US3954397A
Expired / Lapsed
US
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Method for preparing dye solutions
Assignee: Rohm and Haas Co
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Filing: 1973-07-16
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Granted: 1976-05-04
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Expires: 1993-07-16
Abstract
Abstract A method is disclosed for improving the solubility of Lewis acid dyes including metal chelate dyes and acid dyes, in solvent employing a 5- or 6-membered heterocyclic tertiary amine. Dye solutions prepared by this process are useful in dyeing leather, in dyeing coatings and plastic articles, and are especially useful in combination with reactive urethane systems.
Inventors
- 👤 Fred A. Desiderio
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:28
CPC Classifications
C; C09; C09B; C09B67/00; C09B67/0071; C09B67/0072; C09B69/00; C09B69/02; C09B69/04; D; D06; D06P; D06P3/00; D06P3/02; D06P3/04; D06P3/32; Y; Y10; Y10S; Y10S8/00; Y10S8/907; Y10S8/92; Y10S8/926; Y10S8/938
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
132 words
A process for increasing the solubility of a metal chelate or acid dye in a solvent, which comprises dissolving the dye in a solution containing said solvent and a 5- or 6- membered heterocyclic tertiary amine, said solvents being selected from ketones, esters, ethers, aliphatic hydrocarbons, aromatic hydrocarbons, an excess of said tertiary amine or mixtures thereof and said tertiary amine having the following structural formula: ##EQU7## wherein A is oxy or thio, R 1 is an organic radical, R 2 is hydrogen or alkyl and R 3 is hydrogen, phenyl, benzyl, or alkyl or R 2 and R 3 may be joined together with the carbon atom to which they are attached to form a 5- or 6- membered hydrocarbyl ring and n is an integer having a value of 1-2.
Claim 2
Dependent Claim
132 words
A process for increasing the solubility of a metal chelate or acid dye in a solvent, which comprises dissolving the dye in a solution containing said solvent and a 5- or 6- membered heterocyclic tertiary amine, said solvents being selected from ketones, esters, ethers, aliphatic hydrocarbons, aromatic hydrocarbons, an excess of said tertiary amine or mixtures thereof and said tertiary amine having the following structural formula: ##EQU7## wherein A is oxy or thio, R 1 is an organic radical, R 2 is hydrogen or alkyl and R 3 is hydrogen, phenyl, benzyl, or alkyl or R 2 and R 3 may be joined together with the carbon atom to which they are attached to form a 5- or 6- membered hydrocarbyl ring and n is an integer having a value of 1-2.
Claim 3
Dependent Claim
28 words
A process according to claim 1 wherein, in said tertiary amine, R 1 is lower alkyl or acryloxy lower alkyl and R 3 is hydrogen, phenyl or alkyl.
Claim 4
Dependent Claim
63 words
A process according to claim 1 wherein said solvent is a ketone or ester solvent or mixture thereof, and wherein the tertiary amine has the formula ##EQU8## wherein R 5 is hydrogen, R 6 is hydrogen, isopropyl or phenyl or R 5 and R 6 may be joined together with the carbon atom to which they are attached, to form cyclopentyl or cyclohexyl.
Claim 5
Dependent Claim
13 words
A process according to claim 1 wherein the tertiary amine is oxazolidinylethyl methacrylate.
Claim 6
Dependent Claim
80 words
The process of claim 1 wherein the solvent is selected from cyclohexanone, ethyl lactate, pentoxone, butyl acetate, methyl hexyl ketone, methyl amyl acetate, pentylacetate, isobutyl isobutyrate, diisobutylketone, hexyl acetate, a mixed aromatic hydrocarbon, methyl isoamyl ketone, methyl n-butyl ketone, ethylamyl ketone, 2-ethoxyethyl acetate, butyl cellosolve acetate, n-propyl acetate, isobutyl acetate, butyl acetate, i-propyl acetate, ethyl acetate, xylene, toluene, ethyl benzene, benzene, tetrahydrofuran, dioxane, isophorone, methyl ethyl ketone, methyl isobutyl ketone, mesityl oxide, methyl amylketone, chlorobenzene, 1,2-dichloroethylene, methylene dichloride, 1-nitropropane, 2-nitropropane.
Claim 7
Dependent Claim
16 words
The process of claim 1 wherein the solvent is a mixture of cyclohexanone and butyl acetate.
Claim 8
Dependent Claim
119 words
A composition useful in dyeing which comprises: a. a metal chelate dye or an acid dye; b. a 5- or 6- membered heterocyclic tertiary amine of the following formula: ##EQU9## wherein A is oxy or thio, R 1 is an organic radical; R 2 is hydrogen or alkyl; R 3 is hydrogen, phenyl, benzyl or alkyl; or R 2 and R 3 may be joined to form together with the carbon atom to which they are attached, a 5- or 6-membered hydrocarbyl ring and n is an integer having a value of 1 or 2, and c. a solvent selected from a ketone, ester, ether, aliphatic hydrocarbon, aromatic hydrocarbon, an excess of said tertiary amine or a mixture thereof.
Claim 9
Dependent Claim
119 words
A composition useful in dyeing which comprises: a. a metal chelate dye or an acid dye; b. a 5- or 6- membered heterocyclic tertiary amine of the following formula: ##EQU9## wherein A is oxy or thio, R 1 is an organic radical; R 2 is hydrogen or alkyl; R 3 is hydrogen, phenyl, benzyl or alkyl; or R 2 and R 3 may be joined to form together with the carbon atom to which they are attached, a 5- or 6-membered hydrocarbyl ring and n is an integer having a value of 1 or 2, and c. a solvent selected from a ketone, ester, ether, aliphatic hydrocarbon, aromatic hydrocarbon, an excess of said tertiary amine or a mixture thereof.
Claim 10
Dependent Claim
37 words
A composition according to claim 7 wherein said dye is a metal chelate dye, and wherein, in said tertiary amine, R 1 is lower alkyl or acryloxy lower alkyl and R 3 is hydrogen, phenyl or alkyl.
Claim 11
Dependent Claim
77 words
A composition according to claim 7 wherein said dye is a metal chelate dye; wherein said tertiary amine is a 5-membered heterocyclic tertiary amine of the following structural formula: ##EQU10## wherein R 5 is hydrogen, R 6 is hydrogen, isopropyl or phenyl or R 5 and R 6 may be joined together with the carbon atom to which they are attached to form cyclopentyl or cyclohexyl; and wherein said solvent is a ketone, ester or mixture thereof.
Claim 12
Dependent Claim
25 words
A composition according to claim 9 wherein said tertiary amine is oxazolidinylethyl methacrylate; and wherein said solvent is a mixture of cyclohexanone and butyl acetate.
Claim 13
Dependent Claim
15 words
A method of dyeing which comprises treating a substrate with the composition of claim 7.
Claim 14
Dependent Claim
15 words
A method of dyeing which comprises treating a substrate with the composition of claim 8.
Claim 15
Dependent Claim
16 words
A method of claim 12 wherein the substrate is leather or a flexible, polymeric leather-like material.
Claim 16
Dependent Claim
17 words
A leather or leather-like article of manufacture which has been treated with the composition of claim 7.
Claim 17
Dependent Claim
19 words
A leather or flexible, polymeric leather-like article of manufacture which has been treated with the composition of claim 8.
Claim 18
Dependent Claim
19 words
A leather or flexible, polymeric leather-like article of manufacture which has been treated with the composition of claim 9.
Claim 19
Dependent Claim
15 words
A method of dyeing which comprises treating a substrate with the composition of claim 9.
Claim 20
Dependent Claim
31 words
The process of claim 1 wherein the metal chelate dye is selected from Solvent Yellow 88, Solvent Orange 58, Solvent Brown 42, Solvent Brown 43, Solvent Blue 48, Solvent Black 29.
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) | 1979-05-04 | 1979-11-03 | 1980-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-04 | 1983-11-03 | 1984-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-04 | 1987-11-03 | 1988-05-04 | $7700.00 | Window Closed / Lapsed |