Nitrophenylenediamine Dye Patents (Class 8/415)
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Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres
Publication number: 20010049849Abstract: The present application relates to a cosmetic composition intended for treating keratin fibres, comprising, in a support which is suitable for keratin fibres:Type: ApplicationFiled: April 12, 2001Publication date: December 13, 2001Applicant: L'Oreal S.A.Inventors: Roland De La Mettrie, Jean Cotteret, Arnaud De Labbey, Mireille Maubru -
Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers
Publication number: 20010044977Abstract: The present application relates to a cosmetic composition intended for treating keratin fibers, comprising, in a support which is suitable for keratin fibers: (a) at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme; (b) at least one basic amino acid; as well as to processes for treating keratin fibers, in particular processes for dyeing, permanently reshaping or bleaching the hair, using this composition.Type: ApplicationFiled: April 12, 2001Publication date: November 29, 2001Applicant: L'Oreal S.A.Inventors: Roland de la Mettrie, Jean Cotteret, Arnaud De Labbey, Mireille Maubru -
Publication number: 20010044975Abstract: Provided is a hair dye composition containing a direct dye (1). This hair dye composition has markedly high hair dyeing power, has less color fade over time and undergoes a smaller change in the color tone of the dye after storage.Type: ApplicationFiled: March 16, 2001Publication date: November 29, 2001Applicant: Kao CorporationInventors: Kenichi Matsunaga, Hajime Miyabe, Yukihiro Ohashi
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Patent number: 6187057Abstract: The invention discloses a capillary dyeing composition comprising at least one direct dye, characterised in that it further contains a cross-linked polymer with acrylic and/or acrylate units and with acrylamide units. The invention also discloses the use of a cross-linked polymer with acrylic and/or acrylate units and with acrylamide units, in or for the production of a dyeing composition containing at least one direct dye, to improve the tinctorial power of the said composition, particularly after storage at below about 10° C., and particularly at about 4° C. The invention also discloses a method for preserving the tinctorial power, in particular after storage at a temperature below about 10° C., of a dyeing composition containing at least one direct dye, characterised in that an effective amount of the said cross-linked polymer is added to the composition.Type: GrantFiled: May 20, 1998Date of Patent: February 13, 2001Assignee: L'OrealInventor: Mireille Maubru
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Patent number: 6136042Abstract: The invention discloses a capillary dyeing composition comprising at least one direct dye, wherein the composition further comprises a cross-linked polymer with acrylic units and alkyl C.sub.10 -C.sub.30 acrylate units. The invention also discloses the use of cross-linked polymer with acrylic units and alkyl C.sub.10 -C.sub.30 acrylate units in or for the production of a capillary dyeing composition comprising at least one direct dye, to improve the tinctorial power of the composition, particularly after storage at below about 10.degree. C., and in particular at about 4.degree. C. The invention also discloses a method for preserving the tinctorial power of the composition, particularly after storage at below about 10.degree. C., of a dyeing composition containing at least one direct dye, wherein an effective amount of the cross-linked polymer is added to the composition.Type: GrantFiled: May 20, 1998Date of Patent: October 24, 2000Assignee: L'OrealInventor: Mireille Maubru
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Patent number: 5948121Abstract: The present invention relates to a permanent dyeing composition comprising a) above 0 to 1 mg enzyme protein per ml dyeing composition of microbial laccase, b) one or more dye precursor, and c) optionally one or more dye modifiers, the use of the dyeing composition for dyeing keratinous fibers, such as hair, fur, hide, and wool, and a method for permanent dyeing of keratinous fibers.Type: GrantFiled: May 22, 1998Date of Patent: September 7, 1999Assignee: Novo Nordisk A/SInventors: Dorrit Aaslyng, Niels Henrik S.o slashed.rensen, Karen R.o slashed.rb.ae butted.k
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Patent number: 5792221Abstract: A hydroxypropylated 2-nitro-p-phenylenediamine of formula (I), wherein R1 is a C1-4 alkyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl or .gamma.-hydroxypropyl radical; R2 and R3 independently represent a .beta.-hydroxyethyl, .beta.-hydroxypropyl, .gamma.-hydroxypropyl or .beta.,.gamma.-dihydroxypropyl radical, with the proviso that at least one of R1, R2 and R3 is a .gamma.-hydroxypropyl radical, while the other two are not both a .beta.-hydroxyethyl radical; and cosmetically acceptable salts thereof. This compound may be used for directly dyeing hair to give blue through purplish blue shades which are wash-fast, light-fast, waterproof and sweat resistant.Type: GrantFiled: November 25, 1996Date of Patent: August 11, 1998Assignee: L'OrealInventors: Alain Lagrange, Alex Junino, Alain Genet, Jean Cotteret
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Patent number: 5735910Abstract: Novel nitrobenzene compounds of the nitroparaphenylenediamine type substituted by sulphur in the 5-position are disclosed. These compounds are intended especially for the dyeing of keratin fibres and in particular human hair. A process for their preparation, dyeing compositions in which these compounds are present and a dyeing process in which these compositions are used are also disclosed.Type: GrantFiled: December 31, 1996Date of Patent: April 7, 1998Assignee: L'OrealInventors: Alain Lagrange, Alain Genet
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Patent number: 5628799Abstract: A process for dyeing hair by preparing and applying to the hair an aqueous reaction medium comprising a dopa species, a reactive direct dye and an oxidant, said aqueous reaction medium optionally containing at least one hair dyeing agent selected from the group consisting of primary intermediates and couplers and also containing a buffer to maintain the pH in the range from 6 to 10 during the reaction, and removing said aqueous reaction medium from the hair within about one hour following its preparation.Type: GrantFiled: June 7, 1995Date of Patent: May 13, 1997Assignee: Clairol IncorporatedInventors: Gottfried Wenke, Giuseppe Prota
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Patent number: 5516942Abstract: A N1,N4-dihydroxyethylated 2-nitro-p-phenylenediamine of formula (I), wherein R is C3-4 aklyl, and cosmetically acceptable salts thereof, for use in direct dyeing to give blue through purple shades which are wash-fast, light-fast, weatherproof and sweat resistant, and optionally combined with yellow and optionally read or orange-coloured dyes to give natural hues.Type: GrantFiled: December 7, 1994Date of Patent: May 14, 1996Assignee: L'OrealInventors: Alain Lagrange, Alex Junino, Alain Genet, Jean Cotteret
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Patent number: 5496377Abstract: A process for the direct dyeing (or colouring) of keratinous fibres, in particular human keratinous fibres, comprising the step of: directly dyeing the fibres by contacting the fibres (1) with a composition containing at least one direct dye chosen from specific 2-nitro-para-phenylenediamine derivatives and/or nitro derivatives of specific aminophenols, and (2) with a gas containing water vapour, the temperature of the gas being at least 75.degree. C. and the contact time between the gas and the fibres to be dyed not exceeding two minutes. The hair is dyed uniformly over the whole head of hair, from the roots to the ends, regardless of the condition of the hair.Type: GrantFiled: December 16, 1994Date of Patent: March 5, 1996Assignee: L'OrealInventors: Henri Samain, Jean-Michel Sturla
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Patent number: 5380340Abstract: The composition for oxidative dyeing of hair contains at least one coupler and 0.010 to 3.0 percent by weight of at least one developer selected from the group consisting of aminopyrazole derivatives of the formula (I): ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl groups having one to four carbon atoms; n=2 or 3; and physiologically tolerated, water-soluble salts thereof. The developer and coupler substances are present in the composition in a total amount of from 0.1 to 5.0 percent. New pyrazole derivative compounds are also part of the invention.Type: GrantFiled: March 4, 1993Date of Patent: January 10, 1995Assignee: Wella AktiengesellschaftInventors: Hans Neunhoeffer, Stefan Gerstung, Thomas Clausen, Wolfgang R. Balzer
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Patent number: 5199954Abstract: An easily employed, effective and predictable hair dye composition is obtained by combining aryl amines with aryl aldehydes along with an inorganic metal salt having a valence between +1 and +3. By employing this formulation, a permanent, long-lasting, non-fading hair coloring is achieved. In the preferred embodiment, the inorganic metal salt is selected from the group consisting of aluminum chloride, ferric chloride, lithium bromide, manganese chloride, copper chloride, and manganese nitrate. In carrying out the teaching of the present invention, the aryl amine and aryl aldehyde may be applied to the hair separately or in combination, along with the inorganic metal salt. In addition, this inorganic metal salt can be applied after the application and removal of the aryl amine and aryl aldehyde.Type: GrantFiled: February 25, 1992Date of Patent: April 6, 1993Assignee: Shiseido Co., Ltd.Inventors: Thomas M. Schultz, Catherine Grillo, Sanae Kubo
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Patent number: 5186717Abstract: The invention provides dyeing compositions for keratin fibres, which contain at least one dyestuff corresponding to the formula: ##STR1## in which R.sub.1 and R.sub.2 independently of one another denote a hydrogen atom, an alkyl group, a monohydroxyalkyl or polyhydroxyalkyl group, an alkyl group substituted by an alkoxy group, or an aminoalkyl group of which the amino group can optionally be monosubstituted or disubstituted by an alkyl group, and the radical R.sub.2 can also denote a phenyl group or a phenyl group substituted by an alkyl, hydroxyl or amino group, and Z denotes a hydrogen atom or an alkyl group, or their cosmetically acceptable salts. Many of the dyestuffs are novel.Type: GrantFiled: September 25, 1991Date of Patent: February 16, 1993Assignee: L'OrealInventors: Andree Bugaut, Alex Junino, Jean J. Vandenboosche
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Patent number: 5167669Abstract: Dyeing composition for keratinous fibers, especially for human keratinous fibers, characterized in that it contains, in an aqueous medium suitable for dyeing:a) an indole dye; andb) a para-phenylenediamine monosubstituted on one of the amino groups, corresponding to the formula: ##STR1## in which: R.sub.12 denotes a hydrogen atom or a lower alkyl group;R.sub.13 denotes a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; andR.sub.14 denotes a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; R.sub.14 occupying any one of the remaining positions of the benzene ring; as well as the addition salts with an acid, this composition not containing an oxidizing agent other than air.Type: GrantFiled: December 6, 1991Date of Patent: December 1, 1992Assignee: L'OrealInventor: Jean F. Grollier
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Patent number: 5163970Abstract: Compounds of the formula I are described: ##STR1## wherein R.sup.1 and R.sup.2 independently of one another each represent a hydrogen atom, a (C.sub.1 -C.sub.2) alkyl group, a hydroxy (C.sub.2 -C.sub.3) alkyl group or a 2,3-dihydroxypropyl group and X is a fluorine atom, with the proviso that when R.sup.1 or R.sup.2 is hydrogen then the other is not a hydroxy (C.sub.2) alkyl group; processes for their preparation and aqueous hair coloring agents containing these compounds.Type: GrantFiled: August 16, 1991Date of Patent: November 17, 1992Assignee: Hans Schwarzkopf GmbHInventors: Mustafa Akram, Winfried Seidel
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Patent number: 5135543Abstract: Quaternized monoalkylenediamine nitrobenzene compounds of general formula ##STR1## wherein one of Z or Y is the quaternized group ##STR2## the other of Y or Z being H, alkyl hydroxyalkyl or hydroxyalkoxy when it is not said quaternized group, and the use of said compounds in the dyeing of keratinaceous fibers.Type: GrantFiled: September 19, 1991Date of Patent: August 4, 1992Assignee: Clairol IncorporatedInventors: Alexander Chan, Yuh-Guo Pan
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Patent number: 5110318Abstract: A method for non-permanently or semi-permanently coloring hair with an aqueous clay-based composition that involves applying the composition to hair and exposing the hair to heat for a period of time sufficient to dry the composition to a hard and flaky state. The hair coloring composition also can include effective amounts of a reconstruction component (protein), a moisturizer component having sodium hyaluronate, and a shine imparting component having henna extract.Type: GrantFiled: March 14, 1990Date of Patent: May 5, 1992Inventors: Rocco F. Altobelli, Wallace R. Hlavic, Annette Angell-Schram
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Patent number: 5096455Abstract: Dyeing composition for keratinous fibres, especially for human keratinous fibres, characterized in that it contains, in an aqueous medium suitable for dyeing the following composition:a) an indole dye; andb) a para-phenylenediamine monosubstituted on one of the amino groups, corresponding to the formula: ##STR1## in which: R.sub.12 denotes a hydrogen atom or a lower alkyl group;R.sub.13 denotes a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; andR.sub.14 denotes a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; R.sub.14 occupying any one of the remaining positions of the benzene ring; as well as the addition salts with an acid, this composition not containing an oxidizing agent other than air.Type: GrantFiled: July 20, 1990Date of Patent: March 17, 1992Assignee: L'OrealInventor: Jean F. Grollier
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Patent number: 5089025Abstract: The invention relates to the use of compounds corresponding to formula (I) ##STR1## in which one of the substituents R.sup.1 or R.sup.2 is a nitro group while the other is hydrogen, halogen, an amino group, a mono- or dialkylamino group containing C.sub.1-4 alkyl groups, a C.sub.1-4 alkyl or alkoxy group, R.sup.3 and R.sup.4 independently of one another represent hydrogen or a C.sub.1-4 alkyl group, A is a >CHR.sup.6 - or a >C.dbd.O- group, where R.sup.6 is hydrogen or a C.sub.1-4 alkyl group, and R.sup.5 is hydrogen or a C.sub.1-4 alkyl group, or salts thereof as substantive dyes in hair-dyeing compositions.When the substituent groups in formula I represent one of the combinations I-IV shown in the table below, the compounds are novel and are useful in hair-dyeing compositions.______________________________________ R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 A ______________________________________ I: H NO.sub.2 H CH.sub.3 H CH.sub.2 II: H NO.sub.2 CH.sub.3 CH.sub.3 H CH.sub.2 III: NH.sub.2 NO.sub.Type: GrantFiled: January 25, 1991Date of Patent: February 18, 1992Assignee: Henkel Kommanditgesellschaft auf AktienInventors: David Rose, Edgar Lieske, Horst Hoeffkes
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Patent number: 5089026Abstract: A dyeing composition for a keratin fiber which comprises 1,5-dihydroxynaphthalene as a coupling substance, 2-amino-5-hydroxybenzoic acid or a cosmetically acceptable salt thereof as a color developing substance, and a cosmetically acceptable base is disclosed. The dyeing composition for a keratin fiber give a vivid red color tone having a high chroma and an extremely high fastness.Type: GrantFiled: April 25, 1991Date of Patent: February 18, 1992Assignee: Kao CorporationInventors: Hidetoshi Tagami, Jiro Kawase
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Patent number: 5085666Abstract: The invention relates to a process for the preparation of nitroanilines, which consists in reacting an amine RNH.sub.2, or ammonia, with 3,4-methylenedioxynitrobenzene to give the products of the formula: ##STR1## in which R denotes hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl, alkoxyalkyl or aminoalkyl of the formula: ##STR2## in which R.sub.1 and R.sub.2, which are identical or different, denote hydrogen, alkyl or monohydroxyalkyl or polyhydroxyalkyl and n denotes an integer from 2 to 4, or of the formula: ##STR3## in which A denotes OCH.sub.2 or ##STR4## and R.sub.1 denotes --CH.sub.2 CH.sub.2 OH or ##STR5## or their salts.Type: GrantFiled: August 20, 1990Date of Patent: February 4, 1992Assignee: L'OrealInventors: Andree Bugaut, Alex Junino
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Patent number: 5082467Abstract: A dye composition for keratinous fibers is disclosed. The composition comprises a developing substance and, as a coupling substance, a 3,5-diaminopyridine derivative of the following formula (I), ##STR1## wherein R.sup.1 is an alkoxy group or a group ##STR2## wherein R.sup.2 and R.sup.3 may be the same or different and individually represents a hydrogen atom or a hydroxyalkyl group, R.sup.4 a hydroxy, alkoxy, or hydroxyalkyl group, and n is a number of 1-4; or a salt thereof. The composition is capable of dyeing keratinous fibers such as hairs in blue color with a high vividness and with resistances to the light, color change, and discoloration due to shampooing.Type: GrantFiled: January 25, 1991Date of Patent: January 21, 1992Assignee: Kao CorporationInventors: Tadashi Tamura, Akira Kiyomine, Michio Tanaka, Yoshinori Nishizawa, Hidetoshi Tagami, Masahiko Ogawa, Toru Yoshihara, Tsutomu Muraoka, Jiro Kawase
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Patent number: 5073174Abstract: A process for dyeing keratinous fibers comprises a two-step operation in which in the first step the fibers are contacted with an indole dye in a medium suitable for dyeing the fibers, the medium being free from any oxidation catalyst and oxidation catalyst. Thereafter, in the second step the fibers are contacted with a para type oxidation dye precursor in a medium which is also suitable for dyeing the fibers and is free from any oxidation catalyst and oxidation agent. A multi-compartment kit housing the indole dye and para type oxidation dye precursor is also provided.Type: GrantFiled: July 20, 1990Date of Patent: December 17, 1991Assignee: L'OrealInventors: Charles Vayssie, Daniel Bauer, Francoise Richard, Alex Junino
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Patent number: 5067967Abstract: The invention relates to compounds of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 independently of one another each represent a hydrogen atom, a (C.sub.1 -C.sub.2) alkyl group, a hydroxy (C.sub.2 -C.sub.3) alkyl group or a 2,3-dihydroxypropyl group and X is a florine atom or a trifluoromethyl group, processes for their preparation and aqueous hair coloring agents containing these compounds.Type: GrantFiled: April 25, 1990Date of Patent: November 26, 1991Assignee: 501 Hans Schwarzkopf GmbHInventors: Mustafa Akram, Winfried Seidel
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Patent number: 5061289Abstract: Composition for the oxidative dyeing of hair based on a combination of developer substances and coupler substances contains, as developer substance, a diaminopyrazol of the general formula (I), ##STR1## wherein R.sup.1, R.sup.2 and R.sup.4 are identical or different and designate hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl with 2 to 4 carbon atoms, benzyl or phenyl, and R.sup.3 is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl with 2 to 4 carbon atoms, with the proviso that the amino groups are in 3,4 or 4,5 position, or its physiologically tolerated, water-soluble salt, new diaminopyrazol derivatives of the above general formula I are also described herein in which R.sup.1 is methyl or benzyl and the R.sup.2 and R.sup.4 are either benzyl, phenyl, hydrogen, alkyl with 1 to 4 carbon atoms or hydroxyalkyl with 2 to 4 carbon atoms and R.sup.3 is either hydrogen, alkyl with 1 to 4 carbon atoms or hydroxylakyl with 2 to 4 carbon atoms.Type: GrantFiled: August 2, 1990Date of Patent: October 29, 1991Assignee: Wella AktiengesellschaftInventors: Thomas Clausen, Ute Kern, Hans Neunhoeffer
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Patent number: 5047066Abstract: A hair dyeing composition comprising a special developer and a coupling agent is disclosed. The developer is a 4-aminophenol derivative substituted at the 2-position which is represented by the following formula (I), ##STR1## in which X represents a group --NHCOR.sup.1 (R.sup.1 is a linear or branched alkyl group having 1-5 carbon atoms), a group --COOR.sup.2 [R.sup.2 is a hydrogen atom, a linear or branched alkyl group having 1-5 carbon atoms, a monohydroxy alkyl group having 1-5 carbon atoms, a polyhydroxy alkyl group having 1-5 carbon atoms, or a group --(CH.sub.2).sub.n NR.sup.3 R.sup.4 (R.sup.3 and R.sup.4 individually represent a hydrogen atom or a linear or branched alkyl group having 1-5 carbon atoms, and n denotes an integer of 1-5)], a group --CONHR.sup.2, a nitrile group, a group --SO.sub.3 R.sup.2, or a group --SO.sub.2 NR.sub.2.sup.2 (R.sup.2 has the same meaning as defined above and the two R.sup.2 s may be the same or different), or a salt thereof.Type: GrantFiled: June 5, 1989Date of Patent: September 10, 1991Assignee: Kao CorporationInventors: Tsutomu Mano, Jiro Kawase, Daisuke Misu, Michio Obayashi
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Patent number: 5041143Abstract: The present invention relates to a process for preparing a N,N'-disubstituted nitro-para-phenylenediamine (I) according to the following scheme: ##STR1## X denoting a halogen and R a lower alkyl, lower mono- or polyhydroxyalkyl, lower alkoxyalkyl or lower aminoalkyl group, in which the amino group can be mono- or disubstituted with a lower alkyl or lower mono- or polyhydroxyalkyl group, the nitrogen atom of said amino group being able to form part of a heterocyclic system.The invention also relates to the intermediate oxazolidones of formulae (II) and (III), and the new nitro-para-phenylenediamines in which R denotes a lower alkoxyalkyl, lower polyhydroxyalkyl or lower aminoalkyl group, as well as the dyeing compositions for keratinous fibres containing these new nitro-para-phenylenediamines.Type: GrantFiled: December 20, 1989Date of Patent: August 20, 1991Assignee: L'OrealInventors: Gerard Lang, Alex Junino
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Patent number: 5034014Abstract: An aromatic amine, or a cosmetically acceptable salt thereof, is reacted with an aromatic aldehyde in a reaction medium containing water. 2,6-dihydroxypyridine, or a cosmetically acceptable salt thereof, is reacted with hydrogen peroxide in a reaction medium containing water. The two reaction mediums are combined so that both reactions are carried out together on hair. Preferably, the two reactions are carried out together in the same reaction medium. pH is adjusted so that the pH of the common reaction medium is about 5 to 7. Surprisingly, substantially no cross reaction occurs between the two reactions on hair.Type: GrantFiled: June 18, 1990Date of Patent: July 23, 1991Assignee: Clairol, Inc.Inventor: Gottfried Wenke
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Patent number: 4981486Abstract: The present invention relates to the new nitro bezene dye of formula: ##STR1## and the cosmetically acceptable salts of this compound, as well as the process for preparation thereof by condensation of 3-amino-1-propanol with 2-fluoro-5-bis(.beta.-hydroxyethyl)amino-1-nitrobenzene.This blue dye shows excellent solubility in water, a water/alcohol mixture and the usual dyeing media. Furthermore, when used in combination with one or more yellow nitro benzene dyes and optionally other direct dyes, it gives, especially on hair sensitized by treatment such as bleaching or permanent waving, natural shades having good lightfastness and washing resistance.Type: GrantFiled: September 6, 1985Date of Patent: January 1, 1991Assignee: L'OrealInventors: Jean F. Grollier, Jean Cotteret, Alex Junino, Alain Genet
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Patent number: 4931066Abstract: The invention relates to a dyeing composition for keratinous fibres containing, in a suitable vehicle, at least one 2-nitro-para-phenylenediamine direct dye, in free or salified form and also at least one xanthine derivative of formula (II) ##STR1## where n=0 or 1, R'.sub.3 =H, R'.sub.1, R'.sub.2, R'.sub.4 and R'.sub.5 are substituents having various significances, the said compound of formula (II) being in free or salified form. They can be used for dyeing hair.Type: GrantFiled: August 9, 1985Date of Patent: June 5, 1990Assignee: L'OrealInventors: Jean-Francois Grollier, Jean Cotteret, Georges Rosembaum
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Patent number: 4921504Abstract: The compound 4-(N-ethyl-N-2'-hydroxyethyl)-amino-1-(2"-hydroxyethyl)-amino-2-nitrobenze ne, having the formula: ##STR1## is provided for use as a blue coloring nitro dye in a hair dyeing composition that may be directly applied to hair without the use of oxidation agents.Type: GrantFiled: September 12, 1988Date of Patent: May 1, 1990Assignee: Wella AktiengesellschaftInventors: Thomas Clausen, Eugen Konrad
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Patent number: 4910341Abstract: The present invention relates to a process for preparing a N,N'-disubstituted nitro-para-phenylenediamine (I) according to the following scheme: ##STR1## X denoting a halogen and R a lower alkyl, lower mono- or polyhydroxyalkyl, lower alkoxyalkyl or lower aminoalkyl group, in which the amino group can be mono- or disubstituted with a lower alkyl or lower mono- or polyhydroxyalkyl group, the nitrogen atom of said amino group being able to form part of a heterocyclic system.The invention also relates to the intermediate oxazolidones of formulae (II) and (III), and the new nitro-para-phenylenediamines in which R denotes a lower alkoxyalkyl, lower polyhydroxyalkyl or lower aminoalkyl group, as well as the dyeing compositions for keratinous fibres containing these new nitro-para-phenylenediamines.Type: GrantFiled: September 6, 1988Date of Patent: March 20, 1990Assignee: L'OrealInventors: Gerard Lang, Alex Junino
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Patent number: 4886517Abstract: The present invention relates to a composition for dyeing keratinic fibres, and human hair in particular, comprising the azo dye of formula: ##STR1## optionally in combination with at least one nitro benzene dye or with at least one aminoanthraquinone dye or with at least one nitro benzene and at least one aminoanthraquinone dye. The azo dye of formula (II) is nonmutagenic, has good solubility properties in the usual dye carriers, and imparts to hair hues which are stable, particularly to washing. The invention also relates to a process for dyeing human hair by direct coloration which comprises applying the dyeing composition defined above onto the hair, leaving it on the hair for 3 to 60 minutes and then rinsing and drying the hair.Type: GrantFiled: October 31, 1988Date of Patent: December 12, 1989Assignee: L'OrealInventors: Andree Bugaut, Alex Junino, Jean Cotteret
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Patent number: 4875902Abstract: The invention relates to the use of a compound of the formula: ##STR1## in which R denotes an alkyl radical having 1 to 4 carbon atoms, as an antioxidant in oxidation dyeing compositions.Type: GrantFiled: October 16, 1987Date of Patent: October 24, 1989Assignee: L'OrealInventors: Jean F. Grollier, Jean Cotteret
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Patent number: 4863482Abstract: A 2-nitro metaphenylenediamine for use in dyeing keratinous fibers, in particular human hair, has the formula: ##STR1## wherein Z represents a --O--, --S-- or --NH-- radical. R.sub.1, R.sub.2 and R.sub.3 may be identical or different and represent a hydrogen atom or an alkyl, hydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical or an aminoalkyl radical whose amino radical may be mono- or disubstituted by an alkyl or hydroxyalkyl radical. The alkyl and alkoxy radicals contain 1 to 6 carbon atoms. Cosmetically acceptable salts of this compound may also be used.Type: GrantFiled: July 26, 1988Date of Patent: September 5, 1989Assignee: L'OrealInventors: Alex Junino, Nicole Jehanno, Gerard Lang
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Patent number: 4863481Abstract: The invention relates to oxidation dyeing compositions comprising oxidation dyestuff precursors and N-substituted ortho-nitroanilines of the formula: ##STR1## in which R.sub.1 denotes an alkyl, monohydroxyalkyl or polyhydroxyalkyl group, R.sub.2 denotes hydrogen or an amino, monoalkylamino, dialkylamino, mono- or di-(monohydroxyalkyl or polyhydroxyalkyl)-amino, (N-alkyl-N-monohydroxyalkyl or N-alkyl-N-polyhydroxyalkyl)-amino, alkoxy, monohydroxyalkoxy, polyhydroxyalkoxy or aminoalkoxy group and R.sub.3 denotes hydrogen or an alkyl group, at least one of R.sub.2 and R.sub.3 being different from H, with the proviso that if R.sub.1 denotes --CH.sub.2 CH.sub.2 OH, R.sub.2 cannot be di-(monohydroxyalkyl)-amino in an alkaline medium which is non-ammoniacal and comprises an alkali metal or ammonium bisulphite and at least one alkanolamine which is N-(C.sub.1 to C.sub.4 -alkyl-ethanolamine, N,N-di(C.sub.1 to C.sub.4 -alkyl)-ethanolamine, di-(hydroxy-C.sub.2 to C.sub.Type: GrantFiled: January 3, 1983Date of Patent: September 5, 1989Assignee: L'OrealInventors: Christian Monnais, Jean Cotteret
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Patent number: 4845293Abstract: A dyeing composition for keratinous fibres comprising a solvent and at least one dye which is a halogenated 2-nitro-aniline of formula: ##STR1## in which Y is a halogen and Z is a NHR.sub.2 group or Y is hydrogen and Z is a halogen and R.sub.1 and R.sub.2, which may be identical or different, are each hydrogen, an alkyl group, a mono- or polyhydroxylated alkyl group, an alkyl group substituted with an alkoxy or hydroxyalkoxy group, or an aminoalkyl group, the amino group of which is optionally substituted with one or two alkyl or hydroxyalkyl groups, and it being possible for the nitrogen atom of the aminoalkyl group to form part of a heterocycle, all the abve alkyl groups or moieties containing from 1 to 6 carbon atoms,or, if the compound of formula (I) contains an amine group which can be salified, a cosmetically acceptable salt thereof.Type: GrantFiled: February 17, 1987Date of Patent: July 4, 1989Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Nicole Jehanno, Jean J. Vandenbosche
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Patent number: 4834768Abstract: A dyeing composition for the direct coloring of the hair, containing at least one direct dyestuff, and at least one xanthane gum is disclosed.Type: GrantFiled: December 11, 1987Date of Patent: May 30, 1989Assignee: L'OrealInventor: Jean F. Grollier
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Patent number: 4797129Abstract: A dye composition for keratinous fibres comprising a solvent and at least one dye which is a compound of formula: ##STR1## in which R.sub.1 and R.sub.2 are each, independently of each other, hydrogen, an alkyl group, a mono- or polyhydroxylated alkyl group, an alkyl group substituted by an alkoxy or hydroxyalkoxy group, or an aminoalkyl group, the amino group of which is optionally substituted with one or two alkyl or hydroxyalkyl groups, and it being possible for the nitrogen atom also to form part of a heterocyclic ring, all the abovementioned alkyl groups or moieties containing from 1 to 6 carbon atoms, or, of the compound of formula (I) contains an amino group which can be salified, a cosmetically acceptable salt thereof.Type: GrantFiled: February 17, 1987Date of Patent: January 10, 1989Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Nicole Jehanno, Jean J. Vandenbosche
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Patent number: 4764174Abstract: A nitrophenylenediamine dye composition includes a long chain alkyl (8 to 18 carbon chain length) sulfate detergent, such as sodium lauryl sulfate or ammonium lauryl sulfate together with a sultaine (sulfobetaine) surfactant in a ratio of sulfate/sultaine in the range of 1:1 to 10:1, and particularly in the range of 6:1 to 9:1 to achieve unexpectedly increased deposition of specific nitrophenylenediamine dyes onto human hair.Type: GrantFiled: January 30, 1986Date of Patent: August 16, 1988Assignee: Helene Curtis, Inc.Inventor: Myra A. Hoshowski
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Patent number: 4736067Abstract: New dimethyl derivatives of 3-nitro-4-aminoaniline, process for their preparation, and their use for dyeing keratinic fibres.The invention relates to dimethyl derivatives of 3-nitro-4-aminoaniline of formula: ##STR1## in which CH.sub.3 is in position 2 or 5 of the benzene ring and R.sub.1 and R.sub.2 denote independently of each other a hydrogen atom, a lower alkyl group, a lower mono- or polyhydroxyalkyl or a lower aminoalkyl group in which the amino group is optionally mono- or disubstituted by a lower alkyl radical or by a lower mono- or polyhydroxyalkyl radical, it being understood that the two symbols R.sub.1 and R.sub.2 can be simultaneously other than hydrogen only when the mobile CH.sub.3 radical is in position 5, or cosmetically acceptable salts of these compounds, as well as the process for preparing them and their use in dye compositions, in particular for hair, equally for direct coloring and for coloring by an oxidation route.Type: GrantFiled: September 6, 1984Date of Patent: April 5, 1988Assignee: L'OrealInventors: Andree Bugaut, Alain Genet, Jean Cotteret, Alex Junino
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Patent number: 4727192Abstract: The invention relates to a compound of formula ##STR1## in which: X denotes a branched or unbranched alkylene radical containing 2 to 6 carbon atoms, optionally being able to be substituted with one or more hydroxyl radicals;R denotes a hydrogen atom, an alkyl or a mono- or polyhydroxyalkyl radical or an aminoalkyl radical in which the amine group can be mono- or disubstituted with an alkyl radical or with a mono- or polyhydroxyalkyl radical, the nitrogen atom also being able to form part of a heterocyclic system and the alkyl radicals containing 1 to 4 carbon atoms;R' denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl radical;Y and Z denote a nitro and/or --NHR.sub.1 radical, R.sub.Type: GrantFiled: December 13, 1985Date of Patent: February 23, 1988Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Nicole Jehanno
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Patent number: 4725283Abstract: The invention relates to dyeing compositions for direct dyeing of keratinic fibres, containing, in a cosmetically acceptable medium:(a) at least one yellow or green-yellow dye corresponding to the formula (I): ##STR1## in which X=Cl, Br, F, and R.sub.1 and R.sub.2 denote, independently of each other, hydrogen, alkyl, hydroxyalkyl, or alkylaminoalkyl in which the aminoalkyl group may be mono- or disubstituted provided that R.sub.1 and R.sub.2 do not simultaneously denote a hydrogen atom, and(b) at least one blue or violet dye corresponding to the formula: ##STR2## in which R.sub.3 denotes a hydrogen atom or an alkyl, monohydroxyalkyl, polyhydroxyalkyl or alkoxyalkyl radical and R.sub.4 and R.sub.5 have separately the same meanings as R.sub.3 but cannot denote a hydrogen atom.Type: GrantFiled: June 10, 1986Date of Patent: February 16, 1988Assignee: L'OrealInventors: Jean Cotteret, Alex Junino, Gerard Lang
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Patent number: 4704474Abstract: New 1,4-diamino-5-chloro-2-nitrobenzene derivatives are disclosed of the formula I ##STR1## Wherein R.sup.1 and R.sup.2 are the same or different and are each hydrogen, 2-hydroxyethyl or 2,3-dihydroxypropyl, with the proviso, that at least one of said R.sup.1 and R.sup.2 is 2,3-dihydroxypropyl, along with processes for their production, as well as hair coloring compositions containing the same and methods of coloring hair. The compounds are red- to violet-coloring direct dyes, and are readily soluble in water, with favorable toxicological characteristics.Type: GrantFiled: February 26, 1986Date of Patent: November 3, 1987Assignee: Wella AktiengesellschaftInventors: Eugen Konrad, Thomas Clausen
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Patent number: 4690685Abstract: The invention relates to a dyeing composition for keratinous fibres containing at least one 4-bis(.beta.-hydroxyethyl)amino-2-nitro-1-(N-substituted amino)benzene compound in which the substitution is C.sub.1 -C.sub.3 alkyl or .beta.-hydroxyethyl; this composition contains as co-solubilization agent at least one dye of formula (II) ##STR1## in which formula: R.sub.2 denotes a C.sub.2 -C.sub.3 hydroxyalkyl group;R.sub.3 denotes a C.sub.2 -C.sub.3 hydroxyalkyl group; with the proviso that, if R.sub.3 =CH.sub.2 CH.sub.2 OH, R.sub.2 is necessarily an .alpha.-hydroxyethyl or hydroxypropyl radical.Type: GrantFiled: September 26, 1985Date of Patent: September 1, 1987Assignee: L'OrealInventors: Jean-Francois Grollier, Jean Cotteret, Alex Junino, Alain Genet
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Patent number: 4668237Abstract: The invention relates to a composition for dyeing keratinic fibres, especially human hair, which contains 5-nitrovanillin of formula: ##STR1## in an aqueous, alcoholic or hydroalcoholic carrier. This yellow nitro dye makes it possible to obtain stable shades having good light- and shampoo-resistance when it is used by itself or in combination with blue or violet nitrobenzene dyes, and optionally with other direct dyes.Type: GrantFiled: December 23, 1985Date of Patent: May 26, 1987Assignee: L'OrealInventors: Jean F. Grollier, Jean Cotteret, Georges Rosenbaum
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Patent number: 4668236Abstract: The invention relates to a dyeing composition for keratinous fibres containing, in a suitable vehicle, at least one nitrated direct dye of the 2-nitro-paraphenylenediamine series, in which the amino group in position 4 is mono- or disubstituted with lower alkyl or hydroxyalkyl radicals and in which the amino group in position 1 is optionally monosubstituted with a lower alkyl or hydroxyalkyl radial, and the aromatic ring can be substituted or unsubstituted on the remaining positions; the invention consists in introducing into such a composition an imidazolidinedione or one of its substitution derivatives, to improve the solubility of the abovementioned nitrated direct dye by a co-solubilization phenomenon. The invention also relates to a process for dyeing keratinous fibres using such compositions.Type: GrantFiled: June 14, 1985Date of Patent: May 26, 1987Assignee: L'OrealInventors: Jean-Francois Grollier, Jean Cotteret, Georges Rosenbaum
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Patent number: 4666453Abstract: The invention relates to compounds of formula ##STR1## in which X denotes a halogen atom, and R and R' denote a hydrogen atom, an alkyl, polyhydroxyalkyl, hydroxyalkoxyalkyl or alkoxyalkyl radical or an aminoalkyl radical optionally substituted on the nitrogen atom provided that at least one of the groups R and R' is a polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical, and to dye compositions for keratinic fibres in which they are employed, to the preparation process and to intermediates.Type: GrantFiled: June 10, 1986Date of Patent: May 19, 1987Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Ginette Jeanminet
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Patent number: 4637821Abstract: A process for dyeing keratin fibres is disclosed which involved applying:(a) at least one dyestuff of the formula: ##STR1## in which R.sub.1 and R.sub.2 independently designate hydrogen, amino, alkylamino, --NH--aliphatic--(X).sub.m, dialkylamino or --N--(aliphatic-(X).sub.m).sub.2, R.sub.3 designates hydrogen, OH, alkoxy or --O--aliphatic-(X).sub.m "aliphatic" designates an aliphatic radical having 2 to 4 free valencies, m designates an integer from 1 to 3 such that if m=1 X represents OH, Cl, OCH.sub.3 or OCH.sub.2 CH.sub.2 OH, or, if m designates 2 or 3, X designates OH, and R.sub.4 designates hydrogen, alkyl or halogen, with the proviso that at least one of R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, and that, if R.sub.1 and R.sub.2 are both other than hydrogen, R.sub.3 designates hydrogen,(b) at least one dyestuff of the formula: ##STR2## in which R.sub.5 designates hydrogen, amino, aminoalkyl, NH-aliphatic-(X).sub.m, N-(alkyl).sub.2, N-(aliphatic(X).sub.m).sub.2, or NHCH.sub.2 CH.sub.2 NH.sub.Type: GrantFiled: September 30, 1982Date of Patent: January 20, 1987Assignee: L'OrealInventors: Christian Monnais, Jean Cotteret