US3926548A - Sulfonated phenylamino-halotriazine or- diazine surface modified aminated hydrophobic fibers and blends thereof with unmodified aminated hydrophobic fibers - Google Patents

Sulfonated phenylamino-halotriazine or- diazine surface modified aminated hydrophobic fibers and blends thereof with unmodified aminated hydrophobic fibers Download PDF

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US3926548A
US3926548A US296207A US29620772A US3926548A US 3926548 A US3926548 A US 3926548A US 296207 A US296207 A US 296207A US 29620772 A US29620772 A US 29620772A US 3926548 A US3926548 A US 3926548A
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fibers
dye
reserving
yarn
agent
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Kazuo Moriyama
Takashi Iwato
Morihiko Ohno
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Toyobo Co Ltd
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Toyobo Co Ltd
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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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B11/00—Treatment of selected parts of textile materials, e.g. partial dyeing
    • D06B11/0079—Local modifications of the ability of the textile material to receive the treating materials, (e.g. its dyeability)
    • D06B11/0086—Local modifications of the ability of the textile material to receive the treating materials, (e.g. its dyeability) the textile material being one or more yarns
    • 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
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/854—Textiles which contain different kinds of fibres containing modified or unmodified fibres, i.e. containing the same type of fibres having different characteristics, e.g. twisted and not-twisted fibres
    • 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
    • D06P7/00—Dyeing or printing processes combined with mechanical treatment
    • 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
    • Y10S8/929—Carpet dyeing

Definitions

  • An object of the present invention is to provide hydrophobic fibers containing amino groups, which are non-dyeable or differential-dyeable with anionic dyes.
  • Another object of the present invention is to provide hydrophobic fibers containing amino groups which are ferential-dyeable with the use of only anionic dyes.
  • a further object of the present invention is to provide a process for producing the above-mentioned hydrophobic fibers containing amino groups which are nondyeable or differential-dyeable.
  • FIG. 1 is a schematic cross-section of a fiber embodying this invention
  • FIG. 2 is a schematic longitudinal sectional view of an apparatus useful for producing the fibers of this invention.
  • FIG. 1 is a schematic cross-section of a single fiber of the present invention
  • the numeral 1 indicates a layer which has been processed to be dye-reserving to make the fiber non-dyeable or differential-dyeable (hereinafter referred to as dye-reserving layer, for simplicity) and the numeral 2 designates an ordinary dye-acceptable core portion of the fiber.
  • the hydrophobic fiber of the present invention preferably has a dye-reserving layer of a thickness of less than 2 microns on the average. As the thickness of the surface dye-reserving layer exceeds 2 microns on the average, the effect of the present invention is gradually decreased.
  • dye-reserving layer 1 The existence of such dye-reserving layer 1 can be confirmed from the fact that, when the fibers of the present invention are dyed with an anionic dye, especially with a dye having more than three sulfonic acid groups, e.g. Drimarene Brilliant Red X-2B (a reactive dye produced by Sandoz) and are observed under a microscope, the fibers are dyed only from the cut ends.
  • an anionic dye especially with a dye having more than three sulfonic acid groups, e.g. Drimarene Brilliant Red X-2B (a reactive dye produced by Sandoz) and are observed under a microscope
  • the dye-reserving layer 1 is non-dyeable with anionic dyes because the amino groups in that layer of the hydrophobic fiber are blocked by covalent bonds.
  • anionic dyes those having a single sulfonic acid group can pass through the dyereserving layer 1 to dye even the core of the fibers sutficiently.
  • the fibers of this invention can be dyed to have a multicolored effect.
  • another type of dye for example disperse dyes.
  • dyeing with anionic dyes gives dyed articles of bright color and having good fastness to wet treatment and light.
  • Hal H Z Ya NVN It is also possible to obtain more complex multi-colored effects when the dye-reserving layer is formed partly along the length of the hydrophobic fibers.
  • the dyeability can be also varied in various ways by changing, for example, the thickness of the dye-reserving layer, the density of blocking; of amino groups, etc. Also, very attractive miulticolored effects can be obtained by the combination of dyes having different numbers of sulfonic acid groups.
  • the fibers of the present invention are suitable for producing yarn or cloth of a pepper-and-salt effect by the combination with other hydrophobic fibers containing amino groups having different dyeability or with fibers of other types.
  • articles of interior decoration such as carpets, gives multicolored products of seeking effects that have not been obtained in conventional articles.
  • the hydrophobic fibers of the present invention can be produced by reacting a compound having groups capable of linking to amino groups in the fibers to form covalent bonds, with only the surface portion of the fiber.
  • Such compounds having groups capable of forming covalent bonds with amino groups are preferably colorless or white compounds having reactive groups capable of reacting with amino groups, such as halotriazinyl, halopyrimidinyl, haloquinoxalyl, haloacrylamido, vinylsulfo groups, etc., or any other groups that can produce these groups.
  • colored compounds may be also used for the purposes of the present invention.
  • compounds having anionic groups for example, sulfonate, carboxylate, sulfate, phosphate groups, ect., besides the highly reactive groups capable of reacting with amino groups.
  • N Z Y I Hal Hal N f commr- (A) n Hal ⁇ N 7 wherein Hal is F, C] or Br, Z is XY-(A),,, B is H, Cl or F, X is O, S or' -NR, Yis an (n+1)- valent substituted or non-substituted an aromatic or aliphatic group, A is anionic group, n is O or a positive integer, M is H, alkali metal or ammonium, and R is H or a lower alkyl group.
  • the hydrophobic fibers containing amino groups I Hal include polyamide fibers, such as nylon-6, nylon-66;
  • protein-acrylonitrile graft copolymer fibers such as Chinon (produced by Toyobo Co.): fibers of polyesters, polyurethanes, polyacrylonitrile, polypropylene, etc. which have been copolymerized, graft copolymerized or mixed with a compound having an amino group, for example, aminoalkyl acrylate, etc.
  • polyamide fibers are most preferable.
  • the fiber to be treated with the above mentioned compound is usually in the form of fibers, filaments, yarn, but sometimes the treatment may be carried out in respect of the fibers in the form of woven fabrics, knitted fabrics, non-woven fabrics, or paper.
  • One of such methods is to apply the dye-reserving agent to the fibers in a mist-like state, in a manner as shown in FIG. 2, wherein the numeral 3 indicates a means for applying a dye-reserving agent to the fiber a.
  • the reference numeral 4 indicates the main body of the treating apparatus, and the reference numeral 5 designates a supply pipe of high pressure gas.
  • the filaments a to be treated are given the dye-reserving agent at low temperature on the surfaces by the dye-reserving agent applicator 3 and then fed into the treating apparatus 4 through supply rollers 6,6.
  • the filaments a are drawn into the apparatus 4.
  • the filament passage in the apparatus 4 is expanded sharply at the part 9, so that the jet stream turns into a violent turbulent stream therein.
  • the filaments a are also violently vibrated to be opened, and the treating agent partly covering the surfaces of the filaments a leaves the filaments and floats in the form of mist to completely cover only the surface layer of the filaments again.
  • the filaments having this surface deposit of the reserving agent are then dried by a heater 10 positioned at the lower part of the treating apparatus where the reaction on the filament surfaces is completed.
  • the surface-treated filaments are taken-out by delivery rollers 11,11, and wound on a winding roller 12. If a compressed hot air is used as a high pressure gas, the heater 10 is not always necessary.
  • the dye-reserving agent may be directly supplied at the inlet 7 of the treating apparatus or at the spreading part 9. If desired, the agent may be contained in the high pressure gas.
  • the filaments are not necessarily required to be nontwisted yarn but may be soft-twisted yarn of less than 100 T/m.
  • Another example of treatment is that, an article to which the dye-reserving agent has been applied is squeezed and dried at low temperature and then subjected to heat treatment to fix the agent.
  • a further example of treatment is that unstretched filaments to which the dye-reserving agent has been applied is dried and then stretched to fix the agent by the heat developed by the stretching, or is stretched under heating to fix the agent.
  • the article-under treatment should not be brought to a temperature higher than 50C. before drying. If the article is raised above that temperature, the dye-reserving agent may penetrate into the core of the fibers and therefore the fibers of the present invention cannot be obtained. When the temperature is raised after drying, the dye-reserving agent reacts with the amino groups on the fiber surfaces and is fixed, so that it does not diffuse into the core of the fibers.
  • the dye-reserving agent may be used as an aqueous solution or an organic solvent solution. However, it is preferable to use it as an aqueous dispersion with suitable adjustment of the concentration and (wet) pick up such that the fibers take up 0.01 to 0.5% by weight of the agent based on the weight of the fibers.
  • the reactive groups in the agent may react with water and are hydrolyzed, so that the reactivity with amino groups is gradually lowered. Therefore, in such case it is preferable to lower the water solubility of the agent, for example by maintaining the treating liquor at a low temperature or by modifying the sulfonic acid groups into the form of their salts or free acid having slight water solubility or by adding a mineral salt such as sodium sulfate, sodium chloride, etc., so that the hydrolysis proceeds only from the surfaces of the dispersed particles and therefore the agent is kept stable.
  • the methods of forming a dye-reserving surface layer intermittently along the lengthwise direction of the fibers include (1) a method of applying the dye-reserving agent intermittently along the lengthwise direction of the fibers; (2) a method wherein after the agent is applied to the whole surfaces of the fibers and fixed at some parts of the surfaces, the dye-reserving agent on the other parts is removed; and (3) a method wherein after the dye-reserving agent is applied to the whole surfaces of the fibers and fixed, some parts of the surface layer are stripped off.
  • An example of the method (1) is that the travelling yarns are contacted intermittently with a dye-reserving agent-supplying roller.
  • An example of the method (2) is that after the dye-reserving agent is applied and dried, some parts of the agent are fixed on the yarns or fabrics and the yarns or fabrics are then washed to remove the agent in the other parts.
  • a peculiar example of this method is that after the dye-reserving agent is applied to unstretched filaments and dried, the filaments are stretched in some parts and the dye-reserving agent is fixed to the filaments by the heat developed by the stretching. In this case since the filaments are formed into thick-and-thin yarn, the contrasting difference of color is further emphasized to produce an interesting effect.
  • the method (3) is a method of pressing the fibers with a pair of gears, 21 method of scratching some parts of the fiber surfaces with an edge, a method of pressing some parts of the fibers with a hot roller, a method of passing the fibers through sands or glass powder, etc., a method of strongly pressing some parts of the fibers with engraved hot rollers, a method of strongly pressing the fibers superposed with rugged cloth as a lace or rugged paper, with hot rollers, etc.
  • the fibers thus obtained are dyed mainly with anionic dyes including ordinary acid dyes, metallized dyes, direct dyes, reactive dyes, etc., and any of such dyes can be used satisfactorily.
  • the dyeability of the fibers depends on the number of sulfonic acid groups contained in the dye. Examples of the dyes containing a single sulfonic acid group are C.l. Acid Yellow 25, 29, 49, 64, 65, 110, 135, 159, 168, G1. Acid Orange 116, 127, CI. Acid Red 32, 57, 257, 266. 333, 334, CI. Acid Violet 31, 41, Cl. Acid Blue 25, 27, 40, 41, 47, 62, 72, 78, 106, 129, 230, C1.
  • Acid Green 83 C1. Acid Brown 248,etc.
  • dyes containing two sulfonic acid groups are C.l. Acid Yellow 17, 38, 42, 44, 79, CI. Acid Orange 33, CI. Acid Red 37, 154, 157, 168, CI. Acid Violet 48, Cl. Acid Blue 80, 112, 182, 203, CI. Acid Green 27, 4l, etc.
  • dyes containing three or more sulfonic acid groups are C.I. Acid Red 145, CI. Direct Red 95, Cl. Reactive Yellow 2, 12, CI. Reactive Orange 2, CI. Reactive Red 3, 4, 9, 12, 17, 56, CI.
  • EXAMPLE 1 Filament yarn of nylon-6 (1 100 d/68 f), while travelling, was brought into contact with the surface of a rotating roller dipped in a bath consisting of parts by weight disodium hydrogenphosphate water 2 parts by weight and 93 parts by weight.
  • the yarn was then introduced into a treating apparatus as shown in FIG. 2, while a jet stream of high temperature high pressure air at 190C. and 4 kg/cm was blown thereinto so that the yarn was opened into individual filaments and at the same time crimp-processed.
  • the solution of the dye-reserving agent which covered the surfaces of the fibers more or less unevenly was blown off into fine mist-like droplets by the high speed jet stream, and the mist then covered the filaments again uniformly and became fixed by reacting with the amino groups on the surfaces of the fibers.
  • the yarn thus treated and yarn similarly crimp-processed but not treated with the dye-reserving agent were formed into twisted yarn.
  • a carpet was prepared from this twisted yarn and was dyed in a bath containing C.l. Direct Red 95 1% o.w.f. and Ultra N-l (pH adjusting agent produced by Miteshima Chemical Co.) 0.2 g/liter at a liquor ratio of 1:50 and at a temperature of 100C. for 60 minutes. The result was that the yarn treated with the dye-reserving agent was not dyed at all while the yarn not treated was dyed in deep scarlet.
  • Undyed cut piecesof the both yarns were prepared and dyed with the abovementioned ddye. The cross-section of each of them was observed. Both were dyed in quite the same depth of color. It was observed under a microscope, however, that the surface layer of the yarn treated with the dye- 6 reserving agent was not dyed. The thickness of the dye-reserving layer of the treated yarn was about 1 micron when observed by means of microscopic photographs of the cross-sections of the fibers.
  • the content of amino groups as a whole was 55 milliequivalent/kg fibers for the untreated yarn and 53 milliequivalent/kg fibers for the yarn treated with the dye-reserving agent. Thus, there was no substantial difference between the two since the surface layer of which the amino groups were blocked was very thin.
  • EXAMPLE 2 Filament yarn of nylon-6 1 d/68 f), while travelling, was contacted intermittently with the surface of a rotating roller dipped in a bath consisting of 2 parts disodium hydrogenphosphate water 2 parts and 96 parts and immediately introduced into a treating apparatus as shown in FIG. 2 where it was treated as in Example 1. In this way. filament yarn was produced which had an intermittent thin dye-reserving layer (about 1 micron thick) formed evenly on the surface of the filaments.
  • the yarn was then formed into a carpet, which was dyed in a bath consisting of C.l. Acid Brown 248 1.2 7: o.w.f
  • the untreated filament yarn was dyed green, the treated yarn was dyed blue.
  • the cross-section of the treated filaments showed that the thickness of the dye-reserving layer was less than about 2 microns.
  • Exlan H type filaments (acid dye-dyeable acrylic fibers containing amino groups produced by Japan Exlan Company, Limited; 100 d/40 f) were arranged in parallel and were passed through a bath composed of C.l. Reactive Blue 10 and Ultra N-l at a liquorratio of 1:50 at a temperature of 100C. for 60 minutes.
  • the result was that the treated yarn remained white while the untreated yarn was dyed in a deep navy blue to obtain a dyed checked fabric.
  • the cross-section dyeing of the treated filaments showed that the thickness of the dye-reserving layer was less than 2 microns on the average.
  • Chips of nylon-6 having a relative viscosity of 2.5 were melted and spun into filament yarn at a temperature of 260C. and at a winding speed of 800 m/min.
  • the filament yarn was made to take up the following treating liquor in an amount of 6 on the weight of the fibers from an oiling roller, and wound up.
  • Acid Red (containing two 35 sulfonic acid groups) 0.5 7: o.w.f. and Cl. Acid Blue (containing a single sulfonic acid group) 1.2 71 o.w.f.
  • EXAMPLE 7 Chips of nylon-6 having a relative viscosity of 2.5 were melted and spun into filament yarn at a spinning 5Q temperature of 260C. and a winding speed of 800 m/min.
  • the yarn was made to take up a treating liquor composed of spinning oil 15 d water the balance in an amount of 6 on the weight of the fiber from an oiling roller and wound up.
  • This unstretched yarn was stretched four times of the initial length. When the stretched yarn was dyed with Drimarene Brilliant Red X-2B, only the cut ends of the filaments were dyed.
  • This yarn was combined with yarn treated in an oiling bath not containing the compound (b). When the combined yarn was dyed in a bath containing C.l. Reactive Blue 10 (containing 3 sulfonic acid groups) 1.0 7: o.w.f. and C1. Acid Yellow (containing a single sulfonic acid group) 0.3 7: o.w.f.
  • Example 1 the yarn was dyed yellow and deep blue.
  • EXAMPLE 8 Filament yarn of nylon-6 l 100 d/64 f), while travelling, was applied with a treating liquor l composed of $0 No Cl N I 3 N N V I disodium hydrogenphosphate -5 and water the balance and another treating liquor (2) composed of C N O3NO Y m- NH G N N disodium hydrogenphosphate and water the balance.
  • Acid Yellow 49 (containing a single sulfonic acid group) at 100C. for 45 minutes in I the usual way.
  • the result was that the dye-reserving l 5 treated yarn was dyed deeper than the light-dyeable dmdmm hydrogenphosphae 05 yarn.
  • Acid Blue 80 (conand water the balance taming two sulfonic acid groups) in the same was as above, the dye-reserving treated yarn was dyed lighter than the light-dyeable yarn.
  • Reactive Red 3 or Cl Reactive Blue 10 both containmg three sulfonic acid groups) in the same way as W NH Q above, the dye-reserving treated yarn was not substanand tially dyed.
  • the plyed yarn was dyed with a combination of the above-mentioned dyes (each 0.5
  • Hal is fluorine, chlorine or bromine
  • Z is iso lum ro en es ate 4 spinning oil g p p 8' gig NR-phenyl sulfonate
  • B is hydrogen. chlorine or fluoand wutcr ilic hdldncc. rine and R is hdyrogen or lower alkyl.
  • Polyamide fibers according to claim 1 said fibers being mixed with polyamide fibers not having the dyereserved surface layer thereon 6.

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US296207A 1971-10-08 1972-10-10 Sulfonated phenylamino-halotriazine or- diazine surface modified aminated hydrophobic fibers and blends thereof with unmodified aminated hydrophobic fibers Expired - Lifetime US3926548A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4009001A (en) * 1974-05-10 1977-02-22 Burlington Industries, Inc. Process for the production of space-dyed effects on acrylic yarns
US4083682A (en) * 1974-03-14 1978-04-11 Rohm And Haas Company Method for producing variegated nylon yarn
US4300899A (en) * 1977-07-07 1981-11-17 Sandoz Ltd. Triazine and pyrimidine derivatives as reserving agents
WO1991003593A1 (en) * 1989-09-11 1991-03-21 Invicta Group Industries Pty Ltd Textile treatment using triazine as binding agent and sulfonated aromatic hydroxy as barrier agent
WO1991010006A1 (en) * 1990-01-02 1991-07-11 Invicta Group Industries Pty Ltd Textile treatment
US5098774A (en) * 1986-11-14 1992-03-24 Chang John C Divalent metal salts of sulfonated novolak resins and methods for treating fibrous polyamide materials therewith
US5571444A (en) * 1989-09-11 1996-11-05 Invicta Group Industries Pty Ltd. Textile treatment
US5599613A (en) * 1990-06-26 1997-02-04 Westpoint Stevens Inc. Compositions for imparting stain-resistance to polyamide textile products which are lightfast and durable to alkaline washing
CN104497625A (zh) * 2014-11-19 2015-04-08 浙江科永化工有限公司 一种黄色活性染料化合物、其制备方法及用途

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6173025A (ja) * 1984-09-19 1986-04-15 Ishida Scales Mfg Co Ltd 重量判定方法
JPS6173026A (ja) * 1984-09-19 1986-04-15 Ishida Scales Mfg Co Ltd 重量判定方法
GB2207152A (en) * 1987-07-22 1989-01-25 Sandoz Ltd Production of multicolour effects on polyamide fibre material

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1886480A (en) * 1929-04-11 1932-11-08 Chem Ind Basel Dyestuffs containing cellulose residues and process of making same
US3083118A (en) * 1958-03-04 1963-03-26 Tee Pak Inc Method of depositing a polymer of olefinically unsaturated monomer within a polymeric material and the resulting product
US3481682A (en) * 1962-12-06 1969-12-02 Deering Milliken Res Corp Modifying keratinic fibers with unsaturated sulfonic acids and blending fibers so modified with fibers having different dye affinity to obtain products which are differentially dyeable
US3632291A (en) * 1968-02-26 1972-01-04 Ciba Ltd Transfer printing
US3775045A (en) * 1970-06-11 1973-11-27 Ciba Geigy Ag Process for the production of multi-colour effects on natural and synthetic polyamide fibre material

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1886480A (en) * 1929-04-11 1932-11-08 Chem Ind Basel Dyestuffs containing cellulose residues and process of making same
US3083118A (en) * 1958-03-04 1963-03-26 Tee Pak Inc Method of depositing a polymer of olefinically unsaturated monomer within a polymeric material and the resulting product
US3481682A (en) * 1962-12-06 1969-12-02 Deering Milliken Res Corp Modifying keratinic fibers with unsaturated sulfonic acids and blending fibers so modified with fibers having different dye affinity to obtain products which are differentially dyeable
US3632291A (en) * 1968-02-26 1972-01-04 Ciba Ltd Transfer printing
US3775045A (en) * 1970-06-11 1973-11-27 Ciba Geigy Ag Process for the production of multi-colour effects on natural and synthetic polyamide fibre material

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4083682A (en) * 1974-03-14 1978-04-11 Rohm And Haas Company Method for producing variegated nylon yarn
US4009001A (en) * 1974-05-10 1977-02-22 Burlington Industries, Inc. Process for the production of space-dyed effects on acrylic yarns
US4300899A (en) * 1977-07-07 1981-11-17 Sandoz Ltd. Triazine and pyrimidine derivatives as reserving agents
US5098774A (en) * 1986-11-14 1992-03-24 Chang John C Divalent metal salts of sulfonated novolak resins and methods for treating fibrous polyamide materials therewith
WO1991003593A1 (en) * 1989-09-11 1991-03-21 Invicta Group Industries Pty Ltd Textile treatment using triazine as binding agent and sulfonated aromatic hydroxy as barrier agent
US5571444A (en) * 1989-09-11 1996-11-05 Invicta Group Industries Pty Ltd. Textile treatment
WO1991010006A1 (en) * 1990-01-02 1991-07-11 Invicta Group Industries Pty Ltd Textile treatment
US5599613A (en) * 1990-06-26 1997-02-04 Westpoint Stevens Inc. Compositions for imparting stain-resistance to polyamide textile products which are lightfast and durable to alkaline washing
CN104497625A (zh) * 2014-11-19 2015-04-08 浙江科永化工有限公司 一种黄色活性染料化合物、其制备方法及用途

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DE2249361C3 (de) 1980-07-31
DE2249361B2 (de) 1979-11-15
JPS4842188A (ja) 1973-06-19
DE2249361A1 (de) 1973-04-12
GB1403784A (en) 1975-08-28

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