5,6-0-alkylidene glucono-1(4)-lactones and derivatives,...

Details 5,6-0-alkylidene glucono-1(4)-lactones and derivatives,... 5,6-0-alkylidene glucono-1(4)-lactones and derivatives,...

1998-04-13

2001-06-26

Owens, Amelia (Department: 1612)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C549S314000, C549S454000

Reexamination Certificate

active

06251937

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to 5,6-O-alkylidene glucono-1(4)-lactones and to the corresponding derivatives obtained by alkaline hydrolysis or amidation. The invention also relates to processes for the preparation of these compounds and to their uses.
BACKGROUND OF THE INVENTION
Surfactants are made use of in many organic chemistry syntheses.
This is the case, in particular, of emulsion polymerization processes, which offer the advantage of a high rate of reaction and a high degree of polymerization.
The emulsion polymerization, for example in water, generally uses a hydrophobic monomer, a surfactant forming micellar structures and an initiator. The reaction takes place inside the said structures and continues until the monomer is completely converted. Depending on the size of the polymer particles stabilized by the surfactant in the medium, a latex or a suspension is obtained.
Separation of the particles from the medium is made difficult by the presence of a surfactant, which tends to form highly stable emulsions or foams during the extraction step.
To overcome these drawbacks, cleavable surfactants have been proposed, inter alia, which are capable of decomposing into non-surfactant intermediates by an acid hydrolysis.
Among these surfactants, mention may be made of compounds having a labile structure of the 1,3-dioxane type, obtained by condensation of an aliphatic diol and a bromo aldehyde [WANG G. W. et al., JAOCS, Vol. 72, No. 1, pp. 83-87, 1995; JAOCS, Vol. 71, No. 7, pp. 727-730, 1994; JAOCS, Vol. 70, No. 7. pp. 731-732, 1993; J. Colloid and Interface Science, Vol. 173, pp. 49-54, 1995] or by acetalization of N-acetylglucosamine [KIDA T. et al., JAOCS, Vol. 72,-No. 7, pp. 773-780, 1995] or of glucono-1(5)-lactone [KIDA T. et al., JAOCS, Vol. 71, No. 7, pp. 705-710, 1994].
Mention may also be made of compounds having a labile structure of the 1,3-dioxolane type, such as cationic derivatives of alkyl 1,3-dioxolane (in the form of trimethylammonium bromides) [WILK K. A. et al., JAOCS, Vol. 71, No. 1, pp. 81-85, 1994], anionic derivatives containing one or two carboxylate groups [ONO D. et al., JAOCS, Vol. 72, No. 7, pp. 853-856, 1995] and nonionic derivatives obtained from L-galactono-1(4)-lactone.
The preparation of the surfactants which have just been mentioned usually requires many steps in which solvents and/or toxic reactants (for example dimethylformamide, benzene or acrolein) or starting materials that are not readily available (for example L-galactono-1(4)-lactone) are used.
It goes without saying that there is a great demand to have available novel cleavable surfactants which, in addition, are compatible with the skin and mucous membranes, are biodegradable and may be produced on an industrial scale from readily accessible starting materials.
SUMMARY OF THE INVENTION
The present invention thus relates, firstly, to surfactants which satisfy the abovementioned criteria. These surfactants are 5,6-O-alkylidene glucono-1(4)-lactones of formula:
in which R′ and R, which may be identical or different, represent a hydrogen atom or a linear or branched, saturated or unsaturated alkyl radical, the sum of the carbon atoms of R′ and R being between 5 and 42, and preferably between 5 and 21.
The subject of the invention is also a process for the preparation of the abovementioned compounds of formula (I), which consists in reacting glucono-1(5)-lactone with a compound of formula R′—CO—R in the presence of an acid catalyst, R′ and R having the meaning given above.
Another subject of the invention relates to the compounds obtained by alkaline hydrolysis of the abovementioned compounds of formula (I), these compounds corresponding to the formula:
in which:
R′ and R have the meaning given above,
z
n+
represents a cation of an alkali metal or alkaline-earth metal, or a quaternary ammonium of formula:
in which:
R
2
, R
3
, R
4
and R
5
, which may be identical or different, represent an alkyl or hydroxyalkyl radical containing 1 to 18 carbon atoms, an alkylaryl radical containing 7 to 18 carbon atoms or a basic amino acid residue,
and n is the valency of the cation.
Another subject of the invention relates to the compounds obtained by amidation of the abovementioned compounds of formula (I), these compounds corresponding to the formula:
in which:
R′ and R have the meaning given above,
R
1
represents a linear or branched mono- or polyhydroxyalkyl radical containing 2 to 12 carbon atoms and preferably 2 to 6 carbon atoms.
Another subject of the invention relates to compositions, in particular detergent or cosmetic compositions, containing compounds of formula (I) and/or (II) and/or (III).
The invention is described in detail in the following text:
A. PREPARATION OF THE COMPOUNDS OF FORMULA (1)
The alkylidene lactones of formula (I) are obtained by reacting glucono-1(5)-lactone with a compound of formula R′—CO—R in which R′ and R have the meaning given above, in the presence of an acid catalyst and in an anhydrous solvent.
The preferred glucono-1(5)-lactone is D-glucono-1(5)-lactone.
The compound of formula R′—CO—R is most particularly chosen from aldehydes such as n-heptanal, n-octanal, n-nonanal, n-decanal, n-undecanal, n-dodecanal, n-tetradecanal and 10-undecenal and ketones such as 2-heptanone, 2-octanone, 3-octanone, 2-nonanone, 3-nonanone, 2-decanone, 3-decanone, 2-undecanone and 6-undecanone.
The catalyst is generally chosen from hydrochloric acid, sulphuric acid, alkylsulphuric acids such as decyl- or laurylsulphuric acid, sulphonic acids such as benzenesulphonic, para-toluenesulphonic or camphorsulphonic acid, alkylsulphonic acids such as methanesulphonic, decylsulphonic, laurylsulphonic or sulphosuccinic acid or an alkyl sulphosuccinate, for example decyl or lauryl sulphosuccinate, perhalohydric acids such as perchloric acid or hypophosphorous acid, and mixtures of these acids.
Preferably, sulphuric acid, an alkylsulphuric acid, para-toluenesulphonic acid, methanesulphonic acid, sulphosuccinic acid or an alkyl sulphosuccinate, or hypophosphorous acid or a mixture of these acids is used.
The solvent is generally chosen from alkanes such as hexane or heptane, oxide ethers such as diethyl ether, isopropyl ether, dipropyl ether, dibutyl ether, diisobutyl ether, dioxane or diethylene glycol dimethyl ether, halogenated hydrocarbons such as dichloromethane, chloroform or dichloroethane, solvents of the amide type such as N-methylformamide, N,N-dimethylformamide, N,N-dimethylacetamide or N-methyl-2-pyrrolidone, sulphoxides such as dimethyl sulphoxide, nitrites such as acetonitrile, aromatic solvents such as toluene or xylene, and mixtures of these solvents.
Preferably, a mixture of two immiscible solvents is used, for example a mixture of an apolar solvent and a polar solvent, such as a hexane/N,N-dimethylformamide mixture.
The ratio by volume of the apolar solvent to the polar solvent is generally between 0.5 and 10 and preferably between 1 and 4.
In the process according to the invention, from 0.5 to 1.2 molar equivalents and preferably 0.7 to 1 equivalent of the compound of formula R′—CO—R and 0.5×10
−3
to 1 molar equivalent, and preferably 1×10
−2
to 0.5 equivalent, of acid catalyst are generally used per 1 molar equivalent of glucono-1(5)-lactone.
From 2 to 20 weight equivalents, and preferably 4 to 12 equivalents, of solvent are generally used per 1 weight equivalent of glucono-1(5)-lactone.
The reaction is generally carried out at the reflux temperature of the solvent, with trapping out of the water formed by means of a suitable system, for example of the Florentine flask type, at a temperature generally of between 25 and 200° C. and preferably 50 to 120° C.
The reaction time may range from 1 to 50 hours and preferably 5 to 40 hours.
The reaction is generally carried out at a pressure of between 0.013 and 101.325 kPa, and preferably at atmospheric pressure.
After the reaction, the catalyst present in the reaction med

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