent Claim
170 words
A method according to claim 1, wherein, in the formulation, the non-ionic compound, having a hydrotropic action, representing component (2) is a reaction product, having a molecular weight of about 2,000 to 7,000, of (a 1 ) a monohydric to hexahydric alcohol having 1 to 6 carbon atoms, monalkylamines or monoalkylolmonoamines or polyalkylenepolyamines and (a 2 ) 1,2-propylene oxide, a reaction product of an alkylene oxide and a water-insoluble aliphatic monoalcohol having at least 8 carbon atoms, a reaction product of an alkylene oxide and an arylphenol or alkylphenol, a reaction product of a saturated dicarboxylic acid having 3 to 10 carbon atoms and 1,2-propylene oxide or a polypropylene glycol, a reaction product of a fatty acid having 10 to 18 carbon atoms and 1,2-propylene oxide or a polypropylene glycol, a reaction product of a fatty acid having 10 to 18 carbon atoms, a trihydric to hexahydric alcohol and 1,2-propylene oxide or a reaction product of a fatty acid having 10 to 18 carbon atoms, a polyalkylenepolyamine and 1,2-propylene oxide.
Claim 10
Dependent Claim
30 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of ethylene glycol, propylene glycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol or trimethylolethane and 1,2-propylene oxide.
Claim 11
Dependent Claim
55 words
A method according to claim 9, wherein, in the formulation, component (2) is a reaction product of a monoalkylamine or monoalkylolmonoamine having 1 to 6 carbon atoms or a polyalkylenepolyamine of the formula H.sub.2 N(CH.sub.2 CH.sub.2 NH).sub.r CH.sub.2 CH.sub.2 NH.sub.2 in which r is 0 or a number from 1 to 3, and 1,2-propylene oxide.
Claim 12
Dependent Claim
24 words
A method according to claim 10, wherein, in the formulation, component (2) is a reaction product of monoisopropanolamine or ethylene diamine and 1,2-propylene oxide.
Claim 13
Dependent Claim
34 words
A method according to claim 8, wherein, in the formulation, component (2) is an aliphatic, saturated or unsaturated, branched or straight-chain monoalcohol having 8 to 18 carbon atoms, or a mixture of such alcohols.
Claim 14
Dependent Claim
42 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of ethylene oxide, 1,2-propylene oxide or a mixed ethylene-1,2-propylene oxide and an aliphatic, saturated or unsaturated, branched or straight-chain monoalcohol having 8 to 18 carbon atoms.
Claim 15
Dependent Claim
49 words
A method according to claim 13, wherein, in the formulation, component (2) is a compound of the formula R.sub.3 O(CH.sub.2 CH.sub.2 O).sub.s H in which R 3 is a saturated or unsaturated hydrocarbon radical having 8 to 18 carbon atoms and s is a number from 1 to 10.
Claim 16
Dependent Claim
39 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of ethylene oxide, 1,2-propylene oxide or a mixed ethylene-1,2-propylene oxide and an alkylphenol having 4 to 12 carbon atoms in the alkyl part.
Claim 17
Dependent Claim
50 words
A method according to claim 15, wherein, in the formulation, component (2) is a compound of the formula ##STR15## in which R 1 is hydrogen or methyl, p is a number from 4 to 12 and t is a number from 1 to 60, in particular from 1 to 30.
Claim 18
Dependent Claim
26 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of o-phenylphenol and 5 to 15 mols of ethylene oxide.
Claim 19
Dependent Claim
34 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of a saturated dicarboxylic acid having 3 to 10 carbon atoms and 1,2-propylene oxide or a polypropylene glycol.
Claim 20
Dependent Claim
29 words
A method according to claim 18, wherein, in the formulation, component (2) is a reaction product of adipic acid or sebacic acid and 1,2-propylene oxide or a polypropylene glycol.
Claim 21
Dependent Claim
29 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of a fatty acid having 10 to 18 carbon atoms and 1,2-propylene oxide.
Claim 22
Dependent Claim
40 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of a fatty acid having 10 to 18 carbon atoms, a trihydric to hexahydric alcohol having 3 to 6 carbon atoms and 1,2-propylene oxide.
Claim 23
Dependent Claim
53 words
A method according to claim 8, wherein, in the formulation, component (2) is a reaction product of a fatty acid having 10 to 18 carbon atoms, a polyalkylenepolyamine of the formula H.sub.2 N(CH.sub.2 CH.sub.2 NH).sub.n CH.sub.2 CH.sub.2 NH.sub.2 in which n is zero or the number 1, 2 or 3, and 1,2-propylene oxide.
Claim 24
Dependent Claim
32 words
A method according to claim 1, wherein, in the formulation, component (3) is a reaction product of coconut fatty acid, lauric acid, oleic acid or stearic acid and 2 mols of diethanolamine.
Claim 25
Dependent Claim
45 words
A method according to claim 1, wherein component (4) is a compound of the formula R--A--(CH.sub.2 CH.sub.2 O).sub.n --X in which R, A and X are as defined in claim 1 and n is a number from 1 to 9, preferably from 1 to 4.
Claim 26
Dependent Claim
57 words
A method according to claim 24, wherein, in the formulation, component (4) is a compound of the formula R.sub.2 O--(CH.sub.2 CH.sub.2 O).sub.n --X in which R 2 is a saturated or unsaturated hydrocarbon radical, o-phenylphenyl or alkylphenyl having 4 to 12 carbon atoms in the alkyl part, and X and n are as defined in claim 24.
Claim 27
Dependent Claim
39 words
A method according to claim 25, wherein, in the formulation, component (4) is a compound of the formula ##STR16## in which p is a number from 4 to 12 and n and X are as defined in claim 25.
Claim 28
Dependent Claim
41 words
A method according to claim 26, wherein, in the formulation, component (4) is a compound of the formula ##STR17## in which q is a number from 1 to 3 and X 1 is hydrogen, NH 4 or an alkali metal cation.
Claim 29
Dependent Claim
58 words
A method according to claim 1, wherein component (4) is a compound of the formula ##STR18## in which R, A and X are as defined in claim 1, the sum of m 1 , m 2 and m 3 is 2 to 20 and the ratio of ethylene oxide units to propylene oxide units is 1:(1 to 2).
Claim 30
Dependent Claim
28 words
A method according to claim 1, wherein, in the formulation, the compounds representing component (4) are present as an alkali metal salt, ammonium salt or an amine salt.
Claim 31
Dependent Claim
40 words
A method according to claim 1, wherein, in the formulation, component (5) is water, a polyhydric alcohol, which is liquid at room temperature, or an ether, ester or mixed ether-ester thereof, tetramethylurea or a mixture of water and these solvents.
Claim 32
Dependent Claim
59 words
A method of the preparation of a stable concentrated fluid formulation of a metal-free dye, according to claim 1, which comprises mixing the dye with the components (2) and (3), (2) and (4) or (2), (3) and (4) in any desired sequence in water, a water-soluble organic solvent or mixtures thereof, optionally in the presence of conventional formulating assistants.
Claim 33
Dependent Claim
95 words
A method of the preparation of a stable concentrated fluid formulation of a metal-free water-soluble dye, according to claim 1, which comprises separating by-products of the synthesis, water-soluble salts and, optionally a proportion of the water from an aqueous solution or suspension of at least one metal-free water-soluble crude dye, optionally drying the resulting dye formulation, and then mixing it with the components (2) and (3), (2) and (4) or (2), (3) and (4) in any desired sequence in water, a water-soluble organic solvent or mixtures thereof, optionally in the presence of conventional formulating assistants.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-09-19 | 1987-03-21 | 1987-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-09-19 | 1991-03-21 | 1991-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-09-19 | 1995-03-21 | 1995-09-20 | $7700.00 | Window Closed / Lapsed |