US3787181A - Dyeing synthetic hydrophobic fibers with lower alkyl biphenyl carriers - Google Patents

Dyeing synthetic hydrophobic fibers with lower alkyl biphenyl carriers Download PDF

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Publication number
US3787181A
US3787181A US00158082A US3787181DA US3787181A US 3787181 A US3787181 A US 3787181A US 00158082 A US00158082 A US 00158082A US 3787181D A US3787181D A US 3787181DA US 3787181 A US3787181 A US 3787181A
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United States
Prior art keywords
carrier
dyeing
carriers
biphenyl
dyestuff
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Expired - Lifetime
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US00158082A
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English (en)
Inventor
K Dellian
S Lee
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Novartis Corp
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Ciba Geigy Corp
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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
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters 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
    • D06P1/6515Hydrocarbons
    • D06P1/65162Hydrocarbons without halogen
    • 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
    • Y10S8/921Cellulose ester or ether
    • 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

Definitions

  • ABSTRACT A technique for coloring hydrophobic textile fibers with a disperse or basic dyestuff utilizing an alkyl biphenyl carrier.
  • the present invention is directed to a technique for dyeing or printing hydrophobic material with a disperse or basic dyestuff utilizing a carrier to aid penetration of the dyestuff into the fiber.
  • the embployed carrier is an alkyl biphenyl.
  • the present invention is directed to improvement in the method of dyeing textile fibers which do not readily absorb water.
  • the hydrophobic nature of the fiber makes the dyeing of this material difficult and poses practical problems.
  • polyester fibers or fabrics are customarily dyed with disperse acetate dyes or other similar dyes, specially developed for this polyester fiber.
  • disperse acetate dyes or other similar dyes specially developed for this polyester fiber.
  • the nature of these dyes is described in the Chemistry of Synthetic Dyes and Pigments edited by H. Lubs, Rheinhold Publishing Corp., 1855, p. 167 to 174.
  • a few acetate dyes will color the fabric at the boiling point of water, but penetration of the dye is very poor.
  • the prior art has also turned to specific carrier components.
  • the fixation of the dyestuff is either carried out at elevated pressures at temperatures over 100C, or by the thermosol process at temperatures below the softening or melting point of the fabric, e.g., at about 200C for polyester fibers.
  • a preferred technique is the use of dyeing auxiliaries, so-called carriers which aid in providing an easier penetration of the dyestuff into the fiber.
  • biphenyl which has distinct disadvantages. This compound is known to be toxic which causes problems in use and in disposal. Additionally, biphenyl is in dry form, a solid, and added at temperatures close to the boiling point of the dyebath. Recrystallization of this carrier can take place if the temperature is lowered, leading to speckiness or spots on the textile fiber.
  • the carriers of the present invention function in desirable manner of the prior art in facilitating penetration of the dyestuffs into the fiber.
  • the carrier in the dyebath permits an efficient drawing rate of the dyestuff into the fiber and aids in permitting good fastness with uniform shade in the dyeing operation.
  • the disclosed carrier is-a non-toxic agent and is in liquid or easily dissolvable solid form which bypasses serious shortcomings including dissolving and recrystallization problems of prior art carriers.
  • X is an alkyl containing one or two carbon atoms
  • X is hydrogen or an alkyl containing one or two carbon atoms
  • both n and m are separately from one another, integers of 1 to 3.
  • the alkyl biphenyls of the present disclosure reduce appreciably the cost of dyeing hydrophobic synthetic fibers by increasing the utilization and effectiveness of the dyestuff.
  • the carrier in the dyestuff permits an efficient drawing rate of the dyestuff and aids in permitting good fastness with uniform shades in the dyeing operation.
  • the carriers diclosed function in the prior manner of facilitating penetration of the dyestuff into the fiber. Conventional techniques of employing the dyestuff may be employed, such as by the beck, jig, paddle, padder, package machine, and other dyeing method.
  • suitable carriers of the present invention are methyl biphenyl, ethyl biphenyl, and dimethyl biphenyl.
  • a fibrous material includes fibers, yarns, threads, fabric, ribbons, tapes and tabs.
  • a suitable example of a hydrophobic fibrous material is a polyester, such as a high melting polyester containing six membered carbocyclic rings or acid modified carbocyclic rings receptive for cationic dyes.
  • Illustrative of the polyesters that may be employed are polyethylene terephthalate.
  • the general technique of the present invention employing the novel carrier disclosed herein is also applicable to other hydrophobic synthetic materials containing a variety of ester groups in the molecule and being difficult to dye, such as cellulose triacetate and bicarpolyurethane.
  • hydrophobic fibers may be dyed using the present carrier and a wide variety of suitable substrates may be employed.
  • dyestuffs that may be employed in the present invention are known in the art as disperse and basic dyestuffs.
  • suitable disperse dyestuffs are the Color Index C.I. disperse dyes.
  • Illustrative of the basic dyestuffs that may be employed in the present invention are Index C.I. Basic Dyes.
  • the carrier is applied in the form of a solution emulsion or illustratively emulsfying agents may be represented by the following formulae; in which R designates an alkyl group and M is a metal salt such as sodium, potassium, ammonium, or a derivative of ammonia etc.
  • RCOOM 3 n V a wherein R is an alkyl group containing 8 to 24 carbon atoms.
  • ROSO OM wherein R is an alkyl group containing 8 to 24 carbon atoms.
  • RSO3M wherein R is an alkyl group containing l2 to 18 carbon atoms.
  • R f Ar $03M wherein R is an alkyl group containing 3 to 18 carbon atoms and Ar is an aromatic nucleus selected from benzene, naphthalene, anthracene, etc.
  • n is at least one and as high as 10.
  • R Ar (OCH CH2)n OH wherein R is an alkyl group containing 1 to 18 carbon atoms.
  • Ar is a benzene nucleus and n is a number from 4 to 40.
  • R (OCH CH OH wherein R is an alkyl group containing 8 to 24 carbon atoms and n is a number from 4 to 40.
  • R ocu cm oso m wherein R is an alkyl containing 8 to 24 carbon atoms and n is a number equaling l to 4.
  • R C C (OCH CHQ OH wherein R is a fatty radical containing 8 to 24 carbon iP,"l Fl..”l [lu r filtalll 4 m Ra R3 (10) wherein R is an alkyl or amide group containing 8 to 24 carbon atoms, R is hydrogen alkyl or an arakyl group, R is hydrogen or an alkyl group containing 1 to 8 carbon atoms, R is hydrogen, alkyl or arakyl group, and X is an anionic radical, e.g., choloride, sulfate, or sulfate derivative.
  • emulsifying agents which may be employed are lauryl dimethyl, benzyl ammonium chloride, Turkey red oil, sodium lauryl sulfate, sodium dodecyl benzene sulfonate, triethanolamine salt of lauryl sulfate, ethoxylated nonylphenol.
  • An example of a preferred emulsifying agent is the triethanolamine salt of lauryl sulfate.
  • One technique for dyeing comprises adding the dyestuff, such as disperse dyestuff, and emulsified carrier to the dyebath containing the synthetic material.
  • Another method comprises applying the emulsified carrier prior to the dyeing process. This can be done simultaneously during the prescouring operation.
  • the pretreated material is then rinsed and entered into a fresh dyebath containing only the dyestuff.
  • lf printing is employed, it may be carried out in the usual manner by adding the carrier emulsion to the printing paste and printing the fabric on a roller or screen printing unit.
  • the dye is fixed by exposing to steam or heat treatment.
  • the amount of dyeing carrier composition to be added to the dyebath may be varied within relatively wide limits and depends primarily upon the dry weight of the hydrophobic synthetic materials being dyed. Within the broad aspect of the present invention, from about 1 to 15 percent by weight of the dyeing carrier may be employed based on the dry weight of the hydrophobic synthetic material. More satisfactorily, about 2 to 10 percent of the dyeing carrier will be employed.
  • the disclosed carrier of the present invention is not only restricted to be applied alone as the sole carrier in the present disclosure, but can be incorporated into other carriers which are well known in the prior art, such as o-phenyl phenol, methyl salicylate, biphenyl, chlorinated benzene or naphtalenes, methyl naphtalenes and alkyl benzoates, such as for example to an extent of 50% conserving the original characteristics of the employed carrier.
  • the physical form of the alkyl biphenyl carrier is a liquid or easily dissolvable solid.
  • the melting point of 2-methyl biphenyl, 3-methyl biphenyl and 4-methyl biphenyl are respectively 0C, 45C and 49.5C.
  • 4-methyl biphenyl which is a solid at room temperature
  • a eutectic mixture of this component with disclosed biphenyls may be employed which yields a liquid at room temperature.
  • the dyeing carrier is prepared from parts of 3- methyl biphenyl, 15 parts of the triethanol amine salt of dodecylsulfate and 15 parts water; 8 percent of the emulsion, based on the dry weight ofa Dacron polyester fabric, are added at 40C to a dyebath containing 2 percentof the dyestuff of thefollowing formula.
  • the polyester fabric is then loaded in a beck at a liquor ratio 30:1. Running the fabric 10 minutes at 40C, the temperature is raised within 30 minutes, to the boil and kept 1% hours at this temperature. A full orange shade is obtained with very good fastness properties.
  • Disperse Orange 21 lnstead of 8 percent only 6 percent of the carrier emulsion is used.
  • the fabric is dyed in a vivid pink, with excellent lightfastness.
  • EXAMPLE 4 3 percent alginate thickener; percent mineral spirit; a P n d an r bmittsqls a TIEEEQGHFWBEE 350F. After rinsing and soaping a vivid reddish blue was obtained.
  • EXAMPLE 5 A fabric of acid modified polyester. trade name "Dacron 64" is dyed according to example 1 with 1.5 percent the dyestuff of the following formula.
  • the carrier comprises 2- methylbiphenyl, 3-methylbiphenyl, 4-methylbiphenyl or mixtures thereof.
  • alkyl biphenyl carrier includes 4-methyl biphenyl employed in a eutectic mixture.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
US00158082A 1971-06-29 1971-06-29 Dyeing synthetic hydrophobic fibers with lower alkyl biphenyl carriers Expired - Lifetime US3787181A (en)

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US15808271A 1971-06-29 1971-06-29

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US (1) US3787181A (de)
DE (1) DE2229932A1 (de)
FR (1) FR2143842B1 (de)
GB (1) GB1356885A (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4226597A (en) * 1979-06-29 1980-10-07 Olin Corporation Use of 2,4,4,4-tetrachlorobutyl acetate as a dye carrier for disperse dyes
US4270917A (en) * 1978-10-16 1981-06-02 Imperial Chemical Industries Limited Stabilized aqueous dyestuff dispersions
US5009669A (en) * 1988-05-31 1991-04-23 Ciba-Geigy Corporation Aqueous dispensions of 2-(2'-hydroxyphenyl)benzotriazoles
WO1999052361A1 (en) * 1998-04-14 1999-10-21 Reckitt Benckiser Inc. Blooming type germicidal hard-surface cleaners
US6075002A (en) * 1997-11-28 2000-06-13 Reckitt & Colman Inc. Biphenyl based solvents in blooming type germicidal hard surface cleaners
US6100231A (en) * 1997-11-28 2000-08-08 Reckitt & Colman Inc. Biphenyl based solvents in blooming type hard surface cleaners

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1803008A (en) * 1931-04-28 Dyeing
US2394688A (en) * 1944-01-07 1946-02-12 American Viscose Corp Method of dyeing
US2394689A (en) * 1944-01-07 1946-02-12 American Viscose Corp Method of dyeing
US2635942A (en) * 1949-04-27 1953-04-21 Sandoz Ag Dyeing materials made of polyvinyl derivatives
GB915342A (en) * 1959-03-19 1963-01-09 Hoechst Ag Process for dyeing fibres
US3097909A (en) * 1959-09-23 1963-07-16 Ciba Ltd Process for dyeing or printing fibrous materials of aromatic polyesters
US3189400A (en) * 1961-04-20 1965-06-15 Celanese Corp Polyolefin textile dyeing with solvent and dye heated thereon
US3617213A (en) * 1968-12-02 1971-11-02 Robert Curtis Britt Coal tar methyl naphthalene fraction and diphenyl carrier and dyeing therewith

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1803008A (en) * 1931-04-28 Dyeing
US2394688A (en) * 1944-01-07 1946-02-12 American Viscose Corp Method of dyeing
US2394689A (en) * 1944-01-07 1946-02-12 American Viscose Corp Method of dyeing
US2635942A (en) * 1949-04-27 1953-04-21 Sandoz Ag Dyeing materials made of polyvinyl derivatives
GB915342A (en) * 1959-03-19 1963-01-09 Hoechst Ag Process for dyeing fibres
US3097909A (en) * 1959-09-23 1963-07-16 Ciba Ltd Process for dyeing or printing fibrous materials of aromatic polyesters
US3189400A (en) * 1961-04-20 1965-06-15 Celanese Corp Polyolefin textile dyeing with solvent and dye heated thereon
US3617213A (en) * 1968-12-02 1971-11-02 Robert Curtis Britt Coal tar methyl naphthalene fraction and diphenyl carrier and dyeing therewith

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
H.C. Speel et al., The Textile Chemicals and Auxiliaries, 2nd Ed., 1957, pp. 70 71. *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4270917A (en) * 1978-10-16 1981-06-02 Imperial Chemical Industries Limited Stabilized aqueous dyestuff dispersions
US4226597A (en) * 1979-06-29 1980-10-07 Olin Corporation Use of 2,4,4,4-tetrachlorobutyl acetate as a dye carrier for disperse dyes
US5009669A (en) * 1988-05-31 1991-04-23 Ciba-Geigy Corporation Aqueous dispensions of 2-(2'-hydroxyphenyl)benzotriazoles
US6075002A (en) * 1997-11-28 2000-06-13 Reckitt & Colman Inc. Biphenyl based solvents in blooming type germicidal hard surface cleaners
US6100231A (en) * 1997-11-28 2000-08-08 Reckitt & Colman Inc. Biphenyl based solvents in blooming type hard surface cleaners
WO1999052361A1 (en) * 1998-04-14 1999-10-21 Reckitt Benckiser Inc. Blooming type germicidal hard-surface cleaners
US6395697B1 (en) * 1998-04-14 2002-05-28 Reckitt Benckiser Inc. Diphenyl based solvents in blooming type germicidal hard surface cleaners

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Publication number Publication date
FR2143842B1 (de) 1974-12-27
FR2143842A1 (de) 1973-02-09
DE2229932A1 (de) 1973-01-18
GB1356885A (en) 1974-06-19

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