US3925016A - Polyarcrylonitrile basic dyeing process with anionic assistant - Google Patents

Polyarcrylonitrile basic dyeing process with anionic assistant Download PDF

Info

Publication number
US3925016A
US3925016A US314489A US31448972A US3925016A US 3925016 A US3925016 A US 3925016A US 314489 A US314489 A US 314489A US 31448972 A US31448972 A US 31448972A US 3925016 A US3925016 A US 3925016A
Authority
US
United States
Prior art keywords
formula
anionic compound
anionic
dyeing
preparation
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
US314489A
Other languages
English (en)
Inventor
Jaroslav Haase
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 AG
Original Assignee
Ciba Geigy AG
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 AG filed Critical Ciba Geigy AG
Publication of USB314489I5 publication Critical patent/USB314489I5/en
Application granted granted Critical
Publication of US3925016A publication Critical patent/US3925016A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts
    • D06P1/625—Aromatic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
    • 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
    • D06P3/70—Material containing nitrile groups
    • D06P3/76—Material containing nitrile groups using basic 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • ABSTRACT A process for dyeing polyacrylonitrile textile materials with basic dyes in acid aqueous dyeing baths is provided.
  • the process is carried out in the presence of anionic assistants of the formula -R B 1 MG) wherein R represents an alkyl or alkylene radical with 7 to 21 carbon atoms, A is the group COO or OCO, B is a monoor binuclear aromatic radical, R represents hydrogen, hydroxyl, alkyl, alkoxy, cycloalkyl, aryl, aralkyl or halogen and M is an inorganic or organic cation.
  • the assistants display a good retardation and levelling action without the occurrence of blocking effects.
  • the dyed material is levelly dyed in light and dark shades and show good fastness properties.
  • the present invention provides a process for dyeing textile fibre material made from polyacrylonitrile with basic dyes in acid, aqueous dyeing preparations.
  • the process consists in using as dyeing assistant anionic compounds of the formula --A"IEB R Tao wherein R represents an alkyl or alkylene radical with 7 to 21 carbon atoms, A represents the group COO or OCO-, B represents a monoor binuclear aromatic radical, R represents a hydrogen atom, a hydroxyl group, an alkyl, alkoxy, cycloalkyl, aryl or aralkyl radical or a halogen atom, and M represents an inorganic or organic cation.
  • B may be, for example, a benzene, naphthalene or diphenyl radical.
  • R is, for example, a methyl, ethyl, propyl, amyl, decyl, methoxy, ethoxy or also a hydroxybutyl, hydroxyamyl or hydroxydecyl radical, also a cyclopentyl or cyclohexyl radical or a phenyl or benzyl radical, and furthermore too a chlorine, bromine or iodine atom.
  • the anionic compounds correspond to the formula wherein R represents an alkyl or alkylene redical with 11 to 18 carbon atoms, A represents the group COO or OCO--, B represents a benzene, naphthalene or diphenyl radical, R represents a hydrogen atom, an alkyl or alkoxy radical with l to carbon atoms, a 5- or 6-membered cycloalkyl radical, a benzyl or phenyl radical or a halogen atom, and M represents an inorganic or organic cation.
  • Particularly suitable anionic compounds correspond to the formulae wherein R and M have the indicated meanings and R is a hydrogen atom, an alkyl or alkoxy radical with 1 to 4 carbon atoms, preferably a methyl or methoxy group, or is a chlorine or bromine atom.
  • radicals R and R are alkyl and alkylene radicals which may be straight chain or branched, substituted or unsubstituted.
  • suitable substituents are halogen atoms or low molecular alkyl radicals with l to 4 carbon atoms.
  • Particularly suitable radicals R and R are the hydrocarbon radicals of' corresponding saturated and unsaturated fatty acids or fatty alcohols, e.g., the radicals of caprylic, capric, lauric, myristic, palmitic, stearic, arachidic, behenic, decenoic, dodecenoic, tetradecenoic, hexydecenoic or oleic acid. It is also possible to use radicals of polyunsaturated fatty acids, for example those of linoleic or linolenic acid.
  • M is an organic or preferably an inorganic cation.
  • Preferred inorganic cations are those of the alkali metal group, e.g., the lithium, but especially sodium and potassium cation, but also the ammonium ion.
  • organic cations there are used, for example, derivatives of organic amines which contain at least one protonised nitrogen atom, primary, secondary and tertiary monoand polyamines which are optionally further substituted being suitable.
  • the anionic compounds contain preferably at most two mononuclear aromatic radicals which occur independently in the molecule or also, it condensed, form a single binuclear radical. If, for example, B and B are benzene radicals, R and R may be phenyl or aralkyl radicals with up to 10 carbon atoms; but if they are naphthalene radicals, then R, and R should preferably not be aromatic radicals.
  • R represents a hydrogen atom or a methyl or methoxy group
  • M represents sodium, potassium or protonised mono-, dior triethanolamine
  • n represents a number from 11 to 18.
  • the S0 M group is usually in B-position to the CO0 and OCO group and R is preferably a hydrogen atom.
  • R is preferably a hydrogen atom.
  • a substitution in the orthoor meta-position is also possible.
  • the manufacture of the anionic compounds used for the present invention is known and is carried out e.g. by reacting fatty acid derivatives with corresponding phenolic or naphtholic compounds, or by reacting fatty alcohols with benzene or naphthalene derivatives which contain carboxylic acid groups or substituents which can be converted into such groups.
  • the amount of anionic assistant in the dyeing preparations is for example 0.1 to 5 percent, and preferably 1 to 3 percent, relative to the fibre material to be dyed.
  • the dyeing is carried out in liquors which have pH values of about 3 to 6, preferably 3.5 to 5.
  • the pH values are adjusted with mineral acids, or preferably with lower organic acids, such as formic, acetic, oxalic or tartaric acid.
  • the dyestuff preparation according to the invention preferably contains the customary salts and metal halide (preferably zinc chloride) double salts of the known cationic dyes, in particular the methine or azomethine dyes, which contain the indolinium, pyrazolium, imidazolium, triazolium, tetrazolium, oxdiazolium, thiodiazolium, oxazolium, thiazolium, pyridinium, pyrimidinium, or pyrazinium ring.
  • the cited heterocycles can be substituted and/or condensed with aromatic rings.
  • cationic dyes of the diphenylmethane, triphenylmethane, oxazine and triazine series are also possible.
  • dye salts of the arylazole and anthraquinone series with external onium group are also possible.
  • the amount of dye is about 0.5 to 5 percent, relative to the fibre material to be dyed.
  • the dyeing preparations can contain further assistants which are conventionally used in dyeing, for example non-ionic surface active compounds, in particular addition products of ethylene oxide and alcohols, phenols and amines, or organic solvents, in particular ethylene glycol monoethyl ether or thiodiethylene glycol, as well as ethylene carbonate.
  • non-ionic surface active compounds in particular addition products of ethylene oxide and alcohols, phenols and amines, or organic solvents, in particular ethylene glycol monoethyl ether or thiodiethylene glycol, as well as ethylene carbonate.
  • the dyeing process according to the invention can be applied to all acrylic or modacrylic textile materials, i.e., to all textile materials whose fibres are composed of homopolymers or copolymers in which acrylonitrile predominates.
  • Copolymers are for example those of acrylonitrile and other vinyl compounds, such as acrylic esters, acrylic amides, vinyl pyridine, vinyl chloride, vinylidene chloride, copolymers of dicyanoethylene and vinyl acetate, as well as of acrylonitrile block copolymers.
  • the fibre material can be dyed according to the invention in any desired form, for example as flocks, spinning cables, worsted tops, yarn, woven or knitted fabrics.
  • the textile material is dyed by means of known processes, preferably by the exhaust method, in dyeing machines and vessels suitable for the purpose, both under normal pressure and in sealed vessels under pressure.
  • the dyeing preparation according to the invention is appropriately manufactured by making the basic dye into a paste with the amount of acid or buffer salt acid to be used, pouring hot water on to the paste and then treating the resulting dye bath with the anionic assistants as well as, optionally, further assistants conventionally used in dyeing.
  • the preparations possess good stability.
  • the textile material is put into this liquor, which can have a temperature of from 50 to C, and then optionally the temperature of the liquor is increased in order to dye in the temperature range of from 80 to C, preferably at the boiling point of the liquor.
  • the liquor ratios are about 1:10 to 1:50, preferably 1:20 to 1:40.
  • the dyed material is subsequently washed and dried in the customary manner.
  • Dyeings of excellent levelness and good fastness properties are obtained with the process according to the invention for dyeing textile material made from polyacrylonitrile accompanied by the use of anionic assistants.
  • anionic assistants display a good retardation and levelling action without the occurrence of blocking effects.
  • no alteration of shade occurs during the dyeing process.
  • good exhaustion of the liquor is observed.
  • EXAMPLE 1 A fabric made from polyacrylonitrile (25 g) is put at 60C into a litre of dye liquor which contains 0.125 g of a dyestuff mixture consisting of: 25 parts of the dyestuff of the formula 65 parts of the dyestuff of the formula CHO S 3.2 g of glacial acetic acid, ml of 10% aqueous sodium hydroxide solution, and 0.2 g of the assistant of the formula C H COO $0 in solution.
  • the temperature of the dyebath is raised to boiling point and dyeing is carried out for 1 hour at this temperature.
  • the material dyed in this way is thereupon rinsed with lukewarm and cold water and dried. A uniform bluish grey dyeing is obtained under these conditions. No alteration of shade is observed during the dyeing.
  • the anionic assistant mentioned hereinabove is manufactured, for example, in the following way: 53 g of potassium-4-phenolsulphonate and 79 g of oleic acid C IN t ram. I 24 chloride are kept at to C for 20 hours in 20 ml of xylene, while stirring. The reaction mixture is cooled to about 1 10C, then diluted with 400 ml of ligroin, and filtered hot. The solvent is subsequently distilled off in vacuo and the residue is stirred once more with 300 ml 3 of ethyl acetate: alcohol (1:1) and filtered. The filter residue is washed with petroleum ether and dried in vacuo, to give 49.6 g of the water-soluble product of the formula e r1 co0 803K
  • the assistants listed in the following Table were obtained in similar manner.
  • a process for dyeing textile fibre material made from polyacrylonitrile comprising the step of treating the fibre material with a basic dye in an acidic, aqueous preparation, which further comprises as dyeing assistant an anionic compound of the formula CO-, B is benzene, naphthalene or diphenyl, R is hydrogen, hydroxyl, alkyl, hydroxyalkyl, alkoxy, cycloalkyl aryl, aralkyl or halogen, and M represents an inorganic or organic cation.
  • anionic compound is of the formula wherein R is alkyl or alkylene with 11 to 18 carbon atoms and R represents hydrogen, alkyl or alkoxy containing 1 to 10 carbon atoms, or halogen 3.
  • R is hydroxyl.
  • anionic compounds is of the formula wherein R is hydrogen, alkyl or alkoxy containing 1 to 4 carbon atoms, or chlorine or bromine.
  • anionic compound is of the formula SO36 M Rg- OCO wherein R is hydrogen, alkyl or alkoxy containing 1 to 4 carbon atoms, or chlorine or bromine.
  • anionic compound is of the formula in which R, is hydrogen, alkyl or alkoxy containing 1 to 4 carbon atoms, or is chlorine or bromine.
  • M R2- COO pound is of the formula wherein R represents hydrogen, chlorine or bromine or methyl or methoxy, M represents sodium, potassium, protonised mono-, dior triethanolamine, and n represents a whole number from 11 to l8.
  • a process of claim 10, wherein the anionic compound is of the formula (9 c n 00 o so M 22 12.
  • a process of claim 6, wherein the anionic compound is of the formula wherein M represents sodium, potassium, protonised mono-, dior triethanolamine, and n represents a whole number from 11 to 18.
  • anionic compound is of the formula wherein M represents sodium, potassium, protonised mono-, di or triethanolamine, and n represents a whole number from 11 to 18.
  • An acid aqueous dyeing preparation which contains at least one basic dye and an anionic compound of the formula RA B M R2A B M wherein R is an alkyl or alkylene radical with 11 to 18 carbon atoms, A is the group CO-O- or OCO,
  • R is hydrogen, alkyl or alkoxy with 1 to carbon the anionic compound is used. atoms, or halogen, and M is an inorganic or organic 23.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US314489A 1971-12-21 1972-12-12 Polyarcrylonitrile basic dyeing process with anionic assistant Expired - Lifetime US3925016A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1872071A CH550279B (de) 1971-12-21 1971-12-21 Verfahren zum faerben von textilfasermaterial aus polyacrylnitril.

Publications (2)

Publication Number Publication Date
USB314489I5 USB314489I5 (enrdf_load_stackoverflow) 1975-01-28
US3925016A true US3925016A (en) 1975-12-09

Family

ID=4434893

Family Applications (1)

Application Number Title Priority Date Filing Date
US314489A Expired - Lifetime US3925016A (en) 1971-12-21 1972-12-12 Polyarcrylonitrile basic dyeing process with anionic assistant

Country Status (13)

Country Link
US (1) US3925016A (enrdf_load_stackoverflow)
JP (1) JPS4868876A (enrdf_load_stackoverflow)
BE (1) BE793029A (enrdf_load_stackoverflow)
CA (1) CA983659A (enrdf_load_stackoverflow)
CH (2) CH1872071A4 (enrdf_load_stackoverflow)
DE (1) DE2260703A1 (enrdf_load_stackoverflow)
ES (1) ES409831A1 (enrdf_load_stackoverflow)
FR (1) FR2164619B1 (enrdf_load_stackoverflow)
GB (1) GB1367708A (enrdf_load_stackoverflow)
IT (1) IT974151B (enrdf_load_stackoverflow)
NL (1) NL7217106A (enrdf_load_stackoverflow)
SE (1) SE374768B (enrdf_load_stackoverflow)
ZA (1) ZA728775B (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4066395A (en) * 1974-12-02 1978-01-03 Ciba-Geigy Corporation Process for dyeing or printing aromatic polyamide fibres
US4303577A (en) * 1978-12-01 1981-12-01 Monsanto Company Polyamide antiozonants
EP0164786A3 (en) * 1984-06-08 1986-04-02 Shell Internationale Research Maatschappij B.V. A process for the preparation of p-isononanoyloxybenzenenesulphonate
US4867916A (en) * 1986-12-05 1989-09-19 Interox Chemicals Limited Ester manufacture
US4908474A (en) * 1987-06-02 1990-03-13 Interox Chemicals Limited Preparation of esters
WO2002090110A1 (en) * 2001-05-09 2002-11-14 Glen Raven, Inc. Flame-resistant and high visibility fabric and apparel formed therefrom
US20030203688A1 (en) * 2001-05-09 2003-10-30 Campbell Willis D. Flame-resistant and high visibility fabric and apparel formed therefrom
US20040077241A1 (en) * 2001-05-09 2004-04-22 Campbell Willis D. Flame-resistant, high visibility, anti-static fabric and apparel formed therefrom
US20060068664A1 (en) * 2001-05-09 2006-03-30 Gibson Richard M Flame-resistant, high visibility, anti-static fabric and apparel formed therefrom

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4537724A (en) * 1983-05-11 1985-08-27 Ethyl Corporation Alkanoyloxybenzenesulfonate salt production
DE4317075A1 (de) * 1993-05-21 1994-11-24 Bayer Ag Lithiumhaltige Färbereihilfsmittel für Färberei und Druckerei

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2133288A (en) * 1935-09-25 1938-10-18 Nat Aniline & Chem Co Inc Dyeing
US2250098A (en) * 1937-08-03 1941-07-22 Gen Aniline & Film Corp Process of preparing water-containing dyestuff preparations of high concentration
US2310074A (en) * 1938-05-05 1943-02-02 Unichem Chemikalien Handels A Treatment bath
FR1355971A (fr) * 1963-04-24 1964-03-20 Courtaulds Ltd Perfectionnements à la teinture de fibres textiles, plus particulièrement de fibres acryliques
US3164566A (en) * 1961-11-01 1965-01-05 Union Carbide Corp Dyeable linear polyesters modified by a metallosulfophenoxyalkoxy-substituted aromatic dicarboxylic acid or ester
US3451762A (en) * 1964-07-25 1969-06-24 Bayer Ag Process for the continuous coloring of fibres made from natural or synthetic polyamides or of materials containing fibres of this type
DE1938227A1 (de) * 1969-07-28 1971-02-11 Hoechst Ag Verfahren zur Herstellung von Mono- und Dicarbomethoxybenzolsulfonaten
US3619123A (en) * 1967-08-07 1971-11-09 Bayer Ag Process for dyeing fiber materials of synthetic polyamides with acid dyestuffs
US3619122A (en) * 1968-12-26 1971-11-09 Gaf Corp Process for dyeing polyamide fibers
US3687603A (en) * 1967-11-08 1972-08-29 Ciba Geigy Ag Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids
US3713768A (en) * 1970-11-12 1973-01-30 Ciba Geigy Ag Long chain alkane or alkene amido benzene sulfonate assisted dyeing of synthetic linear polyamides
US3718428A (en) * 1970-12-21 1973-02-27 Gaf Corp Alcoholic composition of a cationic dye-alkyl aryl sulfonic acid complex and process of dyeing therewith
US3765835A (en) * 1968-04-25 1973-10-16 Du Pont Anionic dispersion of a salt of a cationic dye and a selected arylsulfonate
US3775056A (en) * 1971-06-30 1973-11-27 M Grossmann Disperse dyes and sulfosuccinate semi esters of polyalkylene glyol ethers of alkylphenols or phenol-formaldehyde condensates

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2133288A (en) * 1935-09-25 1938-10-18 Nat Aniline & Chem Co Inc Dyeing
US2250098A (en) * 1937-08-03 1941-07-22 Gen Aniline & Film Corp Process of preparing water-containing dyestuff preparations of high concentration
US2310074A (en) * 1938-05-05 1943-02-02 Unichem Chemikalien Handels A Treatment bath
US3164566A (en) * 1961-11-01 1965-01-05 Union Carbide Corp Dyeable linear polyesters modified by a metallosulfophenoxyalkoxy-substituted aromatic dicarboxylic acid or ester
FR1355971A (fr) * 1963-04-24 1964-03-20 Courtaulds Ltd Perfectionnements à la teinture de fibres textiles, plus particulièrement de fibres acryliques
US3451762A (en) * 1964-07-25 1969-06-24 Bayer Ag Process for the continuous coloring of fibres made from natural or synthetic polyamides or of materials containing fibres of this type
US3619123A (en) * 1967-08-07 1971-11-09 Bayer Ag Process for dyeing fiber materials of synthetic polyamides with acid dyestuffs
US3687603A (en) * 1967-11-08 1972-08-29 Ciba Geigy Ag Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids
US3765835A (en) * 1968-04-25 1973-10-16 Du Pont Anionic dispersion of a salt of a cationic dye and a selected arylsulfonate
US3619122A (en) * 1968-12-26 1971-11-09 Gaf Corp Process for dyeing polyamide fibers
DE1938227A1 (de) * 1969-07-28 1971-02-11 Hoechst Ag Verfahren zur Herstellung von Mono- und Dicarbomethoxybenzolsulfonaten
US3713768A (en) * 1970-11-12 1973-01-30 Ciba Geigy Ag Long chain alkane or alkene amido benzene sulfonate assisted dyeing of synthetic linear polyamides
US3718428A (en) * 1970-12-21 1973-02-27 Gaf Corp Alcoholic composition of a cationic dye-alkyl aryl sulfonic acid complex and process of dyeing therewith
US3775056A (en) * 1971-06-30 1973-11-27 M Grossmann Disperse dyes and sulfosuccinate semi esters of polyalkylene glyol ethers of alkylphenols or phenol-formaldehyde condensates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chem. Abstracts, Vol. 48, (1954), Column 1771i *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4066395A (en) * 1974-12-02 1978-01-03 Ciba-Geigy Corporation Process for dyeing or printing aromatic polyamide fibres
US4303577A (en) * 1978-12-01 1981-12-01 Monsanto Company Polyamide antiozonants
EP0164786A3 (en) * 1984-06-08 1986-04-02 Shell Internationale Research Maatschappij B.V. A process for the preparation of p-isononanoyloxybenzenenesulphonate
US4867916A (en) * 1986-12-05 1989-09-19 Interox Chemicals Limited Ester manufacture
US4908474A (en) * 1987-06-02 1990-03-13 Interox Chemicals Limited Preparation of esters
US20020168908A1 (en) * 2001-05-09 2002-11-14 Gibson Richard M. Flame-resistant and high visibility fabric and apparel formed therefrom
WO2002090110A1 (en) * 2001-05-09 2002-11-14 Glen Raven, Inc. Flame-resistant and high visibility fabric and apparel formed therefrom
US20030203688A1 (en) * 2001-05-09 2003-10-30 Campbell Willis D. Flame-resistant and high visibility fabric and apparel formed therefrom
US6706650B2 (en) * 2001-05-09 2004-03-16 Glen Raven, Inc. Flame-resistant and high visibility fabric and apparel formed therefrom
US20040077241A1 (en) * 2001-05-09 2004-04-22 Campbell Willis D. Flame-resistant, high visibility, anti-static fabric and apparel formed therefrom
US6787228B2 (en) * 2001-05-09 2004-09-07 Glen Raven, Inc. Flame-resistant and high visibility fabric and apparel formed therefrom
US6946412B2 (en) * 2001-05-09 2005-09-20 Glen Raven, Inc. Flame-resistant, high visibility, anti-static fabric and apparel formed therefrom
US20060068664A1 (en) * 2001-05-09 2006-03-30 Gibson Richard M Flame-resistant, high visibility, anti-static fabric and apparel formed therefrom
US7419922B2 (en) 2001-05-09 2008-09-02 Gibson Richard M Flame-resistant, high visibility, anti-static fabric and apparel formed therefrom
WO2003093544A1 (en) * 2002-04-30 2003-11-13 Glen Raven, Inc. Flame-resistant and high visibility fabric and apparel formed therefrom

Also Published As

Publication number Publication date
JPS4868876A (enrdf_load_stackoverflow) 1973-09-19
FR2164619A1 (enrdf_load_stackoverflow) 1973-08-03
CH1872071A4 (enrdf_load_stackoverflow) 1973-11-15
GB1367708A (en) 1974-09-18
ES409831A1 (es) 1976-09-01
BE793029A (fr) 1973-06-20
FR2164619B1 (enrdf_load_stackoverflow) 1976-06-04
ZA728775B (en) 1973-08-29
SE374768B (enrdf_load_stackoverflow) 1975-03-17
NL7217106A (enrdf_load_stackoverflow) 1973-06-25
DE2260703A1 (de) 1973-06-28
USB314489I5 (enrdf_load_stackoverflow) 1975-01-28
CA983659A (en) 1976-02-17
CH550279B (de) 1974-06-14
IT974151B (it) 1974-06-20

Similar Documents

Publication Publication Date Title
US3925016A (en) Polyarcrylonitrile basic dyeing process with anionic assistant
US2737517A (en) Quaternary ammonium anthraquinone salts
US2235480A (en) Amidelike derivatives and process of making the same
US3076821A (en) (1-amino-2-anthraquinonyl carbonylamino)-alkyl-1uaternary ammonium salts
US3770371A (en) Stable aqueous dispersions of cationic dyestuffs
US3104931A (en) Process for dyeing wool
US2967755A (en) Leveling and stripping agents
US2183754A (en) Process of dyeing
US2716655A (en) Dyes and dye intermediates of the anthraquinone series
US2017119A (en) Treatment of textile and other materials
US2891835A (en) Diquaternary ammonium compounds used in the cationic dyeing of fibers of polyacrylonitrile
US3096142A (en) Process for dye levelling with lactams
US2986444A (en) Production of level dyeings of basic dyestuffs on structures of acrylonitrile polymers
US3652201A (en) Process for the production of dyeings on fiber material consisting of polymeric or copolymeric acrylonitrile
US4074970A (en) Dyeing of synthetic fibers with cationic dyes in the presence of cationic assistants containing hydroxyl and cyclic moieties
US3236582A (en) Process of dyeing polyurethane shaped article with water-soluble reactive dyestuffs
US3281201A (en) Process for dyeing of nylon fibers with premetallized and acid dyestuffs
US3616473A (en) Dyeing-assistants for synthetic fibers
US2155135A (en) Hydroxylated polyamines and their use in dyeing with vat and sulphur dyestuffs
US2263387A (en) Process of dyeing
US3957433A (en) Dyeing additives
US2790003A (en) Basic polyglycol ethers
US3009761A (en) Polyquaternary ammonium compounds
US2094809A (en) Treatment of materials
US3658460A (en) Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds