US2317965A - Process of coloring fibrous materials and the materials obtained thereby - Google Patents

Process of coloring fibrous materials and the materials obtained thereby Download PDF

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US2317965A
US2317965A US332015A US33201540A US2317965A US 2317965 A US2317965 A US 2317965A US 332015 A US332015 A US 332015A US 33201540 A US33201540 A US 33201540A US 2317965 A US2317965 A US 2317965A
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dyeing
dyed
materials
acid
washing
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US332015A
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Bestian Herbert
Nusslein Joseph
Monheim Josef
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GAF Chemicals Corp
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General Aniline and Film Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F4/00—Monocomponent artificial filaments or the like of proteins; Manufacture thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/487—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • 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
    • Y10S8/10—Polyvinyl halide esters or alcohol fiber modification
    • 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
    • Y10S8/21—Nylon
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2164—Coating or impregnation specified as water repellent
    • Y10T442/2197—Nitrogen containing
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352—Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric

Definitions

  • the said products are partly water-soluble and may be applied to the fibrous material in an aqueous solution.
  • the compounds are insoluble or diificultly soluble in water they may be used in the form of their aqueous suspensions or their solutions in organic solvents; also products which'have already been partially polymerized may, if desired, be applied to the material.
  • the compounds are polymerized, suitably by a heat treatment, for instance at 100 C. -l60 C. or a higher temperature, and in this way are incorporated with the fibrous material in a water- Cotton or regenerated cellulose may thus be treated with the compounds according to the above-named formula which are to be considered as urea derivatives, and the compounds may be polymerized on the fiber. In this manner a material is obtained which possesses an increased absorption capacity for acid wool dyestuffs.
  • the cellulose fibers thus pre-treated also show an improved afiinity for the ordinary cotton dyestuffs, the so-called substantive dyestuffs, and the fastness to water and to washing of the dyeings thus obtained is considerably-improved.
  • fibrous materials there are suitable fibers of vegetable or animal origin, furthermore fibers from regenerated cellulose or cellulose derivatives, also mineral or synthetic fibers, for instance glass or asbestos fibers, polyamide and polyvinyl chloride fibers and likewise leathers and hides.
  • the above-named products may likewise be applied on textile materials simultaneously with dyeing bodies and then firmly be fixed on the material by a thermal after-treatment.
  • there may be'obtained vivid dyeings and prints for instance by padding, spraying and printing fabrics from cotton or regenerated cellulose with solutions or suspensions of acid wool V dyestufl's and of urea derivatives which, when dyestuifs capable of being discharged are used, may be discharged-in known manner so as to obtain white or colored effects.
  • aqueous solutions of the products named are mixed with pigments such as titanium dioxide, soot, ultramarine, iron oxide or organic pigments such as azo-dyestufis insoluble in waymerization of the urea compounds the pigments are firmly fixed on the material;
  • the dyeings or prints so obtained are very stable against the usual ashing processes. It is not always necessary apply to the fibrous material a mixture of the pigment dyestufl! and the urea derivative, but the pigment dyestuif may also be prepadded, dried and cross-padded with the solution of the urea derivative.
  • This process of fixing pigments on fibrous materials is especially suitable for uniformly coloring mixed fabrics or mixed structures, for instance union or halfsilk or mixtures from regenerated cellulose and other fibrous materials which do not possess uniform aflinity for dyestuffs.
  • the hydrogen atoms of the ethylene groups may partly or entirely be substituted by methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, decyl, furthermore by phenyl, the methylphenyl radicals, benzyl and orth0, meta and -para-to1yl.
  • Two, three or all of the four hydrogen atoms may likewise be substituted by two, three or four different substituents asnamed above.

Description

Pltented Apr. 27, 1943 UNITED STATES PATENT OFFICE mocsss or comamc rmnous MATE- RIALS'AND THE Mia-ramps onmmnn THEREBY Herbert Bestian, Joseph Niisslein, and Jose! Monheim, Frankfort-on-the-Main, Germany, assignors to General Aniline & Film Corporation, New-York, N. Y., a corporation of Delaware No Drawing. Application April 27, 1940, Serial No. 332,015. In Germany May 27, 1939 2 Claims.
The present invention relates to a process of 'coloringjlbrous materials and to the materials obtained thereby.
We have found that colored effects may be produced on materials of fibrous structure by treating the fibrous materials at any stage of the coloring operation, 1. e., before, during or after the coloring step with products of the general formula: I
C H: CH
or the homologues or the derivatives thereof, wherein R stands for a member of the group consisting of aliphatic and isocyclic radicals, and then polymerizing the monomeric compound or calcium.
In their monomeric form, the said products are partly water-soluble and may be applied to the fibrous material in an aqueous solution. If
the compounds are insoluble or diificultly soluble in water they may be used in the form of their aqueous suspensions or their solutions in organic solvents; also products which'have already been partially polymerized may, if desired, be applied to the material. After the impregnation, the compounds are polymerized, suitably by a heat treatment, for instance at 100 C. -l60 C. or a higher temperature, and in this way are incorporated with the fibrous material in a water- Cotton or regenerated cellulose may thus be treated with the compounds according to the above-named formula which are to be considered as urea derivatives, and the compounds may be polymerized on the fiber. In this manner a material is obtained which possesses an increased absorption capacity for acid wool dyestuffs. The cellulose fibers thus pre-treated also show an improved afiinity for the ordinary cotton dyestuffs, the so-called substantive dyestuffs, and the fastness to water and to washing of the dyeings thus obtained is considerably-improved.
Wool may likewise be pre-treated in the afore- I said manner and then shows an'increased abinsoluble form. The polymerization may be carried through according to the processes described in U. S. Patents No. 2,265,416 issued December 9, 1941, and No. 2,312,863, issued March 2, 1943, both in the name of Herbert Bestian, for Polymerization products.
As fibrous materials there are suitable fibers of vegetable or animal origin, furthermore fibers from regenerated cellulose or cellulose derivatives, also mineral or synthetic fibers, for instance glass or asbestos fibers, polyamide and polyvinyl chloride fibers and likewise leathers and hides. I
By the new process there may be obtained, independently of the tinctorial behavior of the printed or padded materials, novel color effects as a result of the absorption capacity of the products applied for the coloring material. By taking advantage of the behavior of the said products and of the fibrous materials against dyestufis different effects are obtained which may even be far more varied by altering the amount of the product applied and the temperature and duration of the heat-treatment and, if desired, by adding suitable compounds, for instance formaldehyde or compounds yieldsorption capacity for acid dyestuffs. When pretreating in the same manner fibrous materials from cellulose esters or ethers' a material is obtained possessing an increased aifinity for the socalled acetate silk dyestuffs, besides an affinity for acid wool dyestuifs. Furthermore, the treatment with the above-named products may replace the previous mordant operation in the dyeing of cotton with basic dyestuffs or with mordant dyestuffs.
The above-named products may likewise be applied on textile materials simultaneously with dyeing bodies and then firmly be fixed on the material by a thermal after-treatment. In this manner, there may be'obtained vivid dyeings and prints, for instance by padding, spraying and printing fabrics from cotton or regenerated cellulose with solutions or suspensions of acid wool V dyestufl's and of urea derivatives which, when dyestuifs capable of being discharged are used, may be discharged-in known manner so as to obtain white or colored effects.
' Also colored or white pigments may be fixed on the fibrous material by means of urea derivatives.
For instance, aqueous solutions of the products named are mixed with pigments such as titanium dioxide, soot, ultramarine, iron oxide or organic pigments such as azo-dyestufis insoluble in waymerization of the urea compounds the pigments are firmly fixed on the material; The dyeings or prints so obtained are very stable against the usual ashing processes. It is not always necessary apply to the fibrous material a mixture of the pigment dyestufl! and the urea derivative, but the pigment dyestuif may also be prepadded, dried and cross-padded with the solution of the urea derivative. This process of fixing pigments on fibrous materials is especially suitable for uniformly coloring mixed fabrics or mixed structures, for instance union or halfsilk or mixtures from regenerated cellulose and other fibrous materials which do not possess uniform aflinity for dyestuffs.
Dyeings on cellulose with substantive dyestuffs, which dyeings in many cases show an insuflicient fastness to water and to washing may be improved as to their fastness to water and to washing by impregnating them with the urea derivatives in question, for instance by crosspadding. Fastness properties are obtained thereby whichare considerably more improved than in the case of after-treating the dyeings by means of highly molecular amines or ammonium compounds. Dyeings with other dyestuffs, for instance with mordant dyestuffs on cellulose may likewise be improved as to their fastness to water and to washing by after-treating them as described above.
The monomeric starting compounds may be obtained by reaction of aliphatic, cycloaliphatic, aromatic and araliphatic diisocyanates with ethylene imine or the homologues thereof. For instance, by the reaction of ethyleneimine or the homologues and derivatives thereof with aliphatic, aromatic, araliphatic or cycloaliphatic di-isocyanates there may, under suitable working conditions, be obtained products of the general formula:
wherein R stands for a substituent of the group consisting of arylene, alkylene, aralkilene, cycloalkylene and alkylenes the chains of which contain hetero atoms, and X1, X2, X3, X4 stand for substituents of the group consisting of hydrogen, alkyl, aryl and aralkyl.
As starting substances there may, for instance, be used compounds the radical --R-- of which has the following constitution:
CH:, -CH2CH2-, (CHz)a-. (CH2)4, --(CH2)a; the radical may likewise be branched, for instance CH2CHCHrCHr- I CuHs as well as the corresponding metal-and paracompounds,
as well as the corresponding metaand paracompounds and bromine compounds,
20. as well as the corresponding bromine compound;
The radical-R- may likewise be interrupted by hetero atoms, for instance:
The hydrogen atoms of the ethylene groups may partly or entirely be substituted by methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, decyl, furthermore by phenyl, the methylphenyl radicals, benzyl and orth0, meta and -para-to1yl. Two, three or all of the four hydrogen atoms may likewise be substituted by two, three or four different substituents asnamed above.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto:
1. A cotton fabric is printed with a'thickened solution of 20 per cent. strength of the reaction product of hexamethylene-diisocyanate and ethyleneimine, dried' for 8 minutes at 140 C. and dyed with the dyestufi. No. 863 (Schultz, Farbstofl tabellen, 7th edition). The printed parts are dyed vivid pink tints and the dyeing has a good fastness to washing. Similar results are obtained on fabrics from viscose-, cuprammoniumand acetate artificial silk, artificial silk staple fiber and linen. 0n using a cotton ground previously dyed with substantive dyestufi's there are obtained two-coloror intense half-tone effects, according to the ground color used.
2. Glass wool is impregnated with the reaction 75 product from octamethwlene-diisocyanate and alkali ne l-amino-2-mcthoxy-4mitrobenzeuc phcuyl-gainma-ai-id the glass wool may then be dyed dark-brown tints.
3. When cotton is printed with the reaction product from octamethylene-diisocyanate and ethyleneimine, dried for 5 minutes at 130C.-145 C. and dyed with sulfonated 4.4'-diaminodianthrimide without the addition of a chromium salt, a deep-black dyeing of the print is obtained which is fast to washing. A chromium salt may likewise be used, and in this case it is of little diflerence only, whether the chromium salt is applied before, during or after the dyeing operation.
4. A fabric from artificial silk staple fiber is padded with an aqueous solution of per cent. strength of the reaction product from tetramethylene-diisocyanate and ethylene-imine and dried for a short time at 130 C.-145 C. The material is then dyed with the dyestuff obtained by condensation of para-chlorobenzaldehyde and ethyl-benzyl-meta-toluidine, trisulfonation, oxidation and melting with para-phenetidine and a vivid blue dyeing is obtained which is fast to water and to washing. The blue dyeing thus obtained may be discharged .by means of formaldehyde-sulfoxylate to a white which does not change color.- If instead of the blue dyestufi the dyestuff No. 732 (Schultz, l. c.) is used, a brilliant strong yellow dyeing is obtained. If
the latter is printed with adischarge preparation containing the dyestufi No. 1330 (Schultz, l. c.), steamed for 5 minutes in a rapid ager, rinsed and soaped, a deep-blue discharge print is obtained on a yellow ground.
5. A viscose artificial silk fabric is padded with an aqueous solution of 'per cent. strength of the reaction product named in Example 1, dried at 60 C. and overprintedwith a printing paste containing an acid or an acid salt, for instance acetic acid or aluminium sulfate. Thereupon', the material is heated to 140 C., dyed with the azo-dyestuff acetylcyclohexyl-paraphenylenediamine benzoyl-K-acid and soaped for a short time. Half-tone resists are obtained on a red ground.
6. A fibrous material of polyvinyl chloride is padded with a solution of the reaction product from hexamethylene-diisocyanate and ethyleneimine and the chromium complex compoundsv of the azo-dyestuifs from diazotized 1-amino-2- hydroxy-3-nitrobenzene-5-sulfonic acid and beta-- ground and the dyeings obtained are distinctly faster to washing than the ground dyeings.
After having been printed according to Example 1 and heated for 8 minutes to 140 C.
chlorinated or unchlorinated w'ool may likewise be dyed with the dyestufi No. 603 (Schultz, l. 0.).
The printed wool may also be intensely dyed with the dyestufi obtained'by condensation of dinitrostilbene-disulfonic acid with the azo-dyestufl'. para sulfanilic acidalpha naphthylamine. Acetate silk, which has been pro-treated as described in Example 1 and subsequently heated, may likewise be dyed with the azo -dyestufl 2.6- dichloro 4 nitraniline N hydroxyethyl N methyl-meta-toluidine.
By adding to the printing paste 10 per cent. of formaldehyde of 40 per cent. strength or paraformaldehyde the time of heating may be considerably shortened.
8. A cotton fabric printed according to Example 1 is heated for 5 minutes to C. or steamed in a rapid ager, dyed with the disazodyestuif 4.4 diaminodiphenyl 3.3 bisglycolic acidpara-anisidyl-J-acid and subsequently treated with a copper sulfate solution. A darkblue print which is fast to washing is obtained on a blue ground.
9. Muslin from artificial silk staple fiber is printed as described in Example 3, dried at 100 C., dyed with the dyestuff obtained by reduction of the azo-dyestufi acid paranitraniline 1.8-8IlliIlOIlfillhthOl-i.G-(iiS HOlliC acid and reaction with phosgene, and coupled with diazotized para-nitraniline. After soaping the material, a dark-green print is obtained on a a green ground.
10. .A material padded according to Example 4 is dried at 100 C. and dyed with the dyestufi 2-21mino-S-naphtliol-3.6-disulfonic acid hcnzidino mcta-phcnylenediamine incta-plionylcnodiamiue aminobenzoyl-meta aminobenzoy1-J-acid. The
dyeing thus obtained is distinctly more yellowish than a corresponding dyeing produced on a not pre-treated materialand possesses a far better fastness to water and to washing. In comparison with a dyeing on a not pre-treated material which has been diazotized and developed with betanaphthol the shade of'the dyeing obtained as above is somewhat more bluish and shows an improved fastness to water.
- 12. A print produced according to Example 3 is heated for some minutes, on the felt calender. to C. and dyed with the dyestuff obtainable according to Example 2 of U. S. Patent No. 2,044,963 with use of para.para-tetra-hydroxyethyldiamino-meta.meta'-dimethylbenzophenone, and with alum. The printed parts are dyed deepblue tints. Instead of alum there are likewise suited other salts, for instance copper and cobalt salts.
13. Prints, produced as described in Example 1 and heated to 0., are dyed with the dyestufi N0. 1145 (Schultz, l. 0.). good fastness to washing are obtained. If the prints are previously mordanted with formic acid or with formic acid and potassium di-chromate current shades are obtained on dyeing. On previously mordanting with alum, tartar and oxalic acid yellowishred tints are obtained.
14. Prints on cotton produced according to Example 1 are steamed for 5 minutes in a rapid Red-brown tints of azer, treated for a short time in a hot bath containing 2 per cent. of formic acid and 2 per cent. of cobalt nitrate and dyed with the azo-dyestufl 1-sulfanilido-2 para-toluidine1.4- naphtholsub ionic acid, an intense red dyeing of the printed parts being obtained thereby, On addition of hexamethylenetetramine to the printing paste deeper shades may be obtained.
15. A mixed fabric consisting of viscose and cotton, which fabrictends to become streaky on dyeing, is padded with an aqueous solution containing 10 per cent. of the reaction product described in Examples 1 and 3 per cent. of the dyestuff No. 189 (Schultz, l. c.) and heated for 5 minutes to 140 C. A vivid, uniform orange dyeing is obtained which may be discharged to a white. The padding solution may likewise be used. with advantage in spray printing.
16. A printing color consisting of grams of the reaction product according to Example 1, 2 grams of the dyestufi mentioned in Example 5 of German Patent No. 293,352, 53 grams of neutragacanth thickening and 35 grams of water is printed on dulled cuprammonium silk or on a fabric of asbestos fiber, steamed in a rapid ager for 10 minutes and rinsed. The prints obtained have vivid shades and a good fastness to washing.
1?. Cotton material dyed with the dyestuff No. 306 (Schultz, l. c.) is padded with an aqueous solution of 10 per cent. strength of the reaction product mentioned in Example 1, dried and heated for a few minutes to 140 C. This treatment renders the color shades more yellow and distinctly clearer. The fastness to wet processing, particularly to washing at 100 C., is essentially improved thereby. By treating material dyed with the dyestuif No. 510 (Schultz, l. c.) in the same manner there is likewise obtained a dyeing having a considerably better fastness to washing.
18. If a dyeing on tannin-mordanted artificial silk staple fiber, dyed with the dyestuif used in Example 12, is after-treated as described in Example 17 the fastness to washing of the dyeing obtained is quite essentially improved.
19. A cotton fabric is padded with a liquor containing 5 per cent. of the dyestuif No. 86 (Schultz, l. c.) 10 per cent. of the reaction prodnot mentioned in Example 1, 1 per cent. of highly polymerized polyvinyl alcohol and 84 per cent. of water, dried and heated for 5 minutes to 140 C. A brilliant red dyeing of very good iastness to washing is obtained. The fabric may also be padded with the pigment dyestuif and after drying may further be padded with the solution of the above-named reaction product. It is then dried and subsequently heated as described above. Thereby a dyeing is obtained which is particularly fast to rubbing.
We claim:
1. The process of coloring fibrous materials which comprises applying to the material at any stage of the coloring operation a compound of the general formula substituents selected from the group consisting of hydrogen, alkyl, aryl and aralkyl radicals and polymerizing the monomeric compound.
2.'Fibrous materials can'ying a polymer of a compound of the general formula I X1\ /X: I X1\ X1 wherein R stands for a member of the group con- ,sisting of alkylene, arylene, aralkylene, cycloalfor substituents selected from the group consisting of hydrogen, alkyl, aryl and aralkyl radicals and a coloring agent.
HERBERT BESTIAN. JOSEPH NtissLEm. JOSEF' MONI-IEIM.
US332015A 1939-05-27 1940-04-27 Process of coloring fibrous materials and the materials obtained thereby Expired - Lifetime US2317965A (en)

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US2458397A (en) * 1943-11-18 1949-01-04 Courtaulds Ltd Dyeing of nylon fibers by treating with nitrogenous condensation products
US2462428A (en) * 1943-10-29 1949-02-22 Ciba Ltd Process of dyeing glass fibers
US2893892A (en) * 1953-12-10 1959-07-07 Ct Tech Ind Dit I Textile De F Method for the coating of glass threads and tissues with artificial resin
US2908543A (en) * 1956-06-29 1959-10-13 Gen Aniline & Film Corp Aftertreatment of leather dyeings
US2922723A (en) * 1957-01-31 1960-01-26 Johnson & Johnson Product and method of manufacture
US2925313A (en) * 1957-04-29 1960-02-16 Union Carbide Corp Siloxane azo dyestuffs
US2925314A (en) * 1954-02-05 1960-02-16 Basf Ag Process of dyeing and printing cellulose derivatives
US2927839A (en) * 1957-04-29 1960-03-08 Union Carbide Corp Siloxane azo dyestuffs
US2931693A (en) * 1957-04-29 1960-04-05 Union Carbide Corp Silicon azo dyestuff and fibers dyed therewith
US2933416A (en) * 1960-04-19 Process for fixing figments on
US2955053A (en) * 1958-08-20 1960-10-04 Hess Goldsmith & Company Process for selectively coloring glass fabric and resultant article
US2955898A (en) * 1957-04-29 1960-10-11 Union Carbide Corp Thiazine dyestuffs and process of dyeing fibrous material
US2957744A (en) * 1957-04-29 1960-10-25 Union Carbide Corp Silicon-containing ice colors
US2961349A (en) * 1956-08-21 1960-11-22 Hoechst Ag Process for fixing pigments on fibrous materials
US3038776A (en) * 1960-05-17 1962-06-12 Leon H Chance Wrinkle resistant cellulose textiles and processes for producing same
US3079209A (en) * 1960-05-24 1963-02-26 Marble Products Company Of Geo Dyeing natural stones and shells with oil soluble dyes
US3295916A (en) * 1965-09-27 1967-01-03 Allied Chem Production of wash fast colorations with water-soluble metallized azo dyes
US3388964A (en) * 1965-08-19 1968-06-18 Agriculture Usa Shrinkproofing wool with dhsocyanates and ethylenimine

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FR1068657A (en) * 1951-06-28 1954-06-30 Bayer Ag Process for making textiles, etc. water-repellent.
US2764504A (en) * 1952-08-28 1956-09-25 Du Pont Coating process and products therefrom
US2764503A (en) * 1952-08-28 1956-09-25 Du Pont Coating fabrics
BE575304A (en) * 1958-02-10 1900-01-01
US3148164A (en) * 1961-04-21 1964-09-08 Pfersee Chem Fab Means for making textiles water resistant
DE1213373B (en) * 1961-04-22 1966-03-31 Pfersee Chem Fab Water repellent for all kinds of textiles
US3232790A (en) * 1961-06-24 1966-02-01 Pfersee Chem Fab Method for treating textile with perfluoroalkyl compounds and the treated textile
US3150000A (en) * 1961-06-24 1964-09-22 Pfersee Chem Fab Method and means for treating textiles
US3274174A (en) * 1962-02-14 1966-09-20 Pfersee Chem Fab N-1, 1-dihydrofluoroalkyl-n'-alkylene urea
US3535141A (en) * 1967-04-17 1970-10-20 Deering Milliken Res Corp Process for making sail release synthetic textile
US4011613A (en) * 1975-11-18 1977-03-15 The United States Of America As Represented By The Secretary Of Agriculture Durable-press properties in cotton containing fabrics via polymeric N-methylol reagents
JPS595703B2 (en) 1981-12-02 1984-02-06 大和化学工業株式会社 Washing resistance sanitary processing method for textile products
US4696760A (en) * 1983-12-08 1987-09-29 Nippon Shokubai Kagaku Kogyo Co., Ltd. Method for production of aqueous dispersion of N-substituted N',N'-alkylene urea

Cited By (18)

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Publication number Priority date Publication date Assignee Title
US2933416A (en) * 1960-04-19 Process for fixing figments on
US2462428A (en) * 1943-10-29 1949-02-22 Ciba Ltd Process of dyeing glass fibers
US2458397A (en) * 1943-11-18 1949-01-04 Courtaulds Ltd Dyeing of nylon fibers by treating with nitrogenous condensation products
US2893892A (en) * 1953-12-10 1959-07-07 Ct Tech Ind Dit I Textile De F Method for the coating of glass threads and tissues with artificial resin
US2925314A (en) * 1954-02-05 1960-02-16 Basf Ag Process of dyeing and printing cellulose derivatives
US2908543A (en) * 1956-06-29 1959-10-13 Gen Aniline & Film Corp Aftertreatment of leather dyeings
US2961349A (en) * 1956-08-21 1960-11-22 Hoechst Ag Process for fixing pigments on fibrous materials
US2922723A (en) * 1957-01-31 1960-01-26 Johnson & Johnson Product and method of manufacture
US2931693A (en) * 1957-04-29 1960-04-05 Union Carbide Corp Silicon azo dyestuff and fibers dyed therewith
US2927839A (en) * 1957-04-29 1960-03-08 Union Carbide Corp Siloxane azo dyestuffs
US2955898A (en) * 1957-04-29 1960-10-11 Union Carbide Corp Thiazine dyestuffs and process of dyeing fibrous material
US2957744A (en) * 1957-04-29 1960-10-25 Union Carbide Corp Silicon-containing ice colors
US2925313A (en) * 1957-04-29 1960-02-16 Union Carbide Corp Siloxane azo dyestuffs
US2955053A (en) * 1958-08-20 1960-10-04 Hess Goldsmith & Company Process for selectively coloring glass fabric and resultant article
US3038776A (en) * 1960-05-17 1962-06-12 Leon H Chance Wrinkle resistant cellulose textiles and processes for producing same
US3079209A (en) * 1960-05-24 1963-02-26 Marble Products Company Of Geo Dyeing natural stones and shells with oil soluble dyes
US3388964A (en) * 1965-08-19 1968-06-18 Agriculture Usa Shrinkproofing wool with dhsocyanates and ethylenimine
US3295916A (en) * 1965-09-27 1967-01-03 Allied Chem Production of wash fast colorations with water-soluble metallized azo dyes

Also Published As

Publication number Publication date
NL54564C (en) 1943-05-15
BE439195A (en) 1940-08-31
US2314968A (en) 1943-03-30
FR865869A (en) 1941-06-06
BE441247A (en) 1941-04-30
FR879159A (en) 1943-02-16

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