US3716330A - Dyeing synthetics using roller coated molten dye compositions - Google Patents

Dyeing synthetics using roller coated molten dye compositions Download PDF

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US3716330A
US3716330A US00076599A US3716330DA US3716330A US 3716330 A US3716330 A US 3716330A US 00076599 A US00076599 A US 00076599A US 3716330D A US3716330D A US 3716330DA US 3716330 A US3716330 A US 3716330A
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Prior art keywords
dye
fabric
composition
dyestuff
coating
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US00076599A
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K Kitamura
F Takabayashi
F Shibata
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Teijin Ltd
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Teijin Ltd
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Priority claimed from JP44101418A external-priority patent/JPS4841793B1/ja
Priority claimed from JP44103137A external-priority patent/JPS4817229B1/ja
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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
    • D06P1/60—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 polyethers
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • 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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • 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
    • 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

  • ABSTRACT Primary ExaminerGeorge F. Lesmes Assistant Examiner-J. P. Brammer Att0rneyShennan and Shalloway [57 ABSTRACT A process for dyeing fabrics of synthetics fibers which comprised preparing a molten dye composition composed of dyestuff and organic matrix compound which is solid at normal temperature and has compatibility with the dyestuff in molten state, coating the molten composition onto the fabric under the condition not permitting the dyeing of the fabric, then heat-treating the coated fabric to induce the dyeing, and finally removing the remaining coating layer by washing.
  • dip dyeing refers to the practice of immersing the fabric to be dyed in an aqueous dyeing bath and gradually raising the bath temperature.
  • Pad dyeing normally refers to the process comprising immersing the fabric in a dyestuff dispersion, removing from the fabric the excessive dye liquid by squeezing it with mangle, etc., thereafter pre-drying the fabric and heating the same to fix the dye. With this process continuous operation is possible, and the productivity can be advantageously improved.
  • the process still is subject to the following numbers of drawbacks. That is, when dye concentration in the dye-badding bath is increased, the bath becomes susceptible to change with passage of time, e.g., formation of sedimentation due to aggregation of the dyestuff, and the dispersion in the padding bath becomes instable. Consequently, such objectionable results as ending, uneven coloring, formation of specks, etc. take place. Thus the dyestuff concentration in padding bath is inevitably limited. Furthermore, in the pad thermosol process, products of deep color are hardly obtainable because dissipation of dye into the heated atmosphere due to sublimation during the heating for fixing of the dye is conspicuous, and also the soiling of dye-fixing apparatus is heavy.
  • the object of the present invention is to provide a novel method of dyeing fabrics of synthetic fibers, which shows very high productivity and is capable of deep color dyeing with excellent uniformity.
  • Another object of the invention is to provide a novel dyeing method which achieves substantial simplification of procedures and reduction in labor, and exhibits high applicability to production of minor quantities of many different brands.
  • the above objects are accomplished by the subject process for dyeing fabrics of synthetic fibers, which comprises preparing a dyestuff compositioncomposed of at least one dye selected from the group consisting of non-ionic, anionic and-cationic dyes having affinity to said fabric, and organic matrix composed of at least one of aliphatic polyhydric compounds which are solid at normal temperature and melt at temperatures not higher than C.
  • the synthetic fibers are soluble in water or a low boiling point organic solvent, and are at least partially compatible with the dye at molten state, and derivatives of such compounds; heating the composition to form melt thereof; coating the melt onto the fabric under the conditions as will cause no substantial penetration-of the dye into the synthetic fibers; heattreating the coated fabric under the conditions as will allow penetration of the dye component in the coating into the fibers; and thereafter treating the fabric with water or the low boiling point organic solvent to remove the coating.
  • fabric is used in this specification and claims to mean sheet-formed fibrous materials such as woven goods, knit goods, non-woven fabrics, carpet, and film, composed of filaments or spun yarns.
  • at least partially compatible at molten state used in the specification and claims means that the organic matrix employed in the subject process either completely dissolves the dyestuff employed, or at least partially dissolves the dyestuff and uniformly and stably disperses the rest, at molten state.
  • the organic matrix preferably dissolves at least 0.1 wt.% of the used dyestuff at molten state.
  • the most characteristic .features of the subject process reside in the preparation of a melt of non-aqueous dyestuff composition composed of dyestuff and organic matrix which is solid at normal temperature but is easy-melting, and is at least partially compatible with the dyestuff at molten state; coating of the melt onto the fabric to be dyed, forming a uniform coating layer of said dyestuff composition, under the conditions as will cause no substantial penetration of the dye component of the composition into the synthetic fibers constituting the fabric, (i.e., at this stage the fabric is substantially undyed), and the following heat-treatment of the coated fabric to cause penetration of the dye component in the coating layer inside the synthetic fibers and achieve the dyeing of the fabric.
  • the dye component substantially penetrates into the fibers only at the heat-treating stage to achieve dyeing of the fabric. For this reason the heat-treating step may be hereinafter referred to as dye-fixing step.
  • the coating is performed by padding, if dye adsorption takes place during the coating, the dye concentration in the molten dyestuff composition contained in a vessel gradually decreases, causing appreciable change in adsorbed dye concentration between the earlier stage and later stage of the dyeing.
  • the quantitative ratio of dye component in the composition varies with time passage because adsorption rate varies among dyestuffs, occasionally causing such fatal defect in the dyed product such as change in color tone over large areas.
  • the substantial penetration of dye component into synthetic fibers during the coating of molten dyestuff composition onto the fabric, or prevention of such penetration is determined mainly by the two factors of the temperature of molten composition at the coating and the time length during which the composition on the fabric is maintained at that temperature.
  • the higher the temperature, and the longer the continuation of high temperature the greater the tendency of the dye component to penetrate into the synthetic fibers. Therefore, it is generally true that in the coating by immersion of the fabric in a bath of the molten composition, the tendency of dye penetration into the fibers is greater, compared with that in the roller coating, because in the former the composition imparted onto the fabric is maintained at the high temperature for a longer period.
  • the higher is the melting point of organic matrix the greater becomes the tendency of dye penetration into the fibers during the coating.
  • the fabric coated under the conditions as will allow no substantial penetration of the dye component in the molten dye composition into the fibers according to the subject process is either entirely undyed, or at most very slightly dyed appearing like soiling, if washed with water or a low boiling point organic solvent having solubility of the organic matrix. In this sense it will be safe to state that the fabric is substantially undyed.” Therefore, in practicing the subject process, the coating conditions causing substantially no penetration of dye component of the composition into the fibers can be easily empirically determined. That is, by coating the fabric with the molten dye composition in a preliminary test and subjecting the coated fabric to a washing treatment as above-described, the state of dye adsorption onto the fabric can be examined with naked eye, and suitable conditions can be selected from such test result.
  • the fabric thus coated with the dye composition is then heat-treated under the conditions as will allow penetration of the dyestuff component in the coating into the fibers.
  • the dyeing of fabric is accomplished.
  • the main factors for determining if the dye penetration takes place during the heating are the heating temperature, time, and atmosphere. That is, the dye penetration into the fibers is promoted, the higher is the heating temperature, and the longer is the heating time.
  • the ease of penetration also differs depending on the heating atmosphere, i.e. whether the heating is effected in air, or in a vessel of open atmosphere under steam supply, or in a air-tightly closed vessel under elevated pressure and steam supply.
  • the penetration is easier, at a moist state than dry state, and in the presence of moisture, in a closed system at elevated pressure, than in an open system.
  • the preferred heating conditions in accordance with the present invention are normally 150 to 230 for 30 seconds to 40 minutes when dry heat is used; and 140 220C. for 20 seconds to 30 minutes with open system and wet heat. With a closed system and wet heat, the heating at C. is preferably continued for 10 60 minutes.
  • the organic matrix component in the coating layer does not penetrate into the fibers but remains outside of the fibers. Therefore, after fixing the dye component into the fiber by heating, the layer remaining on the fabric, compound mainly of the organic matrix, is removed by washing with water or low boiling point organic solvent which dissolves the organic matrix.
  • the coating step and dye-fixing step of the subject process have been so far described in full details. Although not specified, it should be obvious that the heating must not cause melting of synthetic fibers constituting the fabric, or thermal deterioration to impair handling. From those considerations, the melting temperatures of the organic matrix employed must not exceed at most 80C. above the second order transition temperature of the synthetic fibers composing the fabric.
  • dyestuff composition composed of at least one dye and an organic matrix which is solid at normal temperature and has good compatibility with the dye is used in molten state. Therefore, the dye can be contained at much higher concentrations than those feasible with conventional dye bath, and the molten composition can be uniformly coated onto the fabric even when only minor amount thereof is used, preferably by roller coating system.
  • the sublimation and dissipation of dye into the atmosphere during the heating for dye-fixing as observed in pad thermosol process is substantially eliminated, and therefore deeply dyed fabrics can be obtained with the use of only minor amount of dye.
  • the uniform coating is effected without substantial dyeing of fabric and the dyeing thereof first takes place upon heating of the uniformly coated fabric in accordance with the invention, uniformly dyed fabrics with good handling is readily achieved.
  • the fabric coated with the dye composition of the invention has the unique property of seldom causing contact soil as already mentioned. Therefore, heretofore invariably required cleaning of the apparatus at each change of dyeing brand is unnecessary with the subject process. Consequently continuous dyeing of many brands with each minor quantity is facilitated for the first time.
  • the apparatus In conventional dyeing, the apparatus must be cleansed at each alteration of dyeing brand in order to eliminate the detrimental effect of contact soil which inavoidably takes place. This has been the hindrance to continuous production of many brands of each minor quantity of dyed fabrics as desired for those many years. Again, no mutual contact soil takes place between the fabrics coated with the dye composition of the invention.
  • the pre-drying normally required in pad dyeing is unnecessary. Consequently, non-uniform dyeing due to migration of dye inevitably accompanying the pre-drying step never takes place, and the limitation on the types of fabric to be dyed is completely eliminated.
  • the dye composition employed in this invention is pre-formed into a solid material, it is far easier for handling compared with conventional powdered or liquid dyestuffs, and automatic measuring, supplying, etc. are much facilitated to achieve simplification of procedures and reduction in manual labor.
  • the fabrics useful in the subject process are those composed of one or more of synthetic fibers such as of polyester, polyamide, polyacrylonitrile, polyvinyl chloride, and dyeable-polyolefine, etc.
  • synthetic fibers such as of polyester, polyamide, polyacrylonitrile, polyvinyl chloride, and dyeable-polyolefine, etc.
  • Non-ionic dyes intended in the invention include disperse dyes, vat dyes, developed dyes for synthetic fibers, oil-soluble dyes, and non-ionic fluorescent dyes. Also anionic dyes and cationic dyes are those which form, respectively, free dye anions and dye cations in water.
  • Anionic dyes include, for example, acid dyes, acidic mordant dyes, metal-containing aciddyes, etc., and as cationic dyes, for example, basic dyes may be named.
  • the organic matrix employed in the subject process is at least an aliphatic polyhydric compound or derivative thereof, which is solid at normal temperature and melts at temperatures not higher than at most 80C. above the second order transition temperature of the synthetic fibers employed.
  • the matrix also is soluble in water or low boiling point organic solvents such as aliphatic lower halogenated hydrocarbons, e.g., carbon tetrachloride, perchloroethylene, and
  • trichloroethylene lower aliphatic saturated alcohols of no more than 3 carbons, e.g., methanol, ethanol, and propanol; and acetone; and is at least partially compatible with the employed dye in molten state.
  • Specific examples of such include the following: polyethylene glycol of l,000l0,000 in molecular weight; monoor di-ethers derived from polyethylene glycol and alcohols such as methanol, ethanol, propanol, butanol, octanol, lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, benzyl alcohol, etc., or phenols such as t-butyl phenol, octyl phenol, nonyl phenol, lauryl phenol, octyl-B-naphthol, etc; thioethers derived from polyethylene glycol and mercaptans such as lauryl mercaptan; esters derived from polyethylene
  • Tetronic Tetronic
  • vinyl monomers such as methyl acrylate, methyl methacrylate, and vinyl acetate
  • aliphatic polyhydric alcohols such as sorbitol, arabitol, 2-methyl- 2-propyl-l,S-propanediol, etc.
  • esters of aliphatic polyhydric alcohols such as ethylene glycol monostearate, ethylene glycol distearate, diethylene glycon monopalmitate, triglycerol monostearate, hexaglycerol monostearate, sorbitan monostearate, sorbitan distearate, sorbitan tristearate, glycerine monostearate, glycerine distearate, pentaerythrito
  • polyethylene glycol is the most preferred.
  • the dye composition coated on the fabric is readily solidified to form a coating layer free of contact soil
  • the melting temperature of organic matrix and the ambient temperature should not be too close, because otherwise the solidifying rate of the coating after the application will be reduced. Again the melting temperature should not be too high, because otherwise the melting will be difficult and during the coating operation the tendency of the dye to penetrate into the fabers will be promoted.
  • Preferred range for the melting temperature of organic matrix is 50 C.
  • the composition can contain the dye at a concentration of as high as 30 percent to the total weight of the composition, with high stability. Concentrations higher than that should be avoided, because such will impair the dispersion stability and render the uniform application of the composition difficult.
  • the dye composition of the invention can be formed by homogeneously mixing the dye with organic matrix. In that case, it is also permissible to add other components which. assist uniform deep color dyeing, if
  • antioxidant may be named.
  • decoloration of dye may occur during 1 ⁇ , the heating for dye-fixing, and the decoloration is "presumably caused by oxidation with air.
  • diethanolamine dimethylformamide, dimethylsulfoamide, dimethylacetamide
  • sorbitan monooleate polyoxyethylene sorbitan monolaurate, polyoxyethylene lauryl ether, etc.
  • assistants of dye-fixing which promote fixing of dye such as paraphenyl phenol, orthophenyl phenol, methyl naphthalene, etc. which are the dye-fixing promotor normally utilized for aqueous dyeing of polyester, may be named. Those can be added in minor quantities when necessary.
  • anionic dyes When anionic dyes are used, occasionally the uniformity in application and dyeing is improved when water or an organic acid such as formic or acetic acid is added in a minor quantity (at most 5 wt.% or below) to the dye composition. Obviously, the quantities of those additives should be within the range as will not impair the property of the organic matrix that it is solid at room temperature.
  • the fabric which finished the dye-fixing step may be passed through an acidic aqueous solution. whereupon the dyed color on the fabric may be deepened. This step itself is known as acid shock among the dyeing industry.
  • roller coating is far more desirable for the full exhibition of unique features of subject process.
  • roller coating is convenient for preventing penetration of the dye into the fibers at the time of coating, as already mentioned, and another is that with roller coating, the dye composition containing the dye at a high concentration can be daubed onto the fabric in a minor quantity and with uniformity, consequently improving effective utilization of the dye.
  • the suitable quantity of dye composition ranges 2 50 percent to the weight of fabric.
  • a liquid liquid compatible with the organic matrix onto the fabric assists uniform daubing.
  • a liquid liquid for example, water, perchloroethylene, trichloroethylene, or methanol, acetone, and mixtures thereof, may be named.
  • coated fabric is then subjected to a heat-treatment for fixing the dye.
  • the coated fabric may be forcedly cooled to accelerate solidification of the coating layer, or pre-heated to facilitate the uniform application of dye onto the fabric, in advance of the last heat-treatment.
  • the heated fabric on which the dye is thus fixed is finally washed, to be removed of the coating.
  • the most preferred cleaning agent is water.
  • the washing is often effectively performed by adding an alkaline substance such as sodium carbonate, caustic soda, sodium bicarbonate; reducing agent such as sodium hydrosulfite; and dispersing agent, etc. to water.
  • the aqueous washing may be replaced by washing treatment with low boiling point organic solvent such as perchloroethylene, trichloroethylene, methanol, acetone, etc.
  • the numeral value in the parentheses of the indication such as, for example, polyoxyethylene (20) stearate means the average addition mol number of ethylene oxide.
  • the apparatus used for the coating comprisedtwo coating units disposed in vertical relation and other auxiliary devices such as guide bars to continuously lead the fabric to the coating units, and an expander to outstretch the fabric in the direction of its width to assist smooth supply of the fabric to the rollers.
  • one coating unit consisted of a gravure roll, and a back roller incidental thereto, a knife coater, and a coating bath. The two coating units were so disposed that each one could coat the respective single surface of the fabric fed thereto.
  • the gravure rolls and coating baths were maintained at 70C. by circulation of warm water therethrough.
  • the above melt composition was poured into the coating baths, and continuously coated onto the two sides of woven fabric of polyethylene terephthalate filaments which was fed at a rate of 3 m/min, immediately followed by batch up.
  • the quantity of the coating was 20 to the weight of the fabric.
  • coated fabric was subjected to dye-fixing treatment of various conditions as shown in Table l, to
  • Example II the fabrics dyed in various shades of pink were obtained.
  • the L-values of the fabrics corresponding to the deepness of dyed color were measured with the results shown in Table 2.
  • the same fabric as employed above was dyed under the following conditions: the dye used in Example l was dispersed in water, and to which sodium alginate was added at a concentration of 1 g/l to make an aqueousdye solution. In that procedure, the dye concentration in the solution was so adjusted that the dye pick-up (percent based on the weight of fabric) of the fabric after being immersed in the solution and squeezed with mangle at a fixed squeez ratio should give the various values as specified in Table 2.
  • the dye pick-up (percent) based on the weight of fabric will be referred to as owf.
  • the fabrics were immersed in the so prepared aqueous solutions, squeezed of excessive liquid, air-dried, and fixed of the dye under the identical conditions with those employed in Example 2.
  • the L-values of the dyed fabric obtained of the-control runs are also shown in Table 2.
  • the fabric had an L-value of 73.0, showing the whiteness close to that of the untreated starting fabric. This indicates that substantially no dye adsorption took place at the time of coating. Entirely no contact soil to the back roller, guide roller, etc. during the continuous coating onto both sides of the fabric was observed, and
  • EXAMPLE 2 Under the dyeing conditions of Example 1, the quantity of dye (the same dye as employed in Example 1) applied to the fabric (owf was varied in each run as indicated in Table 2. below, and the mercaptobenzimidazole was replaced by 1 percent to the total weight of the composition of phenothiazine. Also the treated fabric was changed to that woven of highly twisted polyethylene terephthalate filaments, and the conditions for fixing the dye were changed as shown in Table 2. All other conditions being identical with those Table 2 Temp. X Time Atmosphere of owf Dye-fixing (C.) (min) l 2 4 Subject 44.8 39.9 37.7
  • EXAMPLE 3 formula, k V Q and 8 parts of mercaptobenzimidazole were added, and milled for 2 hours in a ball-mill of 60C. Then at the temperature and for the time shown in Table 3a, fabrics woven of polyethylene terephthalate filaments were immersed in the composition, withdrawn, and immediately thrown into cold water to be cooled. Then the fabrics were washed first with 50C. warm water, and then with an aqueous solution containing each 2 g/l of caustic soda, sodium hydrosulfite, and polyoxyethylene (20) stearylamine, at 80C. for 20 minutes. After the subsequent drying, the coated fabrics were measured of their lightness (L-values) as a norm for evaluating the deepness of dyed color, with the results as shown in Table 3a.
  • L-values lightness
  • the color tone of the treated polyethylene terephthalate fabrics of (a) was violet, but under the conditions giving L-values not less than 55, for example, 60 seconds or less at the treating temperature of 140C., and not longer than 1 second at 160C., no dyeing or very slight coloring appearing like soiling took place. Thus it could be said that no substantial dyeing took place.
  • the nylon-6 fabrics obtained in (b) appeared blue, but under the conditions giving L-values of not less than 55, e.g., not longer than 10 seconds at the treating temperature of 140C., and not longer than 1 second at 160C, no substantial dyeing took place ining bath and gravure roll were maintained at 70C., 90C., llC., l40C., and l60C., in each run, by circulation of hot oil.
  • the same dye composition as employed in (a) was applied also to the same fabric as of (a) by gravure roll, at a feed rate of 0.6 m/min. The contact time of the fabric with the heated gravure roll was approximately 0.5 second.
  • the coated fabric was washed similarly to (a), and dried. All the products showed L-values of not less than 55, and were substantially undyed.
  • Example 4 The coating of Example 1 was repeated except that a refined disperse dye of the structural formula,
  • Example 1 was repeated except the following changes: as the dye, a refined disperse dye of the structural formula,
  • EXAMPLE 6 A knit good was dyed under the conditions given in Example 1, except the following changes: that as the starting material, thick knit good made of textured yarns of polyethylene terephthalate filaments was used; that gravure roll of greater coating capacity was employed to apply 20 percent to the weight of the knit good of the dye composition; that the heating for dyefixing was effected by dry heat at 160C. for 20 minutes; and that the washing after the dye-fixing was effected by immersion in perchloroethylene. Thus a knit good uniformly dyed pink throughout the inside of fabric and which had a good handling was obtained.
  • the L-value of the product was 44.2. When the knit good after the coating but before the dye-fixing treatment was washed with hot acetone, the coating layer was substantially completely removed, and the remaining good had an L-value of 73.1. incidentally, the untreated starting material had an L-value of 74.8.
  • the surface thereof was dyed deep pink, and inside of the fibers was dyed in medium to light shade of the pink. Therefore the product had an appearance much inferior to that of the product obtained through the process in accordance with the subject invention. Furthermore, because in the control the coating baths were maintained at high temperatures, the dye in the coating baths was thermally decomposed as the time passed, and consequently occurrence of spots such as specks was observed on the dyed goods. Again the handling of the product of control was flat and coarse, and it was confirmed that the pleasant handling of the starting knit good of textured yarn was remarkably impaired.
  • the padding bath was heated to 200C., and the coating was effected under the condition that the fabric was immersed therein for 30 seconds.
  • the dye component of the molten composition penetrated into the fibers during the coating, and the fabric leaving the padding bath was dyed orange even after the washing.
  • the color tone on the product showed changes with time passage, i.e., at earlier stage of the dyeing the color tone was more reddish and the reddish shade was reduced as time passed. This phenomenon was caused by the difference in dyeing rate of the two dyes employed.
  • the padding bath was maintained at thigh temperatures for a prolonged period in the control run, decomposition of the dyes took place, causing spot formation such as specks.
  • the control product had coarse handling, indicating deterioration of the handling of textured yarn fabric.
  • EXAMPLE 8 Using the fabrics composed of various filaments as shown in Table 6, dyeing was experimented under the conditions given in Example 1, with the following changes: that the dyes indicated in Table 6 were used for dyeing each of the fabrics; that the use of mercaptobenzimidazole was omitted; that the dye-fixing was effected under the heating conditions specified in Table 6, and that the dyed fabrics were washed with 60C. warm water containing 1 g/l of non-ionic surfactant (polyoxyethylene (l5) lauryl ether). The products were uniformly dyed in the shades varying from light to deep. The L-values of the products are also shown in Table 6.
  • EXAMPLE 10 To 320 parts of polyoxyethylene (5) stearic acid amide melted at C., parts of the acid dye employed in Example 9 was added, and dissolved and dispersed in the former by 4 hours milling in a ball mill heated at 70C. The composition was coated onto a fabric woven of nylon-6 filaments similarly to Example 1. The coated fabric was then treated with steam at 190C. for l minute in open system, and thereafter subjected to an acid treatment at 98C. for 1 minute, in an aqueous solution containing 10 g/l of percent formic acid. The fabric was further washed in an aqueous bath containing 2 g/l of sodium carbonate and 2 g/l of nonionic surfactant, at 60C. for 20 minutes.
  • Example 1 I NHCtHn and parts of water were added,.and milled similarly to Example 1.
  • the dye composition retained the property of being solid under normal temperature, under the addition of water, and the homogeneity of the melt was improved.
  • the composition was coated at 70C. onto one surface only of tufted carpet made of textured yarns of nylon-6 filaments, using one gravure coating unit only of the assembly used in Example 1.
  • the gravure roll employed was that having a greater coating capacity.
  • the condition of carpet after the coating was such that the solidified dye composition adhered on the top of pile of the carpet, showing no penetration down to the root of pile.
  • the coated carpet was allowed to stand under dry heat of 100C. for 10 minutes by way of pre-heating. whereupon the coating layer was formed uniformly throughout the height of pile.
  • EXAMPLE 14 Referring to Example 1, the dye composition as formed and melted was poured into a cylindrical iron container, and allowed to cool off to room temperature. Thus a solid, cylindrical dye composition of.5 cm in diameter and l5 cm in length was obtained. Also for making a similar solid, the refined disperse dye used in Example 5 was finely rushed, thoroughly mixed with polyethylene glycol flakes of 4,000 in average molecular weight, in a tumbler at room temperature, and put in the above iron container. As the pressure was reduced from the bottom, the mixture was compression-molded under a pressure of kg/cm exerted by a piston from the top. Thus another solid composition of the similar form was prepared. Separately the melt of dye composition obtained in Example 1 was formed into flakes with flaking machine, and further formed into grains of 3 mm in diameter with a granulating machine.
  • the dye composition employed in the subject process can be made into shaped products of various forms by various methods, because it is solid at normal temperature.
  • a process for dyeing fabrics of synthetic fibers which consists essentially of preparing a dye composition composed of at least one dyestuff selected from the group consisting of non ionic, anionic and cationic dyes having affinity for the synthetic fibers, and an organic matrix comprising at least one member selected from the group consisting of polyethylene glycols of molecular weight of l,000-10,000, polyethylene glycol derivatives selected from the group consisting of ethers and thioethers of polyethylene glycol and adducts of ethylene oxide with aliphatic carboxylic acid amides, adducts of ethylene oxide with aliphatic amines, adducts of ethylene oxide with polypropylene glycol, and esters of a polyhydric alcohol selected from ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, glycerine, pentaerythritol and sorbitan, which are solid at normal temperature and melt at temperatures .not higher than 80C.
  • the fibers are soluble in water or a'low boiling point organic solvent, and are at least partially compatible with the dyestuff in the molten state; heating said dye composition to melt the same; roller coating the molten dye composition onto the fabric under conditions that allow no substantial penetration of the dyestuff into the synthetic fibers;

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US00076599A 1969-09-29 1970-09-29 Dyeing synthetics using roller coated molten dye compositions Expired - Lifetime US3716330A (en)

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JP7757769 1969-09-29
JP44101418A JPS4841793B1 (enrdf_load_stackoverflow) 1969-12-17 1969-12-17
JP44103137A JPS4817229B1 (enrdf_load_stackoverflow) 1969-12-22 1969-12-22
JP3409870 1970-04-21
JP3454670 1970-04-22
JP3515870 1970-04-24

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US (1) US3716330A (enrdf_load_stackoverflow)
CA (1) CA919861A (enrdf_load_stackoverflow)
CH (2) CH1435970A4 (enrdf_load_stackoverflow)
FR (1) FR2063059B1 (enrdf_load_stackoverflow)
GB (1) GB1326259A (enrdf_load_stackoverflow)

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US3966400A (en) * 1973-08-25 1976-06-29 Hoechst Aktiengesellschaft Process and device for the irregular dyeing of textiles
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US4340387A (en) * 1971-11-09 1982-07-20 Ciba-Geigy Corporation Process for the dyeing of fibre material
US5741590A (en) * 1993-09-28 1998-04-21 E. I. Du Pont De Nemours And Company Iridescent fabrics
US20050235435A1 (en) * 2002-06-10 2005-10-27 Franz Gruner Method of dyeing or printing synthetic polyamide fibre materials using reactive dyes
US20060276367A1 (en) * 2005-06-07 2006-12-07 Shah Ketan N Method of neutralizing a stain on a surface
US20070277849A1 (en) * 2006-06-06 2007-12-06 Shah Ketan N Method of neutralizing a stain on a surface
US20080282642A1 (en) * 2005-06-07 2008-11-20 Shah Ketan N Method of affixing a design to a surface
US20090019647A1 (en) * 2005-06-07 2009-01-22 Frazee Glenn R Composition for application to a surface
US20090271933A1 (en) * 2005-06-07 2009-11-05 S.C. Johnson & Son, Inc. Composition For Application To A Surface
US20100154146A1 (en) * 2008-07-02 2010-06-24 S.C. Johnson & Son, Inc. Carpet decor and setting solution compositions
US20110097506A1 (en) * 2005-06-07 2011-04-28 Shah Ketan N Devices for applying a colorant to a surface
US8061269B2 (en) 2008-05-14 2011-11-22 S.C. Johnson & Son, Inc. Multilayer stencils for applying a design to a surface
US8846154B2 (en) 2005-06-07 2014-09-30 S.C. Johnson & Son, Inc. Carpet décor and setting solution compositions
US20210277597A1 (en) * 2020-03-06 2021-09-09 Chaei Hsin Enterprise Co., Ltd. Method for dyeing and removing colored impurities

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US1968856A (en) * 1934-08-07 Treatment of textile materials
US2069210A (en) * 1929-11-07 1937-02-02 Nat Aniline & Chem Co Inc Flavanthrone dyestuff and printing paste
US2901312A (en) * 1955-05-07 1959-08-25 British Rayon Res Ass Process utilizing fluidized beds in the dyeing of fabrics, yarns and the like
US2901311A (en) * 1955-03-04 1959-08-25 Hoechst Ag Process for the printing of fibrous textile material made of polyester fibres
US2928712A (en) * 1960-03-15 Molten urea dyeing process
GB1071074A (en) * 1963-06-19 1967-06-07 Sandoz Ag Dyeing and printing process
US3531238A (en) * 1966-03-23 1970-09-29 Bayer Ag Process for the continuous dyeing or printing with basic dyestuffs of textile materials consisting of polyacrylonitrile

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DE1138735B (de) * 1958-08-19 1962-10-31 Hoechst Ag Bedrucken oder Klotzfaerben von Textilmaterialien
FR1256192A (fr) * 1960-03-24 1961-03-17 Hoechst Ag Procédé de préparation de pâtes à rouleaux d'impression
NL272998A (enrdf_load_stackoverflow) * 1960-12-28

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US1968856A (en) * 1934-08-07 Treatment of textile materials
US2928712A (en) * 1960-03-15 Molten urea dyeing process
US2069210A (en) * 1929-11-07 1937-02-02 Nat Aniline & Chem Co Inc Flavanthrone dyestuff and printing paste
US2901311A (en) * 1955-03-04 1959-08-25 Hoechst Ag Process for the printing of fibrous textile material made of polyester fibres
US2901312A (en) * 1955-05-07 1959-08-25 British Rayon Res Ass Process utilizing fluidized beds in the dyeing of fabrics, yarns and the like
GB1071074A (en) * 1963-06-19 1967-06-07 Sandoz Ag Dyeing and printing process
US3531238A (en) * 1966-03-23 1970-09-29 Bayer Ag Process for the continuous dyeing or printing with basic dyestuffs of textile materials consisting of polyacrylonitrile

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US4340387A (en) * 1971-11-09 1982-07-20 Ciba-Geigy Corporation Process for the dyeing of fibre material
US3966400A (en) * 1973-08-25 1976-06-29 Hoechst Aktiengesellschaft Process and device for the irregular dyeing of textiles
US5741590A (en) * 1993-09-28 1998-04-21 E. I. Du Pont De Nemours And Company Iridescent fabrics
US7396370B2 (en) * 2002-06-10 2008-07-08 Huntsman International Llc Method of dyeing or printing synthetic polyamide fibre materials using reactive dyes
US20050235435A1 (en) * 2002-06-10 2005-10-27 Franz Gruner Method of dyeing or printing synthetic polyamide fibre materials using reactive dyes
US20090271933A1 (en) * 2005-06-07 2009-11-05 S.C. Johnson & Son, Inc. Composition For Application To A Surface
US20100252194A1 (en) * 2005-06-07 2010-10-07 S.C. Johnson & Son, Inc. Composition for application to a surface
US20070089621A1 (en) * 2005-06-07 2007-04-26 Kimball James F Design devices for applying a design to a surface
US20070277848A1 (en) * 2005-06-07 2007-12-06 Shah Ketan N Method of neutralizing a stain on a surface
US8846154B2 (en) 2005-06-07 2014-09-30 S.C. Johnson & Son, Inc. Carpet décor and setting solution compositions
US20060288499A1 (en) * 2005-06-07 2006-12-28 Kimball James F Composition for application to a surface
US7423002B2 (en) 2005-06-07 2008-09-09 S.C. Johnson & Son, Inc. Method of neutralizing a stain on a surface
US20080282642A1 (en) * 2005-06-07 2008-11-20 Shah Ketan N Method of affixing a design to a surface
US20090019647A1 (en) * 2005-06-07 2009-01-22 Frazee Glenn R Composition for application to a surface
US7556841B2 (en) 2005-06-07 2009-07-07 S. C. Johnson & Son, Inc. Method of applying a design to a surface
US20060276367A1 (en) * 2005-06-07 2006-12-07 Shah Ketan N Method of neutralizing a stain on a surface
US7727289B2 (en) 2005-06-07 2010-06-01 S.C. Johnson & Son, Inc. Composition for application to a surface
US8747487B2 (en) 2005-06-07 2014-06-10 S.C. Johnson & Son, Inc. Composition for application to a surface
US7763083B2 (en) 2005-06-07 2010-07-27 S.C. Johnson & Son, Inc. Composition for application to a surface
US7776108B2 (en) 2005-06-07 2010-08-17 S.C. Johnson & Son, Inc. Composition for application to a surface
US20070014921A1 (en) * 2005-06-07 2007-01-18 Kimball James F Method of applying a design to a surface
US20100256263A1 (en) * 2005-06-07 2010-10-07 S.C. Johnson & Son, Inc. Composition for application to a surface
US20110038826A1 (en) * 2005-06-07 2011-02-17 S.C. Johnson & Son, Inc. Composition for application to a surface
US20110097506A1 (en) * 2005-06-07 2011-04-28 Shah Ketan N Devices for applying a colorant to a surface
US7947640B2 (en) 2005-06-07 2011-05-24 S.C. Johnson & Son, Inc. Method of neutralizing a stain on a surface
US8048517B2 (en) 2005-06-07 2011-11-01 S.C. Johnson & Son, Inc. Composition for application to a surface
US8734533B2 (en) 2005-06-07 2014-05-27 S.C. Johnson & Son, Inc. Composition for application to a surface
US8557758B2 (en) 2005-06-07 2013-10-15 S.C. Johnson & Son, Inc. Devices for applying a colorant to a surface
US20070277849A1 (en) * 2006-06-06 2007-12-06 Shah Ketan N Method of neutralizing a stain on a surface
US8499689B2 (en) 2008-05-14 2013-08-06 S. C. Johnson & Son, Inc. Kit including multilayer stencil for applying a design to a surface
US8061269B2 (en) 2008-05-14 2011-11-22 S.C. Johnson & Son, Inc. Multilayer stencils for applying a design to a surface
US20100154146A1 (en) * 2008-07-02 2010-06-24 S.C. Johnson & Son, Inc. Carpet decor and setting solution compositions
US20210277597A1 (en) * 2020-03-06 2021-09-09 Chaei Hsin Enterprise Co., Ltd. Method for dyeing and removing colored impurities
US11473239B2 (en) * 2020-03-06 2022-10-18 Chaei Hsin Enterprise Co., Ltd. Method for dyeing and removing colored impurities

Also Published As

Publication number Publication date
FR2063059A1 (enrdf_load_stackoverflow) 1971-07-02
CA919861A (en) 1973-01-30
GB1326259A (en) 1973-08-08
CH545136A (de) 1973-05-30
FR2063059B1 (enrdf_load_stackoverflow) 1973-11-23
DE2047872B2 (de) 1976-08-19
DE2047872A1 (de) 1971-05-19
CH1435970A4 (enrdf_load_stackoverflow) 1973-05-30

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