Five-membered Hetero Ring Consisting Of One Nitrogen And Four Carbon Atoms Patents (Class 8/574)
  • Patent number: 6306181
    Abstract: The invention relates to novel 4-hydroxyindole derivatives comprising at least one cationic group Z, Z being selected from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring, and aliphatic chains containing at least one quaternized unsaturated ring, to their use as a coupler for the oxidation dyeing of keratinous fibers, to the dyeing compositions comprising them, and to the methods of oxidation dyeing which employ them.
    Type: Grant
    Filed: September 21, 1999
    Date of Patent: October 23, 2001
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 6238440
    Abstract: The present invention relates to a composition for the dyeing of keratinous fibres, especially human hair, which comprises, in a medium appropriate for dyeing: as coupler, at least one compound corresponding to one of the formulae: in which R1 is especially hydrogen, halogen, aryloxy, alkoxy, acyloxy, arylthio, alkylthio, heteroarylthio, heteroaryloxy, etc; R2 and R3 are independent and are especially hydrogen, halogen, alkyl, aryl, alkylthio, arylthio, benzylthio, etc; Za, Zb and Zc are independent and are a nitrogen atom or a carbon atom carrying a radical R4, R5, R6 or R7; R4, R6 and R7 are identical or different and are especially hydrogen, alkyl, aryl, a heterocycle, a halogen, etc; and R5 is especially hydrogen, halogen, acyl, acyloxy or carbamoyl, etc; and at least one oxidation base.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: May 29, 2001
    Assignee: L'Oreal S.A.
    Inventors: Laurent Vidal, GĂ©rard Malle
  • Patent number: 6203580
    Abstract: Compositions for the oxidation dyeing of keratin fibers, comprising, as oxidation base, at least one para-aminophenol, of formula (I) and/or at least one acid-addition salt thereof: in which: R1 represents a hydrogen atom, a linear or branched C1-C4 alkyl radical or a C1-C4 trifluoroalkyl radical, R2 and R3 independently represent a hydrogen atom, a C1-C4 alkyl radical or a C1-C4 monohydroxyalkyl radical, and X, Y and Z independently represent a carbon, nitrogen, oxygen or sulphur atom, wherein the bonds XY and YZ are single or double bonds; a dyeing process using these compositions, novel para-aminophenols and a process for their preparation.
    Type: Grant
    Filed: February 24, 1998
    Date of Patent: March 20, 2001
    Assignee: L'Oreal
    Inventors: Jean Jacques Vandenbossche, Alain Lagrange
  • Patent number: 6203579
    Abstract: A colorant composition for coloring keratin-containing fibers is disclosed having (a) at least one isatin derivative corresponding to the formula I: where R1 and R2 independently of one another represent a hydrogen atom, a halogen atom, a hydroxy group, a (C1-4)-alkyl, hydroxy-(C1-4)-alkyl, tertiary amino-(C1-4)-alkyl, (C1-4)-alkoxy group, an amino group optionally substituted by one or two (C1-4)-alkyl or hydroxy-(C1-4)-alkyl groups, a nitro, carboxy, or sulfo group, and Y is a hydroxy group, a (C1-4)-alkoxy group or an amino group which may be substituted by (C1-4)-alkyl, (C1-4)-alkoxy-(C1-4)-alkyl, carboxy-(C1-4)-alkyl, sulfo-(C1-4)-alkyl or hydroxy-(C1-4)-alkyl groups or which may be part of a heterocyclic 5-, 6- or 7-membered ring, or physiologically compatible salts thereof, and (b) at least one compound containing a primary or secondary amino group or hydroxy group selected from the group consisting of primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic
    Type: Grant
    Filed: October 22, 1999
    Date of Patent: March 20, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moeller, Horst Hoeffkes, Bernd Meinigke, David Rose
  • Patent number: 6200353
    Abstract: Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula at least one coupler comprising a compound of the formula: wherein R is selected from the group consisting of C1 to C2 alkyl and hydroxyethyl, R1 is selected from the group consisting of hydrogen, chlorine, bromine, C1 to C3 alkyl, C1 to C3 alkoxy, C1 to C3 hydroxyalkyl and C1 to C3 hydroxyalkoxy, and X is O, S or NH.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: March 13, 2001
    Assignee: Bristol Myers Squibb Company
    Inventors: Mu-Ill Lim, Linas R. Stasaitis, Yuh-Guo Pan
  • Patent number: 6201126
    Abstract: Compounds of the formula (I) in which A represents N or a cyanomethylene radical, B represents S, O or NH and R1, R2, R3 and x have the meaning given in the description, are highly suitable for dyeing and printing high-molecular-weight materials, in particular automotive cover fabrics.
    Type: Grant
    Filed: June 2, 1997
    Date of Patent: March 13, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventor: Manfred Lorenz
  • Patent number: 6179883
    Abstract: Novel 2-imino-2,3-dihydro-1H-indole derivatives of formula (I) or (II) below: in which: R1, R2 and R3 denote hydrogen, alkyl, carboxyl, alkoxycarbonyl, monohydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl, monoalkylaminoalkyl or dialkylaminoalkyl; R′3 and R4 denote alkyl, carboxyl, alkoxycarbonyl, monohydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl, monoalkylaminoalkyl or dialkylaminoalkyl; R5 denotes hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl, monoalkylaminoalkyl or dialkylaminoalkyl; and the addition salts thereof with an acid, as well as their uses for dyeing keratin fibres.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: January 30, 2001
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 6153764
    Abstract: This invention relates to a process for preparing perylene pigment compositions by reaction of(a) a perylene tetracarboxylic compound;(b) about 0.01 to about 20% by weight, relative to the perylene tetracarboxylic compound, of a non-pigmentary cyclic anhydride or imide of formula (I) ##STR1## wherein W is O or NR.sup.1 (where R.sup.1 is hydrogen, a metal, or optionally substituted alkyl, cycloalkyl, aralkyl, or aryl), R.sup.2, R.sup.3, and R.sup.4 are various combinations of substituents and/or fused-on rings, and the dotted line is an optional double bond representing R.sup.2 --C.dbd.C--R.sup.3 ;(c) ammonia or a primary alkyl, aralkyl, or aryl amine; optionally in the presence of(d) a solvent and/or(e) one or more dispersants.
    Type: Grant
    Filed: January 25, 2000
    Date of Patent: November 28, 2000
    Assignee: Bayer Corporation
    Inventors: Gregory R. Schulz, Michael J. Greene
  • Patent number: 6132475
    Abstract: New p-diaminobenzene derivative compounds of the formula (I): ##STR1## and physiologically compatible water soluble salts thereof are described, wherein X represents oxygen, sulfur, selenium or N-R9. Compositions for dyeing keratin fibers including a combination of coupler and developer substance are described, in which the developer substance includes at least one of the new p-diaminobenzene derivative compounds.
    Type: Grant
    Filed: February 15, 1999
    Date of Patent: October 17, 2000
    Assignee: Wella Aktiengesellschaft
    Inventors: Laurent Chassot, Hans-Juergen Braun
  • Patent number: 6077320
    Abstract: Diiminoisoindoline derivatives or 3-aminoisoindolone derivatives, or tautomeric forms thereof, used as oxidizing-agent-free dye precursors in dyeing keratin fibers, in particular human keratin fibers such as the hair, without an oxidizing agent, in the presence of compounds containing a primary or secondary amine function; dye compositions containing these compounds and to the dyeing devices and processes used.
    Type: Grant
    Filed: December 11, 1997
    Date of Patent: June 20, 2000
    Assignee: L'Oreal
    Inventors: Herve Andrean, Alain Lagrange
  • Patent number: 6063136
    Abstract: The present invention relates to a composition and a dyeing process for the dyeing of keratinous fibers, in particular of human hair, having,as coupler, at least one compound of formula: ##STR1## where Z.sub.a and Z.sub.b, which are different from one another, represent an oxygen or nitrogen atom,and at least one oxidation base.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: May 16, 2000
    Assignee: L'Oreal S.A.
    Inventors: Laurent Vidal, Gerard Malle
  • Patent number: 6042620
    Abstract: New p-diaminobenzene derivative compounds of the formula (I): ##STR1## and physiologically compatible water soluble salts thereof are described, wherein X represents oxygen, sulfur, selenium or N-R9, wherein R9 represents hydrogen, an alkyl group, a hydroxyalkyl group, a phenyl group or an acetyl group; and the remaining R groups each represent variously hydrogen, hydroxy, amino, nitro, nitrile, alkyl, alkoxy, hydroxyalkyl, cyclic or aromatic groups, among others. Compositions for dyeing keratin fibers including a combination of coupler and developer substance are disclosed, in which the developer substance includes at least one of the new p-diaminobenzene derivative compounds.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: March 28, 2000
    Assignee: Wella AG
    Inventors: Hans-Juergen Braun, Laurent Chassot
  • Patent number: 6039769
    Abstract: This invention relates to a process for preparing perylene pigment compositions by reaction of(a) a perylene tetracarboxylic compound;(b) about 0.01 to about 20% by weight, relative to the perylene tetracarboxylic compound, of a non-pigmentary cyclic anhydride or imide of formula (I) ##STR1## wherein W is O or NR.sup.1 (where R.sup.1 is hydrogen, a metal, or optionally substituted alkyl, cycloalkyl, aralkyl, or aryl), R.sup.2, R.sup.3, and R.sup.4 are various combinations of substituents and/or fused-on rings, and the dotted line is an optional double bond representing R.sup.2 --C.dbd.C--R.sup.3 ;(c) ammonia or a primary alkyl, aralkyl, or aryl amine; optionally in the presence of(d) a solvent and/or(e) one or more dispersants.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: March 21, 2000
    Assignee: Bayer Corporation
    Inventors: Gregory R. Schulz, Michael J. Greene
  • Patent number: 6022379
    Abstract: Pyrrole derivatives of 1,4-naphthoquinone and of 1,4-dihydroxynaphthalene, dye compositions containing them and the corresponding dyeing process.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: February 8, 2000
    Assignee: L'Oreal
    Inventors: Sylvie Genard, Herve Andrean, Michel Hocquaux
  • Patent number: 6002018
    Abstract: The invention relates to N-substituted 4-hydroxyindoline derivatives, to their process of synthesis, to their use as couplers for the oxidation of dyeing of keratinous fibers, in combination with at least one oxidation base, and to the dyeing processes in which they are used.
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: December 14, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5993491
    Abstract: Compositions and methods for the oxidative coloring of human hair, wherein the compositions contain as a novel primary dye intermediate a 1-(4-aminophenyl)-2-pyrrolidinemethanol, or a cosmetically acceptable salt thereof. The compositions may also contain at least one other primary intermediate and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations. A preferred dye intermediate in the composition is 1-(4-aminophenyl)-2-pyrrolidinemethanol or cosmetically acceptable salts thereof, which produce intense black colors when used in admixture with a suitable coupling agents, such as 3-aminophenol, in conventional hair dye base formulations.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: November 30, 1999
    Assignee: Bristol-Myers Squibb Company
    Inventors: Mu-Ill Lim, Margaret Popp, Yuh-Guo Pan
  • Patent number: 5972049
    Abstract: Improvements in the disperse dyeing process for hydrophobic textiles by the use of novel dye carrier formulations are disclosed. The carrier composition for use in disperse dyeing of hydrophobic textile material preferably comprises an alkylphthalimide carrier component and a clay dispersing agent. Dye baths and methods of disperse dyeing of a hydrophobic textile material are also disclosed. The use of clay as a dispersing agent allows for the use of carrier compositions with reduced health and environmental hazards without adversely affecting dyeing characteristics.
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: October 26, 1999
    Assignee: Sybron Chemicals Inc.
    Inventors: Calvin M. Wicker, Jr., Otto Bello, Ricky C. Phillips, Robert B. Login
  • Patent number: 5876464
    Abstract: N-(4-Aminophenol) prolineamide and cosmetically acceptable salts thereof are useful as primary intermediates in oxidative hair dyeing. Compositions which contain a hair dye produced by oxidatively coupling N-(4-aminophenol) prolineamide with a coupler in the presence of an oxidizing agent are applied to the hair in oxidative hair dyeing processes.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: March 2, 1999
    Assignee: Bristol-Myers Squibb Company
    Inventors: Mu-Ill Lim, Margaret A. Popp, Yuh-Guo Pan
  • Patent number: 5876465
    Abstract: A composition for dyeing keratin fibres, and in particular human keratin fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing:at least one coupler selected from 2-iminoindoline derivatives of formula (I) and acid addition salts thereof: ##STR1## in which: R.sub.1 represents hydrogen, alkyl, hydroxyalkyl, alkoxycarbonyl or acyl;R.sub.2 represents hydrogen, alkyl, phenyl or arylsulphonyl;R.sub.3 represents hydrogen or alkyl which may be substituted with one or more hydroxyl, alkoxy, amino, alkylamino, dialkylamino, cyano or aryl groups;R.sub.4 and R.sub.5, which may be identical or different, denote hydrogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, dialkylamino, aralkyl, halogen or a nitro group; andat least one oxidation base.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: March 2, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5851237
    Abstract: The invention provides compositions and methods for the oxidative coloring of human hair. The compositions of the invention contain as a primary dye intermediate a 1-(4-aminophenyl) pyrrolidine, or a cosmetically acceptable salt thereof. The compositions may also contain at least one other primary intermediate and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations. Preferred dye intermediates in the compositions of the invention include 1-(4-aminophenyl) pyrrolidine and 1-(4-amino-3-methylphenyl) pyrrolidine, or cosmetically acceptable salts thereof, which produce intense neutral colors when used in admixture with a suitable coupling agents, such as 3-aminophenol, in conventional hair dye base formulations.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: December 22, 1998
    Inventors: James S. Anderson, Michael Y. M. Wong
  • Patent number: 5827330
    Abstract: Water soluble, cationic products useful as hair colorants or for the treatment of skin which are esters or amides formed by reaction of melanin and a quaternary salt containing a reactive amino or hydroxyl group, as well as compositions containing them and methods of using such products to color hair or treat skin are described.
    Type: Grant
    Filed: June 13, 1997
    Date of Patent: October 27, 1998
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Gottfried Wenke, Giuseppe Prota
  • Patent number: 5785717
    Abstract: The present invention relates to a composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising at least one diaminopyrazole derivative as oxidation base in combination with at least one suitably selected heterocyclic coupler, and to the dyeing process using this composition with an oxidizing agent.
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: July 28, 1998
    Assignee: L'Oreal
    Inventors: Mireille Maubru, Marie-Pascale Audousset
  • Patent number: 5769903
    Abstract: The present invention relates to a composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising an oxidation base in combination with at least one suitably selected indole coupler and at least one additional heterocyclic coupler which is also suitably selected, as well as to the dyeing process using this composition with an oxidizing agent.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: June 23, 1998
    Assignee: L'Oreal
    Inventors: Marie-Pascale Audousset, Jean Cotteret
  • Patent number: 5755829
    Abstract: The subject of the invention is a composition for the oxidation dyeing of keratinous fibers containing at least one N-substituted 4-hydroxyindoline derivative as coupler and at least one oxidation base. The invention also relates to new N-substituted 4-hydroxyindoline derivatives, to their process of synthesis, to their use as couplers for the oxidation dyeing of keratinous fibers, in combination with at least one oxidation base, and to the dyeing processes in which they are used.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: May 26, 1998
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5743919
    Abstract: The process of coloring keratin-containing fibers by contacting the fibers with an isatin derivative corresponding to formula (I): ##STR1## in which R.sup.1 is a hydroxy group, an optionally C.sub.1-4 -alkyl- or phenyl-substituted amino group, a C.sub.3-8 alkenyl, dihydroxy-(C.sub.3-6)-alkyl, trihydroxy-(C.sub.4-6)-alkyl, tetrahydroxy-(C.sub.5-6)-alkyl, pentahydroxy-C.sub.6 -alkyl, C.sub.2-4 -aminoalkyl, C.sub.1-4 -sulfoalkyl group, an optionally C.sub.1-4 -alkyl-substituted 2-furylmethyl, 2-thienylmethyl, 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl group or an aralkyl group corresponding to formula (II): ##STR2## in which R.sup.6 and R.sup.7 independently of one another represent hydrogen, halogen atoms, hydroxy groups, amino groups optionally substituted by C.sub.1-4 alkyl or phenyl, C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups, carboxy groups or sulfo groups and R.sup.8 is hydrogen, a C.sub.1-4 alkyl group or a C.sub.2-4 hydroxyalkyl group and x=0, 1 or 2, and R.sup.2, R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: September 17, 1996
    Date of Patent: April 28, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moeller, Horst Hoeffkes
  • Patent number: 5707405
    Abstract: A water-reducible composition comprises A) between about 20 and about 50 wt % of a water-insoluble nigrosine, B) between about 25 and about 40 wt % of a solvent having a flashpoint of at least about 141.degree. F. (61.degree. C.) and a boiling point of at least about 280.degree. F. (138.degree. C.), and C) between about 20 and about 40 wt % of a non-ionic surfactant, the weight percentages being based on total weight of A), B), and C).The composition is prepared by dissolving the nigrosine A) in a C.sub.1 -C.sub.3 alkanol to form an alcohol solution, mixing the alcohol solution with the solvent B) and non-ionic surfactant C, and subsequently stripping the C.sub.1 -C.sub.3 alkanol.
    Type: Grant
    Filed: April 8, 1996
    Date of Patent: January 13, 1998
    Assignee: Morton International, Inc.
    Inventors: Peter A. Caputo, Alejandro Zimin, Sr.
  • Patent number: 5626633
    Abstract: Dyestuffs of the formula (I) ##STR1## wherein n denotes 1 or 2,T denotes O or N--R.sub.0, whereinR.sub.0 denotes H, alkyl, aryl or acyl or, together with R.sub.2 or R.sub.3, forms a 5- to 7-membered ring,R.sub.1 if n=1, denotes aryl, hetaryl or heterocyclylidenemethyl andif n=2, denotes a direct bond or arylene andR.sub.2 and R.sub.3 are independent or cyclic radicals having the meanings given in the description,are employed for bulk dyeing of plastics, preferably thermoplastics.
    Type: Grant
    Filed: December 1, 1995
    Date of Patent: May 6, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventor: Peter Roschger
  • Patent number: 5616150
    Abstract: A composition for coloring keratin-containing fibers containing:(a) at least one isatin derivative corresponding to formula I: ##STR1## wherein R.sup.1 can represent hydrogen, a C.sub.1-4 alkyl group, a C.sub.2-4 hydroxyalkyl group, a C.sub.2-20 acyl group, a phenyl group, and a benzoyl group, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently of one another can represent hydrogen, hydroxy, halogen, nitro groups, sulfo groups, carboxyl groups, C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups or NR.sup.6 R.sup.7 groups and where R.sup.6 and R.sup.7 independently of one another represent hydrogen, C.sub.1-4 alkyl groups or C.sub.2-4 hydroxyalkyl groups, and wherein two adjacent groups R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: April 1, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moeller, Horst Hoeffkes
  • Patent number: 5611817
    Abstract: A process for coloring keratin-containing fibers by contacting the fibers with a composition containing an isatin derivative corresponding to formula I: ##STR1## wherein R.sup.1 is hydrogen, a C.sub.1-4 alkyl group, a C.sub.2-4 hydroxyalkyl group, a C.sub.2-20 acyl group, a benzyl or phenyl group, R.sup.2 is hydrogen, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, a hydroxy, halogen or nitro group, X is a sulfo group --SO.sub.3 H or a carboxyl group --COOH and n is an integer from 0 to 3, including water-soluble salts thereof.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: March 18, 1997
    Inventors: Hinrich Moeller, Horst Hoeffkes
  • Patent number: 5595574
    Abstract: Dye donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer comprising at least one heterocyclic hydrazono dye, wherein said dye corresponds to the general formula:A=N-N=Hetwherein A is a carbocyclic or heterocyclic coupler group or a cyclic reactive methylene system, which may carry at least one substituent, and Het is a heterocyclic nucleus, which may carry at least one substituent.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: January 21, 1997
    Assignee: Agfa-Gevaert N.V.
    Inventors: Wilhelmus Janssens, Luc Vanmaele
  • Patent number: 5571289
    Abstract: Dye donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer comprising at least one heterocyclic hydrazono dye, wherein said dye corresponds to the general formula:A.dbd.N-N.dbd.Hetwherein A is a carbocyclic or heterocyclic coupler group or a cyclic reactive methylene system, which may carry at least one substituent, and Het is a heterocyclic nucleus, which may carry at least one substituent.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: November 5, 1996
    Assignee: AGFA-Gevaert N.V.
    Inventors: Wilhelmus Janssens, Luc Vanmaele
  • Patent number: 5571291
    Abstract: A low-temperature dyeing additive for protein fiber products contains one or more kinds of solvents which are freely miscible with water and having a donor number within the range of 24 to 50 and an acceptor number within the range of 10 to 24 in the presence or absence of a surfactant, in an amount of 0.025 to 40 g per liter of water, has a pH of 3.5 to 9.5. If necessary, it contains tributoxyethyl phosphate in an amount of 0.025 to 4.0 g per liter of water, and/or contains one or more kinds of anions having an enthalpy of hydration (-.DELTA.H.sub.KJ.multidot.mol.sup.-1) of 200 to 290 in an amount of 0.05 to 40 g per liter of water. This low-temperature dyeing additive for protein fiber products serves to relax the higher-order structures of the protein fibers before dyeing or during dyeing, to thereby swell the fibers, thus rendering the fibers readily dyeable without detriment to the properties thereof.
    Type: Grant
    Filed: July 5, 1995
    Date of Patent: November 5, 1996
    Assignee: Tuyaku Co., Ltd.
    Inventor: Sachizumi Koike
  • Patent number: 5554196
    Abstract: Method of marking a surface of an object by means of a laser light beam.A description is given of a method of decorating or marking, for example, synthetic resin objects by means of an UV-laser or IR-laser by coating the object with a layer of a dye precursor and a coupler in a binder. For the precursor use is made of a heterocyclic mono- or bis-arylsulphonylhydrazone and for the coupler use is made of, for example, an indole, aniline, pyrazoline or malonitrile, so that after irradiation with UV-laser light or IR-laser light an azo-dye (XXX) is formed.
    Type: Grant
    Filed: August 1, 1995
    Date of Patent: September 10, 1996
    Assignee: U.S. Philips Corporation
    Inventor: Ytsen Wielstra
  • Patent number: 5542954
    Abstract: A process for the production of aminated cotton fibers by subjecting a raw cotton or cotton-polyester mixture to a modification with a saturated aliphatic compound of 3 to 15 carbon atoms which contains at least one primary, secondary, tertiary, or quaternary amino group and at least one hydrolyzable ester group, in which the saturated radical is straight chain, branched, or cyclic, and may be interrupted by one or more hetero groups and may be substituted by one or more hydroxyl groups. The modification occurs simultaneously with scouring, kiering, or dry mercerizing.
    Type: Grant
    Filed: January 24, 1995
    Date of Patent: August 6, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Schrell, Werner H. Russ
  • Patent number: 5507840
    Abstract: A process for the dyeing of fiber materials with water-soluble anionic dyes, in particular those having a fiber-reactive group, is described, according to which dyeing is carried out using low-electrolyte or entirely electrolyte-free and/or low-alkali or entirely alkali-free dye solutions (dye liquors, printing pastes) and in which a fiber material is used which was modified by means of a saturated straight-chain or branched aliphatic or cycloaliphatic compound which is unsubstituted or substituted by one or more hydroxy groups and contains at least one primary, secondary or tertiary amino group or quaternary ammonium group and at least one hydrolyzable ester group, it also being possible for the aliphatic radical in this compound to be interrupted by one or more hetero groups.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: April 16, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Schrell, Werner H. Russ, Thomas Riehm
  • Patent number: 5498267
    Abstract: Process and use of reactive disperse dyes for dyeing and printing aminated, textile cotton and cotton-polyester blend fabricsHydroxyl-containing materials, in particular fiber materials, such as cellulose fiber materials, which have been modified with an amino-containing compound are dyed as such or in blend with polyester fibers with the aid of a fiber-reactive disperse dye in an aqueous, low-electrolyte or completely electrolyte-free medium and in the absence of an alkaline or alkali-donating agent at a temperature of between 100.degree. and 210.degree. C. Not only the modified cellulose-containing material but also the polyester material can be dyed in one and the same dyeing process with one and the same fiber reactive disperse dye. A uniform overall dyeing not only for modified hydroxyl-containing material but also for polyester material is obtained.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: March 12, 1996
    Assignee: Hoechst AG
    Inventors: Werner H. Russ, Andreas Schrell, Andreas von der Eltz
  • Patent number: 5474578
    Abstract: A hair fiber having a first color is contacted with a dye having the formula I, formula II, formula III or a mixture thereof whereby the fiber has imparted to it a second color, upon subsequent contact with alkaline peroxide the visual appearance of the first color is restored to the fiber.
    Type: Grant
    Filed: October 3, 1994
    Date of Patent: December 12, 1995
    Assignee: Clairol, Inc.
    Inventors: Alexander C. Chan, Alice A. Mayer, Jia-Shen Wang, Gottfried Wenke, Mu-Ill Lim
  • Patent number: 5468258
    Abstract: Dye donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer comprising at least one heterocyclic hydrazono dye, wherein said dye corresponds to the general formula:A=N-N=Hetwherein A is a carbocyclic or heterocyclic coupler group or a cyclic reactive methylene system, which may carry at least one substituent, and Het is a heterocyclic nucleus, which may carry at least one substituent.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: November 21, 1995
    Assignee: Agfa-Gevaert N.V.
    Inventors: Wilhelmus Janssens, Luc Vanmaele
  • Patent number: 5466813
    Abstract: Imine dyes useful in photographic materials have the formula ##STR1## wherein R.sup.1, E.sup.1, E.sup.2, L.sup.1, L.sup.2, L.sup.3,D and m are defined as in the specification.Solid particle dispersions of dyes of formula (I) that contain at least one base-ionizable functional group such as carboxy, sulfonamido, or sulfamoyl are useful as filter dyes in photographic elements.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: November 14, 1995
    Assignee: Eastman Kodak Company
    Inventors: Donald R. Diehl, Margaret J. Helber, Hugh Williamson
  • Patent number: 5427588
    Abstract: The invention relates to indoline compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2 denote hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, nitro, hydroxyl, alkoxy or NHR where R can be hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl;X denotes oxygen or sulfur;R.sub.3 represents --OR.sub.4 or NR.sub.5 R.sub.6 whereR4 denotes alkyl, alkenyl, benzyl, alkoxyalkyl or haloalkyl;R.sub.5 and R.sub.6 denote alkyl;R.sub.1 and R.sub.2 not simultaneously denoting hydrogen or nitro and when R.sub.1 denotes alkyl, alkoxy or mono- or polyhydroxyalkyl, R.sub.2 denotes NHR or hydroxyl,and to their use in dyeing keratinous fibers.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: June 27, 1995
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Jean J. Vandenbosche, Herve Andrean
  • Patent number: 5424452
    Abstract: 1,4-Diketopyrrolo[3,4-c]pyrroles of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, Cl, Br, CH.sub.3, OCH.sub.3, CN or phenyl, and at least one of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is a group--O(CH.sub.2).sub.n X or --O(CH.sub.2 CH.sub.2 O).sub.p CH.sub.2 CH.sub.2 Xwhereinn is an integer from 2 to 12, andp is an integer from 1 to 3,X is a heterocyclic radical selected from the group consisting of pyrrolyl and indolyl, or is a substituted amino group as defined in the specification.Pigment compositions comprising a minor amount of said compounds and diketopyrrolopyrrole pigments have excellent rheological and colouristic properties, especially in paint systems and in printing inks.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: June 13, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Gary Wooden, Guy de Weck, Olof Wallquist
  • Patent number: 5358537
    Abstract: There is disclosed a process and a composition for dyeing polymeric fibers which have limited dye sites and/or difficult to penetrate chemical structures. Briefly stated, the process comprises the steps of contacting polymeric fibers with a dye composition comprising a disperse dye and a swelling agent. The fibers in contact with said dye composition are then preferably heated to a temperature and for a time sufficient to effect dispersion of a portion of said dye into said polymeric fibers. Subsequently, the fibers are treated to remove residual dye composition.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: October 25, 1994
    Assignee: Shaw Industries, Inc.
    Inventors: David R. Kelly, Richard Castle, Christopher Bryant
  • Patent number: 5348557
    Abstract: There is described a process for dyeing sheetlike fiber materials, in particular those made of or containing cellulose fibers, with anionic dyes, in particular those having fiber-reactive groups, which comprises applying an alkali-free and preferably low-electrolyte or completely electrolyte-free aqueous solution of the anionic dye by the inkjet printing spray technique to a fiber material which has been pretreated and modified with a compound that contains one or more primary, secondary or tertiary amino groups or quaternary ammonium groups, which amino/ammonium groups may be part of a heterocycle. There is generally no need for an aftertreatment by washing. The costly treatment of wastewaters resulting from the excess dyeing liquors otherwise obtained is eliminated. If fiber-reactive dyes are used, fixation by means of alkali is not necessary; it is generally effected by a short heat treatment.
    Type: Grant
    Filed: September 23, 1993
    Date of Patent: September 20, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas von der Eltz, Andreas Schrell, Werner H. Russ
  • Patent number: 5215545
    Abstract: Poly(m-phenyleneisophthalamide) fabrics are printed and optionally flame retarded in a two-step process in which the dye diffusion promoting agent N-octyl-2-pyrrolidone optionally with a flame retardant is applied following by printing and print fixation.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: June 1, 1993
    Assignees: Burlington Industries, Inc., ProChroma Technologies, Inc.
    Inventors: Barbara J. Cates, Phillip H. Riggins, David R. Kelly
  • Patent number: 5092904
    Abstract: A method for dyeing fibrous material is provided. The method includes contacting a fibrous material with a mixture of a carrier and a dye soluble or dispersed in the carrier. The improvement comprises the use, as the carrier, of a mixture comprising N-cyclohexyl-2-pyrrolidone and an alkyl or aryl benzoate. The carrier system of the present can be utilized advantageously to dye difficult to dye fibrous material such as aromatic polyamides including Kevlar.RTM. fibers and blends thereof with other fibers.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: March 3, 1992
    Assignee: Springs Industries, Inc.
    Inventor: Nigel E. Neely
  • Patent number: 4994089
    Abstract: The carrier mixture contains N-alkylphthalimides and compounds of the general formula ##STR1## in which R is C.sub.1 -C.sub.7 -alkyl; phenyl, benzyl or phenylethyl, which can be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -alkylcarbonyloxy, hydroxyl or C.sub.1 -C.sub.4 -alkoxycarbonyl,m is 0 or 1,n is 0 or 1, m and n not being 0 at the same time.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: February 19, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank Bartkowiak, Hans Schulze, Wolf-Dieter Schroer, Gunther Boehmke, Karlhans Jakobs, Willi Schossler
  • Patent number: 4985046
    Abstract: There is provided by this invention a process for preparing poly(paraphenylene terephthalamide) fibers dyeable with cationic dyes. The process comprises soaking poly(paraphenylene terephthalamide) fibers in sulfuric acid, washing the fibers and dipping the acid soaked fibers or never-dried PPD-T fibers in an aqueous solution of a dye promoting species. The fibers can then be dried and subsequently dyed.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: January 15, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jon D. Hartzler
  • Patent number: 4981488
    Abstract: Poly(m-phenyleneisophthalamide) fabrics containing N-cyclohexyl-2-pyrrolidone on them are printed with a print paste. Print pastes containing N-cyclohexyl-2-pyrrolidone are also described.
    Type: Grant
    Filed: August 16, 1989
    Date of Patent: January 1, 1991
    Assignees: Burlington Industries, Inc., ProChroma Technologies
    Inventors: Barbara J. Cates, Phillip H. Riggins, David R. Kelly
  • 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: 4886545
    Abstract: This invention provides compositions comprising a compound having the structural formula ##STR1## wherein each X, Y and Z may represent oxygen, sulfur or two hydrogen atoms, provided however that, when Z represents two hydrogen atoms, both X and Y represent oxygen or sulfur and when Z represents oxygen or sulfur at least one of X and Y must represent oxygen or sulfur; m is 2-6; R' is H or a lower alkyl group having 1-4 carbon atoms; n is 0-17 and R is --CH.sub.3, ##STR2## wherein R" is H or halogen. The invention also provides compositions comprising a physiologically-active agent and the hereinabove recited 1-substituted azacycloalkane compound in an amount effective to enhance the penetration of the physiologically-active agent through the skin or other membrane of the body of an animal.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: December 12, 1989
    Assignee: Nelson Research & Development Company
    Inventors: James V. Peck, Gevork Minaskanian