US3816071A - Coloring hydrophobic fibers using carrier of halogenated hydroxybiphenylether - Google Patents

Coloring hydrophobic fibers using carrier of halogenated hydroxybiphenylether Download PDF

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Publication number
US3816071A
US3816071A US00232191A US23219172A US3816071A US 3816071 A US3816071 A US 3816071A US 00232191 A US00232191 A US 00232191A US 23219172 A US23219172 A US 23219172A US 3816071 A US3816071 A US 3816071A
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US
United States
Prior art keywords
carrier
hydroxybiphenylether
halogenated
parts
dyestuff
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00232191A
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English (en)
Inventor
K Dellian
T Furia
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis Corp
Original Assignee
Ciba Geigy Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy Corp filed Critical Ciba Geigy Corp
Priority to US00232191A priority Critical patent/US3816071A/en
Priority to DE19732309906 priority patent/DE2309906A1/de
Application granted granted Critical
Publication of US3816071A publication Critical patent/US3816071A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/24Polyamides; Polyurethanes
    • D06P3/26Polyamides; Polyurethanes using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/651Compounds without nitrogen
    • D06P1/65106Oxygen-containing compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/522Polyesters using basic dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/922Polyester fiber
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

Definitions

  • theprior art has employed in the treatment of the hydrophobic,syntheticfibers elevated pressures with temperatures greater generally than 250 F.
  • dyeingunder'pressure at'elevated temperature is undesirable duezto expensive and complex procedures.
  • the prior art has also turned-to specific carrier components. These carriers aid in the penetration. of the dye into the fiber by causinga swelling of the base substrate.
  • hydrophobic fibers allow satisfactory resultsattemperatures as low as 200 to 210 F although a temperature of 212 F at normal atmospheric pressure ispreferred.
  • carrier components for hydrophobic fibers known in the prior art to be employed' with avariety ofdyes.
  • typical carriers used by the art up to the present time are various derivatives of benzene and. phenol such as orthoand para-phenylphenol, chlorinated benzenes, xylenes, naphthalenes. toluenes, aromatic esters or ethers, and biphenyl. Nevertheless. many of these carrier components have some drawbacks such as lack of availability, undue toxicity, lack of ease of removal from the substrate, effect on lightfastness of color, or influence of buildup of a heavyshade.
  • n is an integer from 0 to 3
  • Y is chlorine or bromine
  • m is an-integer from 0 to 3
  • the sum of n andm is, l, to 3;
  • Thecarrier compounds of the present invention are, in most cases, clear colorlesssolids. They are utilized in the form of. an emulsion or dispersion composition which is added to the, dyebath formulation, printing paste, or prescouringbath. Besides the carrier activity they possess a bacteriostatic, action.
  • the carriers of the present invention are generally colorless, odorless and non-toxic, or nearlyso. They usually do notgaffectthe fastness other than by improving it, and are either non-foaming or very low foaming. Dyeing processes utilizing, the carrier composition of the present invention exhibit a slow drawing of the dyestuff resulting in excellent levelness and extremely good. utilization or exhaustion of the dyestuff.
  • dyestuffs employable in the present invention are well known in the art as disperse and cationicdyestuffs. Illustrative although not limiting of suitable disperse dyestuffs are those listed in the Color Index under the Disperse dye classification.
  • a fabrous material includes fibers,,yarns, threads, fabric ribbons, tapes and tabs.
  • Thedyestuff andemulsified carrier may be added to a bath at temperatureequivalent to the boiling point of water. A time interval of two or three hours is utilized during; which time the fibrous substrate is contacted with the dyebath composition. Thereafter the fabric is washed followed by drying.
  • printing may be carried out in the usual way by adding the carrier emulsionto a paste and'printing the material on a roller or screen printing unit followed by fixing the dye by exposing to steamor. heat treatment.
  • thermosol technique may be utilized by padding the material, with a mixture of a, disperse dye-emulsified carrier of the type disclosed herein followed by drying at to 250 C for l to 30 minutes. Alternatively thennofixing may take place with steam injection at temperature-time conditions as 340 F for l to 30 minutes.
  • hydrophobic materials that do not color readily without theuse of a carrier component.
  • Suitable examples of the hydrophobic material include 3 polyester and acid'modified polyester, polyamide, cationic dyeable polyamide, polypropylene, polyacrylonitrile, and its modified versions, modacrylics, or triacetate.
  • the carriers of this invention are generally employed in the form of an emulsion in order to achieve rapid and uniform distribution of the carriers in the prescouring bath, dyebath, or printing composition.
  • the emulsifying agents which are employed may generally be of the cationic, anionic, or nonionic type of surface active agents familiar to those skilled in the art. Representative of those surface active agents are those of the following formulae in which R is alkyl and M is a metallic cation such as sodium or potassium, or ammonium and derivatives thereof:
  • R-COOM wherein R is an alkyl group containing 7 to 24 carbon atoms.
  • ROSO OM wherein R is an alkyl group containing 7 to 24 carbon atoms.
  • R50 M wherein R is an alkyl group containing 12 to 18 carbon atoms.
  • R-Ar-SO M wherein R is an alkyl group containing 3 to 18 carbon atoms and Ar is an aromatic nucleus selected from benzene, naphthalene, anthracene, etc.
  • R-Ar-(OCH CH2) --OSO3 M 01' wherein R is an alkyl substituent on a benzene ring containing 1 to 18 carbon atoms and Ar is a benzene nucleus and z is at least one and as high as l0.
  • R--A'r--(OCH CH ),--OH wherein R is an alkyl group containing l t o l8 carbon atoms.
  • Ar is a benzene nucleus and z is a number from 4 to 40.
  • R--(OCH CH --OSO M wherein R is an alkyl group containing 8 to 24 carbon atoms and z is a number equaling l to 4.
  • R--C--O--(OCH CH OH wherein R is a fatty radical containing 8 to 24 carbon atoms and z is anumber equaling 4 to 40.
  • R is an alkyl or amido group containing 8 to 24 carbon atoms
  • R is hydrogen, alkyl or an aralkyl group
  • R is hydrogen or an alkyl group containing 1 to 8 carbon atoms
  • R is hydrogen, alkyl or aralkyl group
  • X is an anionic radical, e.g. chloride, sulfate or sulfate derivative.
  • emulsifying agents which may be employed are lauryl dimethyl, benzylammonium chloride, Turkey red oil, sodium lauryl sulfate, sodium dodecyl benzene sulfonate, triethanolamine salt of lauryl sulfate, ethoxylated nonylphenol and the like.
  • the sodium lester sulfate is especially preferred.
  • the emulsifier desirably are of the nonionic or cationic type.
  • Nonionic agents are preferred in most instances.
  • the dye carrier composition is prepared by blending together from about 10 to about 90 parts (by weight) of carrier and from about 10 to about 90 parts (by weight) of the emulsifying agent.
  • the emulsion ordinarily is prepared in water in a known manner.
  • a preferred embodiment employs for 50 parts to 80 parts carrier in conjunction with 20 to 50 parts of emulsifying agent.
  • a composition of about 70 carrier and about 30 parts emulsifier is especially preferred.
  • dye carriers of the present invention besides being generally free of undesirable color, odor, foaming irritant, and toxic properties, are two to three times more effective on a weight to weight bases than previously employed carriers such as biphenyl, methyl naphthalene, o-phenyl and others.
  • a dye carrier composition is prepared by melting 80 parts by weight of 2-hydroxy 2, 4, 4, trichlorodiphenylether, l0 parts of the sodium salt of nonylphenoxypolyethylenoxyl ethanol and 10 parts of the sodium salt of oleyl amylester sulfate. After cooling the mixture is pulverized. The dyebath is loaded at 50 C with Dacron (polyethylene terepthalate) double knit at a liquor ratio of 40:]. Based on the weight of fabric (owf), 2% of the following dyestuff is employed:
  • EXAMPLE 3 A printing paste is prepared containing parts of the carrier composition described in Example 1, 2.5
  • EXAMPLE 6 A dye carrier composition is prepared in like manner as Example 1, but instead of 2 hydroxy 2'4, 4 trichlorodiphenylether, 2 hydroxy 4,4 dichlorodiphenylether is used. In this example, the following dyestuff is added:
  • a liquor ratio of 40:1 is present in the dye bath with 100 pounds of polyethylene terephthalate (Dacron 54) fabric. Initially the bath temperature is at 140 F followed by raising the temperature to boiling over a period of 20 minutes which is maintained for minutes. The fabric is rinsed, soaped, and placed in a bath of 2% hydrosulfite and 2% weight soda ash for 15 minutes at 180 F. A brilliant yellow shade having excellent fastness properties results.
  • Example 11 The procedure of Example I is repeated in all essential respects but instead of Dacron, a fabric of Nylon 66 (polyamidc) is used.
  • rial is a polyamidel said halogen is

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
US00232191A 1972-03-06 1972-03-06 Coloring hydrophobic fibers using carrier of halogenated hydroxybiphenylether Expired - Lifetime US3816071A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US00232191A US3816071A (en) 1972-03-06 1972-03-06 Coloring hydrophobic fibers using carrier of halogenated hydroxybiphenylether
DE19732309906 DE2309906A1 (de) 1972-03-06 1973-02-28 Verfahren zum faerben hydrophober fasern

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00232191A US3816071A (en) 1972-03-06 1972-03-06 Coloring hydrophobic fibers using carrier of halogenated hydroxybiphenylether

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999042650A1 (en) * 1998-02-20 1999-08-26 Milliken Research Corporation Esterified triclosan derivatives as improved textile antimicrobial agents

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2270706A (en) * 1940-03-11 1942-01-20 American Viscose Corp Method of dyeing vinyl polymers
US3385652A (en) * 1963-08-21 1968-05-28 Union Carbide Corp Dyeing polyolefin articles with soluble dye and a short chain polyethylene glycol ether
US3506720A (en) * 1963-02-22 1970-04-14 Geigy Chem Corp Halogenated hydroxy-diphenyl ethers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2270706A (en) * 1940-03-11 1942-01-20 American Viscose Corp Method of dyeing vinyl polymers
US3506720A (en) * 1963-02-22 1970-04-14 Geigy Chem Corp Halogenated hydroxy-diphenyl ethers
US3385652A (en) * 1963-08-21 1968-05-28 Union Carbide Corp Dyeing polyolefin articles with soluble dye and a short chain polyethylene glycol ether

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999042650A1 (en) * 1998-02-20 1999-08-26 Milliken Research Corporation Esterified triclosan derivatives as improved textile antimicrobial agents
US5968207A (en) * 1998-02-20 1999-10-19 Milliken & Company Esterified triclosan derivatives as improved textile antimicrobial agents

Also Published As

Publication number Publication date
DE2309906A1 (de) 1973-09-20

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