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US 5,854,225 AGranted
Compounds derived from cyclodextrin
AssigneeL'oreal
InventorsHerve Richard, Madeleine Leduc
Life of this patent
Estimating the term…
Abstract
The invention relates to cyclodextrin derivatives of formula (I) CD(OH).sub.I (OCOR).sub.m (OR.sub.2).sub.n (1) in which each R.sub.1 independently denotes a C.sub.6 -C.sub.24 alkyl radical or a C.sub.8 -C.sub.24 alkenyl radical, each R.sub.2 independently denotes a C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 hydroxyalkyl radical, and I, m and n are statistical values. The invention also relates to a process for the preparation of the compounds of formula (I) and to the use of these compounds in cosmetics.
Claims19
A compound corresponding to the following general formula (I):
- CD(OH).sub.I (O-C(O)-R.sub.1).sub.m (OR.sub.2).sub.n ( 1)
- in which
- CD denotes a cyclodextrin base skeleton without the hydroxyl groups, wherein said cyclodextrin is .alpha.-, .beta.- or .gamma.-cyclodextrin,
- O-C(O)-R.sub.1 denotes a radical bonded to said cyclodextrin base skeleton, in which each R.sub.1 independently denotes a radical selected from C.sub.11 -C.sub.24 linear or branched alkyl radicals and C.sub.11 -C.sub.24 linear or branched alkenyl radicals,
- OR.sub.2 denotes a radical bonded to said cyclodextrin base skeleton, in which each R.sub.2 independently denotes a radical selected from C.sub.1-C.sub.4 linear or branched alkyl radicals and C.sub.2-C.sub.4 hydroxyalkyl radicals, wherein the hydrogen of the hydroxyl radical of said hydroxyalkyl radical is optionally replaced with a radical comprising at least one radical selected from C.sub.2-C.sub.4 hydroxyalkyl radicals and -COR.sub.1 radicals,
- m denotes the number of O-C(O)R.sub.1 radicals directly bonded to said cyclodextrin base skeleton and is a statistical value other than 0,
- n denotes the number of OR.sub.2 radicals directly bonded to said cyclodextrin base skeleton and is a statistical value other than 0, and
- I denotes the number of hydroxyl groups bonded directly to said cyclodextrin base skeleton and is a statistical value, including 0, such that (I+m+n) is equal to 18, 21 or 24, according to whether said cyclodextrin of said base skeleton is .alpha.-, .beta.- or .gamma.-cyclodextrin, respectively, and further wherein the degree of substitution of cyclodextrin by radicals R.sub.1 ranges from 0.2 to 1.
5 more elements
A method for the preparation of a compound of formula (I)
- CD(OH).sub.I (O-C(O)-R.sub.1).sub.m (OR.sub.2).sub.n ( 1)
- wherein
- CD denotes a cyclodextrin base skeleton without the hydroxyl groups, wherein said cyclodextrin is .alpha.-, .beta.- or .gamma.-cyclodextrin,
- O-C(O)-R.sub.1 denotes a radical bonded to said cyclodextrin base skeleton, in which each R.sub.1 independently denotes a radical selected from C.sub.11 -C.sub.24 linear or branched alkyl radicals and C.sub.11 -C24 linear or branched alkenyl radicals,
- OR.sub.2 denotes a radical bonded to said cyclodextrin base skeleton, in which each R.sub.2 independently denotes a radical selected from C.sub.1 -C.sub.4 linear or branched alkyl radicals and C.sub.2-C.sub.4 hydroxyalkyl radicals, wherein the hydrogen of the hydroxyl radical of said hydroxyalkyl radical is optionally replaced with a radical comprising at least one radical selected from C.sub.2-C 4 hydroxyalkyl radicals and -COR.sub.1 radicals,
- m denotes the number of O-C(O)-R.sub.1 radicals directly bonded to said cyclodextrin base skeleton and is a statistical value other than 0,
- n denotes the number of OR.sub.2 radicals directly bonded to said cyclodextrin base skeleton and is a statistical value other than 0, and
- I denotes the number of hydroxyl groups bonded directly to said cyclodextrin base skeleton and is a statistical value, including 0, such that (I+m+n) is equal to 18, 21 or 24, according to whether said cyclodextrin of said base skeleton is .alpha.-, .beta.- or .gamma.-cyclodextrin, respectively,
- and further wherein the degree of substitution of cyclodextrin by radicals R.sub.1 ranges from 0.2to 1,
- comprising the step of reacting
- (a) a cyclodextrin derivative of formula CD(OR.sub.2).sub.n (OH).sub.I, in which CD, OR.sub.2, and n are as defined above and
- I' denotes the number of hydroxyl radicals bonded directly to said cyclodextrin base skeleton and is a nonzero statistical value such that (I'+n) is equal to 18, 21 or 24, according to whether said cyclodextrin of said base skeleton is .alpha.-, .beta.- or .gamma.-cyclodextrin, respectively with
- (b) p moles of an acid chloride of formula CI-CO-R.sub.1, wherein R.sub.1 is as defined above and p is the total number of radicals R.sub.1
- under conditions sufficient to form said compound of formula (I).
11 more elements
Dependencies are inferred from the claim text.