Concentrated fluid aqueous-alcoholic compositions of...

Colloid systems and wetting agents; subcombinations thereof; pro – Continuous liquid or supercritical phase: colloid systems;... – Aqueous continuous liquid phase and discontinuous phase...

Reexamination Certificate

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C516S900000, C510S123000, C510S490000, C510S535000, C554S052000, C554S068000

Reexamination Certificate

active

06335375

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to concentrated, aqueous-alcoholic, low-viscosity, clear, relatively colourless solutions which are stable over a temperature range of between 5 and 50° C. and which contain at least 50% by weight of alkylamido-propylbetaine corresponding to the general formula (I):
in which R represents the alkyl radical of a fraction of fatty acids of hydrogenated coconut or palm kernel oil type, with an iodine number of not more than 1 (in grams of iodine per 100 g). The approximate composition of such a fraction is, in percentages by weight:
50-65%
lauric acid,
15-26%
myristic acid,
 8-14%
palmitic acid,
 7-15%
stearic acid,
the unsaturated fraction responsible for the low iodine number being represented by less than 1% oleic acid.
In the specification hereinbelow, these alkylamidopropylbetaines will be referred to for simplicity as “betaines”. Their solutions display these qualities only if their composition is chosen precisely in a region of the betaine/ethanol/water diagram normalized to 100 by weight after correction of the NaCl present.
BACKGROUND OF THE INVENTION
Betaines corresponding to the general formula (I) are amphoteric surfactants that are very well tolerated by the skin, they have excellent cleansing and foaming properties and are entirely suitable for making a whole range of surfactant compositions, such as washing agents, cleansing agents (liquid products for washing up by hand), haircare compositions (shampoos) and bodycare compositions (shower gels and bubble baths).
The preparation of this type of betaine is described in many documents, and the processes are known to those skilled in the art, for example U.S. Pat. No. 3,225,074 (American Cyanamid). It consists in reacting a fatty acid or a fatty acid fraction with N,N-dimethyl-1,3-propanediamine (DMAPA) between 140 and 200° C., and then in quaternizing the tertiary amidoamine obtained, of general formula (II):
with monochloroacetic acid in the presence of an alkaline salt or the corresponding salt of this acid, the quaternization reaction usually taking place in aqueous medium. The alkaline chloride, which is often sodium chloride, obtained as a by-product in the reaction, is generally left in this aqueous betaine solution. These aqueous betaines are sold at a concentration in the region of 30% by weight.
Attempts have often been made to prepare industrially betaine solutions that are as concentrated and as fluid as possible, for quite understandable reasons of reducing the transportation and storage costs, without, however, sacrificing the ease of their handling.
A person skilled in the art knows that when the concentration of an aqueous surfactant solution increases, its viscosity also increases. Nevertheless, certain authors have sought to concentrate, by evaporation under reduced pressure, betaine solutions obtained according to the usual processes, but their viscosity increases rapidly and they become pasty at about 40° C. by weight of betaine, then continue to solidify as water is removed therefrom: it is not possible to obtain concentrated solutions via this route. However, it is reported in EP 0,302,329 (Th. Goldschmidt) that it was possible partially to circumvent this difficulty by adjusting the pH of the solution to between 1 and 4.5 with an inorganic acid (hydrochloric, sulphuric or phosphoric acid). The authors thus obtained solutions containing 43 to 44% by weight of betaine (or 53 to 54% solids) with a viscosity in the region of 1000 mPa.s at 25° C. However, the problems of corrosion during storage and transportation, along with the atypical pH of these betaine solutions, limit their use and, moreover, they gel below 16° C.
Another route is that for obtaining betaine in powder form, by spraying fluid solutions at less than 30%. It may be thought to redissolve these powders in suitable solvents, but redissolving these powders is hampered by the formation, when the powder is placed in contact with the solvent, of lumps or gelled pastes which are virtually impossible to redissolve, or at least not within reasonable times that are compatible with industrial activity.
International patent application WO 97/12856 (Henkel) discloses and claims a process for manufacturing surfactants of betaine type with a low salt content (0.98 to 1.01% residual NaCl) by quaternization of tertiary amines and/or tertiary amidoamines with sodium monochloroacetate in an aqueous-alcoholic mixture composed of 5 to 10% by weight of water and 35 to 50% by weight of ethanol and/or isopropanol, this reaction being followed by removal of the salt fraction precipitated, total removal of the solvent and readjustment of the water in the reaction medium in order to bring the solution to the desired active material concentration—in this case 30%. The water/ethanol weight ratio claimed by the authors is typical for a process aimed at removing the NaCl formed during the reaction. A composition of this type formed the subject of U.S. Pat. No. 4,705,893 (KAO), represented by a pentagonal zone of the betaine/water/ethanol ternary diagram defined by the triangular coordinates (80/10/10), (80/15/5), (40/55/5), (40/27.5/32.5) and (52.5/10/37.5). Both of these cases involve processes whose essential aim is to obtain totally aqueous non-concentrated amphoteric surfactant solutions with low salt contents.
A person skilled in the art is familiar with the idea of the possible existence of domains of fluid phases in an amphoteric surfactant/water/solvent system. This idea is pursued in WO 95/14076 (Albright and Wilson), in reality without any concrete teaching other than that of the individual examples reported in that publication, which come closest to the conditions of the present problem, namely, compositions of coco- or lauryl-amidopropylbetaine-salt dissolved in a mixed solvent of water/glycol type.
The problem which still remains is to obtain solutions of hydrogenated coconut or palm kernel oil alkylbetaine which are as concentrated as possible, i.e. at least 50% by weight, clear and relatively colourless, fluid and pumpable (viscosity of less than 1000 mPa.s), stable between 5 and 50° C. for prolonged periods, in order to reduce the packaging, transportation and storage costs, readily manipulable, and which can be formulated in their given state with other surfactants, for example alkyl ether sulphates, alkanolamides or other starting materials forming part, in particular, of the formulations for liquid soaps, shampoos, shower gels and other cosmetic preparations. The use of hydrogenated coconut oil is a restriction imposed by the requirement for these compositions intended for cosmetic uses to have better stability to oxidation than that which might be hoped for the non-hydrogenated natural fractions.
SUMMARY OF THE INVENTION
The present invention provides a solution to this technical problem, which consists in preparing the alkylbetaine by quaternizing the product of reaction of dimethylaminopropylamine with a fatty acid of hydrogenated coconut or palm kernel oil in the presence of small amounts of ethanol, provided that, however, the system remains limited to a quite precise and narrow region of the phase diagram as will now be defined.
The system is determined on betaine/water/ethanol ternary compositions, represented on the ternary diagram in reduced coordinates
B*=[betaine/(betaine+water+ethanol)]·10
2
W*=[water/(betaine+water+ethanol)]·10
2
E*=[ethanol/(betaine+water+ethanol)]·10
2
where betaine has the sense of, and is measured as, betaine=solids−NaCl,
in which the 100% loop relationship applies for the composition B*+W*+E*=100,
all of the betaine, solids, water, ethanol and NaCl magnitudes being expressed on a weight basis, the reduced magnitudes B*, W* and E* appearing as weight %.
With this definition, the betaine considered is a raw betaine, i.e. one consisting of alkylamidobetaine as corresponds to formula I, with a few reactant residues and a few reaction by-products

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