US1883351A - Treatment of cellulose derivatives - Google Patents

Treatment of cellulose derivatives Download PDF

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Publication number
US1883351A
US1883351A US213199A US21319927A US1883351A US 1883351 A US1883351 A US 1883351A US 213199 A US213199 A US 213199A US 21319927 A US21319927 A US 21319927A US 1883351 A US1883351 A US 1883351A
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United States
Prior art keywords
insoluble
parts
compounds
water
derivatives
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Expired - Lifetime
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US213199A
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English (en)
Inventor
Dreyfus Henry
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Henry Dreyfuss Associates LLC
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Henry Dreyfuss Associates LLC
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Classifications

    • 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
    • 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
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/04—Protein or carboxylic compound containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/91—Soap
    • Y10S8/911—Sulfonated
    • 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk
    • 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile
    • 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
    • Y10S8/921—Cellulose ester or ether

Definitions

  • This invention relates to the dyeing, printing or stencilling of cellulose ethers such as methyl cellulose, ethyl cellulose and. benzyl cellulose in the form of artificial silk, yarn,
  • cellulose ethers i. e. cellulose ethers which are insoluble in hot or cold Water
  • cellulose ethers can be dyed, printed or stencilled with coloring matters or organic compounds which are insoluble or practically insoluble in Water or are of relatively low solubility in 1;
  • Water all hereinafter in the claims included in the term relatively water-insoluble coloring compounds
  • Such aqueous dispersions may be obtained for example by grinding (e. g. in colloid mills), by dissolving in a solvent and pouring into Water containing or not containing protective colloids, or by pretreating the coloring matters or compounds with one or more solubilizing agents.
  • solubilizing agents may be specified bodies having oily or fatty char acteristics, namely higher fatty acids or sulphonated or other derivatives thereof containing salt-forming groups such as sulphonicinoleic acid or other sulphated fatty acids or salts of such acids or bodies, for instance their alkali or ammonium salts; carbocyclic compounds containing in their structure one or more salt-forming groups such as naphthenic acids or other carboxylic or sulphonic acids of the cycloparafiins, phenols, sulphonic acids,carboxylic acids,phenolsulphonic acids, sulphonated naphthalene-formaldehyde condensation products or other derivatives of the benzene, naphthalene or anthracene series or other derivatives of the saturated or nonsaturated hydrocarbons containing one or more salt-forming groups or sodium or other salts of any such compounds; Twitchell reagents, i.
  • sulpho-aromatic fatty acids such as sulphobenzene stearic acid or derivatives thereof such as sulphophenol stearic acid or sulpho naphthalene stearic acid, sulpho naphthalene ricinoleic acid or salts of such bodies; sulphite-cellulose lye or constituents thereof, such as lignin sulphonic acid or sodium or other salts thereof; and soluble resin soaps or sodium or other soluble salts or soaps of resin acid.
  • solubilizing agents may be employed either singly or two or more in admixture or in succession. All of these substances are included in the term bodies of oily or fatty characteristics in the appended claims.
  • auxiliary solvents may be used in conjunction with the aforesaid bodies of oily or fatty characteristics or salts thereof for solubilizin or converting into more soluble modifications any Water-insoluble or insufficiently Water-501w ble coloring matters or organic compounds, greatly improved results being obtained in many cases.
  • auxiliary solvents I may mention alkyl or alkylene halides, such as tetrachlorethane or trichlorethylene; paraflins such as cyclohexane, heptane, triethylmethane, l -nonane, nonane; simple or mixed derivatives of the cyclic or aromatic series containing one or more amino, chlor or hydroxy groups such as cresols, alkylanilines, toluidines, chlorphenols, mono or poly chlor benzenes or chlor naphthalenes; aromatic hydrocarbons such as benzene, toluene, xylene, cumene, (C H CH(CH )2), propylbenzene, orthomethylethylbenzene, mesitylene, diphenyl methane, naphthalene; hydrogenated derivatives of aromatic compounds such as hexahydrophenol, hexahydrocresols, lA-hydro- 35
  • auxiliary solvents may be used in conjunction with one or more of the aforesaid bodies of oily or fatty characteristics for the solubilization of insoluble or insufiiciently soluble coloring matters or organic compounds.
  • This process of using auxiliary solvent is of especial use in the solubilization of highly insoluble coloring matters or compounds, which would otherwise require very large and excessive quantities of the bodies of oily orfatty characteristics or salts thereof for their solubilization and practical application although it is to be understood that it may be applied to the dyeing, or otherwise coloring of cellulose ethers with any insoluble or practically 1nsoluble or relatively insoluble coloring matter or compound.
  • any insouble or relatively insoluble coloringmatter or compound may be used for the present invention.
  • I may employ unsulphonated or other relatively insoluble derivatives of the azo class, simple amino bases, unreduced indophenols .(aryl or substituted aryl benzoor naphthoquinone mono-imides) or insoluble or relatively insoluble coloring matters of the following classes -pol arylmethane, oxazine, azine, thiazine, unre uced indigoid or basic derivatives of the anthraqulnone series, e. g.
  • rosaniline base or its alkylated or aryla'ted derivatives pararosaniline base, malachite green base, aminoand aminohydroxyanthraquinones or their derivatives such as 1-paratolylamino-ei-hydroxy anthraqulnone, 1 paratolylamino 4 methylammo-anthraquinone, safranine base and so forth; insoluble or relatively insoluble pyrazolone derivatives,'for example unsulphonated azo de rivatives of'pyrazolone compounds, such as those obtained by coupling 1-phenyl-3- methyl-5-pyrazolone, 0r 1.3-dimethyl-5-pyrazolone with diazotized amino compounds j e. g.
  • the insoluble or relatively insoluble coloring matters or compounds for use in the present invention will usually contain no strongly acidic groups such asthe sulpho group and when basic coloring matters orv compounds are employed they are always used in the form of the base and not in the form of salts such as the-hydrochloride.
  • the insoluble or relatively insoluble coloring matter or compound may be mixed or ground with one or more solubilizing agents, in the presence or absence of water, and the wholeheated if necessary, the solubilized modifications being filtered if desired before addition to the dyebaths or other preparations for dyeing or otherwise coloring the goods containing cellulose ethers.
  • auxiliary solvents are to be used one 'or more of the insoluble or in-
  • dyeings or colorlngs are to be produced by the azoic or development process the insoluble or relatively insoluble component (whether base or developer or both) may be solubilized, as described, and the dyeing or development conducted as usual, either component being applied first to the material.
  • an aqueous dispersion of one or more color ing matters or compounds may be thickened by the use of such substances as starches, flour, gums and the like and applied in the usual manner, followed by such after-treatment as may be required.
  • Mixed goods may be dyed or otherwise colored in uniform or contrasting effects with or without employment of other dyestuffs or components according to the character of the non-ether portion of the goods, said other dyestuffs or components being applied if desired before or after the application of the aforesaid insoluble or relatively insoluble dyestuffs or compounds, or when not deleteriously affected thereby, they may be applied in conjunction therewith.
  • the cellulose ethers may be either fully etherified products or the lower ethers or partially etherified products.
  • Example 1.1 part of a aqueous paste of 2.4-dinitro-4-hydroxy-diphenylamine is ground up with 2 parts of 50% aqueous sodium sulphoricinoleate and the mass is heated and stirred until as homogeneous as possible. Boiling water is then added to make the liquor to a total of 24 parts. The stirred liquor is added to a bath containing 400 parts of soft water. The dyebath is raised to'40 50 C. and 20 parts of insoluble ethyl cellulose artificial silk yarn in hank form are entered, the dyeing temperature being raised to 65 75 C. during half an hour and maintained at that temperature for 1 hour. The goods dyed a yellow shade are lifted, rinsed and dried or otherwise finished as desired.
  • a dyebath is prepared as fol lows:1 partof a 20% paste of stilbenc disazo phenol is pasted with 1 part of a compound obtained by sulphonating a mixture of naphthalene and castor oil. The paste is diluted with 40 parts of boiling soft water and added, through a sieve if necessary to 500 parts of cold water.
  • E mample 3.1 part of 2.4-dinitrobenzeneazo-diethylaniline is pasted with a solution in a sufficient quantity of water of 8 parts of naphthenic acid rendered slightly alkaline with caustic soda.
  • the mass is heated and poured into 100 parts of 2 soap solution, the whole being stirred to produce a good dispersion.
  • the liquor is then filtered into a dyebath and 100 parts of insoluble ethyl cellulose artificial silk yarn in the form of hanks are entered into the dyebath at about 40 C.
  • the temperature is raised during hour to about 75 80 C. and main tained at this temperature for a further hour, after which the goods, now dyed red, are lifted, rinsed and finished as desired.
  • Example 4-1 part of 1-acetylamino-4- oxyanthraquinone is dispersed in 9 parts of water containing 2 parts of glue by means of a colloid mill.
  • the paste is added to 3000 parts of water containing 8 parts of glue.
  • 100 parts of insoluble ethyl cellulose artificial silk yarn in hank form are entered into the cold well stirred dyebath and the temperature raised to 8090 C. during 1 hour, dye- I ing being continued for a further hour.
  • the goods dyed an orange shade may then be lifted, rinsed and dried.
  • Example 5 -1 part of 2.4-dinitro-4-hydroXy-diphenylamine is ground up With about 6 parts of 50% sodium sulphoricinoleate and heated; 4 parts of hexahydrophenol are then added and the heating continued until the mass becomes clear, when it is diluted with 500 parts of cold soft water. The dispersion is then added to a dyebath containing 2000 parts of water. 100 parts of insoluble ethyl cellulose artificial silk yarn in the form of hanks are entered into the bath at about 40 C. and the temperature raised during 1 hour to about 90 0., at which temperature dyeing is continued for a further hour. The goods, dyed a yellow shade, are lifted, rinsed and dried or otherwise finished as desired.
  • the paste is heated to 80 C. and diluted to 25 parts with boiling soft water, and the solution obtained pouredinto 7 50 parts of soft water containing 0.5 parts of olive oil soap in solution.
  • parts of insoluble ethyl cellulose artificial silk yarn in hank form are entered into the dyebath at about C. and the dyeing proceeded with as in the previous example.
  • the goods are dyed a yellow-red shade.
  • dyeing in the claims is to be understood to include printing and stencilling and further the term coloring compound in the claims includes, in addition to coloring matters or dyestuffs, organic compounds which are capable of forming coloring matters or dyestuffs upon the material, for example the components (base or developer or both) used in the azoic or development process of dyeing.
  • said dispersion being prepared by pretreating the compoundwith a solubilizing agent comprising a sodium salt of sulpho-ricinoleic acid and with xylene.
  • Process for dyeing material comprising ethyl cellulose, comprising dyeing the material with an aqueous dispersion of a relatively water-insoluble coloring compound, said dispersion being prepared by pretreating the compound with a solubilizing agent comprising a sodium salt of sulpho-ricinoleic acid and with xylene.

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US213199A 1926-10-08 1927-08-15 Treatment of cellulose derivatives Expired - Lifetime US1883351A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB25012/26A GB285104A (en) 1926-10-08 1926-10-08 Improvements in or relating to the dyeing, printing or stencilling of materials composed of or containing cellulose ethers

Publications (1)

Publication Number Publication Date
US1883351A true US1883351A (en) 1932-10-18

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US213199A Expired - Lifetime US1883351A (en) 1926-10-08 1927-08-15 Treatment of cellulose derivatives

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US (1) US1883351A (enrdf_load_stackoverflow)
BE (1) BE344887A (enrdf_load_stackoverflow)
FR (1) FR641566A (enrdf_load_stackoverflow)
GB (1) GB285104A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2546168A (en) * 1948-07-03 1951-03-27 Celanese Corp Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents
US2546167A (en) * 1948-07-03 1951-03-27 Celanese Corp Acid-fading inhibition using dibenzylethylenediamine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2546168A (en) * 1948-07-03 1951-03-27 Celanese Corp Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents
US2546167A (en) * 1948-07-03 1951-03-27 Celanese Corp Acid-fading inhibition using dibenzylethylenediamine

Also Published As

Publication number Publication date
BE344887A (enrdf_load_stackoverflow)
GB285104A (en) 1928-02-08
FR641566A (fr) 1928-08-07

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