Use of dihydroisoquinolinium salts for treating keratin materials, compositions and implementation processes
A keratin material and keratin fiber technology, applied in hair care, pharmaceutical formulations, cosmetic preparations, etc., can solve problems such as skin irritation
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[0197] According to one embodiment, the heterocycle is selected from:
[0198]
[0199] According to one embodiment, the heterocycle is aromatic and is selected from:
[0200]
[0201] The one or more compounds of formula (I) are preferably selected from the following compounds, their addition salts and also their solvates:
[0202]
[0203]
[0204]
[0205]
[0206] As indicated previously, the one or more compounds of formula (I) according to the invention (preferably compounds 1 to 27), their addition salts and their solvates may be present in the presence of one or more chemical oxidizing agents For lightening keratinous materials such as skin, keratinous fibers, especially human keratinous fibers such as hair, are preferred.
[0207] These chemical oxidizing agents are as described herein below.
[0208] Compositions containing compounds of formula (I)
[0209] Accordingly, the present invention relates to a composition comprising said one or more comp...
Embodiment 1
[0293] Example 1 : Synthesis of 2-(3-imidazol-1-ylpropyl)-3,4-dihydroisoquinolinium bromide (Compound 1)
[0294]
[0295] step 1: Synthesis of 2-(2-bromoethyl)benzaldehyde (a)
[0296]
[0297] 20g of CuBr 2 (1.2 equiv.) was added to 10 g of isochroman (1 equiv.) dissolved in 200 mL of acetonitrile. The mixture was refluxed under nitrogen for 16 hours and then left at room temperature. The mixture was then poured into ice and extracted three times with ethyl acetate. These organic phases were combined, washed with saturated aqueous NaCl, and then washed with NaCl 2 SO 4 dry. All was filtered, evaporated to dryness and purified on a column of silica eluting with petroleum ether. 11.2 g (yield = 70%) of compound (a) were obtained in the form of a yellow oil.
[0298] NMR and mass analysis were consistent with the expected structure.
[0299] Step 2: Synthesis of 2-(3-imidazol-1-ylpropyl)-3,4-dihydroisoquinolinium bromide (compound 1)
[0300]
[0301] 6....
Embodiment 2
[0303] Example 2 : 2-[3-(3-methyl-1H-imidazol-3-ium-1-yl)propyl]-3,4-dihydroisoquinolinium bromide 4-methylbenzenesulfonate (compound 2) Synthesis of
[0304]
[0305] Add 0.4 g (1.1 equivalents) of methyl p-toluenesulfonate to 1 g of 2-(3-imidazol-1-ylpropyl)-3,4-dihydroisoquinolinium bromide dissolved in 50 mL of acetonitrile in compounds. The mixture was refluxed for 16 hours. After evaporation to dryness, the oil obtained was purified on a silica column. 0.8 g (yield = 51%) of compound 2 were obtained in the form of a brown oil.
[0306] NMR and mass analysis were consistent with the expected structure.
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