US3281201A - Process for dyeing of nylon fibers with premetallized and acid dyestuffs - Google Patents
Process for dyeing of nylon fibers with premetallized and acid dyestuffs Download PDFInfo
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- US3281201A US3281201A US204616A US20461662A US3281201A US 3281201 A US3281201 A US 3281201A US 204616 A US204616 A US 204616A US 20461662 A US20461662 A US 20461662A US 3281201 A US3281201 A US 3281201A
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/13—Fugitive dyeing or stripping dyes
- D06P5/138—Fugitive dyeing or stripping dyes fugitive dyeing
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/245—Polyamides; Polyurethanes using metallisable or mordant dyes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/907—Nonionic emulsifiers for dyeing
Definitions
- the dyeing of a nylon was carried out by employing dispersed or acetate dyestuffs because of their great covering power and their insensitivity to variations in constitution normally encountered in the manufacture of nylon fibers. But, however, the use of dispersed or acetate dyestuffs was limited in application because of their lack of fastness to light and washing. With the advent of the application of acid dyes, milling dyes and neutral dyeing premetallized dyes to a nylon fiber, yarn or fabric, the problem of fastness to light and washing was alleviated but here again these dyes appeared extremely sensitive to variations in the composition of the nylon fiber in that the dyes did not level and did not yield well-penetrated dyeings. In addition, a further difficulty encoun tered has been the necessity for complete stripping of uneven dyeings because of the lack of available leveling agents.
- a primary object of this invention is to provide a new and improved aqueous dyebath suitable for dyeing nylon.
- a further object of this invention is the provision of a new and improved process for dyeing nylon.
- Still another object of this invention is the provision of a new and improved process for even and level dying of nylon without streaks and variations in depth of shade.
- a still further object of the invention contemplates the feature of an aqueous dyebath composition suitable for stripping dyestuffs from an unevenly dyed nylon fiber, yarn or fabric and re-dyeing of the unevenly dyed nylon fiber, yarn or fabric.
- the attainment of one or more of the above objects of the invention is accomplished by treating nylon with an aqueous dyebath containing a water-soluble, non-ionic surface active agent containing a polyoxyalkylene chain and derived from an active hydrogen-containing compound.
- a further embodiment of this invention is directed to the feature of enhancing the leveling action and is accomplished by the employment of a combination of a non-ionic surface active agent containing a polyoxyalkylene chain with an activator. It has been found that the aforesaid combination is particularly useful for stripping and redyeing of unevenly dyed nylon and in the case of neutral dyeing premetallized colors, the affinity 3,281,201 Patented Oct.
- the non-ionic surface active agents which have been found unusually effective as leveling agents for premetallized and acid type dyestuffs are the nonylphenoxypolyoxyethylene glycols containing 84 to 88% combined ethylene oxide. Indeed, it is quite surprising to find that the non-ionic surface active agents of the class described above provide optimum leveling action on nylon since experimental data indicates that such specificity of action is lacking in nonylphenol-ethylene oxide adducts containing or 90 percent ethylene oxide and octyl and dodecylphenol-ethylene oxide adducts containing percent combined ethylene oxide.
- the activators which can be employed to enhance the leveling action of the aforesaid non-ionic surface active agents include ammonia and relatively non-volatile organic amines and amides which are water-soluble to the extent of at least one weight percent.
- they Preferably and in addition to the degree of desired water solubility of the organic amines and amides, they should have boiling points of at least 70 C. or greater at atmospheric pressure. It is also preferred that they should not be highly odoriferous.
- organic amines and amides which find utility in carrying out the process of the invention include alkyl amines, alkenyl amines, alkanolamines, aromatic and heterocyclic amines such as methylamine, ethylamine, triethylamine, di-n-propylamine, isopropylamine, diisopropylamine, butylamine, dibutylamine, amylamine, diamylamine, triamylamine, ethanolamine, propanolamine, dimethylaminoethanol, ethylaminoethanol, isopropylaminoethanol, dibutylaminoethanol, acetamide, caproamide, caprylamide, pyrrolidone, N- methyl pyrrolidone, piperazine, pyridine, morpholine, morpholone, N-methyl morpholone and the like.
- alkyl amines alkenyl amines, alkanolamines, aromatic and heterocycl
- Another class of activators which are useful in the process of the invention are amides reacted with from one to three molar proportions of ethylene oxide such as N- (beta-hydroxylethyl)-n-butyranilide, N (beta hydroxyethyl)-n-caproamide, N (beta hydroxyethyl) caprylamide, N-(beta-hydroxyethyl)-n-caproanilide, N-betahydroxyethoxyethyl-n-caproamide, N beta hydroxyethoxyethyl caprylamide and N-hydroxyethoxyethyl derivatives of caproamide, caprylamide, n-butyranilide, n-caproanilide and the like.
- nonylphenoxypolyoxyethylene glycol surfactant above-described which is employed in carrying out the process of the invention is not necessarily a critical feature of the invention.
- Recommended amounts which can be employed to secure advantageous results can vary from 0.25 to 10.0% by weight based on the weight of fiber although amounts less than or greater than the above recommendation can be employed if desired.
- the amount of activator to be employed for stripping and redyeing of unevenly dyed nylon in combination with surfactant is not a critical feature of the invention.
- Advantageous results can be obtained by employing amounts of activator varying from 1.0 to 2.0 percent by weight based on the weight of fiber.
- the acid-generating salts which can be readily employed with facility in carrying out the process of this invention are the ammonium salts of inorganic and organic acids.
- Representative ammonium salts include ammonium acetate, ammonium borate, ammonium carbonate, ammonium citrate, ammonium formate, ammonium oxalate, ammonium persulfate, ammonium sulfate, ammonium tartarate and the like.
- the process of the invention is admirably suited for use with all types of nylon superpolymers and comprises the reaction products of polymer-forming compositions containing amide-forming groups, for example, reaction materials comprising bi-functional molecules containing at least two reactive groups which are complementary to reactive groups in other molecules and which include the complementary amide-forming groups.
- reaction materials comprising bi-functional molecules containing at least two reactive groups which are complementary to reactive groups in other molecules and which include the complementary amide-forming groups.
- These synthetic polycarbamates which comprise the self-polymerization products of monoa-mine monocarboxyli-c acids containing at least five carbon atoms in the chain separating the amino function and the carboxyl function and those synthetic linear polycarbamates derived from the reaction of suitable diamines with suitable dicarboxylic acids in substantially equirnolar amounts.
- amino acids, diamines, and dicarboxylic acids are intended to include the equivalent amide-forming derivatives of these reactants.
- amino acid polycarbonamides yield the amino acid hydrochloride
- diamine-dicarboxylic acid polycarbamates yield the dicarboxylic acid and diamine hydrochloride.
- the average number of carbon atoms separating the amide groups in the nylons is at least two.
- nylons are characterized by the recurrence in the molecule of the groups -NRCO wherein R is a member of the group consisting of hydrogen and monovalent hydrocarbon radicals, as a part of the main chain of atoms in the polymer.
- Particularly useful nylons applicable in the process of the invention are the simple unsubstituted nylons, such as those formed by the reaction of tetramethylene diamine and adipic acid, tetramethylene diamine and suberic acid, tetramethylene diamine with sebacic acid, hexamethylene diamine and 'adipic acid, or the polymerization products of n-epsiloncaprolactam.
- polymers formed from the reaction of two or more diamines with dicarboxylic acids and/or two or more dicarboxylic acids with diamines are contemplated as providing suitable nylons for practice in the instant invention.
- the dyestuffs which can be advantageously employed in carrying out the process of the invention are readily available in commerce and well known and described in the literature and patented arts.
- the acid dyestuffs suitable for use herein are those water-soluble dyes commonly employed for dyeing wool, and contain at least one carboxylic, sulfonic, sulfone or sulfonamide group or a substituted derivative thereof and are applied from a neutral to acid aqueous medium.
- a great number of them are the azo type (mono-, di-, and polyazo dyestuffs).
- other groups of acid dyes are also operative in carrying out the process of this invention and include, for example, the quinoline, pyrazolone, and dior triphenylmethane colors, the acid anthraquinones, the dyes derived from xanthene such as the eosines, phthaleins and sulforhodamines and the chromoxan dyes derived from oxytrimellitinic acid.
- the dyestuffs may be pre-metallized, such dyestuffs being generally described as metallized acid or metallized azo dyestuffs.
- mordant acid dyestuffs are also operative herein, such dyestuffs being metallized on the fiber in the usual manner, subsequent to treatment in accordance with the process of the instant invention.
- metallized and mordant acid dyestuffs suitable for use in the process of this invention contain in the 0,0 positions relative to an azo linkage, well known groups, for example hydroxyl or carboxyl groups and the like, which are capable of forming complexes with metals.
- the amount of dyestuif employed in the aqueous dyebath will vary depending on the results desired. Ordinarily, from about 1 to about 8 ounces of commercially available dyestulf (about 0.75 to 6.0 per- 'cent by weight) of liquor is sufficient to achieve satisfactory results.
- nylon fabric is immersed in a water bath containing the water-soluble, non-ionic surface active agent having a poly-oxyalkylene chain as described above and circulated therein for a period of about 5 minutes. Subsequently, a dyestulf previously dissolved and diluted, is added to the water bath containing the surface active agent and the nylon fabric. The material is then run for a suitable period of time such as about 10 minutes with the temperature being raised to about 200 F. over a period of 45 minutes and dyeing continued at this temperature for a period of about an hour. At the end of the dyeing cycle, the bath is dropped and the fabric rinsed well in water at a temperature of about F.
- an acid splitting salt previously dissolved in water
- an acid splitting salt is added in aliquot portions if desired, preferably over a period of about /2 hour whereupon the bath is reheated to the aforesaid higher temperature and maintained at that temperature for a period of about 1 hour.
- the bath is then dropped and the fabric rinsed well in water at 80F. and dried. In this manner, the original unevenly dyed and poorly penetrated fabric will be well penetrated, evenly dyed and show the original depth of shade.
- Example 1 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant, prepared by condensing ethylene oxide with nonylphenol until the product contains '86 weight percent of combined ethylene oxide, whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff, prepared by diazotizing 2- aminophenol 4-dimethyl sulfonamide, coupling with 1- acetylarnino-7-naph-thol and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F.
- a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains '86 weight percent of combined ethylene oxide, whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff, prepared by diazotizing
- Example 2 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 Weight percent of combined ethylene oxide whereupon there is added 1 percent by Weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing anthranilic acid, coupling with phenyl methyl pyrazolone and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour.
- a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 Weight percent of combined ethylene oxide whereupon there is added 1 percent by Weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing anthran
- Example 3 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestutf prepared by diazotizing Z-amidophenol 4-sulfonamide, coupling with phenyl methyl pyrazolone and metallized with chromium.
- a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestutf prepared by diazotizing Z-amidophenol 4-sulfonamide, coupling with phenyl methyl pyrazolone and metall
- the fabric is nm for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a wellpeuetrated level dyeing.
- Example 4 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing a 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestulf prepared by diazotizing 4-chloro, Z-amidophenol, coupling with phenyl methyl pyrazolone 4-dimethyl sulfonamide and metallized with chromium.
- the fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
- Example 5 whereupon the temperature is raised to 200 F. over a' period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
- Example 6 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by reducing and diazotizing 4-chloro-5-nitro, 2-amidophenol, coupling with l-naphthol 3-sulfonamide and metallized with chromium.
- the fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour.
- the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
- Example 7 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on Weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by Weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 2- amidophenol, 4-dimethyl sulfonamide, coupling with the bis diethyl sulfonamide of H acid and metallized with cobalt.
- the fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour.
- the bath is dropped and the fabric is rinsed well in water at F. There is obtained a well-penetrated level dyeing.
- Example 8 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 2-amidophenol 4-dimethyl sulfonamide, coupling with the bis diethyl sulfonamide of H acid and metallized with chromium.
- the fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour.
- the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
- Example 9 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 2- chloro, 4-amidophenol, coupling with phenyl methyl pyrazolone 3-sulfonamide and metallized with cobalt. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
- a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains
- Example 10 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 4- nitro, 2-amidophenol, coupling with phenyl methyl pyrazolone 3-sulfonamide and metallized with cobalt. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
- a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains
- Example 11 An unevenly dyed piece of spun nylon prepared by the procedure of Example 1 except that the nonionic surfactant was omitted from the dyebath, was leveled by immersing the same in a'bath maintained at a temperature of 160 F adding percent by weight based on weight of fabric of previously dissolved nonylphenoxypolyoxyethylene glycol containing 86.0 percent by weight of combined ethylene oxide and 2 percent by weight based on weight of fabric of triethanolarnine. The temperature of the bath is raised slowly to 205 F. to 210 F. and maintained at this temperature for 1 /2 hours. The bath is then cooled to 190 F.
- Example 12 Unevenly dyed fabric prepare-d by the method of EX- ample 7 without nonionic surfactant, was leveled and well-penetrated by treating according to the procedure set forth in Example 11.
- Example 13 Unevenly dyed fabric prepared by the method of EX- ample 8 without nonionic surfactant, was leveled and wellpenetrated by treating according to the procedure set forth in Example 11.
- a process for producing a level, well-penetrated dyeing on nylon material which comprises dyeing said material in a dyebath consisting essentially of water, a
- Water-soluble dyestufi selected from the group consisting of acid and metallized acid dyestufis and a nonylphenoxypolyoxyethylene glycol containing from 84-88 weight percent combined ethylene oxide.
- the dyestuif is a premetallized acid dyestufi prepared by diazotizing 2- aminophenol 4-dimethylsulfonamide, coupling with 1- acetylarnino-7-naphthol and metallized with chromium.
- the dyestufi is a premetallized acid dyestuff prepared by diazotizing anthranilic acid, coupling with phenyl methyl pyraz'olone and metallized with chromium.
- the dyestulf is a premetallized acid dyestufi? prepared by diazotizing 2- amidophenol 4-sulfonamide, coupling with phenyl methyl pyrazolone and metallized with chromium.
- the dyestui f is a premetallized acid dyestuff prepared by diazotizing 4- chloro Z-amidophenol, coupling with phenyl methyl pyrazolone and metallized with chromium.
- the dyestuff is a premetallized acid dyestutf prepared by diazotizing 4- chloro 2-amidophenol, coupling with beta-naphthol and metallized with cobalt.
- the dyestufr' is a premetallized acid dyestutf prepared by diazotizing 4-chloro- S-nitro 2-amidophenol, coupling with l-naphthol 3-sulfonarnide and metallized with chromium.
- the dyestuff is a premetallized acid dyestuff prepared by diazotizing 2- amidophenol 4-dimethylsulfonamide, coupling with the bis-diethylsulfonamide of H acid and metallized with cobalt.
- the dyestuff is a premetallized acid dyestuif prepared by diazotizing 2- amidophenol 4-dimethylsulfonamide, coupling with the bis-diethylsulfonamide of H acid and metallized with chromium.
- the dyestui'l is a premetallized acid dyestuif prepared by diazotizing 2- chloro 4-amidophenol, coupling with phenyl methyl pyrazolone 3-sulfonami-de and metallized with cobalt.
- the dyestuff is a premetallized acid dyestuif prepared by diazotizing 4- nitro 2-arnidophenol, coupling with phenyl methyl pyrazolone 3-sulfonamide and metallized with cobalt.
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Description
United States Patent 3,281 201 PROCESS FOR DYEING 6F NYLON FIBERS WITH PREMETALLIZED AND ACID DYESTUFFS Henry R. Mautner, Leonia, N.J., and William L. Fickert, Lansdale, Pa., assignors to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware N0 Drawing. Filed June 22, 1962, Ser. No. 204,616 11 Claims. (Cl. 8-42) The present invention relates to the art of dyeing. More patricularly, this invention relates to a process for dyeing of fibers, yarns and fabrics composed of polycarbonamide superpolymers, more familiarly and hereinafter referred to as nylon, and an aqueous dyebath suitable therefor.
Heretofore, according to customary practices, the dyeing of a nylon was carried out by employing dispersed or acetate dyestuffs because of their great covering power and their insensitivity to variations in constitution normally encountered in the manufacture of nylon fibers. But, however, the use of dispersed or acetate dyestuffs was limited in application because of their lack of fastness to light and washing. With the advent of the application of acid dyes, milling dyes and neutral dyeing premetallized dyes to a nylon fiber, yarn or fabric, the problem of fastness to light and washing was alleviated but here again these dyes appeared extremely sensitive to variations in the composition of the nylon fiber in that the dyes did not level and did not yield well-penetrated dyeings. In addition, a further difficulty encoun tered has been the necessity for complete stripping of uneven dyeings because of the lack of available leveling agents.
Thus, a primary object of this invention is to provide a new and improved aqueous dyebath suitable for dyeing nylon.
A further object of this invention is the provision of a new and improved process for dyeing nylon.
It is still another object of this invention to provide a process for the dyeing of nylon which will produce level, well-penetrated dyeings on said nylon.
It is a further object of this invention to provide a process for dyeing nylon fibers. with neutral dyeing premetallized colors which produces dyed fibers, yarns and fabrics characterized by excellent light and fastness and wetfastness. 7
Still another object of this invention is the provision of a new and improved process for even and level dying of nylon without streaks and variations in depth of shade.
A still further object of the invention contemplates the feature of an aqueous dyebath composition suitable for stripping dyestuffs from an unevenly dyed nylon fiber, yarn or fabric and re-dyeing of the unevenly dyed nylon fiber, yarn or fabric.
These and other objects of the invention will become further apparent from the detailed description of the invention hereinafter.
The attainment of one or more of the above objects of the invention is accomplished by treating nylon with an aqueous dyebath containing a water-soluble, non-ionic surface active agent containing a polyoxyalkylene chain and derived from an active hydrogen-containing compound.
A further embodiment of this invention is directed to the feature of enhancing the leveling action and is accomplished by the employment of a combination of a non-ionic surface active agent containing a polyoxyalkylene chain with an activator. It has been found that the aforesaid combination is particularly useful for stripping and redyeing of unevenly dyed nylon and in the case of neutral dyeing premetallized colors, the affinity 3,281,201 Patented Oct. 25, 1966 of non-ionic surfactant-activator combination for the dyestutf is so great that the dyestutf is removed from the nylon fiber, yarn or fabric into the aqueous dyebath so that when acid-generating salts are added to the dyebath, the dyestuffs in the bath are gradually released upon continued dyeing and return evenly and uniformly to the nylon fiber, yarn or fabric.
The non-ionic surface active agents which have been found unusually effective as leveling agents for premetallized and acid type dyestuffs are the nonylphenoxypolyoxyethylene glycols containing 84 to 88% combined ethylene oxide. Indeed, it is quite surprising to find that the non-ionic surface active agents of the class described above provide optimum leveling action on nylon since experimental data indicates that such specificity of action is lacking in nonylphenol-ethylene oxide adducts containing or 90 percent ethylene oxide and octyl and dodecylphenol-ethylene oxide adducts containing percent combined ethylene oxide.
The activators which can be employed to enhance the leveling action of the aforesaid non-ionic surface active agents include ammonia and relatively non-volatile organic amines and amides which are water-soluble to the extent of at least one weight percent. Preferably and in addition to the degree of desired water solubility of the organic amines and amides, they should have boiling points of at least 70 C. or greater at atmospheric pressure. It is also preferred that they should not be highly odoriferous. Representative organic amines and amides which find utility in carrying out the process of the invention include alkyl amines, alkenyl amines, alkanolamines, aromatic and heterocyclic amines such as methylamine, ethylamine, triethylamine, di-n-propylamine, isopropylamine, diisopropylamine, butylamine, dibutylamine, amylamine, diamylamine, triamylamine, ethanolamine, propanolamine, dimethylaminoethanol, ethylaminoethanol, isopropylaminoethanol, dibutylaminoethanol, acetamide, caproamide, caprylamide, pyrrolidone, N- methyl pyrrolidone, piperazine, pyridine, morpholine, morpholone, N-methyl morpholone and the like.
Another class of activators which are useful in the process of the invention are amides reacted with from one to three molar proportions of ethylene oxide such as N- (beta-hydroxylethyl)-n-butyranilide, N (beta hydroxyethyl)-n-caproamide, N (beta hydroxyethyl) caprylamide, N-(beta-hydroxyethyl)-n-caproanilide, N-betahydroxyethoxyethyl-n-caproamide, N beta hydroxyethoxyethyl caprylamide and N-hydroxyethoxyethyl derivatives of caproamide, caprylamide, n-butyranilide, n-caproanilide and the like.
The amount of nonylphenoxypolyoxyethylene glycol surfactant above-described which is employed in carrying out the process of the invention is not necessarily a critical feature of the invention. Recommended amounts which can be employed to secure advantageous results can vary from 0.25 to 10.0% by weight based on the weight of fiber although amounts less than or greater than the above recommendation can be employed if desired. Similarly, the amount of activator to be employed for stripping and redyeing of unevenly dyed nylon in combination with surfactant is not a critical feature of the invention. Advantageous results can be obtained by employing amounts of activator varying from 1.0 to 2.0 percent by weight based on the weight of fiber.
The acid-generating salts which can be readily employed with facility in carrying out the process of this invention are the ammonium salts of inorganic and organic acids. Representative ammonium salts include ammonium acetate, ammonium borate, ammonium carbonate, ammonium citrate, ammonium formate, ammonium oxalate, ammonium persulfate, ammonium sulfate, ammonium tartarate and the like.
The process of the invention is admirably suited for use with all types of nylon superpolymers and comprises the reaction products of polymer-forming compositions containing amide-forming groups, for example, reaction materials comprising bi-functional molecules containing at least two reactive groups which are complementary to reactive groups in other molecules and which include the complementary amide-forming groups. These synthetic polycarbamates which comprise the self-polymerization products of monoa-mine monocarboxyli-c acids containing at least five carbon atoms in the chain separating the amino function and the carboxyl function and those synthetic linear polycarbamates derived from the reaction of suitable diamines with suitable dicarboxylic acids in substantially equirnolar amounts. It is to be understood that reference herein to the amino acids, diamines, and dicarboxylic acids is intended to include the equivalent amide-forming derivatives of these reactants. Upon hydrolysis, the amino acid polycarbonamides yield the amino acid hydrochloride and the diamine-dicarboxylic acid polycarbamates yield the dicarboxylic acid and diamine hydrochloride. Further, the average number of carbon atoms separating the amide groups in the nylons is at least two.
The nylons are characterized by the recurrence in the molecule of the groups -NRCO wherein R is a member of the group consisting of hydrogen and monovalent hydrocarbon radicals, as a part of the main chain of atoms in the polymer. Particularly useful nylons applicable in the process of the invention are the simple unsubstituted nylons, such as those formed by the reaction of tetramethylene diamine and adipic acid, tetramethylene diamine and suberic acid, tetramethylene diamine with sebacic acid, hexamethylene diamine and 'adipic acid, or the polymerization products of n-epsiloncaprolactam. In addition, polymers formed from the reaction of two or more diamines with dicarboxylic acids and/or two or more dicarboxylic acids with diamines are contemplated as providing suitable nylons for practice in the instant invention.
The dyestuffs which can be advantageously employed in carrying out the process of the invention are readily available in commerce and well known and described in the literature and patented arts. In general, the acid dyestuffs suitable for use herein are those water-soluble dyes commonly employed for dyeing wool, and contain at least one carboxylic, sulfonic, sulfone or sulfonamide group or a substituted derivative thereof and are applied from a neutral to acid aqueous medium. A great number of them are the azo type (mono-, di-, and polyazo dyestuffs). However, other groups of acid dyes are also operative in carrying out the process of this invention and include, for example, the quinoline, pyrazolone, and dior triphenylmethane colors, the acid anthraquinones, the dyes derived from xanthene such as the eosines, phthaleins and sulforhodamines and the chromoxan dyes derived from oxytrimellitinic acid. The dyestuffs may be pre-metallized, such dyestuffs being generally described as metallized acid or metallized azo dyestuffs. The mordant acid dyestuffs are also operative herein, such dyestuffs being metallized on the fiber in the usual manner, subsequent to treatment in accordance with the process of the instant invention. As metallized and mordant acid dyestuffs suitable for use in the process of this invention, those preferred contain in the 0,0 positions relative to an azo linkage, well known groups, for example hydroxyl or carboxyl groups and the like, which are capable of forming complexes with metals.
In general, the amount of dyestuif employed in the aqueous dyebath will vary depending on the results desired. Ordinarily, from about 1 to about 8 ounces of commercially available dyestulf (about 0.75 to 6.0 per- 'cent by weight) of liquor is sufficient to achieve satisfactory results.
In carrying out the process of the instant invention, a
nylon fabric is immersed in a water bath containing the water-soluble, non-ionic surface active agent having a poly-oxyalkylene chain as described above and circulated therein for a period of about 5 minutes. Subsequently, a dyestulf previously dissolved and diluted, is added to the water bath containing the surface active agent and the nylon fabric. The material is then run for a suitable period of time such as about 10 minutes with the temperature being raised to about 200 F. over a period of 45 minutes and dyeing continued at this temperature for a period of about an hour. At the end of the dyeing cycle, the bath is dropped and the fabric rinsed well in water at a temperature of about F.
In carrying out the process of the invention when employing an unevenly dyed piece of nylon fabric, fiber or yarn, satisfactory leveling and stripping can be obtained by introducing the unevenly dyed piece of nylon fabric into 30 to 1 liquor ratio bath at F. and adding to said bath a non-ionic surfactant of the class described and an amine and subsequently raising the temperature slowly to a temperature in the range of from 205 to 210 F. while maintaining this temperature for a period of from 1 to 2 hours. Subsequently, the bath is cooled to a temperature of F. whereupon an acid splitting salt, previously dissolved in water, is added in aliquot portions if desired, preferably over a period of about /2 hour whereupon the bath is reheated to the aforesaid higher temperature and maintained at that temperature for a period of about 1 hour. The bath is then dropped and the fabric rinsed well in water at 80F. and dried. In this manner, the original unevenly dyed and poorly penetrated fabric will be well penetrated, evenly dyed and show the original depth of shade.
The following examples, in which parts are by Weight unless otherwise indicated, will serve to illustrate the practice of the instant invention and are considered representative of the scope of the invention and are not to be regarded as a limitation thereof. In all cases, the dyeing was carried out in 30 to 1 liquor ratio bath.
Example 1 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant, prepared by condensing ethylene oxide with nonylphenol until the product contains '86 weight percent of combined ethylene oxide, whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff, prepared by diazotizing 2- aminophenol 4-dimethyl sulfonamide, coupling with 1- acetylarnino-7-naph-thol and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric in rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing which exhibits good fastness to washing, light and rubbing.
Example 2 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 Weight percent of combined ethylene oxide whereupon there is added 1 percent by Weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing anthranilic acid, coupling with phenyl methyl pyrazolone and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the faoric is rinsed well in Water Example 3 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestutf prepared by diazotizing Z-amidophenol 4-sulfonamide, coupling with phenyl methyl pyrazolone and metallized with chromium. The fabric is nm for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a wellpeuetrated level dyeing.
Example 4 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing a 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestulf prepared by diazotizing 4-chloro, Z-amidophenol, coupling with phenyl methyl pyrazolone 4-dimethyl sulfonamide and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
Example 5 whereupon the temperature is raised to 200 F. over a' period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
Example 6 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by reducing and diazotizing 4-chloro-5-nitro, 2-amidophenol, coupling with l-naphthol 3-sulfonamide and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
Example 7 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on Weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by Weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 2- amidophenol, 4-dimethyl sulfonamide, coupling with the bis diethyl sulfonamide of H acid and metallized with cobalt. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at F. There is obtained a well-penetrated level dyeing.
Example 8 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 2-amidophenol 4-dimethyl sulfonamide, coupling with the bis diethyl sulfonamide of H acid and metallized with chromium. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
Example 9 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 2- chloro, 4-amidophenol, coupling with phenyl methyl pyrazolone 3-sulfonamide and metallized with cobalt. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
Example 10 A nylon suiting fabric is circulated for a period of five minutes in an aqueous dyebath containing 2.0 percent by weight based on weight of fabric of a nonionic surfactant prepared by condensing ethylene oxide with nonylphenol until the product contains 86 weight percent of combined ethylene oxide whereupon there is added 1 percent by weight based on weight of fabric, of a previously dissolved and diluted dyestuff prepared by diazotizing 4- nitro, 2-amidophenol, coupling with phenyl methyl pyrazolone 3-sulfonamide and metallized with cobalt. The fabric is run for ten minutes whereupon the temperature is raised to 200 F. over a period of 45 minutes and dyeing continued at this temperature for one hour. At the end of the dyeing cycle, the bath is dropped and the fabric is rinsed well in water at 80 F. There is obtained a well-penetrated level dyeing.
Example 11 An unevenly dyed piece of spun nylon prepared by the procedure of Example 1 except that the nonionic surfactant was omitted from the dyebath, was leveled by immersing the same in a'bath maintained at a temperature of 160 F adding percent by weight based on weight of fabric of previously dissolved nonylphenoxypolyoxyethylene glycol containing 86.0 percent by weight of combined ethylene oxide and 2 percent by weight based on weight of fabric of triethanolarnine. The temperature of the bath is raised slowly to 205 F. to 210 F. and maintained at this temperature for 1 /2 hours. The bath is then cooled to 190 F. whereupon a solution of ammonium acetate, corresponding to 5 percent by weight based on weight of fabric, is added in three portions over a period of twenty minutes. Subsequently, the bath is reheated to 205 F. to 210 F. for a period of one hour whereupon the bath is dropped and the fabric rinsed well in water at 80 F, extracted and dried. The original, uneven,poorly penetrated fabric is well-penetrated, evenly dyed and exhibits original depth of shade.
Example 12 Unevenly dyed fabric prepare-d by the method of EX- ample 7 without nonionic surfactant, was leveled and well-penetrated by treating according to the procedure set forth in Example 11.
Example 13 Unevenly dyed fabric prepared by the method of EX- ample 8 without nonionic surfactant, was leveled and wellpenetrated by treating according to the procedure set forth in Example 11.
What is claimed is:
1. A process for producing a level, well-penetrated dyeing on nylon material which comprises dyeing said material in a dyebath consisting essentially of water, a
Water-soluble dyestufi selected from the group consisting of acid and metallized acid dyestufis and a nonylphenoxypolyoxyethylene glycol containing from 84-88 weight percent combined ethylene oxide.
2. The process of claim 1 wherein the dyestuif is a premetallized acid dyestufi prepared by diazotizing 2- aminophenol 4-dimethylsulfonamide, coupling with 1- acetylarnino-7-naphthol and metallized with chromium.
3. The process of claim 1 wherein the dyestufi is a premetallized acid dyestuff prepared by diazotizing anthranilic acid, coupling with phenyl methyl pyraz'olone and metallized with chromium.
4. The process of claim 1 wherein the dyestulf is a premetallized acid dyestufi? prepared by diazotizing 2- amidophenol 4-sulfonamide, coupling with phenyl methyl pyrazolone and metallized with chromium.
5. The process of claim 1 wherein the dyestui f is a premetallized acid dyestuff prepared by diazotizing 4- chloro Z-amidophenol, coupling with phenyl methyl pyrazolone and metallized with chromium.
6. The process of claim 1 wherein the dyestuff is a premetallized acid dyestutf prepared by diazotizing 4- chloro 2-amidophenol, coupling with beta-naphthol and metallized with cobalt.
7. The process of claim 1 wherein the dyestufr' is a premetallized acid dyestutf prepared by diazotizing 4-chloro- S-nitro 2-amidophenol, coupling with l-naphthol 3-sulfonarnide and metallized with chromium.
8. The process of claim 1 wherein the dyestuff is a premetallized acid dyestuff prepared by diazotizing 2- amidophenol 4-dimethylsulfonamide, coupling with the bis-diethylsulfonamide of H acid and metallized with cobalt.
9. The process of claim 1 wherein the dyestuff is a premetallized acid dyestuif prepared by diazotizing 2- amidophenol 4-dimethylsulfonamide, coupling with the bis-diethylsulfonamide of H acid and metallized with chromium.
10. The process of claim 1 wherein the dyestui'l is a premetallized acid dyestuif prepared by diazotizing 2- chloro 4-amidophenol, coupling with phenyl methyl pyrazolone 3-sulfonami-de and metallized with cobalt.
11. The process of claim 1 wherein the dyestuff is a premetallized acid dyestuif prepared by diazotizing 4- nitro 2-arnidophenol, coupling with phenyl methyl pyrazolone 3-sulfonamide and metallized with cobalt.
References Cited by the Examiner UNITED STATES PATENTS I Mooradian 819 2,739,868 3/1956 Shanley 8-19 2,743,231 4/1956 Klein 2 855 2,828,180 3/1958 Sertorio.
2,915,472 12/1959 Pressner 8-55 2,952,506 9/1960 Dellis 855
Claims (1)
1. A PROCESS FOR PRODUCING A LEVEL, WELL-PENETRATED DYEING ON NYLON MATERIAL WHICH COMPRISES DYEING SAID MATERIAL IN A DYEBATH CONSISTING ESSENTIALLY OF WATER, A WATER-SOLUBLE DYESTUFF SELECTED FROM THE GROUP CONSISTING OF ACID AND METALLIZED ACID DYESTUFFS AND A NONYLPHENOXY POLYOXYETHYLENE GLYCOL CONTAINING FROM 84-88 WEIGHT PERCENT COMBINED ETHYLENE OXIDE.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US204616A US3281201A (en) | 1962-06-22 | 1962-06-22 | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
US464887A US3410648A (en) | 1962-06-22 | 1965-05-10 | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US204616A US3281201A (en) | 1962-06-22 | 1962-06-22 | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
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US3281201A true US3281201A (en) | 1966-10-25 |
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US204616A Expired - Lifetime US3281201A (en) | 1962-06-22 | 1962-06-22 | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3410648A (en) * | 1962-06-22 | 1968-11-12 | Gaf Corp | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
US3480378A (en) * | 1964-03-21 | 1969-11-25 | Bayer Ag | Process for dyeing linear polyester fiber materials |
US3519377A (en) * | 1962-02-08 | 1970-07-07 | Teijin Ltd | Printing polyester textiles with a disperse dye paste containing an alkyl amide or alkylene diamide |
US3963418A (en) * | 1974-08-01 | 1976-06-15 | E. I. Du Pont De Nemours And Company | Yellow disazo acid dye solution |
US3986827A (en) * | 1972-08-29 | 1976-10-19 | E. I. Du Pont De Nemours And Company | Storage-stable concentrated aqueous solution of disazo acid dye |
US4381186A (en) * | 1980-03-19 | 1983-04-26 | Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa Spa | Process for dyeing polyamidic textile materials, in particular high dyeing speed polyamides with acid dyes and alkaline reactants |
US4927429A (en) * | 1987-05-04 | 1990-05-22 | Burlington Industries, Inc. | Process of dyeing synthetic fabrics using high-boiling ester solvents |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2723178A (en) * | 1951-02-10 | 1955-11-08 | American Cyanamid Co | Method of controlling the migration of metallized dyes between dye bath and fabric |
US2739868A (en) * | 1951-01-13 | 1956-03-27 | Fmc Corp | Method of dyeing peroxide-bleached wool |
US2743231A (en) * | 1951-12-08 | 1956-04-24 | Heyden Chemical Corp | Process for the dyeing of nylon fibers and fabrics with 5-chlorosalicylic acid |
US2828180A (en) * | 1952-05-31 | 1958-03-25 | Anonima Italiana Colori E Affi | Water-in-oil dyestuff emulsions and their application to the dyeing and printing of cloths and fibers |
US2915472A (en) * | 1956-01-09 | 1959-12-01 | Pressner Samuel | Brightening compositions |
US2952506A (en) * | 1956-08-24 | 1960-09-13 | Chemstrand Corp | Process for even and level dyeing of filament nylon fabrics |
-
1962
- 1962-06-22 US US204616A patent/US3281201A/en not_active Expired - Lifetime
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2739868A (en) * | 1951-01-13 | 1956-03-27 | Fmc Corp | Method of dyeing peroxide-bleached wool |
US2723178A (en) * | 1951-02-10 | 1955-11-08 | American Cyanamid Co | Method of controlling the migration of metallized dyes between dye bath and fabric |
US2743231A (en) * | 1951-12-08 | 1956-04-24 | Heyden Chemical Corp | Process for the dyeing of nylon fibers and fabrics with 5-chlorosalicylic acid |
US2828180A (en) * | 1952-05-31 | 1958-03-25 | Anonima Italiana Colori E Affi | Water-in-oil dyestuff emulsions and their application to the dyeing and printing of cloths and fibers |
US2915472A (en) * | 1956-01-09 | 1959-12-01 | Pressner Samuel | Brightening compositions |
US2952506A (en) * | 1956-08-24 | 1960-09-13 | Chemstrand Corp | Process for even and level dyeing of filament nylon fabrics |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3519377A (en) * | 1962-02-08 | 1970-07-07 | Teijin Ltd | Printing polyester textiles with a disperse dye paste containing an alkyl amide or alkylene diamide |
US3410648A (en) * | 1962-06-22 | 1968-11-12 | Gaf Corp | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
US3480378A (en) * | 1964-03-21 | 1969-11-25 | Bayer Ag | Process for dyeing linear polyester fiber materials |
US3986827A (en) * | 1972-08-29 | 1976-10-19 | E. I. Du Pont De Nemours And Company | Storage-stable concentrated aqueous solution of disazo acid dye |
US3963418A (en) * | 1974-08-01 | 1976-06-15 | E. I. Du Pont De Nemours And Company | Yellow disazo acid dye solution |
US4381186A (en) * | 1980-03-19 | 1983-04-26 | Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa Spa | Process for dyeing polyamidic textile materials, in particular high dyeing speed polyamides with acid dyes and alkaline reactants |
US4927429A (en) * | 1987-05-04 | 1990-05-22 | Burlington Industries, Inc. | Process of dyeing synthetic fabrics using high-boiling ester solvents |
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