US3927973A - Method for coloring fibrous material composed of phenolic resins - Google Patents

Method for coloring fibrous material composed of phenolic resins Download PDF

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US3927973A
US3927973A US351884A US35188473A US3927973A US 3927973 A US3927973 A US 3927973A US 351884 A US351884 A US 351884A US 35188473 A US35188473 A US 35188473A US 3927973 A US3927973 A US 3927973A
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water
dye
fibers
fibrous structures
phenolic
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Syunya Ida
Norio Endo
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Kanebo Ltd
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Kanebo 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
    • D06P1/90—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
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65168—Sulfur-containing compounds
    • D06P1/65193—Compounds containing sulfite or sulfone groups
    • 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
    • D06P1/922—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 hydrocarbons
    • 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
    • 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
    • D06P3/002—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using basic 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
    • D06P3/003—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using vat or sulfur 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
    • D06P3/004—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using dispersed 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
    • D06P3/007—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated preparing dyes in situ
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
    • D06P5/2066—Thermic treatments of textile materials
    • D06P5/2077—Thermic treatments of textile materials after 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • This invention relates to a method for coloring fibers or fibrous structures prepared from phenolic resins. More specifically, this invention relates to a method for uniformly coloring phenolic fibers or their structures in deep fast colors.
  • phenolic fibers As is well known, fibers composed of phenolic resins (to be referred to simply as phenolic fibers) have poor affinity with dyes and extremely low dyeability for a variety of reasons such as their compact fibrous structure, the lack of dye-affinitive groups, or their high negative surface potential. It is very difficult therefore to color phenolic fibers uniformly in deep fast colors.
  • Fibers having a compact fibrous structure and no dye-affinitive groups such as polyester fibers or polypropylene fibers, are colored at a temperature as high as 1 to 130C. using dyes having a small molecular volume, or using a dye liquor containing a carrier material (swelling agent) such as ortho-phenylphenol, chlorobenzene, a salicylic acid ester or a benzoic acid ester in order to give satisfactory dyeings.
  • a carrier material such as ortho-phenylphenol, chlorobenzene, a salicylic acid ester or a benzoic acid ester
  • the phenolic fibers can scarcely be colored substantially even at 1 10 to 130C. using a carrier material such as those mentioned above, and it has been difficult to provide colored phenolic fibers which are useful for practical applications.
  • Certain kinds of such difficulty-dyeable synthetic fibers have previously been colored, for example, by a method wherein a substance having dye-affinitive groups, such as a polymer having a free amino group, is incorporated in a spinning solution, and fibers obtained by spinning this solution are dyed by conventional methods, a method wherein a pigment is incorporated in a spinning solution beforehand, and the spinning solution is spun to form colored fibers, or a method wherein a pigment is fixed to the surface of the fibers by a binder to color the fibers are also known.
  • a substance having dye-affinitive groups such as a polymer having a free amino group
  • wool, cellulosic fibers or polyamide synthetic fibers are dyed by a method wherein a dye liquor is uniformly applied to the fibers and then the fibers are treated with saturated or superheated steam, a method wherein the fibers are likewise treated with steam containing an acid, or a method wherein the fibers are treated with a vapor of water containing an aromatic or alicyclic compound such as phenol, ophenylphenol, ochloropheno1, B-naphthol, m-cresol, cyclohexanol, aniline, N-methylaniline, N-dimethylaniline, N-ethylaniline, or N-diethylaniline.
  • an aromatic or alicyclic compound such as phenol, ophenylphenol, ochloropheno1, B-naphthol, m-cresol, cyclohexanol, aniline, N-methylaniline, N-dimethylaniline, N-ethylani
  • a primary object of this invention is to provide an improved method for coloring fibers composed of phenolic resins and their structures (to be referred to generically as phenolic fibrous materials).
  • a secondary object of this invention is to provide a method for uniformly coloring phenolic fibrous material in deep fast colors.
  • Another object of this invention is to provide a method for coloring phenolic fibrous materials that can be utilized industrially.
  • a method for coloring fibers or fibrous structures composed of phenolic resins which comprises applying a dye liquor to the fibers or fibrous structures, and then contacting them with a vapor of at least one compound selected from the group consisting of N,N-dialkyl acetylamides, dialkyl sulfoxides, ketones, alcohols, aliphatic amines and dioxane, or a mixed vapor of such compound and water.
  • fibers composed of phenolic resins denotes uncured fibers formed by melt spinning, or wet spinning, etc. of a prepolymer of the novolak or resol type prepared from a phenol (e.g., phenol, cresol, xylenol, ethylphenol, phenylphenol, amylphenol, bisphenol A, or resorcinol) and an aidehyde (formaldehyde, acetaldehyde, para-formaldehyde, hexamethylene tetramine, furfural, glutaraldehyde, or glyoxal), or the cured products thereof obtained by curing such uncured fibers with a curing agent such as an aldehyde in the presence of an alkaline or acidic catalyst.
  • a curing agent such as an aldehyde in the presence of an alkaline or acidic catalyst.
  • the phenolic fibers can be produced by any known method, we will not describe it here.
  • the phenolic fibers to be dyed by the method of this invention may be composed of a phenolic resin alone, or a blend of a major proportion of the phenolic resin with a minor proportion (generally, 1-40% by weight) of another fiber-forming polymer.
  • a minor proportion generally, 1-40% by weight
  • the amount of the fiber-forming polymer should be as small as possible, preferably up to 30 by weight, when the blend is used, or the phenolic fibers should be composed solely of the phenolic resin.
  • the fiber-forming polymer that can be used include polyamide resins such as nylon 6, nylon 11, nylon 12, nylon 66, nylon 610, nylon 61 1, nylon 612, and blends of two or more of these with each other; polyester resins such as polyethylene terephthalate, polyesters derived from the same constituent elements as polyethylene terephthalate with part of ethylene glycol replaced by other known glycols, polyesters derived from the same constituent elements as polyethylene terephthalate with the terephthalic acid replaced by orthoor metaphthalic acids, other known aliphatic dicarboxylic acids or blends of two or more of these with each other; polyester ethers such as polyethylene hydroxybenzoate, and polyolefin resins such as polyethylene, polypropylene, and ethylene-propylene copolymer, or blends of two or more of these with each other.
  • polyester resins such as polyethylene terephthalate, polyesters derived from the same constituent elements as polyethylene terephthalate with part of ethylene glycol replaced by
  • fibrous structures composed of phenolic resins used in the present specification and claims denotes a fibrous product such as a web, yarn, woven fabric, knitted fabric, non-woven fabric, carpet, batt or laminated cloth composed of the phenolic fibers alone or a composite of the phenolic fibers and other natural, semisynthetic or synthetic fibers.
  • the coloring of these phenolic fibrous materials can be performed by the known methods usually employed to dye usual fibrous materials.
  • coloring denotes coloring in a broad sense, and therefore, includes (a) the dip dyeing whereby a fibrous material is dyed as dipped in a dye solution, (b) the pad dyeing whereby a dye solution is padded on a fibrous material, and then the fibrous material is heated, and (c) the printing whereby a printing paste is applied to a fibrous material, and the material is then heated to color the printed portions.
  • the dye liquor used in accordance with the process of this invention may be in the form of a solution containing a dye (especially in the case of dip dyeing) or a paste containing a dye (pad dyeing and printing).
  • the application of a dye liquor to the phenolic fibrous materials by the pad dyeing or printing process can be effected, for example, by padding an aqueous dye solution containing about to 50 by weight, based on the material to be dyed, of a dye and if desired a small amount of a viscosity regulator, or by printing a paste-like dye liquor containing about 5 to 50 by weight, based on the weight of the fibrous material to be dyed, ofa dye, about 0.l l0 by weight, based on the total weight of the liquor, of a size, and water.
  • the fibrous material is treated with steam either as such or after drying.
  • the dyes that are usually used in the dyeing of natural, semi-synthetic or synthetic fibrous materials can be used in accordance with the method of this invention for dyeing the phenolic fibrous materials.
  • vat dyes azoic dyes, cationic dyes, disperse dyes, metal-containing dyes, acid dyes, direct dyes, reactive dyes, and chrome dyes.
  • the azoic dyes, cationic dyes, disperse dyes and vat dyes have good dyeability with regard to the phenolic fibers, and can be conveniently used in the present inventioh.
  • Typical examples of these dyes are as follows:
  • Cationic dyes Cationic dyes of the azo, diphenylmethane, triphenylmethane, xanthene, acridine, quinoline, methine, thiazole, azine, thiazine, and oxazine types. Specific examples are Sumiacryl Orange G (C.l. Basic Orange 2!), Sumiacryl Brilliant Red BB, Sumiacryl Red 68 (C.l. Basic Violet 7), Sumiacryl Brown (C.l. Basic Orange 30), Sumiacryl Blue 66 (C.l. Basic Blue 22), Diacryl Brilliant Pink R (C.l. Basic Red Diacryl Blue 2RL (C.l. Basic Blue 59), Diacryl Green 2BL' 4 (C.l. Basic Green 77), and Diacryl Violet BRL (C.l.
  • Disperse dyes Disperse dyes of the azo, anthraquinone, nitro, aminoquinone and methine types. Specific examples are Dianix Fast Orange R-FS, Dianix Fast Red B-FS, Dianix Red Brown R-FS, Kayalon Polyester Violet BNF (C.l. Disperse Violet 30), Kayalon Polyester Pink BSF (C.l. Disperse Red 55), Sumikalon Red FB (C.l. Disperse Red 60), Sumikalon Blue R (C.l. Disperse Blue 71 and Sumikalon Dark Blue RB (C.l. Disperse Blue 55).
  • Vat dyes Vat dyes of the anthraquinone and indigozoyl types. Specific examples are Caledon Orange Brown 26 (C.l. Vat Orange 14), Caledon Red B (C.l. Vat Red 41), Mikethrene Violet FFBN (C.l. Vat Violet l3) Nihonthrene Dark Blue BO (C.l. Vat Blue 20), Caledon Olive OMW (C.l. Vat Green 26), and lndanthrene Black Brown RV (C.l. Vat Brown 56).
  • Examples of the size to be incorporated in the dye liquor include starch, sodium alginate, tragacanth gum, gum arabic, gelatin, dextrin, British gum, carboxymethylcellulose, methyl cellulose, hydroxyethyl cellulose, carboxymethyl starch, polyvinyl alcohol, poly(- sodium acrylate), kerosene, and 1,l ,l-trichloroethane. Of these, kerosene and Lt .l-trichloroethane are especially suited for preparing an emulsion paste. These sizes can also be used as a viscosity regulator of the dye liquor. They, however, should not be dissolved at the time of steam treatment to destroy the printed pattern or should not be coagulated to make it difficult to remove them.
  • the phenolic fibrous material to which the dye liquor has been applied by any of the above-mentioned dyeing methods is treated with steam by the method of this invention either as such or after drying. Accordingly, the method of this invention has the advantage of being applicable also to the pad roll process.
  • the drying of the fibrous material before steam treatment is usually performed at a temperature of to l20C., preferably to C, although it differs according to the dyeing method used.
  • the steaming treatment in accordance with this invention can be achieved by contacting the material, to which a dye liquor has been applied, with a vapor of at least one compound selected from the group consisting of N,N-dialkyl acrylamides, dialkyl sulfoxides, ketones, alcohols, aliphatic amines and dioxane or a mixed vapor of this compound with water.
  • the two alkyl moieties in the N,N-dialkyl acylarnides and the dialkyl sulfoxides are the same or different, and suitably a lower alkyl group containing 1 to 5 carbon atoms, such as a methyl or ethyl group.
  • the acyl is a residue of an acid, for example, a formyl, acetyl or propionyl group.
  • the preferred N,N-dialkyl acylamides are N,N-dimethyl formamide, N,N-diethyl formamide, N,N-dimethyl acetamide, N,N-diethyl acetamide, and methylethyl N,N-acetamide.
  • Dimethyl sulfoxide and diethyl sulfoxide are the preferred dialkyl sulfoxides.
  • ketones that can be used in this invention are expressed by the formula wherein R and R, may be the same or different, and represent an alkyl group, preferably a lower alkyl group having 1 to carbon atoms, or a phenyl group, or R and R, together may form an alkylene group, especially a hexylene group.
  • Examples of the ketones suitably used in this invention are acetone, diethyl ketone, methyl ethyl ketone, acetophenone, and cyclohexanone.
  • TheK alcigli lols are expressed by the formula wherein R, is an alkyl group, preferably a lower alkyl group having up to 4 carbon atoms, an aralkyl group such as a benzyl group, or a heterocyclic group such as a furfuryl or tetrahydrofurfuryl group.
  • R is an alkyl group, preferably a lower alkyl group having up to 4 carbon atoms, an aralkyl group such as a benzyl group, or a heterocyclic group such as a furfuryl or tetrahydrofurfuryl group.
  • Suitable examples of the alcohols are methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec.-butyl alcohol, tert.-butyl alcohol, benzyl alcohol, furfuryl alcohol and tetrahydrofurfuryl alcohol.
  • the aliphatic amines used in accordance with the method of this invention may be primary, secondary and tertiary, or either monoamines or diamines. Furthermore, the aliphatic groups may be replaced by hydroxyl groups. Preferably, the aliphatic groups contain not more than 5 carbon atoms.
  • aliphatic amines that can be suitably used are methyl amine, dimethyl amine, trimethyl amine, monoethyl amine, diethyl amine, triethyl amine, n-propyl amine, isopropyl amibe, n-butyl amine, ethylene diamine, isobutyl amine, sec.-butyl amine, tertbutylamine, monoethanol amine, and isopropanol amine.
  • n-butyl alcohol, iso-butyl alcoho], dioxane, acetone, and N,N-dimethyl formamide are especially suitable.
  • these compounds may be used alone or in admixture of two or more, or further as admixture with water.
  • the compounds are contained preferably in a total amount of at least 5 by weight based on the mixed vapor.
  • the most suitable proportion of these compounds differs according to the types of the compounds used.
  • the proportion is not less than 5 by weight for acetone, not less than by weight for methyl amine, ethyl amine, and diethyl ketone, not less than by weight for n-propanol, iso-propanol, sec-butanol, tertbutanol, propyl amine and methyl ethyl ketone, not less than 30 by weight for n-butanol, iso-butanol and dimethyl amine, not less than 40 by weight for N,N- dimethyl formamide, furfuryl alcohol, dioxane and diethyl amine, not less than 50 by weight for N,N- dimethyl acetamide, methanol, ethanol, trimethyl amine, triethyl amine,
  • the mixed vapor of the above compounds and water can be easily prepared by mixing vapors of the compounds with steam, or heating an aqueous solution containing these compounds, or by blowing steam into the above compounds.
  • the phenolic fibrous material to which a dye liquor has been applied is contacted with vapors of the above compounds or mixed vapors of water and the above compounds in a steaming chamber, for example, by feeding the vapors into a closed chamber in which the fibrous material is placed.
  • the temperature of the vapors with which the fibrous material comes into contact differs according to the form, type and amount of the fibrous material used, the method of dyeing the material, the type of the dye used, the types of the above compounds, the amounts of these compounds in the mixed vapor, etc., but in general it is to 150C, preferably to 140C.
  • the fibers are swollen excessively during steaming. This contributes to increased diffusion of the dye, but on the other hand, causes the fixed dye to bleed out, thus reducing the dyeability. Furthermore, the tenacity of the fibers decreases, or the dye is decomposed during the treatment. If it is too low, no effective energy for fixing the dye to the material can be obtained. Accordingly, the optimum steaming temperature can be easily determined by those skilled in the art on a trial-and-error basis.
  • the time required for contacting the fibrous material with the vapors can be varied over a wide range according to various factors such as the form and type of the fibrous material, the type of the dye, or the amounts and types of the above compounds. Usually, it is 20 minutes to minutes, preferably about 30 to 90 minutes.
  • the fibrous material which has been steamed as described above is then subjected to a finishing treatment in accordance with a customary method.
  • a fibrous material dyed with a disperse dye and then steamed is washed with water, and then with an aqueous solution containing hydrosulfite, soda ash and a nonionic surface active agent, and finally dried.
  • the fibrous material is dyed with an azoic dye, cationic dye or vat dye and then steamed as described above, it is washed with water and then with an aqueous solution containing a non-ionic surface active agent, and finally dried.
  • the steaming treatment in accordance with the method of this invention promotes the diffusion of the dye adhered to the fibrous material into its interior, and makes it possible to obtain dyeings having uniform, deep fast colors. Furthermore, since the specific compounds used for the steaming treatment have high solubility in water, they do not give rise to difficulty of removal as in the case of the conventional carrier dyeing.
  • the method of the present invention makes it possible to color difficulty-dyeable phenolic fibrous materials in uniform deep colors with fastness characteristics without using any specific apparatus or costly chemicals. [t is therefore very useful for commercial application.
  • the vapor of the above specific compounds or the mixed vapors of the above compounds and water do not merely exhibit a swelling action on the fibers, but have an effect of neutralizing negative potential on the surfaces of the fibers and facilitating the diffusion of the dye into the fibers.
  • This unique function and effect are clearly seen from the fact that when the phenolic fibrous material is colored by dip dyeing in a dye liquor containing methyl amine, dimethyl amine, ethyl amine, diethyl amine, ethylene diamine, methanol or ethanol, the dye is not at all fixed to the fibers, or even when a cloth to which the dye has been applied is heated in a bath of the above compounds, the dye is not fixed to the fibers.
  • Table 1 Dyed by dipping in a dye liquor consisting of 30 4: (based on the weight of the dye liquor) of ethylamine and 30 '7: (based on the weight of the material to he dyed) of a dye for 60 minutes at l30'C.
  • the dyeings had a light fastness of class 4, laundering fastness of class 4, and a rubbing fastness of class 5.
  • EXAMPLE 2 A tweed produced from a ply yarn composed of the same phenolic fibers as used in Example 1 was dipped in a dye liquor of the following formulation, and squeezed to an extent of Formulation Hydroxyethyl cellulose (viscosity regulator) 0.4 Kg
  • Viscosity of the dye liquor I200 centipoises The tweed was then dried at C. for 5 minutes, and contacted with a mixed steam held at ll0C. and consisting of 50 of isopropanol amine and S0 of water for 60 minutes.
  • the treated tweed was washed with water, and then with a reductive wash liquid consisting of l g/l of hydrosulfite, 0.5 g/l of soda ash, l g/l of a non-ionic surface active agent and water at 80C. for 20 minutes, followed by washing with water and drying.
  • the dyed cloth was colored in a bluish deep black.
  • Formulation Diacryl Navy Blue BP (cationic dye, product of Mitsubishi Chemical Co. Ltd.)
  • Emulsion consisting of 50% of kerosene and 50% of water (viscosity regulator) Water Viscosity of the dye liquor 8000 centipoises
  • the fabric was then dried at 90C., and then contacted with a mixed vapor held at 125C. and consisting of 50 25 of methanol and S of water for 60 minutes.
  • the fabric was then washed with water, and washed with an aqueous solution containing 1 g/l of a non-ionic surface active agent for 3 minutes at 80C., followed by washing with water, and drying.
  • the resultant fabric had a beautiful blue pattern.
  • EXAMPLE 4 A plain weave fabric of the same structure as used in Example 1 was dipped in a dye liquor of the following formulation, and squeezed to an extent of Formulation Dianix Fast Brilliant Red BS (disperse dge, product of Mitsubishi hemical Co., Ltd.) 150 g 1,1 ,l-trichloroethane 850 g After application of the above dye liquor, the fabric was reductively washed for 3 minutes at 80C., washed with water, and dried. The dyed fabric was colored brilliant red.
  • Dianix Fast Brilliant Red BS diserse dge, product of Mitsubishi hemical Co., Ltd.
  • EXAMPLE 5 A knitted fabric produced from a ply yarn composed of the same phenolic fibers as used in Example 1 was dipped in a dye liquor of the following formulation, and squeezed to an extent of 70 Formulation Carbox methyl cellulose Dianix as! Red 28 (disperse dye, product of Mitsubishi Chemical Co., Ltd.) Water I I Viscosity of the dye liquor 800 centrpoises 1 Bi ig After application of the above dye liquor, the fabric was contacted with a mixed vapor held at C. and consisting of 10 of acetone and 90 of water for 60 minutes while being rotated on a roll (without prior 1 l drying).
  • the fabric was washed with water, and then washed with a reductive wash liquor consisting of 1 g/l of hydrosulfite, 0.5 g/l of soda ash, 1 g/l ofa non-ionic surface active agent and water at 80C. for 20 minutes,
  • the resul- 5 l fi g i g g tant dyed fabric was colored red.
  • bffi a ia d ye fc h titar isonl The above procedure was repeated using mixed va- 6 Aftefthe pp 5 pors of water with various ketones as shown in Table 5. above and sample was treated with The results are shown in Table 5.
  • Table 7 Aniline 50 0.29 Run D d t Water 50 yelng ens
  • the washed with water and the washed with a reductive treated fabric was washed with water, and then washed wash liquor consisting of 1 g/l of hydrosulfite, 0.5 g/l of 3 reductive wash quot conslslmg l 8" of y' soda ash, l g/l of non-ionic surface active agent and drQsumte 1 g/l of Soda log/l of non'lofllc Surface water at 80C. for 20 minutes, followed by washing acme agem f f at 80 0 20 "mules, with water and drying.
  • the resulting curtain material lowefj by washmg l and drymg-
  • the resultant was Cobred in a beautiful green color fabric was colored in a reddish deep brown.
  • EXAMPLE 8 A woven fabric produced from a ply yarn composed of the same phenolic fibers as used in Example 1 was dipped in a dye liquor of the following formulation, and squeezed to an extent of 57 Formulation Carboxymethyl cellulose (viscosity regulator) Dianix Brown R-E (disperse dye, product of Mitsubishi Chemical Co., Ltd.)
  • EXAMPLE 9 A woven fabric produced from monofilaments composed of the same phenolic fibers as used in Example I was dipped in a dye liquor of the following formulation, and squeezed to an extent of Fonnulation TD 1200 (predi fi ing agent) 9 Kg TD Brilliant R (color developer, product of Daito Chemical Co., Ltd.) 2 Kg TD Bordeaux 25 (color developer, product of Daito Chemical Co., Ltd.) 4 Kg Sodium alginate l Kg Water 84 Kg After application of the above dye liquor, the fabric was dried for 10 minutes at C, and treated with a vapor of the compositions shown in Table 9 at C. for 60 minutes.
  • TD 1200 predi fi ing agent
  • 9 Kg TD Brilliant R color developer, product of Daito Chemical Co., Ltd.
  • Kg TD Bordeaux 25 color developer, product of Daito Chemical Co., Ltd.
  • Kg Sodium alginate l Kg Water 84 Kg After application of the above dye liquor,
  • the treated fabric was washed with water, and then washed with an aqueous solution containing 1 gll of a nonionic surface active agent at 80C. for 20 minutes, followed by washing with water. Then, the fabric was treated with an aqueous solution containing 6 of 65 sulfuric acid and 3 of sodium nitrite for 30 minutes at 100C, followed by washing with warm water and cold water. The results are shown in Table 9.
  • EXAMPLE 10 A woven fabric produced from a ply yarn composed of the same phenolic fibers as mentioned in Example I was printed with a dye liquor of the following formulation.
  • a method for coloring fibers or fibrous structures composed of phenolic resins which comprises:
  • said dye liquor is a solution, emulsion or paste containing a dye.
  • said dye liquor contains a disperse dye, azoic dye, cationic dye or vat dye.
  • a method for printing fibrous structures composed of a phenolic resins which comprises:

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US351884A 1972-04-20 1973-04-17 Method for coloring fibrous material composed of phenolic resins Expired - Lifetime US3927973A (en)

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FR (1) FR2181071B1 (enrdf_load_stackoverflow)
GB (1) GB1417503A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3993442A (en) * 1974-09-19 1976-11-23 The Carborundum Company Anionic dyeing of novoloid fibers
US20030104163A1 (en) * 1996-09-16 2003-06-05 Basf Corporation, Inc. Colored fibers having resistance to ozone fading
US20040132375A1 (en) * 2000-10-16 2004-07-08 Toyotaka Fukuhara Thermal insulating material for housing use and method of using the same
US20080073615A1 (en) * 2006-07-24 2008-03-27 Sumitomo Chemical Company, Limited Method for producing resorcin/formaldehyde resin

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3967925A (en) * 1974-09-19 1976-07-06 The Carborundum Company Cationic dyeing of novoloid fibers
DE4432833A1 (de) * 1994-09-15 1996-03-21 Basf Ag Verfahren zum Färben von Melamin-Formaldehyd-Kondensationsprodukten
US11315803B2 (en) 2020-05-12 2022-04-26 International Business Machines Corporation Stress mitigation in organic laminates

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2524811A (en) * 1946-09-20 1950-10-10 Interchem Corp Dyeing plastic articles with an aqueous dispersion of dye dissolved in a plasticizer
US3519377A (en) * 1962-02-08 1970-07-07 Teijin Ltd Printing polyester textiles with a disperse dye paste containing an alkyl amide or alkylene diamide
US3606988A (en) * 1967-08-08 1971-09-21 Bayer Ag Process for dyeing nitrogen-containing fibre materials
US3667898A (en) * 1969-05-26 1972-06-06 Dow Chemical Co Process for dyeing textile materials from organic solvent media
US3716521A (en) * 1971-03-31 1973-02-13 Carborundum Co Etherified or esterified phenolic resin fibers and production thereof
US3723558A (en) * 1969-10-01 1973-03-27 Krupp Gmbh Production of pure p-xylene

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2524811A (en) * 1946-09-20 1950-10-10 Interchem Corp Dyeing plastic articles with an aqueous dispersion of dye dissolved in a plasticizer
US3519377A (en) * 1962-02-08 1970-07-07 Teijin Ltd Printing polyester textiles with a disperse dye paste containing an alkyl amide or alkylene diamide
US3606988A (en) * 1967-08-08 1971-09-21 Bayer Ag Process for dyeing nitrogen-containing fibre materials
US3667898A (en) * 1969-05-26 1972-06-06 Dow Chemical Co Process for dyeing textile materials from organic solvent media
US3723558A (en) * 1969-10-01 1973-03-27 Krupp Gmbh Production of pure p-xylene
US3716521A (en) * 1971-03-31 1973-02-13 Carborundum Co Etherified or esterified phenolic resin fibers and production thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3993442A (en) * 1974-09-19 1976-11-23 The Carborundum Company Anionic dyeing of novoloid fibers
US20030104163A1 (en) * 1996-09-16 2003-06-05 Basf Corporation, Inc. Colored fibers having resistance to ozone fading
US20040132375A1 (en) * 2000-10-16 2004-07-08 Toyotaka Fukuhara Thermal insulating material for housing use and method of using the same
US20080073615A1 (en) * 2006-07-24 2008-03-27 Sumitomo Chemical Company, Limited Method for producing resorcin/formaldehyde resin

Also Published As

Publication number Publication date
DE2319491A1 (de) 1973-10-31
FR2181071A1 (enrdf_load_stackoverflow) 1973-11-30
GB1417503A (en) 1975-12-10
FR2181071B1 (enrdf_load_stackoverflow) 1976-09-10
JPS539311B2 (enrdf_load_stackoverflow) 1978-04-05
DE2319491C3 (de) 1979-01-18
DE2319491B2 (de) 1978-05-24
JPS491876A (enrdf_load_stackoverflow) 1974-01-09

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