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    • 13. 发明申请
    • POLYMERIC HAIR DYES
    • US20110088173A1
    • 2011-04-21
    • US12812785
    • 2009-01-07
    • Sophie Marquais-BienewaldChristian CremerOlof WallquistRoberg Hochberg
    • Sophie Marquais-BienewaldChristian CremerOlof WallquistRoberg Hochberg
    • A61K8/41A61Q5/10C09B44/16
    • C09B69/106A61K8/4946A61K8/69A61K8/84A61K2800/57A61Q5/02A61Q5/065A61Q5/12
    • Disclosed are polymeric dyes obtained by the reaction of (a) a basic polycondensate with (b) an electrophilic dye of formula (2) P—X—Ya+ Ana−; wherein the basic polycondensate (a) is obtained by the reaction of (a1) an amine of formula (I) in the presence of an anhydrous solvent with an ammonium salt (a2) with a cyanamide; wherein R1, R2, R3 and R4 independently from each other are hydrogen; or C1-C4alkyl, which may be substituted by amino, hydroxy, cyano or C1-C4alkoxy; A is C2-C20alkylene, which may be substituted or interrupted by one or more than one hetero atoms; P is a reactive grouping capable of reacting with a nitrogen nucleophile; X is a linkage group selected from C1-C30alkylene, C2-C12alkenylene, C5-C10arylene, C5-C10cycloalkylene and C1-C10alkylene(C5-C10arylene) which may be interrupted and/or terminated at one or both ends by one or more than one —O—, —S—, —N═, —N(R5)—, —S(O)—, SO2, —(CH2CH2—O)1-5—, —(CH2CH2CH2—O)1-5—, —C(O)—, —C(O)O—, —OC(O)—, (II), —CON(R5)—, —C(NR5R6)2—, —(R5)NC(O)—, —C(S)R5— or an optionally substituted, saturated or unsaturated, fused or non-fused aromatic or nonaromatic (hetero)cyclic bivalent radical optionally comprising at least one heteroatom; —O—; —S—; —N(R5)—; —S(O)—; —SO2—; —(CH2CH2—O)1-5—; —C(O)—; —C(O)O—, —OC(O)—; (III); —CON(R5)—; —SO2N(R5)—; —C(NR5R6)2—; —(R5)NC(O)—; —C(S)R5—; saturated or unsaturated, fused or non-fused aromatic or nonaromatic bivalent radical optionally comprising at least one heteroatom; which is optionally substituted by C1-C30alkyl, C1-C30alkoxy, C2-C12alkenyl, C5-C10aryl, C5-C10cycloalkyl, C1-C10alkyl(C5-C10arylene), halogen or hydroxy; or the direct bond; Y is a residue of an organic dye; R5 and R6 independently from each other are hydrogen; unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted d-C14alkyl; C2-C14alkenyl; C6-C10aryl; C6-C10aryl-C1-C10alkyl; or C5-C10alkyl(C5-C10aryl); a is 1, 2 or 3; and An is an anion. The dyes are distinguished by their depth of shade and their good fastness properties to washing, such as, for example, fastness to light, shampooing and rubbing.
    • 14. 发明申请
    • Triarylmethane Dyes
    • US20090151091A1
    • 2009-06-18
    • US11992876
    • 2006-09-27
    • Christian CremerOlof Wallquist
    • Christian CremerOlof Wallquist
    • A61K8/46C07D403/06C07C233/88C07C229/54A61K8/49
    • A61K8/46A61K8/49A61K8/492A61Q5/10C09B11/04C09B49/126
    • Disclosed are triarylmethane dyes of formula (1) D1-(Z1J)r-Y1—S-A, wherein A is hydrogen; a radical of formula (1b) *—S—Y2-(Z2)-D2; or a radical of formula (1c) *—S—Y3; Y1 and Y2 independently from each other are unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1-C10alkylene; C5-C10cycloalkylene; C5-C10arylene; or —C5-C10arylene-(C1-C10alkylene); Y3 is an unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C1C10alkyl; C5-C10cycloalkyl; C5-C10aryl; or —C5-C10aryl-(C1-C10alkyl); Z1 and Z2 independently from each other are *—(CH2)p—C(O)—**; *—(CH2CH2—O)—**; *—(CH2)p—C(O)O—**; *—(CH2)p—OCO—**; —(CH2)p—N(R1)—**; —(CH2)p—CON(R1)—**; —(CH2)p—(R1)NC(O)—**; -0-; —S—; —S(O)—; —S(O)2—; or a cationic biradical of a substituted or unsubstituted aromatic or heteroaromatic compound of the formula (1a); (1b); (1c); (1d); or (1e); wherein the asterix * indicates the linkage to D1 and/or D2; the asterix ** indicates the linkage to Y1 and/or Y2; W1 is N or a radical of CR5; R1, R2, R3, R4 and R5 independently from each other are hydrogen; C1-C14alkyl; C2-C14alkenyl; C5-C10aryl; C5-C10aryl-(C1-C10alkyl); or —C1-C10alkyl(C5-C10aryl); D1 and D2 independently from each other are hydrogen; or the residue of an organic dye selected from the radical of formula (1f), wherein B1 and B2, independently from each other are C6-C10aryl; or a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6; B3 is C6-C10arylene, or a bivalent radical of a 5-7-membered heterocyclic compound, which may be substituted by C1-C12alkyl, C1-C12alkoxy, phenyl, hydroxy, halogen, sulfonic acid, carboxylate, or by the radical —NR6R7 or —OR6; R6 and R7 independently from each other are hydrogen; or C1-C12alkyl, which may be substituted by hydroxy or C6-C10aryl; or R6 and R7 together with the linking nitrogen atom form a 5 to 7 membered heterocyclic ring; or R6 and R7 together with the linking nitrogen atom form a piperidine ring of formula (1b)* 1H **. wherein the asterix(*) is directed to Z1 or Z2 respectively; and the asterix(**) is directed to the linking nitrogen atom; wherein one of D1 and D2 is not hydrogen; An is an anion; p is a number from O to 5; r is O or 1; and s is a number from 1 to 5. The compounds are useful for the dyeing of organic materials, such as keratin fibers, preferably human hair.
    • 18. 发明申请
    • Oxazine Disulfide Dyes
    • US20090229059A1
    • 2009-09-17
    • US11992878
    • 2006-09-27
    • Christian CremerOlof Wallquist
    • Christian CremerOlof Wallquist
    • A61K8/49C09B19/00C09B17/02C09B21/00C09B49/06A61Q5/10
    • C09B19/00A61K8/49A61Q5/065A61Q5/10C09B17/02C09B21/00C09B49/06
    • Disclosed are oxazine disulfide dyes of formula (1) D1-(Z1)r-Y1—S-A, wherein A is hydrogen; or a radical of formula (1a)*—S—Y2-(Z2)r-D2; Y1 and Y2 independently from each other are unsubstituted or substituted, straight-chain or branched, interrupted or uninterrupted C—1—C—10alkylene; C5-C10cycloalkylene; C5-C10arylene; or —C5-C10arylene-(C1-C10alkylene); Z1 and Z2 independently from each other are *—(CH2)p—C(O)—**; *—(CH2CH2—O)S—**; *—(CH2)p—C(O)O—**; *—(CH2)p—OCO—**; *—(CH2)P—N(R1)—**; formula 1(g); —(CH2)p—CON(R1)—**; *—(CH2)p—(R1)NC(O)—**; , 0-; —S—; —S(O)—; —S(O)2—; or a cationic biradical of a substituted or unsubstituted aromatic or heteroaromatic compound of the formula (1a); (1b); (1c); (1d); or (1e); wherein the asterix * indicates the linkage to D1 and/or D2; the asterix ** indicates the linkage to Y1 and/or Y2; W1 is N or a radical of CR5; R1, R2, R3, R4 and R5 independently from each other are hydrogen; C1-C14alkyl; C2-C14alkenyl; C5-C10aryl; C5-C10aryl-(C1-C10alkyl); or —C1-C10alkyl(C5-C10aryl); D1 and D2 independently from each other ar the residue of an organic dye selected from the radical of formula (1f); R6 and R7 independently from each other are hydrogen; C1-C20alkyl; C1-C20alkoxy; C3-C6cycloalkyl; C5-C10aryl; anellated aromatic groups; carboxylate; or sulfonate groups; R8, R9 and R10, R11 and R12 each independently from each other are hydrogen; unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C1-C14alkyl, C2-C14alkenyl, C6-C10aryl, C6-C10aryl-C1-C10alkyl or C5-C10alkyl(C5-C10aryl); or R8 and R9 or R10 and R11, together with the linking nitrogen atom form a 5 to 7 membered carbocyclic ring which may contain one or more than one hetero atom; or R8 is linked to C1 together with N+ forming a 5-7 membered carbocyclic ring; or R9 is linked to C2 together with N+ forming a 5-7 membered carbocyclic ring; X is —O—; or —N(R9)—; or —S—; p is a number from 0 to 5; r is 0 or 1; and s is a number from 1 to 5. The compounds are useful for the dyeing of organic materials, such as keratin fibers, preferably human hair.
    • 19. 发明申请
    • Nitrosulfide dyes
    • US20090130045A1
    • 2009-05-21
    • US11921810
    • 2006-06-14
    • Christian CremerOlof Wallquist
    • Christian CremerOlof Wallquist
    • A61K8/46C07C321/20
    • A61Q5/10A61K8/418A61K8/46C09B49/02C09B51/00
    • Disclosed are nitro-sulfide dyes of formula (1), their salts, isomers, hydrates and other solvates, wherein R1, R2, R3, independently from each other are hydrogen; C1-C20alkyl or C1-C20alkoxy, which may be substituted by one or more C1-C5alkoxy, halogen, —NH2, mono-C1-C5alkylamino, di-C1-C5alkylamino, —NO2 or hydroxy; C3-C6cycloalkyl; —C(O)H; —C(O)—C1-C5alkyl; —C(O)OH; —C(O)O—C1-C5alkyl; halogen; NO2; OH; SH; phenyl, which may be substituted by one or more C1-C5alkyl, C1-C5alkoxy, halogen, —NH2, mono-C1-C5alkylamino, di-C1-C5alkylamino, —NO2 or hydroxy; or a radical of formula (1a) —NR4R5, wherein R4 and R5 independently from each other are hydrogen; C1-C12alkyl, which may be substituted by one or more C1-C5alkyl, C1-C5-alkoxy, hydroxy or —(CO)—H; —(CO)—C1-C5alkyl; phenyl or phenyl-C1-C4alkyl, wherein the phenyl moiety may be substituted by one or more C1-C5alkyl, C1-C5alkoxy, halogen, —NH2, mono-C1-C5alkylamino, di-C1-C5alkylamino, —NO2, carboxy or hydroxy; or a radical of formula (2); wherein at least one of the radicals R1, R2 or R3 is NO2; Y1 is C1-C10alkylene; C5-C10cycloalkylene; C5-C10arylene; or C5-C10arylene-(C1-C10alkylene); Z1 is the direct bond; formula (3); or a cationic biradical of a saturated, aromatic or heteroaromatic group; Q1 is —C(O)—; —C(O)O—; —OCO—; —N(R6)—X2—; —CON(R6)—; —(R6)NC(O)—; —O—; —S—; —S(O)—; or —S(O)2—; X1 and X2 independently from each other are the direct bond; C1-C10alkylene; C5-C10cycloalkylene; C5-C10arylene; or C5-C10arylene-(C1-C10alkylene); and R6, R7 and R8 independently from each other are hydrogen; C1-C14alkyl; C2-C14alkenyl; C6-C10aryl; C6-C10aryl-C1-C10alkyl; or C1-C10alkyl(C5-C10aryl); m is 1; or 2; U is hydrogen, if m is 1; or the direct bond, if m is 2; with the proviso that the method does not comprise contacting hair with an enzyme of the type of a protein disulfidisomerase (EC 5.3.4.1). Further, the present invention relates to novel sulfide compounds, compositions thereof, especially comprising other dyes, and to processes for their preparation.