Azo, Acridone, Or Quinone Dye Patents (Class 8/662)
  • Patent number: 4908437
    Abstract: The invention relates to novel thienone compounds useful in dyeing fibers, of the formula: ##STR1## where R.sup.1 is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or C.sub.1 -C.sub.4 -monoalkylcarbamoyl or -dialkylcarbamoyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.8 -alkyl, substituted or unsubstituted phenyl, furyl, thienyl or halogen,X is nitrogen or CR.sup.4 where R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano or substituted or unsubstituted phenyl, andR.sup.3 is an aniline, thiazole, indole, styrol or isoindole radical, with the proviso that if R.sup.1 is cyano, X is CH and R.sup.3 is 4-dimethylaminophenyl or styryl, then R.sup.2 is not methyl or phenyl and that if R.sup.1 is cyano, X is CH and R.sup.3 is phenyl or 4-methoxyphenyl, then R.sup.2 is not phenyl.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: March 13, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Johannes P. Dix, Helmut Reichelt, Masahiro Hayashi
  • Patent number: 4881943
    Abstract: A disperse monoazo dye of the formula: ##STR1## wherein each of R and R.sup.3 represents a lower alkyl radical, R.sup.1 represents a lower alkyl or C.sub.3 -C.sub.6 alkenyl radical andR.sup.2 represents a C.sub.2 -C.sub.6 alkyl radical carrying a hydroxy or acyloxy substituent.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Brierley, Ronald W. Kenyon, Denis R. A. Ridyard
  • Patent number: 4880432
    Abstract: Disclosed is a process for preparing particles colored with a dye which comprises: (a) forming, by a free radical dispersion polymerization process in a nonaqueous solution, polymeric particles having attached thereto stabilizing copolymers with at least one functional group capable of undergoing a chemical reaction with a dye, the particles having an average diameter of from about 0.1 to about 20 microns; (b) adding a dye to the polymeric particles having attached thereto stabilizing copolymers; and (c) effecting a chemical reaction between the dye and the stabilizing copolymers that results in the dye becoming covalently bound to the polymeric particles. Also disclosed is a liquid electrophotographic developer composition comprising a liquid medium, a charge control agent, and colored polymeric toner particles prepared as stated above and having an average diameter of from about 0.5 to about 5 microns.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: November 14, 1989
    Assignee: Xerox Corporation
    Inventors: Luke S. Egan, Mitchell A. Winnik, Francoise M. Winnik
  • Patent number: 4874392
    Abstract: A Monoazo compounds of the formula ##STR1## wherein D is a diazo component radical of the 4-nitrophenyl series, thienyl-2 series, thiazolyl-2 series or 5-nitrobenzoisothiazolyl-3 series,R.sub.1 is hydrogen; C.sub.1-2 alkyl; C.sub.1-2 alkoxy; formylamino; (C.sub.1-4 alkyl)carbonylamino; (C.sub.1-4 alkyl)carbonylamino the alkyl group of which is substituted by 1 to 3 substituents independently selected from halo, C.sub.1-3 alkoxy, cyano, phenyl, phenoxy and benzyloxy; (C.sub.2-4 alkenyl)carbonylamino; halo(C.sub.2-4 alkenyl)carbonylamino; benzoylamino; benzoylamino the phenyl group of which is substituted by 1 to 3 substituents independently selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; (C.sub.1-4 alkoxy)carbonylamino; (C.sub.1-4 alkoxy)carbonylamino the alkyl moiety of which is substituted by 1 to 3 substituents independently selected from halo, C.sub.1-3 alkoxy, cyano, phenyl, phenoxy and benzyloxy; (C.sub.8-14 alkyl)carbonylamino or (C.sub.8-14 alkoxy)carbonylamino,R.sub.2 is C.sub.
    Type: Grant
    Filed: July 29, 1987
    Date of Patent: October 17, 1989
    Assignee: Sandoz Ltd.
    Inventor: Beat Henzi
  • Patent number: 4851012
    Abstract: A mixture of monoazo dyestuffs which contains one or more dyestuffs of the formula I ##STR1## and one or more dyestuffs of the formula II ##STR2## wherein R.sup.1 and R.sup.2 independently of one another each denote linear or branched alkyl with 1 to 6 carbon atoms, R denotes linear or branched alkyl with 1 to 5 carbon atoms and Hal denotes chloro or bromo, are outstandingly suitable for dyeing and printing hydrophobic materials.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: July 25, 1989
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Hubert Kruse, Reinhard Kuhn, Margareta Boos
  • Patent number: 4802889
    Abstract: Monoazo dyestuff of the formula ##STR1## wherein R.sup.1 is 4 alkyl having 1 to 3 carbon atoms, andR.sup.2 is methyl, ethyl or alkoxy having 1 to 4 carbon atoms hich is unsubstituted or substituted by methoxy or ethoxy is useful for dyeing and printing hydrophobic fibers a blue color.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: February 7, 1989
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Bte,uml/u/ hler, Horst Tappe, Reinhard Kuhn, Albert Bode, Margareta Boss
  • Patent number: 4780106
    Abstract: Metal-free compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, and acid addition salts of metal-free compounds of said formula and 1:1 and 1:2 metal complexes thereof, whereinB is hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy; C.sub.2-4 alkyl substituted by hydroxy; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo; --A--NH--R.sub.2 ; --A'.sub.4 --N(R.sub.7).sub.2 ; --A.sub.4 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar. or --N(R.sub.7).sub.2,R is hydrogen; C.sub.1-4 alkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.
    Type: Grant
    Filed: June 10, 1987
    Date of Patent: October 25, 1988
    Assignee: Sandoz Ltd.
    Inventors: Helmut Moser, Manfred Greve, Reinhard Pedrazzi, Roland Wald
  • Patent number: 4773915
    Abstract: Azo dyestuffs of the formula ##STR1## wherein R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxyethoxy andX denotes acyl,are distinguished by good levelling properties and good allround fastness properties. They dye polyester fibres in a bright blue shade.
    Type: Grant
    Filed: January 7, 1987
    Date of Patent: September 27, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Kruckenberg, Klaus Leverenz, Hans-Gunter Otten
  • Patent number: 4772292
    Abstract: A dyestuff mixture for coloring synthetic fibers a yellow color contains as component A a dyestuff of the formula ##STR1## and as component B a different yellow disperse dyestuff species.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: September 20, 1988
    Assignee: Cassella Aktiengesellschaft
    Inventors: Manfred Hahnke, Ulrich Buhler, Albert Bode
  • Patent number: 4760004
    Abstract: Compounds of the formulae I, II and III ##STR1## in which R is --F, --Cl, --Br, C.sub.1 -C.sub.18 alkoxy, and n is the number 0, 1, 2 or 3, are suitable in particular for use as photoconductive substances.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: July 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Alain C. Rochat, Edward E. Jaffe, Jin Mizuguchi
  • Patent number: 4722737
    Abstract: The azo dyestuff of the formula ##STR1## having the interplanar spacings D/.ANG. 3.13, 3.36, 4.85, 9.26 and 13.94 for the five strongest lines having the relative intensity use 98, 89, 82, 100 and 87 is distinguished, compared to known modifications by an increased dye bath stability.
    Type: Grant
    Filed: February 10, 1987
    Date of Patent: February 2, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Brandt, Klaus Leverenz
  • Patent number: 4693725
    Abstract: An aqueous liquid dye composition improved in storage stability, which comprises a bifunctional reactive dye of the following formula, ##STR1## wherein D is an organic dye residue having at least one sulfonic acid group, R.sub.1 and R.sub.2 are independently a hydrogen atom or an unsubstituted or substituted lower alkyl group, A is an substituted or substituted phenylene or naphthylene group, X is a halogen atom, and Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a splittable group by an alkali, in an amount of 5 to 50% by weight based on the weight of the liquid dye composition, the liquid dye composition having a pH value of from 3 to 7.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: September 15, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriaki Yamauchi, Shinnei Ikeou, Kunihiko Imada
  • Patent number: 4693726
    Abstract: Process for dyeing cellulose fibers or cellulose blend fibers, which comprises dyeing the fibers mentioned with water-soluble reactive dyes which contain in the dye molecule at least once the structural element of the formula ##STR1## in which Y denotes a hydroxyl, hydroxymethyl, alkoxy C.sub.1 -C.sub.4, aldehyde, carboxamide, monoalkyl C.sub.1 -C.sub.4 -carboxamide, dialkyl C.sub.1 -C.sub.4 -carboxamide, monophenyl carboxamide, cyano, alkyl C.sub.1 -C.sub.4 -oxycarbonyl or sulfo group or a halogen atom, in an aqueous medium within the pH range 4-11.
    Type: Grant
    Filed: April 3, 1986
    Date of Patent: September 15, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Peter Mischke, Gerd Konig, Hartmut Springer
  • Patent number: 4659333
    Abstract: The invention relates to a process for fixing azo, metal complex azo and formazan dyes on textile fabrics with hot steam to give stable shades, which process comprises fixing textile fabrics dyed or printed with said dyes in hot steam that contains at least 0.5% by volume of air.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: April 21, 1987
    Assignee: CIBA-GEIGY Corporation
    Inventor: Andres Schaub
  • Patent number: 4655786
    Abstract: The invention relates to a process for dyeing hydrophobic fibre material under HT conditions with unformulated disperse dyes from an aqueous liquor, which process comprises dissolving one or more such dyes in water, in the temperature range from 70.degree. to 100.degree. C., with a surfactant or mixture of surfactants which has a hydrotropic action on disperse dyes, feeding the dye solution into a dyeing apparatus which contains water heated to 70.degree. to 100.degree. C. and substrate, and subsequently heating the dye liquor to dyeing temperature, or dissolving the dye at a temperature of over 100.degree. C. under pressure by means of the surfactant or mixture of surfactants which has a hydrotropic action on the dye, feeding the solution into a closed dyeing apparatus which contains water heated to 100.degree. to 150.degree. C. and substrate, and, in both cases, carrying out dyeing in the temperature range from 120.degree. to 150.degree. C. with constant circulation of the dye liquor.
    Type: Grant
    Filed: November 8, 1984
    Date of Patent: April 7, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Navratil, Heinz Abel
  • Patent number: 4623397
    Abstract: Compounds of the formula I ##STR1## in which each R.sub.1, independently, is hydrogen, C.sub.1-8 alkyl, C.sub.2-3 alkyl substituted by one or two substituents selected from the group consisting of halo, hydroxy, cyano, methoxy, ethoxy and (C.sub.1-2 alkoxy)carbonyl or cyclohexyl, and each R.sub.2 and R.sub.3, independently, is hydrogen, chlorine, bromine, methyl, methoxy or ethoxy, their production and use as pigments for the mass pigmentation of, for example, viscose, surface coatings such as oil and water base paints and lacquers and inks, pigment printing, textile coating and pigmenting paper in the mass.
    Type: Grant
    Filed: October 10, 1984
    Date of Patent: November 18, 1986
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul
  • Patent number: 4617381
    Abstract: A process is disclosed for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 starting with the product of the basic condensation of para-nitrotoluene-ortho-sulfonic acid in the form of its tetrasodium reaction mass or the wet filter cake separation of the solids from said mass and the reaction liquids or the dry technical grade sodium complex which is the dried filter cake. The solid starting material is suspended in a lower alkanol/water medium; the suspension is acidified to a pH below about 2.5 to acidify each sulfo moiety on the chromophore and to form the free inorganic salt; this acidified suspension is heated to assure completion of the metathetical salt-forming reaction; after sufficient heating, the mixture of the acidified chromophore and the salt is neutralized to a pH in the range 6.0 to 7.
    Type: Grant
    Filed: September 11, 1984
    Date of Patent: October 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: James W. Hinson, Jo A. Cleverdon
  • Patent number: 4604100
    Abstract: The invention describes a process for the preparation of granular dye formulations by melt granulation, using a polyethylene glycol as melt vehicle. The essential feature of the invention is that a start is made from the dye which contains water, for example from the aqueous filter cake or synthesis solution, and adjusting the moisture content of the granular formulations to 1 to 30% by partial evaporation of water from the dye/polyethylene glycol melt.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: August 5, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Schneider, Heinz Knies, Gerhard Kaudela
  • Patent number: 4541831
    Abstract: Described is a process for the production of substantially dustless water-soluble dye or optical brightener compositions, which process comprises mixing a dry, solid inorganic salt, heated to at least 50.degree. C., with a mixture of at least one dye or optical brightener, an adhesive as e.g. sorbitol, a dust binding surface active agent and further additives. Such compositions are negligibly dusty to dustfree, and retain these properties even after storage for months, particularly in the case where spray-dried material is used.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: September 17, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Gunther, Kurt Hintermayr
  • Patent number: 4492586
    Abstract: Dispersants, especially well suited for use with insoluble dyes, are produced by reacting hydroxyl benzyl alcohol compounds with sulfonated lignin derivatives. The dispersants have high levels of heat stability, coupled with desirable dye reduction, staining, foaming, milling and viscosity-reducing properties. Dyestuffs, dye pastes and dye baths, as well as methods utilizing them, are provided.
    Type: Grant
    Filed: June 25, 1981
    Date of Patent: January 8, 1985
    Assignee: Reed Lignin, Inc.
    Inventor: Stephen Y. Lin
  • Patent number: 4462820
    Abstract: A method of using mono- or dibromodicyanomethane for controlling harmful organisms in water, in aqueous systems, in oil or in fuels is disclosed. The compounds act extremely rapidly in very low concentrations.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: July 31, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Reinhardt Grade, Joachim Lorenz
  • Patent number: 4460375
    Abstract: A dyeing-stable modification (.beta.-modification) of the dyestuff of the formula (I) ##STR1## which has the X-ray diffraction diagram shown in FIG. 1 and having the characteristic reflections at the following glancing angles and relative intensities:______________________________________ [.theta.] 2.74 4.27 4.70 5.50 8.74 11.24 12.44 relative 100 72 40 23 27 32 26 intensity ______________________________________a process for its preparation by heating the dyestuff of said formula (I) of the dyeing-unstable .alpha.-modification, characterized by an X-ray diffraction diagram having the characteristic reflections at the following glancing angles and relative intensities ______________________________________ [.theta.] 3.55 4.15 5.35 9.45 10.41 12.71 13.89 relative 42 100 35 24 34 94 48 intensity ______________________________________at temperatures of 60.degree. to 120.degree. C. in an organic solvent, and its use for dyeing fiber materials made of cellulose esters or synthetic linear polyesters.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: July 17, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Sommer, Manfred Schneider, Rudolf Schickfluss
  • Patent number: 4452609
    Abstract: Azo compounds of the formula ##STR1## wherein R.sub.1 is alkyl, alkenyl, aralkyl, aryl or hetaryl,R.sub.2 is hydrogen or alkyl,R.sub.3 is hydrogen, alkyl, halogen, OR.sub.1 etc.R.sub.4 is hydrogen, alkyl, aralkyl, aryl or cycloalkyl,R.sub.5 is hydrogen, alkyl, alkenyl or aralkyl,Y is cyano, halogen, trifluoromethyl, nitro or SO.sub.2 R.sub.1,Y.sub.1 is halogen or preferably cyano,X.sub.1 is hydrogen or a substituent with a Hammet .sigma. para value of -0.3 to +0.3,X.sub.2 is hydrogen, halogen etc.,are useful for dyeing polyester fibre materials in clear red to violet shades with good general fastness properties.
    Type: Grant
    Filed: December 13, 1982
    Date of Patent: June 5, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rainer Hamprecht
  • Patent number: 4422854
    Abstract: Transfer printing supports impregnated or printed with a formulation containing a dyestuff of the formula I ##STR1## in which R.sup.1 is alkyl having from 1 to 4 carbon atoms, R.sup.2 is hydrogen or has the meaning of R.sup.1, R.sup.3 is methyl, methoxy or ethoxy, and R.sup.4 is hydrogen, methyl, methoxy or ethoxy, or containing mixtures of such dyestuffs, a process for the manufacture of these supports, which comprises impregnating or printing the support material with formulations containing a dyestuff of the formula I or mixtures of such dyestuffs, and the use of these supports for the dyeing and printing of flat web or sheet structures of synthetic or natural materials according to the heat transfer printing process.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: December 27, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Hahnle, Manfred Schneider, Claus Schuster, Rudolf Schickfluss
  • Patent number: 4416665
    Abstract: Water-insoluble azo dyestuff of the formula ##STR1## its manufacture and its use as the dyestuff in the dyeing and printing of hydrophobic fiber materials.
    Type: Grant
    Filed: September 21, 1981
    Date of Patent: November 22, 1983
    Assignee: Cassella Aktiengesellschaft
    Inventors: Horst Tappe, Kurt Roth
  • Patent number: 4405330
    Abstract: Navy mixtures which contain dyes of the formula I ##STR1## where X is chlorine or bromine,Y is hydrogen, methoxy or ethoxy andR is N(C.sub.2 H.sub.5).sub.2, N(CH.sub.2 CH.dbd.CH.sub.2).sub.2 or N(C.sub.2 H.sub.4 OCOCH.sub.3).sub.2,the mixtures being composed of 10-70% of dyes with Y.dbd.H and R=N(C.sub.2 H.sub.5).sub.2, 5-40% of dyes with Y=OCH.sub.3 or OC.sub.2 H.sub.5 and R.dbd.N(CH.sub.2 --CH.dbd.CH.sub.2).sub.2 and 5-80% of dyes with Y=OCH.sub.3 or OC.sub.2 H.sub.5 and R=N(C.sub.2 H.sub.4 OCOCH.sub.3).sub.2.The novel mixtures have excellent tinctorial properties and give very fast dyeings on synthetic polyesters.
    Type: Grant
    Filed: October 8, 1982
    Date of Patent: September 20, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Helmut Degen, Guenter Hansen, Reinhold Krallmann, Wolf-Dieter Kermer
  • Patent number: 4395264
    Abstract: The present invention relates to a process for coupling beta-naphthol with a diazotized amine as follows:1. (a) Dissolving a beta-naphthol in water with a strong base(b) Precipitating the beta-naphthol with a strong acid and(c) Cooling the slurry.2. Adding a diazotized amine to the beta-naphthol solution and3. Increasing the pH in two steps, first with a strong base and then with a weak base.
    Type: Grant
    Filed: November 6, 1981
    Date of Patent: July 26, 1983
    Assignee: BASF Wyandotte Corporation
    Inventor: George W. Fenwick
  • Patent number: 4389213
    Abstract: The invention relates to the use of water-soluble compounds obtained by esterifying alkylene oxide adducts on alcohols having 10 to 24 C atoms with carboxylic acids having up to 22 C atoms and carrying 1 to 6 carboxyl groups as preparation agents for dyestuffs which are insoluble to sparingly soluble in water and preparations which contain a dyestuff having a particle size of less than about 5 .mu.m and one of the preparation agents mentioned.
    Type: Grant
    Filed: April 23, 1982
    Date of Patent: June 21, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Schneider, Hubert Kruse, Konrad Opitz
  • Patent number: 4386934
    Abstract: Navy dye mixtures which contain, as essential components, compounds of the general formula I ##STR1## where X is chlorine or bromine, Y is methoxy or ethoxy, and R is ##STR2## NHC.sub.2 H.sub.4 CN, NHCH.sub.2 CH.dbd.CH.sub.2 or N(C.sub.2 H.sub.4 OCOCH.sub.3).sub.2, and wherein the dye of the above formula where X is Br, Y is OCH.sub.3 or OC.sub.2 H.sub.5 and R is N(C.sub.2 H.sub.4 OCOCH.sub.3).sub.2 is present in an amount of 25-45%, based on the total weight of the mixture, are very useful for dyeing synthetic polyesters.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: June 7, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Helmut Degen, Guenter Hansen, Reinhold Krallmann, Wolf-Dieter Kermer
  • Patent number: 4380452
    Abstract: A process for dyeing and printing cellulose-containing textile material, wherein the dye used is a compound of the general formula I ##STR1## where K is the radical of a coupling component of the pyridone, pyrazole or indole series,one of the radicals X, Y and Z is a carboxylic acid ester group of a total of 2 to 19 carbon atoms, a carboxamide group of a total of 1 to 19 carbon atoms, an unsubstituted or substituted sulfonic acid phenyl ester group or a sulfonamide group of a total of 6 to 18 carbon atoms, andthe remaining substituents X, Y and Z are hydrogen, methyl, chlorine, bromine or nitro.
    Type: Grant
    Filed: July 29, 1981
    Date of Patent: April 19, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Werner Juenemann, Gunther Lamm
  • Patent number: 4377390
    Abstract: Dyestuffs of the formula ##STR1## wherein R denotes hydrogen or alkyl,X denotes R, Cl or Br,m and p denotes 0 or 1,n denotes 2 to 4,A denotes oxygen or --NR-- andB denotes C.sub.1 -C.sub.8 -alkyl, alkenyl, cycloalkyl, aralkyl or aryl,are especially suitable for the dyeing of polyester-materials; they give deep yellow dyeings with good light fastness properties.
    Type: Grant
    Filed: May 27, 1981
    Date of Patent: March 22, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl H. Schundehutte, Henning Reel, Winfried Kruckenberg
  • Patent number: 4374640
    Abstract: A dyestuff useful for dyeing and printing synthetic, hydrophobic fibers or mixtures thereof with cellulose fibers and stable under dyeing conditions is a .beta.-modification of a compound of the formula ##STR1## having an X-ray diffraction pattern under Cu-K.alpha.-radiation with high intensity lines at a diffraction angle in .theta. degrees of 3.75, 6.40 and 12.35;medium intensity lines at a diffraction angle in .theta. degrees of 6.60, 7.30, 7.60, 7.90, 8.10, 8.35, 9.30, 9.70, 9.90, 10.20, 10.50, 12.70 and 13.90;and low intensity lines at a diffraction angle in .theta. degrees of 5.65, 8.75, 11.25, 11.70, 13.35, 15.10 and 15.55; which is prepared by heating at 50.degree.-150.degree. C. the .alpha.-modification of said compound, which is unstable under dyeing conditions.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: February 22, 1983
    Assignee: Cassella Aktiengesellschaft
    Inventors: Horst Tappe, Hans Mayer, Klaus Hofmann
  • Patent number: 4368055
    Abstract: Hydrophobic synthetic fabrics dyed in deep shades utilizing disperse dyes can be improved in solvent bleeding properties by subjecting the dyed fabric to treatment comprising exposure to an aqueous alkaline solution at elevated temperatures prior to the usual heat setting of the dyed fabric. The process is particularly useful for polyester fabrics derived from aromatic polyesters.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: January 11, 1983
    Assignee: BASF Wyandotte Corporation
    Inventors: Gert Motzkus, Kurt Fohn
  • Patent number: 4368054
    Abstract: Liquid compositions of nitro group-containing aniline compounds containing no sulfonic acid and/or carboxylic acid groups and having a melting point of below 140.degree. C., especially those suitable for use as diazo component in ice color dyeing, which contain 20 to 70% of this nitro-aniline, 5 to 80 weight % of a castor oil oxethylated with 25 to 60 mols of ethylene oxide, and 5 to 65 weight % of N-methyl-pyrrolidone as solvent. By simply mixing these components clear solutions are obtained which can be diazotized within a few seconds by means of an aqueous sodium nitrite solution and thus give diazonium salt solutions free from residue. These diazonium salt solutions can be used in simple manner and very advantageously as developing baths or liquors for producing water-insoluble azo dyestuffs on the fiber according to the ice color technique.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: January 11, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hasso Hertel
  • Patent number: 4359321
    Abstract: Dispersants, especially well suited for use with insoluble dyes, are produced by reacting hydroxyl benzyl alcohol compounds with sulfonated lignin derivatives. The dispersants have high levels of heat stability, coupled with desirable dye reduction, staining, foaming, milling and viscosity-reducing properties. Dyestuffs, dye pastes and dye baths, as well as methods utilizing them, are provided.
    Type: Grant
    Filed: September 3, 1981
    Date of Patent: November 16, 1982
    Assignee: American Can Company
    Inventor: Stephen Y. Lin
  • Patent number: 4336025
    Abstract: Water-soluble compounds of the formula ##STR1## wherein A is an aryl radical, X represents identical or different groups of the formula --CH.sub.2 --CH.sub.2 -- and --CH.sub.2 --CH(CH.sub.3)--, R--CO-- denotes identical or different radicals of a carboxylic acid having up to 22 C atoms, n represents identical or different numbers from 8 to 150, p is a number from 1 to 10 and m represents 0 up to (p-0.5), are suitable for the preparation of colorants, particularly disperse dyestuffs or vat dyestuffs.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: June 22, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Schneider, Hubert Kruse, Konrad Opitz
  • Patent number: 4332588
    Abstract: By the slow stepwise heating up of an aqueous suspension of the crystallographically amorphous dye of the formula ##STR1## which dye is unstable to dyeing, to a temperature of 90.degree.-100.degree. C. with a halting point at 40.degree.-60.degree. C., this dye can be transformed completely into the crystalline .alpha.-modification.The novel dye modification can be easily converted, without increase of viscosity, into thinly liquid formulations which are readily pourable, which form no sediment, and which are excellently suitable for producing printing pastes, for example for printing polyester fabric.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: June 1, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Eugster, Stefan Koller
  • Patent number: 4329144
    Abstract: By suspension of the melt of the known crystallographically amorphous dye of the formula ##STR1## which is unstable to dyeing, in water at a temperature of 90.degree. to 130.degree. C., this dye can be caused to crystallize. There is obtained a crystalline granulate in which the dye is completely in the novel .epsilon.-modification.The novel dye modification is stable in dispersion under dyeing conditions, and has no tendency to flocculate.
    Type: Grant
    Filed: December 15, 1980
    Date of Patent: May 11, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Eugster, Stefan Koller
  • Patent number: 4327999
    Abstract: It is possible by heating at temperatures of between 65.degree. and 200.degree. C. to convert the known .alpha.-modification of the azo dye of the formula ##STR1## which is unstable to dyeing, completely into the .beta.-modification which is stable to dyeing. The modification transformation can be performed either with the solid dye or with a suspension thereof in an organic, preferably aromatic, solvent.The novel dye modification is stable in dispersion under dyeing conditions, and shows no tendency to flocculate.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: May 4, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Koller, Peter Eugster, Suresh C. Agarwal
  • Patent number: 4323363
    Abstract: Hazy or frosty appearance of mixtures of polyester and cellulosic fibers when dyed with disperse dyes is suppressed by adding to the aqueous dye bath a small amount of low copolymer of acrylamide or the like with a water-soluble maleic or fumaric acid ester, and with or without an additional water-soluble vinyl compound, all as defined infra. The copolymer is normally a liquid miscible with water in all proportions at 10.degree. C. or below. Disperse dye is fixed to the polyester fibers by heating as in the Thermosol process. Dyes for the cellulosic fibers can also be included in the dye bath so that the cellulosic fibers are also dyed in the same treatment. Alternatively the cellulosic fibers can be separately dyed, preferably after the polyester fibers are dyed.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: April 6, 1982
    Assignee: Cassella Aktiengesellschaft
    Inventors: Gert Brachten, Friedrich Engelhardt, Heinz Helling, Joachim Ribka
  • Patent number: 4319880
    Abstract: The invention relates to a novel crystallographic modification (".beta.-modification") being stable under dyeing conditions of the dyestuff of the formula ##STR1## which is characterized by an X-ray diffraction pattern as shown in FIG. 1 with characteristic reflexes at the following glance angles .theta. (CuK.sub..alpha. radiation) with the relative intensities:______________________________________ .phi. 3.71 6.62 7.85 8.6 9.43 10.51 11.8 12.57 relat. 67 44 34 36 60 60 46 100 intensity ______________________________________to processes for their manufacture and to their use for dyeing fibrous materials of cellulose esters or of synthetic linear polyesters or blended fabrics of these polyesters and wool or rayon.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: March 16, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Konrad Opitz, Rudolf Schickfluss
  • Patent number: 4306874
    Abstract: A sublimable monoazo dyestuff of the formula ##STR1## wherein X is alkyl of 1-4 carbon atoms is used as the dyestuff in the process for printing synthetic, hydrophobic materials, treated cellulose materials or materials containing both by transfer printing using formulations containing said sublimable monoazo dyestuff.
    Type: Grant
    Filed: August 1, 1980
    Date of Patent: December 22, 1981
    Assignee: Cassella Aktiengesellschaft
    Inventors: Horst Tappe, Claus Schuster
  • Patent number: 4305718
    Abstract: A process for dyeing and printing cellulose-containing textile material, wherein the dye used is a compound of the general formula I ##STR1## where K is the radical of a coupling component of the pyridone, pyrazole or indole series,one of the radicals X, Y and Z is a carboxylic acid ester group of a total of 2 to 19 carbon atoms, a carboxamide group of a total of 1 to 19 carbon atoms, an unsubstituted or substituted sulfonic acid phenyl ester group or a sulfonamide group of a total of 6 to 18 carbon atoms, andthe remaining substituents X, Y and Z are hydrogen, methyl, chlorine, bromine or nitro.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: December 15, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loffler, Werner Juenemann, Gunther Lamm
  • Patent number: 4305719
    Abstract: Disclosed is copolyester material dyed with at least one azo or anthraquinone type dye, said copolyester material having an inherent viscosity of at least 0.4 and containing in copolymerized form from about 0.3 to about 5.0% by weight of one or more of the stabilizing moieties having the general formula ##STR1## where R and R.sub.1 are each a chemical bond or an alkylene group of 1-6 carbons; R.sub.2 is alkyl, cycloalkyl, or aryl; R.sub.3 represents 1-5 groups each independently selected from H, Cl, F, alkyl, cycloalkyl, alkoxy, aryl or aryloxy; wherein all of the above alkyl and alkylene moieties comprising or being part of the R.sub.2 or R.sub.3 groups contain from 1-8 carbons, and wherein all of the above alkyl, alkylene, aryl and cycloalkyl moieties may be substituted with up to three of a variety of substituents such as halogen, alkyl of 1-8 carbons, alkoxy of 1-8 carbons, aryl, cycloalkyl and CN.
    Type: Grant
    Filed: June 25, 1980
    Date of Patent: December 15, 1981
    Assignee: Eastman Kodak Company
    Inventors: Joseph S. Zannucci, Bobby J. Sublett, Wayne P. Pruett
  • Patent number: 4293306
    Abstract: A process for the dyeing or printing of a hydrophobic organic fibrous material containing or consisting of polyester, wherein(a) the fibrous material is dyed (.alpha.) from an aqueous dispersion with a dyestuff of the formula (1) indicated below at a pH value between 2 and 9 and at a temperature above 100.degree. C. or at about 100.degree. C. in the presence of a carrier, or (.beta.) by impregnating it with an aqueous dispersion of a dyestuff of the formula (1), said dispersion having a pH value between 2 and 9, and subsequently exposing the fibrous material so treated to a short heat treatment between about 180.degree. and 210.degree. C.
    Type: Grant
    Filed: February 6, 1980
    Date of Patent: October 6, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Hoyer, Willi Steckelberg, Walter Deucker, Rudolf Schickfluss
  • Patent number: 4290770
    Abstract: The invention relates to the coloration of artificial or synthetic materials. There is used as disperse dyestuff a compound of the general formula: ##STR1## in which R.sub.1 represents a hydrogen atom or a nitro group, R.sub.2 represents a hydrogen or halogen atom or a nitro, trifluoromethyl, alkyl or alkoxy group and R.sub.3 represents a hydrogen or halogen atom or a cyano group.
    Type: Grant
    Filed: December 31, 1979
    Date of Patent: September 22, 1981
    Assignee: P C U K Produits Chimiques Ugine Kuhlmann
    Inventor: Manfred C. Rau
  • Patent number: 4274829
    Abstract: Process for the continuous dyeing of synthetic fibre materials from organic solvents, wherein the material, preheated to at least 100.degree. C., is impregnated with a halogenated hydrocarbon impregnating liquor containing dyestuff or optical brightener to give a liquor absorption of more than 100%, and is then passed through a vapor zone filled with halogenated hydrocarbon at a temperature above the boiling point of the halogenated hydrocarbon in such a manner that during passage of the material through this zone the liquor becomes concentrated on the material, whereby(a) the amount of solvent on the material is not increased by condensation of halogenated hydrocarbon vapor, and(b) more than 5% of liquor is present on the material when it emerges from the vapor zone, so that the material during its passage through this vapor zone never becomes dry.
    Type: Grant
    Filed: October 4, 1978
    Date of Patent: June 23, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Jacques Zurbuchen
  • Patent number: 4264326
    Abstract: New disperse dyestuffs which may be used especially for the coloration of artificial or synthetic materials correspond to the general formula: ##STR1## in which R.sub.1 represents a hydrogen or halogen atom or a nitro, alkyl or alkoxy group and R.sub.2 represents a hydrogen or halogen atom or a cyano group. These dyestuffs provide colorations of very fast yellow to orange shades on polyester fibers.
    Type: Grant
    Filed: November 21, 1979
    Date of Patent: April 28, 1981
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventor: Manfred C. Rau
  • Patent number: 4252530
    Abstract: White patterns on synthetic fiber textiles or patterns of a different color on a colored background are produced by dyeing the material with a dyestuff dischargeable to white, drying the material, printing the material with a discharge resist paste and heating the treated material to 100.degree.-230.degree. C. wherein the discharge agent is a base which produces a pH of at least 8 in a 5% strength aqueous solution.
    Type: Grant
    Filed: August 14, 1979
    Date of Patent: February 24, 1981
    Assignee: Cassella Aktiengesellschaft
    Inventors: Joachim Ribka, Horst Tappe, Kurt Roth, Hans-Jurgen Weyer
  • Patent number: 4249275
    Abstract: For dyeing and printing cellulose fibers swollen with water-miscible swelling agents or fibre blends containing these fibres, the fibres are treated with dyestuffs of the general formula ##STR1## wherein R.sub.1 represents aryl,R.sub.2 represents halogen, CN, CF.sub.3, NO.sub.2, Q.sub.1, --OQ.sub.1, --COOQ.sub.1, CONQ.sub.1 Q.sub.2 or --NHCOQ.sub.1,R.sub.3 represents H, halogen, CN, CF.sub.3, Q.sub.1 or --OQ.sub.1 andK represents the radical of a coupling component,whereinQ.sub.1 denotes alkyl or aryl andQ.sub.2 denotes hydrogen, alkyl or aralkyl,and the dyestuffs are fixed by heat treatment.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: February 10, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Hugl, Gerhard Wolfrum, Henning Reel, Werner Kunnel, Robert Kuth, Wilhelm Gohrbandt