US3685957A - Process for dyeing polyester fibers with nitrodiphenylamine dyestuff - Google Patents
Process for dyeing polyester fibers with nitrodiphenylamine dyestuff Download PDFInfo
- Publication number
- US3685957A US3685957A US54020A US3685957DA US3685957A US 3685957 A US3685957 A US 3685957A US 54020 A US54020 A US 54020A US 3685957D A US3685957D A US 3685957DA US 3685957 A US3685957 A US 3685957A
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- US
- United States
- Prior art keywords
- dyestuff
- bis
- polyester fibers
- dyeing
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B51/00—Nitro or nitroso dyes
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/19—Nitro dyes
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
-
- 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
- Y10S8/933—Thermosol dyeing, thermofixation or dry heat fixation or development
Definitions
- Polyester fibers present particular dyeing problems, arising at least in part out of the hydrophobic nature of such fibers.
- the class of dyes known as disperse dyestuffs has come to have the widest application. These dyestufls are essentially water-insoluble products applied in a finely divided condition from a dispersion.
- the dyeing difficulties associated with polyester fibers have been met by the development of special methods for the application of disperse dyes to the fibers. Of these methods, the one known as the Pad/Thermofix method has become of increasing infportance since it is particularly adapted for high-speed, continuous dyeing operations.
- a fabric is padded by passing it through an aqueous suspension of the dyestuif and squeezing the fabric between closely-set rollers in order to remove excess dye liquor.
- the dyestuff is only loosely attached to the fiber at this point.
- the dyestuff is then fixed on the fiber by subjecting the material to a short, intensive heat-treatment at elevated temperatures of the order of about 120220 C. It is evident that a dyestuif, in order to be suitable for application by this method, must be fast to sublimation or else it will wholly or partially volatilize from the fiber during the heat-treatment step.
- A represents a single bond or a divalent radical which is an aliphatic straight or branched chain hydrocarbon of from 1 to 12 carbon atoms, such as ethylene, butylene, isobutylene, 3-methylhexylene, hexylene and the like (lower alkylene of from 1-12 carbon atoms), a metaor para-phenylene radical, a para-diphenylene radical or a radical of the formula in which B is CH 0, S0 8-8, or S; R, and R represent hydrogen, lower alkyl (from 1-7 carbon atoms) such as methyl, ethyl, propyl or butyl, hydroxyalkyl, (hydroxy lower alkyl such as hydroxymethyl,
- the aromatic rings represented by the symbol A can be substituted by the same substituents as are recited in the definition of R and R
- the nitrodiphenylamines employed in the present invention are prepared by combining compounds of the formula wherein A, R and R have the meanings given above and X is halogen, preferably chlorine, with an aromatic amine of the formulae NH and NH1 where R and R have the meanings ascribed above and can be the same or different.
- certain aliphatic amines (alkylamines of from 2-10 carbon atoms) can also be employed.
- these amines are 3-methoxypropylamine, 2-hydroxybutylamine and 3-chloropropylamine and especially cyclohexylamine.
- the dyestuffs obtained when these amines are employed as reactants produce bright greenish fellow dyeings o fexcellent sublimation fastness and good light fastness.
- the compounds of the formula OzN N are prepared by acylating a primary or secondary diamine of the formula where R R and A have the meanings given above with a suitable acylating agent, such as 3-nitro-4-chlorobenzenesulfonyl chloride in aqueous medium or with solvent with or without heating and, preferably, in the presence of a proton acceptor.
- a suitable acylating agent such as 3-nitro-4-chlorobenzenesulfonyl chloride in aqueous medium or with solvent with or without heating and, preferably, in the presence of a proton acceptor.
- the preferred nitrodiphenylamines employed in the present invention are those wherein A is a straight or branched chain alkylene of from 2-6 carbon atoms, and especially ethylene, methylethylene, and propylene: R and R are hydrogen or hydroxy lower alkyl of from 2 to 6 carbon atoms, and especially hydrogen, or hydrogen for one of R and R and hydroxy lower alkyl for the other; Y and Z the same or different and phenyl, monoalkylphenyl, monoalkoxyphenyl, monohydroxyalkylphenyl wherein the side chain contains from 2-6 carbon atoms and is attached to the o, m, or p position; and cyclohexyl; and especially phenyl.
- the said dyestuffs are preferably used in a finely divided form and the dyeing is carried out in the presence of a dispersing agent, such as sulphite cellulose or waste liquor or a combination of different wetting and dispersing agents.
- a dispersing agent such as sulphite cellulose or waste liquor or a combination of different wetting and dispersing agents.
- Dyestuff preparations of this kind can be made by known methods, for example, by grinding the dyestuff(s) either in dry or wet form with or without the addition of a dispersing agent.
- the dyestuffs used in the invention are especially suitable for dyeing by the so-called thermofixation or Pad/ Thermofix method, in which the fabric to be dyed is impregnated advantageously at a temperature not exceeding 60 C. with an aqueous dispersion of the dyestuff, which may contain 1 to 50% of urea and a thickening agent, especially sodium alginate, and the fabric is squeezed in the usual manner.
- the squeezing is prefer- 4 ably carried out so that the goods retain 50 to of their weight of dye liquor.
- the dyestutf is fixed by subjecting the impregnated fabric to a heat treatment at temperatures above 100 C., for example, at a temperature ranging from 220 C., it being of advantage to dry the fabric prior to this treatment, for example, in a current of warm air.
- the padding liquor contains a dyestuff suitable for dyeing cotton, for example, a direct dyestuff or vat dyestuff, or a so-called reactive dyestuff, i.e. a dyestuff capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestuff containing a chlorotriazine or chlorodiazine residue.
- a dyestuff suitable for dyeing cotton for example, a direct dyestuff or vat dyestuff, or a so-called reactive dyestuff, i.e. a dyestuff capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestuff containing a chlorotriazine or chlorodiazine residue.
- an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of two or more of these agents.
- an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of two or more of these agents.
- the dyeings produced on polyester fibers by the process of the invention are advantageously given an aftertreatment, for example, by heating them with an aqueous solution of a non-ionic detergent.
- the dyestuffs may be applied by printing.
- a printing color which, in addition to the usual printing assistants, such as wetting and thickening agents, contains the finely dispersed dyestuff, if desired, in admixture with one of the aforesaid cotton dyestuffs, and, if desired, in the presence of urea and/or an agent capable of binding acid.
- polyester defines synthetic polymeric polyesters, such as the highly polymeric linear polyesters, the molecules of which have recurring monomeric units connected by ester linkages.
- Dibasic acids for example, aromatic acids, such as terephthalic acid, diphenyl-4,4'-dicarboxylic acid and/or diphenylsulfone-4,4'-dicarboxylic acid and dihydroxy compounds, for example, glycols, such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and/ or butylene glycol, as well as other diols, such as 1,4-bis (hydroxymethyl)-hexahydrobenzene, 1,4-cyclohexandiol can be used as the monomers to form the polymeric polyesters, and preferably the condensation product of terephthalic acid and ethylene glycol or 1,4- bis (hydroxymethyl) hexahydrobenzene.
- Typical commercial examples of such fibers are Dacron, Terylene, Fortrel, Trevira, Terlanca, Kodel, Vicron, etc. They are disclosed, for example, in US. Pat. No. 2,901,466 and British Pats. Nos. 578,079; 579,462; 588,497 and 596,688.
- the present invention is, of course, equally applicable to the dyeing of blends of polyester fibers and cellulosic fibers.
- the latter term includes native cellulose, such as linen or, more particularly, cotton, as well as regenerated cellulose, such as viscose of cuprammonium rayon.
- Example 1 50 g. by weight of N,N' ethylene bis 4 chloro- 3 nitrobenzene 1 sulfonamide, 22 g. of aniline, 50 g. of anhydrous sodium acetate, and 650 g. of 95% ethanol are stirred for 24 hours at 130 C. in an autoclave. The reaction mass is cooled, filtered and washed with ethanol. The collected precipitate is washed with hot water, filtered, and washed until free of salts. The product, N,N'- ethylene bis 4 phenylamino 3 nitrobenzenc 1- sulfonamide, obtained in a yield of 45 g., gives yellow dyeings on polyester fibers.
- the N,N' ethylene bis 4 chloro 3 nitrobenzenel-sulfonamide employed above is prepared in the following manner: 6 g. by weight of ethylenediamine are dissolved in 60 g. of water at 2 C. To this solution there are added over a period of minutes, with stirring, 73 g. of a wet paste containing 51 parts of 4 chloro 3 nitrobenzene 1 sulfonyl chloride and the balance water. The mixture is heated, with agitation, during 30 minutes, to 60 C. The neutrality is then maintained over 2 hours by the gradual addition of 16.5 g. of a 50% by weight solution of sodium hydroxide in water. The precipitate is recovered by filtration and washed thoroughly with water. 45 g. by weight of product are obtained, recrystallized from ethanol and collected as a colorless crystalline powder melting at 221-2225 C.
- Example 2 51.4 g. by weight of N,N-methylethylene-bis-4-chloro-3-nitrobenzene-l-sulfonamide and 22.5 g. of aniline are added to a solution of 110 g. sodium acetate in 73 g. water at 90 C. and heated for hours at 115 to 120 C. with stirring. The reaction mixture is diluted with 80 g. of water and filtered. The solids are washed thoroughly with hot water and dried. 60.5 g. of N,N'- methylethylene bis-4-phenylamino-3-nitrobenzene-l-sulfonamide giving yellow shades on polyester fibers are obtained.
- Example 3 54.6 g. of N,N'-p-phenylene-bis-4-chloro-3-nitrobenzene-l-sulfonamide and 22.5 g. of aniline are added to a solution of 110 g. sodium acetate in 73 g. water at 90 C. and heated for 20 hours at 120 C. with stirring. The reaction mixture is diluted with 80 g. of water and filtered. The solids are washed thoroughly with hot water and dried. 59 g. of N,N'-p-phenylene-bis-4-phenylamino- 3-nitrobenzene-l-sulfonamide, giving yellow shades on polyester fibers are obtained.
- N,N'-p-phenylene-bis-4-chloro 3 nitrobenzene-lsulfonamide employed above is prepared in the following manner: To a stirred mixture of 11 g. by weight of p-phenylene-diamine, 24 g. of anhydrous sodium acetate and 45 g. of acetone there are added, with external cooling, at 10-25 C., 73 g. of a wet paste containing 51 g. of 4-chloro-3-nitrobenzene-l-sulfonyl chloride and the balance water. The reaction mass is heated and a temperature of 55 C. is maintained for 30 minutes. The reaction mass is diluted with water, filtered, the precipitate washed with ethanol, and then with hot water.
- Example 4 50 g. by weight of N,N'-ethylene-bis-4-chloro-3-nitrobenzene-l-sulfonamide and 24 g. of cyclohexylamine are added to a solution of 120 g. of sodium acetate in g. of water at C. and heated for 18 hours at 116 C. with stirring. The reaction mixture is diluted with 200 g. of water and filtered. The solids are washed thoroughly with hot water and dried. 58 g. of N,N-ethylene-bis-4- cyclohexylamino 3 nitrobenzene-l-sulfonamido giving greenish-yellow shades on polyester fibers are obtained.
- Example 5 51.3 g. by weight of N,N-(1,3-propylene-bis)-4-chloro-3-nitrobenzene-l-sulfonamide and 22 g. of 3-methoxypropylamine are stirred in a solution of 120 g. of sodium acetate in 80 g. of water at 116 C. for 18 hours. The reaction mixture is diluted with 250 g. of water, cooled until the oily product solidifies, and filtered. The solids are thoroughly washed with water, and then with methanol. 52.5 g. of N,N'-(1,3-propylene-bis)-4-w-methoxypropylamino 3 nitrobenzene-l-sultonarnide giving greenish-yellow shades on polyester fibers are obtained.
- Example 6 The dyes listed below are prepared by the method of Example 2 or 5 as indicated, opposite each compound. They give yellow dyeings on polyester fibers characterized by good penetration and excellent fastness to light and sublimation.
- Example 7 15 g. of N,N-ethy1ene-bis-4-phenylamino-3-nitro-benzene-l-sulfamide (Example 1) are brought to a state of fine dispersion by milling in a ball mill with parts of the condensation product of naphthalene-Z-sulfonic acid with formaldehyde and 75 g. of water.
- An aqueous preparation containing 67 g. of the above dyestutf dispersion and 0.5 g. of sodium alginate per liter is padded onto fabric of polyethylene terephthalate fiber and squeezed to 65% pick-up.
- the padded material is then air dried and subsequently heat dried at 220 C. for 1 minute.
- the dyed fabric is scoured for 5 minutes at the boil in a solution containing 3% of sodium di-iso-butylnaphthalene monosulfate and 5% sodium carbonate and then dried.
- a yellow dyeing is obtained, characterized by good penetration and excellent fastness to light and sublimation. Similar results are obtained when poly(1,4-cyclohexylene-dimethylene terephthalate) is used in place of polyethylene terephthalate fiber in the above example.
- Example 8 The procedure of Example 7 is repeated, except that g. each of the yellow dyes listed in Examples 2-6 are employed for the dispersion. A yellow dyeing is obtained in each instance characterized by good penetration and excellent fastness to light and sublimation.
- Example 7 The procedure of Example 7 is repeated, except that a total of 15 g. of each of the dyes of Examples 2 and 3 are employed. Satisfactory dyeings are obtained. Combinations of the other dyestuffs as mentioned in Examples 2-6 can be similarly employed.
- Process for coloring polyester fiber which comprises applying to fibrous material of synthetic polyester an aqueous dispersion of a compound of claim 1.
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- Engineering & Computer Science (AREA)
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Abstract
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5402070A | 1970-07-10 | 1970-07-10 |
Publications (1)
Publication Number | Publication Date |
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US3685957A true US3685957A (en) | 1972-08-22 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US54020A Expired - Lifetime US3685957A (en) | 1970-07-10 | 1970-07-10 | Process for dyeing polyester fibers with nitrodiphenylamine dyestuff |
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US (1) | US3685957A (en) |
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1970
- 1970-07-10 US US54020A patent/US3685957A/en not_active Expired - Lifetime
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: CIBA-GEIGY CORPORATION, NEW YORK Free format text: MERGER;ASSIGNOR:TOMS RIVER CHEMICAL CORPORATION;REEL/FRAME:003947/0757 Effective date: 19811102 Owner name: CIBA-GEIGY CORPORATION, A CORP. OF N.Y. Free format text: MERGER;ASSIGNOR:TOMS RIVER CHEMICAL CORPORATION;REEL/FRAME:004124/0150 Effective date: 19811022 Owner name: CIBA-GEIGY CORPORATION Free format text: MERGER;ASSIGNOR:TOMS RIVER CHEMICAL CORPORATION;REEL/FRAME:003947/0757 Effective date: 19811102 |