Use of dihydroisoquinolinium double derivatives for treating keratin materials, compositions and implementation processes
11406579 · 2022-08-09
Assignee
Inventors
Cpc classification
International classification
C07D401/06
CHEMISTRY; METALLURGY
Abstract
The present invention relates to the use of one or more dihydroisoquinolinium double salts for treating keratin materials, in particular keratin fibres, especially human keratin fibres such as the hair. The invention also relates to a process for treating keratin materials using said salts and optionally in the presence of one or more chemical oxidizing agents. A subject of the invention is also a composition for lightening keratin materials, comprising one or more dihydroisoquinolinium double salts as defined below and one or more chemical oxidizing agents. The present invention also relates to one or more particular dihydroisoquinolinium double salts and also to compositions containing them, in particular compositions comprising a physiologically acceptable medium.
Claims
1. A method for lightening human hair, the method comprising: applying to said human hair at least one compound of formula (I), the tautomeric forms thereof, the addition salts thereof, or the solvates thereof optionally in the presence of at least one chemical oxidizing agent: ##STR00030## wherein in formula (I): R.sub.1, R.sub.2, R.sub.3, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9 and R′.sub.10, independently of each other, are chosen from: a hydrogen atom; a halogen atom, a C.sub.1-C.sub.6 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, C.sub.1-C.sub.6 alkoxy, cyano, or amino —NR.sub.aR.sub.b groups, a C.sub.1-C.sub.6 alkoxy radical; a hydroxyl radical; an amino radical —NR.sub.aR.sub.b, an aminocarbonyl radical —CONH.sub.2, or a carboxyl radical —CO.sub.2H, R.sub.4 and R′.sub.4 together form a divalent radical L such that L is chosen from a linear or branched, saturated or unsaturated C.sub.1-C.sub.15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur, R.sub.a and R.sub.b are chosen from, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated C.sub.1-C.sub.6 alkyl radical, Anion denotes an organic or mineral anion or mixture of anions which ensures the electrical neutrality of the compounds of formula (I).
2. The method according to claim 1, wherein a radical chosen from the radicals R.sub.i and a radical chosen from the radicals R′.sub.j when i=j, together form: a divalent radical L representing a linear or branched, saturated or unsaturated C.sub.1-C.sub.15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur, or a single bond.
3. The method according to claim 1, wherein a radical chosen from the radicals R.sub.i and a radical chosen from the radicals R′.sub.j when i and j are identical and are equal to 3 or 4, together form a divalent radical L, or a covalent single bond.
4. The method according to claim 1, wherein: R.sub.1 and R′.sub.1 are identical to each other, R.sub.2 and R′.sub.2 are identical to each other, R.sub.3 and R′.sub.3 are identical to each other, R.sub.5 and R′.sub.5 are identical to each other, R.sub.6 and R′.sub.6 are identical to each other, R.sub.7 and R′.sub.7 are identical to each other, R.sub.8 and R′.sub.8 are identical to each other, R.sub.9 and R′.sub.9 are identical to each other, R.sub.10 and R′.sub.10 are identical to each other and, independently from one pair to another, are chosen from a hydrogen atom; a halogen atom, a C.sub.1-C.sub.6 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, cyano, C.sub.1-C.sub.6 alkoxy, or amino NR.sub.aR.sub.b groups, a C.sub.1-C.sub.6 alkoxy radical; a hydroxyl radical; an amino radical NR.sub.aR.sub.b, an aminocarbonyl radical —CONH.sub.2, or a carboxyl radical —CO.sub.2H, R.sub.4 and R′.sub.4 together form a divalent radical L such that L is chosen from a linear or branched, saturated or unsaturated C.sub.1-C.sub.15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur, R.sub.a and R.sub.b, independently of each other, are chosen from a hydrogen atom or a linear or branched, saturated or unsaturated C.sub.1-C.sub.6 alkyl radical.
5. The method according to claim 1, wherein: R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3, R′.sub.3, R.sub.5, R′.sub.5, R.sub.6, R′.sub.6, R.sub.7, R′.sub.7, R.sub.8, R′.sub.8, R.sub.9 and R′.sub.9 denote a hydrogen atom, R.sub.4 and R′.sub.4 together form a divalent radical L such that L represents a saturated linear C.sub.1-C.sub.15 alkylene radical, optionally substituted with at least one hydroxyl group or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur, L optionally denoting a saturated, linear or branched C.sub.2-C.sub.10 alkylene radical, optionally substituted with at least one hydroxyl group or interrupted with at least one non-adjacent heteroatom chosen from oxygen.
6. The method according to claim 1, wherein the at least one compound of formula (I), the tautomeric forms thereof, the addition salts thereof, and/or the solvates thereof are chosen from the following compounds, the tautomeric forms thereof, the addition salts thereof, and/or the solvates thereof: TABLE-US-00007
7. A method for improving the oxidizing activity of at least one chemical oxidizing agent, the method comprising: applying to human hair at least one compound of formula (I), the tautomeric forms thereof, the addition salts thereof, or the solvates thereof in the presence of at least one chemical oxidizing agent: ##STR00040## wherein in formula (I): R.sub.1, R.sub.2, R.sub.3, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9 and R′.sub.10, independently of each other, are chosen from: a hydrogen atom; a halogen atom, a C.sub.1-C.sub.6 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, C.sub.1-C.sub.6 alkoxy, cyano, or amino —NR.sub.aR.sub.b groups, a C.sub.1-C.sub.6 alkoxy radical; a hydroxyl radical; an amino radical —NR.sub.aR.sub.b, an aminocarbonyl radical —CONH.sub.2, or a carboxyl radical —CO.sub.2H, R.sub.4 and R′.sub.4 together form a divalent radical L such that L is chosen from a linear or branched, saturated or unsaturated C.sub.1-C.sub.15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur R.sub.a and R.sub.b are chosen from, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated C.sub.1-C.sub.6 alkyl radical, Anion denotes an organic or mineral anion or mixture of anions which ensures the electrical neutrality of the compounds of formula (I).
Description
EXAMPLE
Example 1
Synthesis of 2,2′-butane-1,4-diyldi-3,4-dihydroisoguinolinium dibromide (compound 1)
(1) ##STR00029##
(2) 10 g of 3,4-dihydroisoquinoline (4 eq.) are placed in a 250 mL three-necked flask in 75 mL of toluene, followed by addition of 2.28 mL of 1,4-dibromobutane (1 eq.). The mixture is refluxed with vigorous stirring for 15 hours. The beige-brown precipitate is filtered off under vacuum and under argon and washed with diisopropyl ether and then dried under vacuum over P.sub.2O.sub.5.
(3) The product is recrystallized from 80 mL of n-propanol and is isolated in the form of a beige-coloured powder (5.15 g, yield=56.5%).
(4) The analyses are in accordance with the expected product.
Example 2
(5) I. Preparation of the Compositions
(6) The following formulations are prepared:
(7) Preparation of Formulation A:
(8) TABLE-US-00003 Chemical name g % 2-Octyldodecanol 11.5 Liquid petroleum jelly 74.5 Oxyethylenated lauryl alcohol (2 OE) 3 Oxyethylenated sorbitan mono laurate (4 OE) 11
(9) Preparation of the Oxidizing Formulation B (HQ2):
(10) TABLE-US-00004 Chemical name g % Glycerol 0.5 (50% linear 70/30 C.sub.13/C.sub.15)alkyl ether carboxylic 0.85 acid monoethanolamide (2 OE) Tetrasodium pyrophosphate decahydrate 0.02 50% hydrogen peroxide solution (200 vol. 12 aqueous hydrogen peroxide solution) Disodium tin hexahydroxide 0.04 Diethylenetriaminepentaacetic acid, pentasodium 0.15 salt as an aqueous 40% solution Cetylstearyl alcohol/oxyethylenated (30 OE) 2.85 cetylstearyl alcohol mixture Deionized water 83.59
(11) Preparation of Compositions 1 and 2 for Evaluation on Locks:
(12) Compositions 1 to 2 were obtained from the following ingredients:
(13) TABLE-US-00005 Composition 1 Composition 2 2,2′-Butane-1,4-diyldi-3,4 — 30 mg dihydroisoquinolinium dibromide (1) Formulation A 1 g 1 g Oxidizing formulation B (H.sub.2O.sub.2) 1.5 g 1.5 g 20% Aqueous ammonia NH.sub.4OH Drops Drops .fwdarw. pH = .fwdarw. pH = 9.5 9.5
(14) After preparation, compositions 1 and 2 are applied to natural 250 mg locks with a tone depth of 4. After a leave-on time of 30 minutes at a temperature of 27° C., the locks are washed with shampoo, rinsed and dried.
(15) The colorimetric data are then measured with a Minolta CM-3610d spectrophotometer:
(16) TABLE-US-00006 Composition 1 Composition 2 Lightening (L*) 23.8 29.5
(17) It is noted that greater lightening is obtained with composition 2 according to the invention than with composition 1.
(18) In particular, it is noted that the presence of the dihydroisoquinolinium double salts makes it possible to improve the oxidizing power of hydrogen peroxide and thus to boost its activity (comparison between composition 1 and composition 2).