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(12) United States Patent (10) Patent No.: US 8,268,014 B2 Fröhling (45) Date of Patent: *Sep

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(12) United States Patent (10) Patent No.: US 8,268,014 B2 Fröhling (45) Date of Patent: *Sep USOO8268O14B2 (12) United States Patent (10) Patent No.: US 8,268,014 B2 Fröhling (45) Date of Patent: *Sep. 18, 2012 (54) HAIR DYEING COMPOSITION compounds of formulae (2); (3) and (4): wherein D is the radical of a diazo component of the formula (2a); (2b); (2c); (75) Inventor: Beate Fröhling, Neustadt (DE) (2d); (2f); (2g) or (2h). The invention also relates to the dyeing methods for dyeing keratinous fibers comprising Such dyeing (73) Assignee: BASFSE Ludwigshafen (DE) composition. (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 (1) U.S.C. 154(b) by 0 days. R6 2 Rs This patent is Subject to a terminal dis- R O R4 claimer. NN O nN.1 (21) Appl. No.: 13/148,685 R k 2 (22) PCT Filed: Feb. 19, 2010 -- (2) D-N (86). PCT No.: PCT/EP2010/052097 Y-k S371 (c)(1), (3) (2), (4) Date: Sep. 30, 2011 D-N-K" (87) PCT Pub. No.: WO2010/097338 H 4. PCT Pub. Date: Sep. 2, 2010 R11 (4) (65) Prior Publication Data / \ R-N+ \ R13 US 2012/OO17931 A1 Jan. 26, 2012 o N-y (30) Foreign Application Priority Data / S1 R15 W Feb. 25, 2009 (EP) ..................................... 09 153589 V (51) Int. Cl. R14 A61O 5/10 (2006.01) (2a) CO7D 265/00 (2006.01) X (52) U.S. Cl. ............. 8/405; 8/407; 8/409; 8/426; 8/466; : l 8/565; 8/567; 8/568; 8/570; 8/572; 8/574; le 544/103 Rs (58) Field of Classification Search .............. 8/405, 407, (2b) 8/409, 426,466, 565, 567,568,570, 572, X R10 8/574; 54.4/103 - / See application file for complete search history. ( N-N (56) References Cited ? 9 U.S. PATENT DOCUMENTS R17 (2c) 3,369,970 A 2, 1968 McLaughlin 6,190.421 B1 2/2001 Rondeau / y NRIs FOREIGN PATENT DOCUMENTS : 2W R19 DE 382987O A1 4f1989 \\ (Continued) (2d) R OTHER PUBLICATIONS 20 STIC Search Report dated Jan. 31, 2012.* : \ (Continued) R21w / \ Primary Examiner — Eisa Elhilo R22 (74) Attorney, Agent, or Firm — Shiela A. Loggins R23 o (57) ABSTRACT The invention relates to hair dyeing composition comprising (a) a dye of formula (1); (b)ant least one dye selected from the 14 Claims, No Drawings US 8,268,014 B2 Page 2 FOREIGN PATENT DOCUMENTS WO 2004/O19897 A1 3, 2004 DE 199594.79 A1 T 2001 WO 2006,108458 A 10, 2006 EP 318294 A2 5, 1989 OTHER PUBLICATIONS EP T14954 A2 6, 1996 GB 1249 438 A 10, 1971 J. F. Corbett: The Chemistry of Hair-Care Products, JSCDAug. 1976, GB 1408 734 A 1Of 1975 p. 290. WO 95,01772 A1 1/1995 English Language Abstract of DE 19959479. WO WO95/O1772 * 1/1995 English Language Abstract of DE 3829870. WO 95/15144 A1 6, 1995 English Language Abstract of WO 00/10519. WO 97.20545 A1 6, 1997 English Language Abstract of EP 714954. WO OO 10519 A1 3, 2000 WO O3,022233 A 3, 2003 * cited by examiner US 8,268,014 B2 1. 2 HAR DYEING COMPOSITION (2a) The present invention relates to a composition for dyeing X keratinous fibres, in particular human keratinous fibres Such : as hair, comprising, in an appropriate dyeing medium, at least le N: a mixture of at least 2 cationic direct dyes of a given formula, Rs compositions thereof, to processes for their preparation and to (2b) their use in the dyeing of organic material. Such as keratin X R10: fibers, wool, leather, silk, cellulose or polyamides, especially keratin-containing fibres, cotton or nylon, and preferably 10 hair, more preferably human hair. N-N. It is known, for example, from WO95/01772, WO ? 95/15144, EP 714954 and EP318294 that cationic dyes can R (2c) 7 be used to dye organic material, for example keratin, silk, 15 cellulose or cellulose derivatives, and also synthetic fibres, for N-R example polyamides. Cationic dyes exhibit very brilliant / xN* " shades. A disadvantage is their unsatisfactory fastness to y R19 hydrolysis and to light, their frequently inadequate stability under reducing or oxidizing conditions, and their frequently R16 O (2d) unsatisfactory storage stability (see: John F. Corbett: “The R20 Chemistry of Hair-Care Products', JSCD August 1976, page 290). The actual technical problem of the present invention was to provide brilliant dyes that are distinguished by deep dyeing 25 having good fastness properties with respect to washing, light, shampooing and rubbing, and that preferably exhibit satisfactory stability under reducing or oxidizing dyeing con ditions, for the dyeing of organic material. Accordingly, the present invention relates to a hair dye 30 composition, comprising Kis the radical of a coupling component selected from aniline derivatives; phenol derivatives; naphthalene derivative; (a) a dye of formula X is —CH= —O—; —S ; or —N(R-7) : R. R. R. and Raindependently from each other are hydro 35 gen; or C-C alkyl; R N R (1) 6 2 5 Rs and R independently from each other are hydrogen; An: C-C alkyl; or C-C alkoxy: R R4 R, and R independently from each other are unsubstituted or OH-, C-C alkoxy-, halogen-, amino-, C-C-mono or N-N-N-N- 40 -dialkylamino-substituted C-Calkyl; or phenyl: R R3 Rs is hydrogen; C-C alkyl, Cl; or nitro: Ro is hydrogen; C-Calkyl: Cl; nitro; amino; or (b) at least one dye selected from the compounds of formulae C-C mono- or C-Cadialkylamino; R is hydrogen; C-C alkyl, or CN: 45 R is unsubstituted or OH or CN-substituted C-C alkyl: (2) R is hydrogen; or C-C alkyl, -- Ra and Rs independently from each other are hydrogen: D-NV An: C-C alkyl, or C-Calkoxy; or N-K Ra and Rs together with the nitrogen and carbon atoms (3) 50 joining them together form a 5-or 6-membered ring; D-N-K" Re and Rao independently from each other are hydrogen; An and C-C alkyl, hydroxy: Cl; nitro, amino, C-C mono- or H dialkylamino; (4) R7, Rs. R. R. R. and R2 independently from each 55 other are hydrogen; or C-C alkyl; / R is hydrogen; or C-C alkyl; and R-N+ \ \ , is An is a colorless anion. o N-N C-Coalkyl is for example, methyl, ethyl, propyl, isopro An: pyl. n-butyl, Sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pen V-R-15 60 tyl, 2,2'-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl, n-octyl, 1,1,3,3'-tetramethylbutyl or 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tredecyl, tetradecyl, pentadecyl. ( ). haxadecyl or eicosyl. R14 C-Coalkenyl is for example allyl, methallyl, isopropenyl, 65 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-me wherein thyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso-dodece D is the radical of a diazo component of the formula nyl, n-dodec-2-enyl or n-octadec-4-enyl. US 8,268,014 B2 3 4 Aryl is for example naphthyl and preferably phenyl. -continued Heterocyclic organic radical is, for example, a five-mem (2h) bered nitrogen-containing hetero-cyclic radical Such as imi dazolyl pyrazolyl, triazolyl pyrrolyl pyrrolidinyl, oxazolyl or thiazolyl, a six-membered nitrogen-containing heterocy clic radical Such as piperazinyl, piperidinyl, pyridinyl or mor pholinyl, or a bicyclic radical which possesses a fused-on five-membered nitrogen-containing heterocycle and a six membered aromatic ring. Such as benzoxazolyl, indolylben 10 Even more preferred are hair dye compositions, wherein in Zothiazolyl, benzimidazolyl or benzotriazolyl. formulas (2) Preferred is a hair dye composition, wherein informula (1) K is the radical of formula of component (a) R. R. R. and Raindependently from each other are hydrogen; or C-C alkyl. (2i) More preferred is a hair dye composition, wherein compo 15 R25 nent (a) corresponds to formula -(). (5) N O-CH n wherein C. H Rs is hydrogen; hydroxy: C-C alkyl, C-C alkoxy; nitro: N N O n amino; mono-C-C-alkylamino; di-C-C alkylamino; or a radical of formula H 25 Preferably Rs is hydrogen; or C-C alkyl. More preferably, in formulas (2a) and (2b) 30 R, and Ro independently from each other are C-C alkyl, and even more preferred are hair dye compositions, wherein in formula (2a) wherein X is NR; and 35 R. R., and Rs independently from each other are hydro Rs is hydrogen; or C-C alkyl. gen; or C-C alkyl. Preferred are hair dye compositions, wherein Preferred are also hair dye compositions wherein D is a radical of formula K is the radical of formula 40 (2e) (2k) NH2 O HO Br. 45 OH NH (2f) 50 Most preferred are hair dye compositions comprising (a) a dye of formula (1), and (b) at least one dye selected from the compounds of formulae 55 (2g) (6) 60 US 8,268,014 B2 5 6 -continued (7) (6) HO N N HO 5 VN ( ) \ N O-CH N+(CH3)3Cl le N ( ) (8) HO N+(CH3)3C-: HN N (7) N NO \-( ) 15 HO s N N (9) 8 HO HO (8) H.N- )-N HN N N \ ( ) 25 2 V ( ) NO ( ) (10) (9) O NH2 HO Br HN \ O ICl 35 N NH N+(CH3)3C-:(CH3)3Cl-, ( ) NH OH (11) \ \ 40 N+(CH3)3Cl-, and N N N (10) O NH2 / O \ M | Nt Br / 45 / (12) N N"(CH3)3Cl.-- NV NH OH NR 50 / \ Also preferred are hair dying compositions, comprising (a) a dye of formula (1), and FN (b) the dyes of formulae \ and 55 (13) / (6) N HO 2-N ( - Nt\ Y-K)-n 60 O-CH\, ( ) Preferred are also hair dying compositions, comprising 65 (a) a dye of formula (1), and N+(CH3)3Cl- and/or (b) at least one dye selected from the compounds of formulae US 8,268,014 B2 7 8 -continued The hair dye composition according to the present inven (11) tion of may be used in combination with at least one single direct dye different from the dyes of component (a) and (b).
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