US3273954A - Mixtures of quaternary ammonium dye assistants and dyeing retanned leather therewith - Google Patents

Mixtures of quaternary ammonium dye assistants and dyeing retanned leather therewith Download PDF

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US3273954A
US3273954A US304662A US30466263A US3273954A US 3273954 A US3273954 A US 3273954A US 304662 A US304662 A US 304662A US 30466263 A US30466263 A US 30466263A US 3273954 A US3273954 A US 3273954A
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Prior art keywords
leather
dyeing
quaternized
carbon atoms
shade
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US304662A
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Wachsmann Hubert
Bindler Jakob
Erny Max
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Novartis AG
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JR Geigy AG
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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
    • 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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/32—Material containing basic nitrogen containing amide groups leather skins
    • 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
    • Y10S8/90—Basic emulsifiers for dyeing
    • Y10S8/901—Quaternary ammonium salts
    • 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
    • Y10S8/907—Nonionic emulsifiers for 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/919—Paper

Definitions

  • these agents are bound very quickly and predominantly in places on the leather surface where there are greater amounts of tanning agent present so that uneven dyeing results.
  • cationic recharging of the surface generally leads to disturbances in subsequent anionic fatliquoring.
  • the treatment liquor to be used according to the invention must contain at least one anionic dyestufi' and, as shade-deepening agent, a quaternized salt of a condensation product produced from the following components:
  • the treatment liquor can contain still further auxiliaries used in dyeing or leather treatment.
  • the aliphatic monoamines and polyamines serving as component (a) in the formation of the said shade'deepening agent must contain one higher alkyl or alkenyl radical preferably with from 10 to 20* carbon atoms, such as the decyl, dodecyl, tetradecyl, hexadecyl, octadecyl or eicosyl or oleyl radical, as lipophilic radical, and from one to six amino nitrogen atoms.
  • the alkylene chain between two neighboring amino nitrogens is an uninterrupted chain 3,273,954 Patented Sept. 20, 1966 containing from 2 to 3 carbon atoms and is of one of the following configurations:
  • amines are, therefore, mono-higher alkylor monohigher alkenyl-substituted ammonia, ethylenediamine; propylenediamine, di-ethylenetriamine, triethylenetetramine, diaminodiethyl ether or bis-(aminoethyl)- glycol ether and the like, or mixtures of such amines which are substituted in the aforesaid manner.
  • the polyglycol ethers obtained are quaternized with the ester of a lower saturated aliphatic alcohol preferably methanol or ethanol or an araliphatic alcohol, particularly benzyl or phenylethyl, lower-alkyl-benzyl, chlorobenzyl or bromobenzyl alcohol with a strong acid, e.g.
  • an ester such as dimethy or diethyl sulfate, ethyl chloride, bromide or iodide or benzyl chloride, p-toluene sulfonic acid methyl or ethyl ester, methane sulfonic acid methyl or ethyl ester, chloroor bromo-acetic acid methyl or ethyl ester, or chloro- 0r bromo-propionic acid methyl or ethyl ester, but preferably with dimethyl sulfate, to form the shade-deepening agent, according to the invention.
  • an ester such as dimethy or diethyl sulfate, ethyl chloride, bromide or iodide or benzyl chloride, p-toluene sulfonic acid methyl or ethyl ester, methane sulfonic acid methyl or ethyl este
  • Very good shade-deepening and levelling action is obtained by the use of a condensation product of an aliphatic polyamine of the structure defined above containing from 2 to 4 basic nitrogen atoms and an alkyl or alkenyl radical of 10 to 20 carbon atoms, with ethylene oxide in a molar ratio of 10:1 to 200:1 quaternized with a lower alkyl sulfate, tosylate or mesylate.
  • the polyglycol ether produced from 1 equivalent of octadecyl diethylenetriarnine and 20 equivalents of ethylene oxide and quaternized with dimethyl sulfate has been found to give optimal results.
  • auxiliaries which can be contained in the treatment liquor are analogously quaternized addition products of less than 10 equivalents of ethylene oxide.
  • a dyebath of the type described hereinbefore which contains a shadedeepening mixture consisting of (I) a shade deepening agent of components (a) and (b), and optionally (c), as defined above, and at least one of the following (II) basic fixing agents, used hitherto for after-treatment of dyeings with anionic dyestuffs: on cellulose, namely (1) a quaternary salt of an organic tertiary monoamine having per molecule one amino group and from one to two aliphatic or cycloaliphatic radicals having at least 1-0 and preferably not more than 30 carbon atoms, as the substituent or substituents of the amino nitrogen, the remaining one or two nitrogen bonds being substituted with lower alkyl; such amines being, for instance, N-dodecyl-N,N-dimethylor -dietihyl-amine l-(p-methylphenyl)-l-amino
  • di-tertiary diamines e.g. N,N,N',N'-tetramethyl-ethylenediamine with (b) aliphatic dihalides, especially dichlorides, dibromides or di-iodies, the carbon chain of which contains 2 to 6 carbon atoms and is uninterrupted or interrupted by one to two oxygen atoms, in molar ratio of from 2:3 to 3:2, particularly valuable compounds being, for example, the condensation product of 2 moles of N,N,N', N",N"-pentarnethyl-diethylenetriamine and 3 moles of'fl, l3-dichlorodiethyl ether or the condensation product of N,N,N',N'-tetramethyl-ethylenediamine and 1,4-dibromobutane;
  • aliphatic dihalides especially dichlorides, dibromides or di-iodies, the carbon chain of which contains 2 to 6 carbon atoms and is uninterrupted or interrupted by one to two oxygen atoms,
  • peralkylated polyethylene polyamines such as are obtained by polymerisation of ethylene imine, subsequently quaternized With lower alkyl halides, especially chlorides, bromide and iodides, or di(lower alkyl)sulfates.
  • the anionic dyestuffs used in the dyebaths for leather according to the invention are those usual in leather dyeing. They can be of any class of dyestuffs; preferably they are of the easily accessible azo, anthraquinone, phthalocyaninc or nitro class of dyestuffs. Examples of azo dyestuffs are unmetallized or metallized, e.g.
  • anthraquinone dyestuffs are condensation products of 1-amino-2-sulfo-4-bromoanthraquinone or 1,4-dihydroxyanthraquinone with preferably aromatic-amines, in particular with an aniline or phenylene-diamine.
  • dyestuffs preferably contain acid, water solubilizing groups, especially sulfonic acid groups; in addition they can contain the following substituents: lower alkyl, lower alkoxy, hydroxyl, amino, lower alkanoylamino, lower alkanoyl carbamyl and sulfamyl groups, including N-substituted, preferably monoor dilower alkylor N-phenyl or benzylsubstituted carbamyl or sulfamyl, lower alkoxycarbonyl, phenoxy-sulfonyl, lower alkylphenoxy-sulfonyl, chlorophenoxyor bromophenoxy-sulfonyl, lower alkyl-sulfonyl, phenylsulfonyl, lower alkyl-phenylsulfonyl, chloroor bromo-phenylsulfonyl uitro, cyano, trifiuoromethyl groups,
  • the dyebaths according to the invention may also contain further auxiliary agents such as polycondensation products of poly-(halogenoalkyl)-amines and amines, or polycondensation products of w-aminoalkyl halides or w-aminoalkanol sulfates the carbon chain of which can be interrupted by hetero atoms and the amino group of which can be primray, secondary or tertiary, such as quaternized polycondensation products of ,B-aminoethyl halides or of 'y-arninopropyl halides; or quaternary compounds from dimethylamine with epichlorohydrin or with glycerin-1x,oU-dichlorohydrin, or quaternized polycondensation products of carboxylic acid amides or N-monoalkylamides having 4
  • auxiliary agents such as polycondensation products of poly-(halogenoalkyl)-amines and amines,
  • the leather is treated with the dye liquor to be used according to the invention either in the dye bath at temperatures of 4060 C. for about 45 to preferably not longer than minutes, or by spraying or brushing.
  • the content in the dye bath of quaternary ammonium compounds as defined under (1) supra is advantageously up to at least about 0.1 and 3%, and preferably 0.3 to 1.5% by weight, that of any cation-active poly-compounds present such as the basic fixing agents defined under (II) from at least about 0.05 up to not more than 1.5%, and preferably 0.1 to 0.8% calculated on the wet leather which has been pressed out to a water content of about 50%.
  • Example 1 grams (g.) of re-ta-nned chrome leather (shaved weight) are circulated in a solution of 0.5 g. of the azo dyestufi Acid Black 1 Color Index (C.I.) No. 20,470 and water for 30 minutes at 60 in a small rotating drum. A mixture of 0.4 g. of a condensation product of 1 equivalent octadecyl diethylenetriamine and 20 equivalents of ethylene oxide quaternized with dimethyl sulfate as well as 0.1 g.
  • C.I. azo dyestufi Acid Black 1 Color Index
  • Example 3 Equally advantageous leather dyeings are obtained by using, instead OLf the, in all, 0.5 g. of the mixture of additives mentioned in Example 1, 0.2 g. of the polyglycol ether produced from octadecyl diethylenetriamine and 20 gram-equivalents of ethylene oxide quaternized with diethyl sulfate and 0.1 g. of the polycondensation product of 1,4-dibromobutane and N,N,N.',N-tetramethylenediamine; otherwise following the procedure in Example 1.
  • Example 4 beautifully rfast dyeings are obtained on replacing the, in all, 0.5 g. of the combination of additives mentioned in Example 1 by 1 g. d the polyglycol ether produced from octadecyl diethylenetriamine and 20 gramequivalents of ethylene oxide quaternized with dimethyl sulfate, and by 0.5 g. of the polyglycol ether obtained by polyaddition of oleylamine with 5 gram-equivalents of ethylene oxide, 1 gram-equivalent of styrene oxide and 1 gram-equivalent of propylene oxide and by otherwise following the same procedure.
  • Example 5 Beautiful deep leather dyeings are obtained on using the additives mentioned in Example 4 in amounts of 0.5 g. of each instead of 1 g. and 0.5 g. respectively; otherwise the procedure given in Example 1 is followed.
  • Example 6 Equally beautiful dyeings are obtained by repeating Example 1, but replacing the combination of additives used in Example 1 by 0.4 g. of the polyglycol ether produced from octadecyl propylenediamine or from lauryl diethylenetriamine or from cetyl ethylened-iamine or from stearyl ethylenediamine and 20 gram-equivalents of ethylene oxide quaternized with dimethyl sulfate and by 0.1 g. of l-(p-methylp henyl)-1-aminododecane, quaternized with methyl bromide.
  • the polyglycol ether produced from octadecyl propylenediamine or from lauryl diethylenetriamine or from cetyl ethylened-iamine or from stearyl ethylenediamine and 20 gram-equivalents of ethylene oxide quaternized with dimethyl sulfate and by 0.1 g. of l-(p-methylp
  • Example 7 The same dyeing effects are also attained by replacing the 0.1 g. of quaternized l-(p-methylphenyl)-l-aminododecane mentioned in Example 6 by the same amounts of N-dodecyl-N,N-dimethylamine quaternized with benzyl chloride or by poly-N-,8 chloroethyl-N,N-diethylamine or by polyethyleneimine quaternized with methyl iodide.
  • Example 8 100 g. of re-tanned chrome leather (shaved weight) are circulated in a solution of 0.5 g. of Cl. Acid Brown 188 in 500 ml. of water for 30 minutes at 60? in a small rotating drum. 1 g. of the polyglycol ether produced from octadecyl diethylenetriamine and SO gram-equivalents of ethylene oxide quaternized with dimethyl sulfate in 5 ml. of water are added through the hollow shaft of the rotating drum and the drum is run for 20 minutes. Another 0.5 g. of the dyestulf mentioned are then added, the drum is run for another 20 minutes, 0.3 g. of 85% formic acid in 3 ml. of water are finally added and the drum is again rotated for 20 minutes. The leather is then fat-liquored in the usual way in the same bath and finished.
  • Example 9 By using, instead of the 1 g. of the additive mentioned in Example 8, the same amounts of the analogous polyglycol ethers derived from oleylamine, dodecylamine, hexadecylamine or octadecylarnine and otherwise following the procedure described in Example 8, equally good dyeings are obtained.
  • An aqueous dyeing liquor for the dyeing of re-tanned leather in deep color shades comprising, as essential ingredients (1) an anionic leather dyestuff,
  • a shade-deepening mixture consisting essentially of (I) the quaternized salt of a condensation product (a) an aliphatic amine containing, per mole cule, from one to six amino nitrogen atoms, one lipophilic N-substituent being a member selected from the group consisting of alkyl with from 10 to 20 carbon atoms and alkenyl with from 10 to 20 carbon atoms, and, between every two adjacent amino nitrogens in amines with more than one nitrogen atom, a linking member selected from the group consisting of CH CH CH -CH CH CH2OH- CH3 -CH -CH OCH CH and CH; -CI-I OCHzCH2OCHzCH2- (b) from 10 IR) 200 moles, per mole of (a),
  • a member selected from the group consisting of styrene oxide and propylene oxide quaternized with a member selected from the group consisting of the esters of a strong acid with one of the following: a lower saturated aliphatic alcohol, benzyl alcohol, phenyl-ethyl alcohol, chlorobenzyl alcohol, bromobenzyl alcohol and lower alkyl-benzyl alcohol; and
  • a shade-deepening mixture consisting essentially of (I) the quaternized salt of a condensation product (a) an aliphatic amine containing per molecule from one to six amino nitrogen atoms, one lipophilic N-substituent being a member selected from the group consisting of alkyl with from 10 to 20 carbon atoms and alkenyl with from 10 to 20 carbon atoms, and, between every two adjacent amino nitrogens in amines with more than one nitrogen atom, a linking member selected from the group consisting of (b) from 10 to 200 moles, per mole of (a),
  • a member selected from the group consisting of styrene oxide and propylene oxide quaternized with a member selected from the group consisting of the esters of a strong acid with one of the following: a lower saturated aliphatic alcohol, benzyl alcohol, phenyl-ethyl alcohol, chlorobenzyl alcohol, bromobenzyl alcohol and lower alkyl-benzyl alcohol; and
  • a basic fixing agent selected from the group consisting of (i) a quaternary salt of an organic tertiary monoamine having per molecule from 1 to 2 alkyl radicals of at least 1 and not more than 30 carbon atoms, said alkyl radical being a substituent of the amino nitrogen atom, the remaining nitrogen bonds being substituted with lower alkyl, and (ii) the condensation product of (a) a polytertiary polyamine with from 2 to 5 amino nitrogen atoms, two to four of which are tertiary nitrogen atoms, and with a linking alkylene chain of 2 to 3 carbon atoms between every two adjacent amino nitrogen atoms, with 8) a straight chain aliphatic dihalide the halogen atoms of which are of an atomic number ranging from 17 to 53 and the aliphatic chain of which is 2 to 6 carbon atoms interrupted by from 0 to 2 oxygen atoms, the molar ratio of (oz) to (/3) ranging from about 2:3 to 3
  • a shade-deepening mixture for use in aqueous dyebaths for the dyeing of re-tanned leather with anionic leather dyes which mixture consists essentially of (I) the quaternized salt of a condensation product of (a) an aliphatic amine containing, per molecule, from one to six amino nitrogen atoms, one lipophilic N-substituent being a member selected from the group consisting of alkyl with from 10 to 20 carbon atoms and alkenyl with from 10 to 20 carbon atoms, and, between every two adjacent amino nitrogens in amines with more than one nitrogen atom, a linking member selected from the group consisting of (b) from 10 to 200 moles, per mole of (a), of
  • ethylene oxide and (c) from 0 to 2 moles, per mole of (a), of a member selected from the group consisting of styrene oxide and propylene oxide, quaternized with a member selected from the group consisting of the esters of a strong acid with one of the following: a lower saturated aliphatic alcohol, benzyl alcohol, phenyl-ethyl alcohol, chlorobenzyl alcohol, bromobenzyl alcohol and lower alkyl-benzyl alcohol; and
  • a basic fixing agent selected from the group consisting of (a) a quaternary salt of an organic tertiary monoamine having per molecule from 1 to 2 alkyl radicals of at least 10 and not more than 30 carbon atoms, said alkyl radical being a substituent of the amino nitrogen atom, the remaining nitrogen bonds being substituted with lower alkyl, and (b) the condensation product of (a) a polytertiary polyamine with from 2 to '5 amino nitrogen atoms, two to four of which are tertiary nitrogen atoms, and with a linking alkylene chain of 2 mo 3 carbon atoms between every two adjacent amino nitrogen atoms, with (,8) a straight-chain aliphatic dihalide, the halogen atoms of which are of an atomic number ranging from 17 to 53 and the aliphatic chain of which is of 2 to 6 carbon atoms interrupted by from (l to 2 oxygen atoms, the molar ratio of (oz) to (,6) ranging from about
  • a shade-deepening mixture for use in aqueous dyebaths for the dyeing of re-tanned leather with anionic leather dyes which mixture consists essentially of (I) a condensation product of 1 equivalent of octadecyl diethylenetriamine and 20 gram equivalents ethylene oxide, quaternized with dimethyl sulfate, and
  • (II) a polycondensation product of 2 moles of N,N,N',N",N" pentamethyl diethylene triamine and 3 moles of ,B,,B-dichlorodiethyl ether, in a weight ratio of (I) to (II) equal to about 4:1.
  • a shade-deepening mixture for use in aqueous dyebaths for the dyeing of re-tanned leather with anionic leather dyes which mixture consists essentially of (I) a condensation product of 1 equivalent of oleylamine with 20 equivalents of ethylene oxide, 1 equivalent of styrene oxide and 1 equivalent. of propylene oxide, quaternized with dimethyl sulfate, and

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US304662A 1962-09-14 1963-08-26 Mixtures of quaternary ammonium dye assistants and dyeing retanned leather therewith Expired - Lifetime US3273954A (en)

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CH1094662A CH415542A (de) 1962-09-14 1962-09-14 Verfahren zum Färben von Leder

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355243A (en) * 1963-06-11 1967-11-28 Geigy Ag J R Process for the dyeing of polyacrylonitrile fibers
US4290767A (en) * 1978-09-29 1981-09-22 Ciba-Geigy Corporation Process for slop-padding textile cellulose material
US4717390A (en) * 1985-01-30 1988-01-05 Sandoz Ltd. Method for dyeing leather with water-soluble sulpho group-containing sulphur dyes
US4717389A (en) * 1985-06-05 1988-01-05 Sandoz Ltd. Hair-reserving dyeing of wool- and fur-bearing skins
US20050153860A1 (en) * 2003-12-19 2005-07-14 Shankang Zhou Hydrophobic polyamine ethoxylates

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228369A (en) * 1933-12-20 1941-01-14 Gen Aniline & Film Corp Dyeing animal fibrous materials
GB705335A (en) * 1950-12-29 1954-03-10 Ciba Ltd Process for dyeing leather
DE960178C (de) * 1952-12-21 1957-03-21 Bayer Ag Verfahren zur Verbesserung der Echtheitseigenschaften substantiver Faerbungen auf Cellulosefasern
US2967755A (en) * 1957-02-05 1961-01-10 Sandoz Ltd Leveling and stripping agents
FR1261845A (fr) * 1959-07-08 1961-05-19 Geigy Ag J R Nouveaux composés tensio-actifs non ioniques et leur préparation
US3097039A (en) * 1963-07-09 Hoas oh
US3104931A (en) * 1958-03-11 1963-09-24 Ciba Geigy Corp Process for dyeing wool

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097039A (en) * 1963-07-09 Hoas oh
US2228369A (en) * 1933-12-20 1941-01-14 Gen Aniline & Film Corp Dyeing animal fibrous materials
GB705335A (en) * 1950-12-29 1954-03-10 Ciba Ltd Process for dyeing leather
US2763528A (en) * 1950-12-29 1956-09-18 Ciba Ltd Process for dyeing leather with acid and direct dyes
DE960178C (de) * 1952-12-21 1957-03-21 Bayer Ag Verfahren zur Verbesserung der Echtheitseigenschaften substantiver Faerbungen auf Cellulosefasern
US2967755A (en) * 1957-02-05 1961-01-10 Sandoz Ltd Leveling and stripping agents
US3104931A (en) * 1958-03-11 1963-09-24 Ciba Geigy Corp Process for dyeing wool
FR1261845A (fr) * 1959-07-08 1961-05-19 Geigy Ag J R Nouveaux composés tensio-actifs non ioniques et leur préparation

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355243A (en) * 1963-06-11 1967-11-28 Geigy Ag J R Process for the dyeing of polyacrylonitrile fibers
US4290767A (en) * 1978-09-29 1981-09-22 Ciba-Geigy Corporation Process for slop-padding textile cellulose material
US4717390A (en) * 1985-01-30 1988-01-05 Sandoz Ltd. Method for dyeing leather with water-soluble sulpho group-containing sulphur dyes
US4717389A (en) * 1985-06-05 1988-01-05 Sandoz Ltd. Hair-reserving dyeing of wool- and fur-bearing skins
US20050153860A1 (en) * 2003-12-19 2005-07-14 Shankang Zhou Hydrophobic polyamine ethoxylates
WO2005063850A1 (en) * 2003-12-19 2005-07-14 The Procter & Gamble Company Hydrophobic polyamine ethoxylates

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GB1006918A (en) 1965-10-06
CH415542A (de) 1966-06-30
BE637366A (en)van)

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