Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
This invention relates to the use of polycarboxylic acid compounds, aqueous compositions comprising the same, cosmetic compositions comprising the same, in particular, hair care compositions, and their use for the treatment of hair, and a process for the treatment of hair comprising the use of said cosmetic compositions.
1. An aqueous composition comprising a compound
hydrocarbon
wherein the compound has the formula:
wherein R 4 is selected from the group consisting of hydroxy or F,
wherein F is selected from:
—O—C(O)—R 3 —C(O)OH, and
—NR 1 —C(O)—R 3 —C(O)OH,
wherein R 1 is selected from the group consisting of hydrogen, or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
wherein R 3 is selected from a single bond or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms, which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
with the proviso that R 3 is not —CH═CH—,
with the proviso that at least two of R 4 are F, or
wherein the compound has the formula:
wherein one of R 5 is hydroxy and one of R 5 is a group of the formula
and wherein F is as defined above and the dotted line is the bond to the carbon atom, or
wherein the compound is a mixture of the following two isomers:
and
wherein F is as defined above, and
wherein the compound or mixture is present in an amount of from about 0.1 to about 20 weight percent based on the weight of the aqueous composition.
2. The aqueous composition of claim 1 wherein the optional substituents of the groups R 1 , and R 3 are selected from the groups consisting of hydroxyl, amino and halogen, and the number of the substituents is up to 5.
3. The aqueous composition of claim 1 wherein R 1 is selected from the group consisting of hydrogen, n-, iso-, or tert.-C 1 -C 22 -alkyl, C 2 -C 22 -alkoxyalkyl, C 5 -C 30 -cycloalkyl, C 6 -C 30 -aryl, C 6 -C 30 -aryl(C 1 -C 6 )alkyl, C 6 -C 30 -alkylaryl, C 2 -C 22 -alkenyl, C 2 -C 22 -alkenyloxyalkyl, which optionally can be each substituted by hydroxyl and halogen, and which optionally can contain one or more ether groups (—O—).
4. The aqueous composition of claim 1 , wherein R 3 is selected from the group consisting of a single bond and straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 18, and which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, and wherein R 3 is optionally substituted by one or more groups selected from hydroxyl groups, amino groups, and carboxy groups.
5. The aqueous composition of claim 1 , wherein R 3 is derived from a dicarboxylic acid of the formula:
wherein R 3 is as defined above, such as optionally substituted aliphatic, saturated or unsaturated or aromatic dicarboxylic acids.
6. The aqueous composition of claim 1 , wherein F is selected from the group consisting of the formulas:
wherein the dotted line in the above formulae represents the bond to the oxygen atom, and wherein there are a least two groups F.
7. A process for the manufacture of the aqueous composition of claim 1 which comprises mixing water with the compound or mixture of compounds which is made by a process, selected from the group consisting of the following processes:
(A) Reacting at least one compound having at least two epoxy groups, which optionally may have one or more hydroxyl groups, with at least one di- or tricarboxylic acid compound,
(B) Reacting at least one compound having at least one epoxy group, which optionally may have one or more hydroxyl groups, with at least one di- or tricarboxylic acid compound, and subsequently subjecting the reaction product to the reaction with at least one acid anhydride,
(C) Reacting at least one polyhydroxy compound with at least one acid anhydride,
(D) Reacting at least one polyamine compound with at least one acid anhydride.
8. The aqueous composition according to claim 1 , further comprising at least one surfactant and/or metal salt.
9. The aqueous composition according to claim 8 , wherein the weight ratio of said surfactant and/or metal salt to the compound or mixture of compounds, is at least 0.06.
10. The aqueous composition according to claim 1 , comprising from 0.5 to 15 wt-%, of the compound or mixture of compounds, based on the weight of the aqueous composition.
11. The aqueous composition according to claim 8 , wherein the surfactant is selected from cationic, nonionic, betaine and anionic surfactants.
12. The aqueous composition according to claim 8 , wherein the surfactant is selected from hydrocarbon-based or silicone-based emulsifiers.
13. The aqueous composition according to claim 8 , wherein the surfactant is present in an amount of from about 0.05% to about 15% by weight of the aqueous composition.
14. The aqueous composition according to claim 1 , further comprising at least one additional additive, selected from the group consisting of
a) organic diluents or solvents,
b) proteins, preferably keratin,
c) emollients or fatty substances,
d) preservatives,
e) skin protecting ingredients,
f) conditioning agents,
g) oxidizing agents,
h) reducing agents,
i) tannins,
j) metal salts, and
k) further auxiliaries selected from pH adjusting agents, thickeners, lipids, amino acids, sugars, fragrances, sunscreen agents, vitamins, pearlescent agents, gelling agents, trace elements, sequestering agents, antioxidants, humectants, anti-hair loss agents, anti-dandruff agents, propellants, ceramides, polymers, fillers, nacres, colorants, and mixtures thereof,
with the proviso that oxidizing agents and reducing agents are not present simultaneously in a given composition.
15. The aqueous composition according to claim 1 having the composition:
Ingredient
Weight-%
The compound or
0.05 to 20
mixture of compounds
hydrocarbon or silicone
0 to 15,
based surfactant
water
q.s. to add to 100%
diluents/solvents
0 to 95%,
protein, preferred keratin
0 to 15,
emollients/fatty substance
0 to 15%,
preservatives
0 to 5%,
skin protecting ingredients
0 to 15%,
conditioning agents
0 to 15%,
oxidizing agents
0 to 15%,
reducing agents
0 to 15%,
tannins
0 to 15%,
metal salts
0 to 15%,
hair dyeing agent
0 to 15%,
further auxiliary agents
0 to 15%,
wherein the wt-percentages relate to the complete weight of the aqueous compositions.
16. A cosmetic composition comprising the aqueous composition of claim 1 .
17. A hair treatment cosmetic composition comprising the cosmetic composition of claim 16 .
18. The hair treatment cosmetic composition according to claim 17 , which is selected from a hair shampoo composition, hair care composition, hair conditioning composition, hair strengthening composition, hair coloration or dyeing composition, hair color deepening composition, hair combability improving composition, anti-frizz composition, hair rinse-off and leave-on compositions.
19. A process for the treatment of hair which comprises the steps of providing a cosmetic composition according to claim 16 , and applying said cosmetic composition to said hair.
20. A process for the treatment of hair according to claim 19 , which further comprises the step of dyeing the hair.
21. A method for the treatment of hair, which comprises the step of applying the aqueous composition of claim 1 to said hair.
22. The method according to claim 21 is for strengthening of hair, for hair color retention, for hair color enhancement, for hair color deepening, for hair color protection, for shaping of hair, for hair conditioning, for hair smoothening or softening, for hair straightening, or for improving manageability of the hair.
23. A compound having the formula:
wherein R 4 is selected from the group consisting of hydroxy or F, with the proviso that at least two of R 4 are F and F is selected from:
—O—C(O)—R 3 —C(O)OH, and
—NR 1 —C(O)—R 3 —C(O)OH,
wherein
R 1 is selected from the group consisting of hydrogen, or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
and
R 3 is selected from a single bond or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms, which optionally contain one or more groups selected from —O—, NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
with the proviso that R 3 is not —CH═CH—,
and salts thereof.
24. A compound having the formula:
wherein one of R 5 is hydroxy and one of R 5 is a group of the formula
and wherein F is selected from:
—O—C(O)—R 3 —C(O)OH, and
—NR′—C(O)—R 3 —C(O)OH,
wherein
R 1 is selected from the group consisting of hydrogen, or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms which optionally contain one or more groups selected from —O—, NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
and
R 3 is selected from a single bond or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms, which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
with the proviso that R 3 is not —CH═CH—,
and salts thereof,
and the dotted line is the bond to the carbon atom.
25. A compound which is a mixture of the following two isomers:
and
wherein F is selected from:
—O—C(O)—R 3 —C(O)OH, and
—NR 1 —C(O)—R 3 —C(O)OH,
wherein
R 1 is selected from the group consisting of hydrogen, or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
and
R 3 is selected from a single bond or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals which have up to 100 carbon atoms, which optionally contain one or more groups selected from —O—, —NH—, —C(O)—, —C(S)—, tertiary amino groups
and quaternary ammonium groups
with the proviso that R 3 is not —CH═CH—,
and salts thereof.
26. A compound having the formula: