US 11,696,884 B2
Compositions comprising menthol compounds as smoothing agents
Cécile Kalem, Issy-les-Moulineaux (FR); Dominik Stuhlmann, Holzminden (DE); Aurélie Trunet, Levallois Perret (FR); and Denis Brouard, Saint Ouen (FR)
Assigned to Symrise AG, Holzminden (DE)
Appl. No. 15/554,791
Filed by Symrise AG, Holzminden (DE)
PCT Filed Feb. 17, 2016, PCT No. PCT/EP2016/053394
§ 371(c)(1), (2) Date Aug. 31, 2017,
PCT Pub. No. WO2016/139066, PCT Pub. Date Sep. 9, 2016.
Claims priority of application No. 15157677 (EP), filed on Mar. 4, 2015.
Prior Publication US 2018/0042832 A1, Feb. 15, 2018
Int. Cl. A61K 8/49 (2006.01); A61Q 19/00 (2006.01); A61K 8/42 (2006.01); A61K 8/37 (2006.01); A61K 8/34 (2006.01); A61Q 5/10 (2006.01); A61Q 5/04 (2006.01); A61Q 5/08 (2006.01); A61Q 5/12 (2006.01)
CPC A61K 8/498 (2013.01) [A61K 8/34 (2013.01); A61K 8/345 (2013.01); A61K 8/37 (2013.01); A61K 8/375 (2013.01); A61K 8/42 (2013.01); A61K 8/4973 (2013.01); A61Q 5/04 (2013.01); A61Q 5/08 (2013.01); A61Q 5/10 (2013.01); A61Q 5/12 (2013.01); A61Q 19/005 (2013.01); A61K 2800/244 (2013.01)] 3 Claims
 
1. A method of permanent hair dyeing, comprising the following steps
(i) mixing all the components of a composition consisting of:
(a) menthol compounds corresponding to formulas (I), (II) and/or (III)

OG Complex Work Unit Chemistry
in which X represents —Y or —COZ and Y represents the following groups:
 
 
 (i) a linear or branched alkyl or hydroxyl alkyl radical containing
 
 
 1 to 6 carbon atoms or an allyl radical;
 
 (ii) a hydroxy or dihydroxyalkyl radical containing 1 to 6 carbon
 
 
 atoms;
 
 (iii) a radical —OCR1;
 
 (iv) a radical —OCO(M)OH;
 
 (v) a radical —OCO—S;
 
 (vi) a radical —OC(CH2)nCOR2;
 
wherein
 
 
 M represents a linear or branched alkyl and/or alkenyl radical
 
 
 containing 1 to 10, preferably, 1 to 4 carbon atoms;
 
 S represents a carbohydrate radical containing 5 to 12 carbon
 
 
 atoms, preferably, a fructose, a glucose or a sucrose radical;
 
 n stands for 0 or for numbers of 1 to 6, preferably, of 2 to 3;
 
 R1 represents a linear or branched alkyl- or hydroxyl alkyl radical
 
 
 containing 1 to 6, preferably, 1 to 2 carbon atoms or an allyl
 
 
 radical;
 
 R2 represents a hydroxyl radical or a radical —NR3R4;
 
 R3 and R4, independently of one another, represent hydrogen or a
 
 
 linear or branched alkyl or hydroxyl alkyl radical containing
 
 
 1 to 6, preferably, 1 to 2 carbon atoms,
 
while Z represents the following groups:
 
 
 (vii) a radical NR5R6, or
 
 (viii) a radical NHR7,
 
wherein
 
R5, R6 independently of one another, represent hydrogen or a linear
 
 or branched alkyl or hydroxyl alkyl radical containing 1 to
 
 6, preferably, 1 to 2 carbon atoms, a phenyl radical or an
 
 alkoxyphenyl radical containing 1 to 6, preferably, 1 to 2
 
 carbon atoms in the alkoxy radical;
R5, R6, R7 represent a radical —(CH2)nCOOR8;
R8 represents a linear or branched alkyl or hydroxy alkyl
 
 radical containing 1 to 6, preferably, 1 to 2 carbon atoms,
 
 and
n stands for 0 or for numbers of 1 to 10, preferably, of 1 to 4,
 
 and
 
(b) a cosmetically acceptable carrier, and
(c) a hair colouring formulation and/or a hair straightening formulation having a pH of from 6.5 to 12; and consisting of
(c-1) at least one separately provided oxidizing agent, and
(c-2) at least one oxidation base, and
(c-3) at least one synthetic dye, and/or
(c-4) at least one natural dye,
wherein the composition is in the absence of menthofuran, and applying the obtained mixture onto the hair of a person having a sensitive scalp:
(ii) leaving the mixture of step (i) on the hair for a defined time; then
(iii) rinsing the hair.