Hair-treatment compositions comprising oligoesters

Details Hair-treatment compositions comprising oligoesters Hair-treatment compositions comprising oligoesters

1999-11-23

2002-07-30

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100, C510S119000

Reexamination Certificate

active

06426063

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to hair-treatment compositions, for example hair shampoos, hair conditioners, hair treatments, containing polyesters.
DESCRIPTION OF THE RELATED ART
Frequent bleaching, permanent waving and coloring, but also frequent washing of the hair with degrease surfactants, results in damage to the structure of the hair. The hair becomes brittle and loses its shine. Furthermore, the hair becomes electrostatically charged upon combing, and the roughened surface of the hair causes matting and knotting of the hair. As a result, combing is hindered. Hair-treatment compositions with a combability-improving and conditioning action have thus achieved considerable importance.
Compositions of this type are, for example, frequently distributed in wet hair in the form of a clear haircare conditioner, an aerosol foam or else in emulsion form as so-called cream rinses after the hair has been washed and, depending on the type of hair-treatment composition, either rinsed out with water after a contact time of a few minutes, or else left on the hair.
Active ingredients which are used to improve the structure of the hair are mainly cationic, in particular quaternary ammonium compounds, such as cetyltrimethylammonium chloride, alone or in combination with a variety of waxy additives, such as, for example, hydrocarbons, fatty alcohols and fatty acids. Hair cleansing and hair conditioning in two stages is time-consuming, meaning that many consumers prefer hair compositions with a combined cleansing and conditioning action.
A number of conditioning active ingredients are available for the preparation of conditioning shampoos.
These include oils and oil-like substances such as, for example, liquid hydrocarbon compounds, fatty alcohols, monocarboxylic acid esters, polyalcohol esters, silicones, both soluble, such as, for example, dimethicone copolyols, and insoluble silicones, for example polydimethylsiloxane, and cationic surface-active agents and cationic polymers.
DE-A-195 00 841 discloses hair shampoos based on anionic surfactants and which, in addition to cationic polymers and polysiloxanes, also have alkyloligoglucosides and protein fatty acid condensates. DE-A-44 38 115 proposes hair-treatment compositions comprising alkyl and/or alkenyl oligoglycosides and/or fatty acid N-alkylpolyhydroxyalkylamides and protein abietic acid condensates. Conditioning shampoos which comprise silicones are described in various patents (U.S. Pat. No. 2,826,551, U.S. Pat. No. 3,964,500, U.S. Pat. No. 4,364,837, GB 849,433, U.S. Pat. No. 4,741,855, U.S. Pat. No. 4,788,006 and U.S. Pat. Nos. 4,902,499, 4,704,272 and in EP 0 461 593). DE 30 48 075 describes the use of quaternary polymers as conditioning agents in hair-treatment compositions.
Hair-treatment compositions comprising the abovementioned constituents often have the disadvantage that their foaming ability is not always satisfactory. This refers on the one hand to the height of the base foam, and also on the other hand to foam stability, in particular in hard water. A further disadvantage is that hair shampoos often leave a rough feel on the hair after they have been rinsed out and impair combability. Cationic agents which are frequently used for haircare impart a sticky feel to damp hair and weigh dry hair down.
Surprisingly, we have found that the incorporation of polyesters into into hair-treatment compositions, significantly improves foaming ability, foam structure and dry combability. In addition, they reduce the rate at which the hair becomes greasy again, and have an antistatic and feel-improving action, and feel pleasant on the skin. They make dry hair loose, shiny and easy to untangle.
Polyesters, under the name of Soil Release Polymers (SRP), have been used for some time in detergent and surface-active cleansers and in fiber preparation because of their soil-release action and for improving the antistatic and slip properties of textile fibers.
The German laid-open specifications DE-A-16 17 141 and DE-A-22 00 911 describe the incorporation of polyterephthalate/polyoxyethylene glycol copolymers or a mixed polymer of polyethylene glycol and polyethylene terephthalate in detergents for improving wash-off of oily/greasy soilings from cotton/polyester blends. U.S. Pat. No. 3,557,039 describes the synthesis of a polyester starting from dimethyl terephthalate and ethylene glycol in the presence of a catalyst; in the synthesis given in U.S. Pat. No. 3,959,280, polyethylene oxide is additionally used as reactant. EP-A-066 944 relates to textile-treatment compositions which comprise a copolyester of ethylene glycol, propylene glycol, aromatic dicarboxylic acid and sulfonated aromatic dicarboxylic acid in specific molar ratios.
SUMMARY OF THE INVENTION
The invention provides hair-treatment compositions comprising oligoesters of the formula
in which
R
1
and R
7
are hydrogen or linear or branched C
1
- to C
18
-alkyl,
R
2
and R
6
are ethylene,
R
3
is o-, m- or p-phenylene,
R
4
is ethylene,
R
5
is ethylene, 1,2-propylene or random mixtures of any composition of the two,
n
1
and n
5
independently of one another are a number between 1 and 500,
n
2
is a number from 10 to 140,
n
3
is a number from 0 to 12,
n
4
is a number from 7 to 40.
Preferably, independely of one another,
R
1
and R
7
are hydrogen or linear or branched C
1
- to C
4
-alkyl, R
3
is p-phenylene,
n
1
and n
5
are a number from 3 to 45,
n
2
is a number from 18 to 70,
n
3
is a number from 0 to 5,
n
4
is a number from 8 to 12,
n
3
+n
4
is a number from 12 to 18 or from 25 to 35.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The oligoesters according to the invention are synthesized from the dicarboxylic acid HOOC—R
3
—COOH or its dimethyl ester, preferably dimethyl terephthalate, ethylene glycol and/or propylene glycol, polyethylene glycol and optionally C
1
- to C
18
-alkylpolyethylene glycol by carrying out a transesterification with addition of a catalyst by heating to temperatures of from 160 to about 220° C. firstly at atmospheric pressure and while distilling off the methanol, and then effecting condensation under reduced pressure at temperatures of from 160 to about 240° C. while distilling off excess glycols. Transesterification and condensation catalysts from the prior art are suitable, such as, for example, titanium tetraisopropoxide, dibutyltin oxide or antimony trioxide/calcium acetate.
These oligoesters can be incorporated into any type of hair-treatment composition, for example into shampoos, cream rinses, hair conditioners, hair lotions, waving compositions or aerosol foams. The content of oligoesters in these haircare compositions can vary within wide limits and is generally from 0.1 to 5% by weight, preferably from 0.5 to 3% by weight, in particular from 1 to 2% by weight, based on the hair-treatment composition.
Moreover, the hair-treatment compositions according to the invention comprise the constituents customary in this connection, essentially anionic, nonionic, cationic, zwitterionic or amphoteric surfactants, and auxiliaries and additives such as emulsifiers, refatting agents, biogenic active ingredients, film formers, preservatives, pearlizing agents, dyes.
Anionic surfactants are, in particular, the following compound d their mixtures: alkali metal salts, ammonium salts, amine salts and salts of aminoalcohols of the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamide sulfates and ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidosulfonates, alkylarylsulfonates, &agr;-olefinsulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamidosulfosuccinamates, alkyl sulfoacetates, alkylpolyglycerol carboxylates, alkyl phosphates, alkyl ether phosphates, alkyl sarcosinates, alkyl polypeptidates, alkylamidopolypeptidates, alkyl isethionates, alkyl taurates.
Salts of saturated and unsaturated fatty acids, such as oleic acid, ricinoleic acid, palmitic acid, stearic acid, copra oil acid salts or hydrogenated copra oil acid salts, and alkylpolyethoxycarboxylates

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