Naphthalene dicarboxylic acid diester or polyesters for conferring luster and stabilizing color for hair

FIELD: organic chemistry, cosmetics.

SUBSTANCE: invention relates to naphthalene dicarboxylic acid diester or polyester of the formula (I) , or their mixture and used for conferring luster and/or stabilizing color for hair wherein each among R¹ that can be similar or different is taken among group consisting of alkyl group comprising from 1 to 22 carbon atoms, diol of the formula: HO-R²-OH and polyglycol of the formula: HO-R³-(O-R²)_m-OH wherein R² and R³ are similar or different and each represents alkylene group with unbranched or branched chain comprising from 1 to 6 carbon atoms and wherein each m and n represents a number from 1 to 100, or their mixtures. Indicated diesters or polyesters of the formula (I) or (II) are effective in stabilization of compounds that represent UV-A-filters of derivative of dibenzoylmethane and providing their enhanced effectiveness for prolonged time.

EFFECT: valuable cosmetic properties of compounds.

9 cl, 3 ex

The present invention relates to compositions for topical application to the hair to give Shine and stabilization of natural and/or received in the dyeing of hair color. More specifically, the present invention relates to the use of diesters and/or polyesters naphthaleneboronic acid, which unexpectedly turned out to be effective in the treatment and stabilization of hair color from fading. The diesters and polyesters naphthaleneboronic acid stabilize the natural color of hair and color-treated hair and make it Shine. In addition, as described in more detail in the patent application, now U.S. patent No. 5993789, compositions absorb UV radiation.

BACKGROUND of INVENTION AND prior art

It is well known that ultraviolet light having a wavelength between about 280 nm or 290 nm and 320 nm (UV-b) is harmful to human skin, causing burns that are harmful when getting a good sun tan. UV-a radiation in the production of tanning of the skin can also cause damage, especially in the case of very weakly pigmented, sensitive skin, resulting in reduced skin elasticity and rugosity.

Therefore, the sunscreen composition should include both UV-a and UV-b filters to prevent damage the value of human skin for the most part of the sun's rays within the entire range from approximately 280 nm to approximately 400 nm.

UV-b filters, which are very widely commercially used in sunscreen compositions are esters parameterstring acid, such as 2-ethylhexylacrylate, usually called octylmethoxycinnamate or PARSOL® MOA with ethyl radical, attached to 2-position main exiles long chain; oxybenzone, octisalate.

UV-a filters, most commonly used in commercial sunscreen compositions are derived dibenzoylmethane, particularly 4-(1,1-dimethylethyl)-4’-methoxydibenzoylmethane (PARSOL® 1789) and 4-isopropylbenzylamine (EUSOLEX 8020). Other derivatives dibenzoylmethane specified as UV-a filters are described in U.S. patent No. 4489057; 4387089, 4562067 and 5670140, incorporated herein as references. It is well known that the above-described and most commonly used UV-a filters, especially derivatives dibenzoylmethane, such as PARSOL® 1789, lack of photochemical stability when used alone or in combination with the above-described most often commercially used UV-b filters. In accordance with this, when used alone or when combined with UV-b filter, such as 2-ethylhexylacrylate (PARSOL® MCX), oxybenzone and/or octisalate, PARSOL® 1789 becomes less photochemically stable, which makes it necessary inflicted is of frequent multiple coatings on the skin for sufficient protection from UV radiation.

In accordance with one aspect of the present invention discovered, quite unexpectedly, that the inclusion of diapir and/or polyester of one or more naphthalenesulphonic acids of the formula (I) in cosmetic sunscreen ready preparative form, which contains UV-absorber derived dibenzoylmethane, particularly PARSOL® 1789, and/or 4-isopropylbenzylamine (EUSOLEX 8020), derived dibenzoylmethane photochemically stabilized, so contains the derived dibenzoylmethane sunscreen composition without additional or more sunscreen agents such as oxybenzone and/or octylmethoxycinnamate (ESCALOL 567), is more effective for filtering UV And radiation; the composition filters more UV-a radiation for longer periods of time, and therefore there is no need to apply sunscreen ready preparative shape as often, at the same time maintaining effective protection of the skin from UV-a radiation.

In accordance with another important advantage of the present invention, it was found that the diesters and polyesters naphthalenesulphonic acids can also absorb UV light in the most damaging range of approximately 280-300 nm, especially have absorption peaks for wavelength 280 and 295 nm, is shown in Fig.9.

Adding the two is relating UV-b filter compounds, such as octylmethoxycinnamate, octisalate and/or oxybenzone, the compositions of the present invention can be unexpected to maintain effective protection hair color and can protect against UV radiation both in the UV-a and UV-b region without the usual sunscreen additives or additives, such as octocrylene and/or titanium dioxide. The composition has unexpectedly high SPF (sun protection factor) without solid additives such as titanium dioxide, which provides an excellent feeling when applied, it can easily be applied in the form of a solid cover for full coverage and sun protection actions. In preferred compositions the ratio of compounds which are UV-a filter, to compounds which are UV-b filter is in the range of about 0.1:1 to about 3:1, preferably approximately from 0.1:1 to about 0.5:1, very preferably approximately from 0.3:1 to about 0.5:1. Quite unexpectedly, that the preferred compositions of the present invention have unexpectedly high SPF, for example, higher than SPF 12 in one preferred composition, and higher than SPF 20 in another preferred composition, with the addition of small amounts of other UV-b and UV-a filters to PARSOL® 1789 and without the use of solid blocking compounds, such as Tio₂.

In accordance with another what they aspect of the present invention, the diesters and polyesters naphthaleneboronic acid give the hair Shine and/or stabilize hair color from fading, especially in the case of hair containing synthetic dye.

SUMMARY of the INVENTION

Briefly, the present invention relates to giving luster and/or protecting hair color compounds, including fluids and/or polyester naphthaleneboronic acid, resulting in the provision of UV acquisitions.

Active, giving luster and/or stabilizing hair color compounds of the present invention are diesters and polyesters naphthaleneboronic acid. The diesters and polyesters are the reaction products (a) naphthaleneboronic acid, having the structure:

and (b) alcohol having the structure R¹HE, or a diol having the structure HO-R²-OH, or polyglycol having the structure HO-R³-(O-R²-)_m-OH, in which R¹represents an alkyl group with unbranched or branched chain, having from 1 to 22 carbon atoms, R²and R³are the same or different and each represents alkylenes group having from 1 to 6 carbon atoms, and in which the type, each equal to from 1 to about 100, preferably from 1 to about 10, more preferably from 2 to about 7 or mixtures thereof.

Fluids of the present invention has the structure (III):

where R¹ is the above values.

The diesters and polyesters naphthaleneboronic acid of the present invention have the General formula (I):

where R²and R³are the same or different and each represents alkylenes group having from 1 to 6 carbon atoms, and n is from 1 to about 100, preferably from 1 to about 10, more preferably from 2 to about 7.

In the alternative case, the stabilizing hair color diesters and polyesters of the present invention can be locked in the end position of the alcohol or acid. Locked in the end position, the polyesters have the structural formula (II):

where R¹and R²and n have the meanings specified above in relation to formula (I). Two R¹in the formula (II) may be the same or different.

The preferred diesters and polyesters of the present invention have srednevekovoy molecular weight of approximately 244 to about 4000, and more preferably from about 450 to about 1500. To achieve the full advantages of the present invention fluids or polyester must have srednevekovoy molecular weight of from about 500 to about 1000.

Naphthaleneboronic acid selected from the group consisting of

1,2-naphthalenemethanol key is lots; 1,3-naphthaleneboronic acid,

1,4-naphthaleneboronic acid; 1,5-naphthalenemethanol acids;

1,6-naphthaleneboronic acid; 1,7-naphthalenemethanol acids;

1,8-naphthaleneboronic acid; 2,3-naphthalenemethanol acids;

2,6-naphthaleneboronic acid; 2,7-naphthaleneboronic acid and mixtures thereof. Preferred dicarboxylic acids are 2,6-, 1,5 - and 1,8-naphthalenesulphonate acid.

Alcohol R¹OH may be, for example, methanol, ethanol, propanol, isopropyl alcohol, n-butanol, sec-butanol, isobutyl alcohol, tert-butyl alcohol, amyl alcohol, 1-hexanol, 1-octanol, 1-decanol, istelrooy alcohol, 1-undecanol, 1-dodecanol, 1-tridecylamine alcohol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol, 1-eicosanol, 1-docosanol, 2-ethylhexyloxy alcohol, 2-butyloctyl, 2-buildecon, 2-hexyldecanol, 2-octillery, 2-hexyldecanol, 2-octyldodecanol, 2-decyltetradeceth and mixtures thereof.

Glycol or polyglycols may be, for example, ethylene glycol, propylene glycol, 1,2-propandiol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropyleneglycol, tripropyleneglycol, methylpropanol, 1,6-hexanediol, 1,3-butanediol, 1,4-butanediol, PEG from PEG-4 through PEG-100, from BCPs BCPs-9 to GPR-34, pentilenglikol, neopentylglycol, trimethylpentanediol, 1,4-cyclohexanedimethanol, 2,2-dimethyl-1,3-disappear to the diol, 2,2,4,4-tetramethyl-1,3-cyclobutanediyl and mixtures thereof.

It has been unexpectedly discovered that these diesters and polyesters naphthalenesulphonic acids are very effective in giving Shine to hair and maintaining the desired natural color or dyed hair, at the same time, providing hair sunscreen effect, when they are contained in the composition in amounts of at least about 0.1 wt.% up to 20 wt.%, preferably from about 0.2% to 10 wt.%, more preferably from about 0.5 to 10 wt.%.

In accordance with one aspect of the present invention is to provide a composition, which includes fluids or polyester of one or more naphthaleneboronic acid as a compound that gives Shine to hair, and in the quality of the connection, protecting hair color, and these compounds are diesters and/or polyesters naphthaleneboronic acid, have the formula (I) or (II).

Another aspect of the present invention is to provide a composition for application to human hair, which photochemically stabilizes derivatives dibenzoylmethane, particularly PARSOL® 1789, and capable of increasing the sun protection factor (SPF), achievable for sunscreen compositions containing derivatives dibenzoylmethane.

Another aspect of the present invention is the reating a superior, stable compositions containing fluids and/or polyester naphthaleneboronic acid, which increases the efficiency of the sunscreen compounds derived dibenzoylmethane, particularly 4-(1,1-dimethylethyl)-4’-methoxydibenzoylmethane (PARSOL® 1789), in SPF and duration of action for the protection of human hair.

Another aspect of the present invention is the creation of a stable sunscreen compositions with a wide range of actions for local application to human hair, which has a SPF of at least 12 and provides significant protection from solar UV radiation full range (280-400 nm), includes approximately 4-15 wt.% ester and/or polyester naphthaleneboronic acid and contains less than 7%, preferably less than 6.1% of the sunscreen composition, of additives selected from the group of oxybenzone and avobenzone (PARSOL® 1789).

Another aspect of the present invention is to provide a moisturizing composition for topical application to human hair, which provides SPF value of at least 20 and includes approximately 4-15 wt.% ester and/or polyester naphthaleneboronic acid.

The above and other aspects and advantages of the present invention will become clearer from the following detailed description and preferred embodiments, taken the combination with graphics.

A BRIEF DESCRIPTION of GRAPHIC MATERIALS

Figure 1 is a graph showing the photostability PARSOL® 1789, or 4-(1,1-dimethylethyl)-4’-methoxydibenzoylmethane as a function of concentration used as photostabilization esters naphthalenesulphonic acids of the present invention;

Figure 2 is a graph showing the photostability (photostability) or the ability of UV-absorbing sunscreen composition containing 1 wt.% azobenzene when exposed to UV light with varying wavelengths;

Figure 3 is a graph showing the photostability or the ability of UV-absorbing sunscreen composition containing 1 wt.% avobenzone at stabilization 4 wt.% one of the polyesters naphthaleneboronic acid of the present invention;

Figure 4 is a graph showing the photostability or the ability of UV-absorbing sunscreen composition containing 1 wt.% avobenzone at stabilization 8 wt.% one of the polyesters naphthaleneboronic acid of the present invention;

Figure 5 is a graph showing the photostability of sunscreen compositions containing 3 wt.% oxybenzone/1% of avobenzone without photostabilization of the present invention;

6 is a graph showing the photostability of sunscreen the composition is, containing 3 wt.% oxybenzone/1 wt.% avobenzone and 8 wt.% one of which photostabilization polyesters naphthalenesulphonic acids of the present invention;

Fig.7 is a graph showing the photostability of sunscreen composition containing 1 wt.% avobenzone and 4 wt.% octocrylene of photostabilizer;

Fig is a graph showing the photostability of sunscreen composition containing 1 wt.% avobenzone and 4 wt.% oligomer (MW=~1500) ether naphthaleneboronic acid of the present invention, and

Fig.9 is a graph showing the UV-absorption naphthaleneboronic acid of example 1 at a 17.5 ppm in tetrahydrofuran (THF).

A DETAILED description of the PREFERRED OPTIONS ACCOMPLISHMENTS

Preferred compositions of the present invention include, optionally, from about 0.5% to about 5%, preferably from about 0.5% to about 3% which is the UV-a filter derived dibenzoylmethane, such as 4-(1,1-dimethylethyl)-4’-methoxydibenzoylmethane (PARSOL® 1789) and from about 1% to about 10 wt.% diapir and/or polyester of one or more naphthalenesulphonic acids as photostabilizer/a solubilizer for the derived dibenzoylmethane having the formula (I) or (II).

/p>

where each of R¹that may be the same or different, represents an alkyl group having from 1 to 22 carbon atoms, or a diol having the structure HO-R²-OH, or polyglycol having the structure HO-R³-(O-R²-)_m-OH, where R²and R³identical or different, represent, each, alkylenes group with unbranched or branched chain, having from 1 to 6 carbon atoms, where m and n are each equal to the number of from 1 to about 100, preferably from 1 to about 10, more preferably from 2 to about 7, or a mixture.

Compounds of formula (I) and (II) are well known for use in other purposes.

EXAMPLES

Example 1

Photostabilizers action of a polyester of 2,6-naphthaleneboronic acid and tripropyleneglycol with terminal blocking group 2-butyloctyl was determined as follows. First, following finished formulation containing 1% PARSOL® 1789, obtained in the usual way by dissolving PARSOL® 1789 in the oil phase and the preliminary mixing of the aqueous phase, followed by emulsification of the oil by adding it to the aqueous phase:

The photostability PARSOL® 1789 was determined by the distribution of measured quantities of emulsions on slides 5 cm²Vitroskin, ZAT is m irradiation slides solar moduliruem device. Measurements of absorption in the UV-a range (315-380 nm) was performed Labsphere UV Transmittance Analyzer before and after irradiation and the results compared.

After radiation 5 MED (minimal erythema dose) attenuation of UV-And-acquisitions through PARSOL® 1789 was significantly lower in the finished formulation containing PARSOL® 1789 in combination with 4% and 8% of polymer naphthaleneboronic acid when compared with ready preparative form that only contains PARSOL® 1789 (compare figure 2, 3 and 4). In addition, the weakening of the absorption in the UV-A region is way related to the concentration of the polymer naphthaleneboronic acid, as can be seen in graph 1.

Example 2

Photostabilizers action of a polyester of 2,6-naphthaleneboronic acid, tripropyleneglycol and diethylene glycol with terminal blocking group of 2-ethylhexanol were compared octocrylene, well-known photostabilization for PARSOL® 1789. The following ready preparative forms received in the usual way, and each contained 1% PARSOL® 1789 and 4% or octocrylene or polyester of 2,6-naphthaleneboronic acid:

After the test according to the Protocol described above in example 1, the following results were obtained:

This test showed that the polyester obtained from naphthaleneboronic acid is comparable with octocrylene in his ability to photostability PARSOL® 1789.

Example 3

The following example is a preferred finish preparative form for topical application to human hair to give hair Shine and for the stabilization of natural and dyed synthetic hair dye from fading:

GIVING HAIR SHINE AND COLOR STABILIZATION HAIR DIETHYLHEXYLPHTHALATE

Procedure

1. Gently mix the ingredients.

2. Add ingredients In the order listed.

1. The method of stabilization of color containing natural or synthetic dye hair by applying a composition in a cosmetically acceptable medium containing from 0.1 to 20 wt.% which is a stabilizing connection diapir or polyester naphthaleneboronic acid selected from the group consisting of compounds of the formula (I), formula (II), formula (III) and mixtures thereof:

where each R¹that may be the same or different, selected from the group consisting of alkyl groups having from 1 to 22 carbon atoms; a diol having the structure HO-R²-OH, and polyglycol having the structure HO-R³-(O-R²-)_m-OH, where R²and R³identical or different, represent each alkylenes group with unbranched or branched chain, having from 1 to 6 carbon atoms, and where m and n are each equal to the number of from 1 to about 100, or mixtures thereof.

2. The method according to claim 1, characterized in that the composition additionally includes optional derived dibenzoylmethane in the amount of from about 0.5 to about 5%, and where the molar ratio of the specified defimage or polyester compounds having the formula (I), (II) or (III), and specified derivative dibenzoylmethane is approximately from 0.1:1 to about 10:1.

3. The method according to claim 2, characterized in that the molar ratio of the specified defimage or polyester compounds having the formula (I), (II) or (III), and specified derivative dibenzoylmethane is approximately from 0.1:1 to approximately 0.3:1.

4. The method according to claim 3, characterized in that the derived dibenzoylmethane selected from the group consisting of 4-(1,1-dimethylethyl)-4’-methoxydibenzoylmethane, 4-isopropylbenzylamine and their mixtures.

5. The method according to claim 4, characterized in that the derivative dibenzoylmethane is 4-(1,1-dimethylethyl)-4’-methoxydibenzoylmethane.

6. The method according to claim 5, characterized in that the derived dibenzoylmethane include in the composition in an amount from about 0.5 to 3 wt.% song.

7. The method according to claim 1, characterized in that the fluids naphthalene-dicarboxylic acid is a compound of formula III where each R¹is ethylhexyloxy group.

8. A way of brightening the hair of a person by applying the composition in a cosmetically acceptable medium, including fluids or polyester naphthaleneboronic acid selected from the group consisting of compounds of the formula (I), formula (II), formula (III) and mixtures thereof:

where each R¹that may be the same or different, selected from the group consisting of alkyl groups having from 1 to 22 carbon atoms; a diol having the structure HO-R²-OH, and polyglycol having the structure HO-R³-(O-R²-)_m-OH, where R²and R³identical or different, represent each alkylenes group with unbranched or branched chain, having from 1 to 6 carbon atoms, where m and n are each equal to the number of from 1 to about 100, or mixtures thereof.

9. The method according to claim 8, characterized in that the fluids naphthalene-dicarboxylic KIS is the notes is a compound of formula III where each R ¹is ethylhexyloxy group.