Sulfur Dye (sulfur-organic Reaction Product Dye) Patents (Class 8/652)
  • Patent number: 4950306
    Abstract: Process for dyeing and printing cellulosic fiber materials with vat dyes in the presence of enediols as reducing agents and alkali, using in addition small amount of organic water-miscible solvents, for example low molecular weight alcohols, when reducing the vat dyes. The vatting of the vat dyes proceeds uniformly and completely within a relatively short time, and the resulting vat dyes are reproducible and notable for high levelness and fastness properties.
    Type: Grant
    Filed: July 27, 1989
    Date of Patent: August 21, 1990
    Assignee: Ciba-Geigy Corporatioin
    Inventors: Walter Marte, Paul Rys
  • Patent number: 4917706
    Abstract: Liquid compositions of sulfur dyes in reduced form are obtained by reducing a sulfur dye in an alkaline medium to which no sulfide reducing agent has been added, preferably employing a reducing sugar as reducing agent and a sulfur dye which has been washed to remove inorganic salts therefrom.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: April 17, 1990
    Assignee: Sandoz Ltd.
    Inventor: Laszlo A. Meszaros
  • Patent number: 4886518
    Abstract: A process for dyeing cellulose fibres or cellulose-containing blend fibres with vat dyes, sulfur dyes, leuco vat ester dyes or azoic dyes by the pad dyeing process without incurring ending, in which an aqueous dyeing liquor is used which, aside from the dye, contains a colorless compound of the formula ##STR1## or of the formula ##STR2## where Q is ##STR3## or .dbd.N--, Y is hydrogen, halogen, cyano, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkylsulfonyl,V and W, independently of each other, are each R.sub.2 --X.sub.2 --, R.sub.3 --X.sub.3 --, hydroxyl C.sub.1 --C.sub.5 alkoxy or an unsubstituted or C.sub.1 --C.sub.5 alkyl-- or C.sub.5 --C.sub.6 cycloalkyl-monosubstituted or --disubstituted amino group, the alkyl radical being unsubstituted or substituted by hydroxyl, cyano, sulfo or sulfato,R.sub.1, R.sub.2 and R.sub.3, independently of one another, are each an aromatic or heteroaromatic radical,X.sub.1, X.sub.2 and X.sub.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: December 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Sire
  • Patent number: 4886549
    Abstract: Specific vatting accelerators according to claims 1 and 2 are described. These can be added to a vat dye or sulfur dye composition, or to a dye bath or printing paste containing a vat dye or sulfue dye, by virtue of which an improvement of dye yield, particularly on cellulose materials, is obtained.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: December 12, 1989
    Assignee: Ciba-Geiegy Corporation
    Inventor: Zdenek Koci
  • Patent number: 4838896
    Abstract: A mixture of a textile auxiliary (T) obtained by reacting epichlorohydrin and ammonia in defined mole ratio, and a polymeric compound (P) which is a water-soluble homopolymer of a mono- or di-allylamine, or a water-soluble copolymer consisting of mono-, di- or tri-allylamine units may be used as an aftertreatment agent for fixation of anionic and sulphur dyeings on cellulosic fibres. The treated dyeings have better fastness properties than dyeings treated with either (T) or (P) alone.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: June 13, 1989
    Assignee: Sandoz Ltd.
    Inventors: Bruno Kissling, Tibor Robinson
  • Patent number: 4810254
    Abstract: The wet-fastness properties of cellulose materials dyed with sulfur dyestuffs is improved by treating the cellulose materials, before, during or after dyeing, with a polymer which is a copolymer or homopolymer of a monomer of the formula ##STR1## wherein R.sup.1 and R.sup.2 denote, for example, hydrogen or (C.sub.1 -C.sub.22)-alkyl; R.sup.3 and R.sup.4 denote hydrogen or methyl; and Y.sup..crclbar. denotes, for example, a monovalent anion.
    Type: Grant
    Filed: January 27, 1988
    Date of Patent: March 7, 1989
    Assignee: Cassella Aktiengesellschaft
    Inventors: Wolfgang Bauer, Karl-Heinz Keil, Gert Nagl, Manfred Kaiser, Joachim Steinbach, Klaus Sternberger
  • Patent number: 4801303
    Abstract: Polyester-cotton blend textile substrates are dyed with a disperse dye and then with a sulfur dye from the same dyebath which is maintained at a temperature no higher than 105.degree. C. when the sulfur dye is present therein and which preferably contains glucose as the reducing agent for the sulfur dye.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: January 31, 1989
    Assignee: Sandoz Ltd.
    Inventors: Mark S. Carlough, Laszlo A. Meszaros
  • Patent number: 4723961
    Abstract: The alkaline reoxidation of vat and sulfur vat dyes by means of hydrogen peroxide is difficult to control and to keep constant. By using agents which split off hypochlorite in the heat, for example sodium N-chloro-p-toluenesulfonamide, at pH values above 8 it is possible according to the invention even to reoxidize reliably combinations of these dyes having different oxidation behaviors. At the same time it became possible to combine the necessary soaping process with reoxidation.
    Type: Grant
    Filed: September 9, 1986
    Date of Patent: February 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Heinrich O. Bernhardt
  • Patent number: 4717389
    Abstract: A hair-reserving penetration dyeing of the leather side of wool- or fur-bearing skins is obtained by dyeing the wooled or fur skins in aqueous medium with hydrosoluble sulpho-group-containing sulphur dyes (a) in the presence of dye-substantive uptake assistant (b) and of non-ionic and/or anionic hydrophilic dispersants (c) and optionally in the presence of leather fatting agents (d).
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: January 5, 1988
    Assignee: Sandoz Ltd.
    Inventor: Rudolf Seitz
  • Patent number: 4519805
    Abstract: Specific vatting accelerators according to claims 1 and 2 are described. These can be added to a vat dye or sulfur dye composition, or to a dye bath or printing paste containing a vat dye or sulfur dye, by virtue of which an improvement of dye yield, particularly on cellulose materials, is obtained.
    Type: Grant
    Filed: December 29, 1981
    Date of Patent: May 28, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Zdenek Koci
  • Patent number: 4488880
    Abstract: The reoxidation of sulfur dyestuffs in an acid medium is associated with disadvantages, such as pollution of the environment, the risk of corrosion on equipment etc. Admittedly oxidation in an alkaline medium does not have these disadvantages, but it is, in turn, more difficult to control (dependence on pH and constancy of color shade).These difficulties are eliminated in accordance with the invention if the textile material containing cellulose fibers which has the sulfur dyestuffs in the reduced form applied and fixed thereto is subjected to the oxidative action of sodium benzenesulfochloroamide or p-toluenesulfochloroamide under alkaline conditions in order to develop the dyestuff. This can be carried out either continuously or discontinuously.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: December 18, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Heinrich Bernhardt
  • Patent number: 4465490
    Abstract: A process for the continuous dyeing of fabric webs, in which the fabric web is impregnated at a temperature between 20.degree. and 95.degree. C. with an aqueous liquor which contains dissolved and/or dispersed dyestuffs and squeezed, and the dyestuffs are fixed in a steam/air mixture, which comprises fixing the dyestuff without the impregnated fabric having been dried at an intermediate stage, keeping the dry temperature of the steam/air mixture between 110.degree. and 140.degree. C., adjusting the steam content of the steam air mixture in such a way that the wet temperature of the moist fabric web is between 50.degree. and 95.degree. C., and fixing the dyestuffs for at least 20 seconds.
    Type: Grant
    Filed: February 16, 1983
    Date of Patent: August 14, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Ulrich von der Eltz
  • Patent number: 4456453
    Abstract: The simultaneous oxidation and fixation are effected in the presence of a stable aqueous composition comprising an oxidation agent selected among the iodates and bromates of alkaline metals and a fixation agent selected among thermo-hardenable cationic resins.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: June 26, 1984
    Assignee: Manufacture de Produits Chimiques Protex
    Inventor: Jean Balland
  • Patent number: 4418014
    Abstract: The process for recovering recyclable sulphur from a strongly colored solution obtained from the production of sulphur dyestuffs containing alkali metal sulfides, alkali metal polysulfides, sulphur dyestuffs or mixtures thereof comprising(a) mixing said solution at an alkaline pH with a decolorizing amount of an iron or zinc compound which is a hydroxide or the salt of an inorganic acid whereby a precipitate is formed,(b) separating the precipitate to isolate a decolorized solution, and either(c) precipitating elemental sulphur from the decolorized solution by adding sulphur dioxide or alkali metal thiosulfate under acidic conditions, and(d) separating the precipitated elemental sulphur, or(e) recycling the decolorized solution for use in the manufacture of sulphur dyestuffs.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: November 29, 1983
    Assignee: Cassella Aktiengesellschaft
    Inventor: Georg Daniek
  • Patent number: 4403995
    Abstract: New sulphur dyestuffs are prepared by reacting sulphur with a 4-hydroxydiphenylamine of the formula ##STR1## wherein R and R.sup.1 denote hydrogen or alkyl having 1 to 4 carbon atoms and the nucleus A has at least one free ortho-position in relation to the imino group, in a first stage at an elevated temperature to form a thiazine compound which is then sulphurized in a second stage in a water-soluble solvent at an elevated temperature to produce the sulphur dyestuff, and wherein a molar ratio of first stage reactants of 1:(2 to 2.4) between the 4-hydroxydiphenylamine compound and sulphur is maintained.
    Type: Grant
    Filed: February 18, 1982
    Date of Patent: September 13, 1983
    Assignee: Cassella Aktiengesellschaft
    Inventor: Dieter Cornelius
  • Patent number: 4371373
    Abstract: Oxidation of dyeings with reduced vat and sulfur dyes, is accomplished in an improved manner with sodium chlorite under acid conditions of preferably pH 4.5-6 at 30.degree.-65.degree. C. in the presence of chelating agents which prevent the release of chlorine or chlorine compounds, such chelating agents being selected from derivatives of amino carboxylic acids, such as EDTA, and hydroxyalkane phosphonic acids.
    Type: Grant
    Filed: January 3, 1979
    Date of Patent: February 1, 1983
    Assignee: Manufacture de Produits Chimiques Protex
    Inventor: Jean Balland
  • Patent number: 4322214
    Abstract: Textile materials such as fiber and cloth can be dyed more satisfactorily with sulfur dyes or sulfurized vat dyes by allowing an organic mercapto compound and/or an organic sulfur compound capable of generating mercapto groups under dyeing conditions to be present in dye baths. Still more improved dyeing results may be obtained by allowing a sulfite salt compound to be further present in such dye baths.
    Type: Grant
    Filed: April 9, 1980
    Date of Patent: March 30, 1982
    Assignee: Asahi Chemical Company Limited
    Inventors: Osamu Manabe, Masayasu Utsunomiya, Morihiro Kamiyama, Michiaki Tsutsui, Masayuki Matsumoto
  • Patent number: 4321054
    Abstract: An acidic, aqueous oxidant including ionized bromate, iodate and a soluble molybdenum-containing material.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: March 23, 1982
    Assignee: The Dow Chemical Company
    Inventors: Ralph A. Davis, Randy C. Stauffer
  • Patent number: 4310332
    Abstract: The present invention relates to a process for the oxidation of sulphur dyes, particularly when they are incorporated in natural or regenerated cellulose textile fibres such as cotton, which employs an alternative oxidant to the ecologically undesirable dichromate now used. The process employs two steps, in the first of which the sulphur dyed textile is contacted with dilute hydrogen peroxide, very conveniently having a pH of 3-5 and at a temperature of from 40-80.degree. C. and in the second step, the textile is then contacted with a dilute solution of activator often ferric sulphate, preferably at pH 3-4 and from 0.1 to 1.0 g/l activator concentration. The process can be effected with relatively minor alteration or addition to existing equipment.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: January 12, 1982
    Assignee: Interox Chemicals Limited
    Inventor: Philip B. Curzons
  • Patent number: 4309178
    Abstract: In the processs for isolating solid sulphur dyestuffs from crude sulphur dyestuff melts, the improvement comprises adding 10.sup.-4 to 1% by weight, relative to the amount of dyestuff, of an organic flocculating auxiliary to the crude dyestuff melt to produce a filterable dyestuff precipitate and then separating said precipitate.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: January 5, 1982
    Assignee: Cassella Aktiengesellschaft
    Inventors: Georg Daniek, Artur Meyer, Wolf Weidemuller
  • Patent number: 4300904
    Abstract: The dyeing of cotton in glycol and glycol ether solvents containing direct or sulfur dyes is disclosed. Prior to dyeing, the fabric is treated with an aqueous solution to swell the fibers. When the pretreated cotton is dyed in solvent containing 0.25% to 2% potassium thiocyanate it results in improved color saturation. The instant invention is extremely effective for either cotton or cotton/polyester blends.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: November 17, 1981
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Eugene J. Blanchard
  • Patent number: 4300903
    Abstract: A padding auxiliary is used in a dyeing process using a padding liquor wherein the padding auxiliary is an aqueous solution or dispersion containing(a) 20 to 50 percent by weight of a mixture of 50 to 100 percent by weight of a compound of the following formula ##STR1## and 50 to 0 percent by weight of a compound of the following formula ##STR2## (b) b percent by weight of a compound of the formula ##STR3## and (c) c percent by weight of a compound of the formula ##STR4## wherein b is a number from 0 to 5, c is a number from 0 to 5 and the numbers for b and c are chosen such that the sum of the numbers for b and c is a number from 1 to 10;R.sup.1, R.sup.2 and R.sup.3 are independently an aliphatic moiety with 5 to 12 carbon atoms or an araliphatic moiety with 7 to 13 carbon atoms;X.sym., Y.sym. and Z.sym. is each independently an alkali metal cation, ammonium cation or a cation of an alkylamine or hydroxyalkylamine wherein the alkyl has 1-12 carbon atoms;R.sup.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: November 17, 1981
    Assignee: Cassella Aktiengesellschaft
    Inventors: Friedrich Engelhardt, Karl-Heinz Keil, Gerhard Weckler, Klaus Sternberger
  • Patent number: 4285695
    Abstract: An improved sodium hydrosulfite dye reducing composition is described for reducing vat or sulfur dye in aqueous dye bath solutions, comprised of sodium dithionite, at least 1 percent sodium sulfite by weight of sodium dithionite, and stabilized by alkali metal hydroxide, the improvement characterized by including in this composition an effective surface crust inhibiting amount of an anionic surfactant selected from the group consisting of alkyl sulfates, alkyl aryl phosphate esters, N-acyl-N-alkyl taurates, .alpha.-olefin sulfonates, alkyl aryl disulfonates, dodecylated oxydibenzene sulfonates, and mixtures thereof.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: August 25, 1981
    Assignee: Olin Corporation
    Inventors: Richard L. Doerr, Michael Scardera
  • Patent number: 4279615
    Abstract: Polyester fiber materials are colored by contacting them with aqueous compositions containing an organic pigment or a vat dyestuff or both and an oxpropylate of a mono- to hexahydric alkanol of 2 to 6 carbon atoms (containing 20 to 60 propylene oxide units) and fixing in a manner which is common for polyester. The colorations are fast to migration, especially to bleeding into PVC-coatings.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: July 21, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Sienling Ong
  • Patent number: 4252533
    Abstract: Dyeing and printing with sulfur dyestuffs involves dissolving the dyestuff by reduction. The dissolved reduced dyestuff is applied to the material to be dyed or printed and the dyestuff is reconverted into in soluble dyestuff by oxidation. The present invention improves the prior art by using as the dyestuff reducing agent a compound of the formula ##STR1## or an alkali metal salt thereof, wherein R is --H or --OH and R' is --H, --CH.sub.3 or --CH.sub.2 OH.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: February 24, 1981
    Assignee: Cassella Aktiengesellschaft
    Inventors: Christian Heid, Konrad Mix, Heinz Dickmanns, Erwin Krusche
  • Patent number: 4244690
    Abstract: According to this invention, there is provided an improved method of dyeing fibrous products characterized in that, in the dyeing of fibrous products using an oxidation-reduction dyeing type dye and an aqueous alkali solution of thiourea dioxide as a reducing solution, the reduction of the dye with the said aqueous alkali solution of thiourea dioxide is carried out in the presence of one or more substances selected from the group consisting of saturated aliphatic ketones having 3 to 10 carbon atoms, saturated aliphatic ketocarboxylic acids having 3 to 10 carbon atoms and alicyclic ketones having 3 to 10 carbon atoms.
    Type: Grant
    Filed: February 15, 1979
    Date of Patent: January 13, 1981
    Assignee: Tokai Denka Kogyo Kabushiki Kaisha
    Inventors: Kanji Sato, Kazuyoshi Kushibe, Masaru Nishii, Yasuhiro Kanaya, Yasumasa Kawabe
  • Patent number: 4242091
    Abstract: Process for the continuous dyeing of textile webs made from cellulose fibers or wool, or mixtures containing such fibers, with reactive or sulfur dyestuffs in reduced form, or with reactive or acid dyestuffs, which comprises preheating the textile material to temperatures of from 97.degree. to 104.degree. C. by means of IR radiators or microwaves while maintaining a residual moisture corresponding at least to the water retention amount (normal humidity) of the fibers, and subsequently treating it with steam for 10 to 300 seconds without applying additional pressure, in order to fix the dyestuffs.
    Type: Grant
    Filed: December 14, 1979
    Date of Patent: December 30, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erich Feess, Walter Birke, Joachim Steinbach
  • Patent number: 4240791
    Abstract: According to this invention, there is provided a method of dyeing fibrous products characterized in that, in the dyeing of fibrous products using an oxidation-reduction dyeing type dye and an aqueous alkali solution of thiourea dioxide as a reducing solution, the reduction of the dye with the said aqueous alkali solution of thiourea dioxide is carried out in the presence of one or more dialdehyde compounds selected from dialdehyde compounds represented by the general formulaOHC--R--CHO (I)in which R is a saturated or unsaturated aliphatic or aromatic organic compound radical.
    Type: Grant
    Filed: February 15, 1979
    Date of Patent: December 23, 1980
    Assignee: Tokai Denka Kogyo Kabushiki Kaisha
    Inventors: Kanji Sato, Kazuyoshi Kushibe, Masaru Nishii, Yasuhiro Kanaya, Yasumasa Kawabe
  • Patent number: 4218219
    Abstract: Green sulfur dyestuff is produced by reacting phenothiazine in sulfuric acid with an oxidizing agent, condensing the oxidized phenothiazine with p-nitrosophenol and thionating with sulfur and sodium sulfide the condensate in a bake or reflux process.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: August 19, 1980
    Assignee: Cassella Aktiengesellschaft
    Inventors: Gert Nagl, Joachim Ribka, Heinz Dickmanns, Ulrich Gotsmann