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US4160642A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for preparing dye solutions

Assignee: Rohm and Haas Co
•
Filing: 1975-09-17
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Granted: 1979-07-10
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Expires: 1995-09-17
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Abstract

Abstract A method is disclosed for improving the solubility of Lewis acid dyes including metal chelate dyes and acid dyes, in solvents employing a copolymer based on a monomer containing 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 08:05
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: 23
Claim 1
Independent Claim 46 words
A process for increasing the solubility of a hydroxyazo metal chelate dye in an effective solvent substantially free from active hydrogen atoms as determined by the Zerewitinoff Method which comprises treating said dye with a copolymer of oxazolidinylethyl methacrylate and one or more monomers copolymerizable therewith.
Claim 2
Dependent Claim 46 words
A process for increasing the solubility of a hydroxyazo metal chelate dye in an effective solvent substantially free from active hydrogen atoms as determined by the Zerewitinoff Method which comprises treating said dye with a copolymer of oxazolidinylethyl methacrylate and one or more monomers copolymerizable therewith.
Claim 3
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.
Claim 4
Dependent Claim 37 words
A process for preparing a urethane compatable dye solution which comprises treating a metal chelate dye with a copolymer of oxazolidinylethyl methacrylate and one or more monomers copolymerizable therewith in a mixture of cyclohexanone and butyl acetate.
Claim 5
Dependent Claim 37 words
A process for preparing a urethane compatable dye solution which comprises treating a metal chelate dye with a copolymer of oxazolidinylethyl methacrylate and one or more monomers copolymerizable therewith in a mixture of cyclohexanone and butyl acetate.
Claim 6
Dependent Claim 197 words
A composition useful in dyeing which comprises a solution of: (a) a metal chelate dye or acid dye; (b) a 5- or 6- membered heterocyclic tertiary amine copolymer wherein the tertiary amine has the formula: ##STR7## 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 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 1-2; said tertiary amine being copolymerized with one or more monomers selected from ##STR8## wherein R 7 is hydrogen or lower alkyl and R 8 is a straight, branched or cyclic radical having from 2 to 14 carbon atoms, and ##STR9## wherein R 9 and R 10 are the same or different radicals selected from hydrogen, halo, lower alkanoyloxy, cyano, formyl, phenyl, carbamoyl or epoxy; and (c) a solvent substantially free from active hydrogen atoms as determined by the Zerewitinoff Method selected from a ketone, ester, ether, aliphatic hydrocarbon, aromatic hydrocarbon or an excess of said tertiary amine.
Claim 7
Dependent Claim 197 words
A composition useful in dyeing which comprises a solution of: (a) a metal chelate dye or acid dye; (b) a 5- or 6- membered heterocyclic tertiary amine copolymer wherein the tertiary amine has the formula: ##STR7## 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 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 1-2; said tertiary amine being copolymerized with one or more monomers selected from ##STR8## wherein R 7 is hydrogen or lower alkyl and R 8 is a straight, branched or cyclic radical having from 2 to 14 carbon atoms, and ##STR9## wherein R 9 and R 10 are the same or different radicals selected from hydrogen, halo, lower alkanoyloxy, cyano, formyl, phenyl, carbamoyl or epoxy; and (c) a solvent substantially free from active hydrogen atoms as determined by the Zerewitinoff Method selected from a ketone, ester, ether, aliphatic hydrocarbon, aromatic hydrocarbon or an excess of said tertiary amine.
Claim 8
Dependent Claim 38 words
A composition as in claim 4 wherein R 1 of the tertiary amine is a radical of the formula ##STR10## wherein R 4 is hydrogen or lower alkyl and m is an integer having a value of 2-3.
Claim 9
Dependent Claim 15 words
A method of dyeing which comprises treating a substrate with the composition of claim 4.
Claim 10
Dependent Claim 16 words
The method of claim 6 wherein the substrate is leather or a flexible, polymeric leather-like material.
Claim 11
Dependent Claim 16 words
The composition of claim 4 wherein the copolymer is composed of methyl methacrylate and oxazolidinylethyl methacrylate.
Claim 12
Dependent Claim 18 words
The composition of claim 4 wherein the copolymer is composed of methyl methacrylate, butyl acrylate and oxazolidinylethyl methacrylate.
Claim 13
Dependent Claim 13 words
A composition which comprises the composition of claim 4 and a reactive polyurethane.
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 15 words
A method of dyeing which comprises treating a substrate with the composition of claim 9.
Claim 16
Dependent Claim 16 words
The method of claim 11 wherein the substrate is leather or a flexible, polymeric leather-like material.
Claim 17
Dependent Claim 16 words
The method of claim 12 wherein the substrate is leather or a flexible, polymeric leather-like material.
Claim 18
Dependent Claim 189 words
A process for increasing the solubility of a metal chelate dye or acid dye in an effective solvent substantially free from active hydrogen atoms as determined by the Zerewitinoff Method, which comprises dissolving the dye in an effective solution containing said solvent and a 5- or 6-membered heterocyclic tertiary amine copolymer, said tertiary amine having the following structural formula: ##STR11## wherein A is oxy or thio, R 1 is a copolymerizable 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; said tertiary amine being copolymerized with one or more monomers selected from ##STR12## wherein R 7 is hydrogen or lower alkyl and R 8 is a straight, branched or cyclic radical having from 2 to 14 carbon atoms, and ##STR13## wherein R 9 and R 10 are the same or different radicals selected from hydrogen, halo, lower alkanoxyloxy, cyano, formyl, phenyl, carbamoyl or epoxy.
Claim 19
Dependent Claim 189 words
A process for increasing the solubility of a metal chelate dye or acid dye in an effective solvent substantially free from active hydrogen atoms as determined by the Zerewitinoff Method, which comprises dissolving the dye in an effective solution containing said solvent and a 5- or 6-membered heterocyclic tertiary amine copolymer, said tertiary amine having the following structural formula: ##STR11## wherein A is oxy or thio, R 1 is a copolymerizable 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; said tertiary amine being copolymerized with one or more monomers selected from ##STR12## wherein R 7 is hydrogen or lower alkyl and R 8 is a straight, branched or cyclic radical having from 2 to 14 carbon atoms, and ##STR13## wherein R 9 and R 10 are the same or different radicals selected from hydrogen, halo, lower alkanoxyloxy, cyano, formyl, phenyl, carbamoyl or epoxy.
Claim 20
Dependent Claim 38 words
A process as in claim 15 wherein R 1 of the tertiary amine is a radical of the formula ##STR14## wherein R 4 is hydrogen or lower alkyl and m is an integer having a value of 2-3.
Claim 21
Dependent Claim 16 words
The process of claim 15 wherein the copolymer is composed of methyl methacrylate and oxazolidinylethyl methacrylate.
Claim 22
Dependent Claim 18 words
The process of claim 15 wherein the copolymer is composed of methyl methacrylate, butyl acrylate, and oxazolidinylethyl methacrylate.
Claim 23
Dependent Claim 21 words
The process of claim 15 wherein the 5- or 6-membered heterocyclic amine is from 2 to 25 percent of the copolymer.

References Cited (Backward Citations)

US2205355A Cited
US2328900A Cited
US3190850A Cited
US2901473A Cited
US3037006A Cited
US3661923A Cited
US3743626A Cited
US3954397A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-07-09 1983-01-08 1983-07-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-07-09 1987-01-08 1987-07-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-07-09 1991-01-08 1991-07-10 $7700.00 Window Closed / Lapsed

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