Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-11-14
2000-08-15
Lee, Howard C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 30, 536 43, 536 45, 536 46, 536 52, 536 553, 536119, 536124, C07H 504, C07H 100, C08B 1100, C08B 3100
Patent
active
061038857
DESCRIPTION:
BRIEF SUMMARY
The invention pertains to a process for the amidation of a material having at least one carboxyl-containing polysaccharide. The invention also pertains to hydrophobe modified carboxyl groups-containing polysaccharides so obtainable.
A process for the amidation of a material having at least one carboxyl-containing polysaccharide has been disclosed in U.S. Pat. No. 4,963,664 to Yalpani et al. In the described process a material having at least one carboxyl-containing polysaccharide is reacted with an ammonium donor having the general formula >NH in order to convert the carboxyl groups into amide groups. This method, however, appears unviable. The exemplified process involves unsuitably long reaction times and displays a low conversion, which, all in all, prohibits employing the process on a commercially acceptable scale. Furthermore, the disclosed method, while yielding quaternary ammonium modified polysaccharide, even fails to produce the desired result of amidation. Typical ammonium donors disclosed are ammonia, ammonium salts, primary and secondary amines, polypeptides, proteins, etc. While Yalpani thus directs the man of ordinary skill in the art to employing numerous amines as the ammonium donor, the disclosure is silent on such modification as will render the carboxyl groups-containing polysaccharides hydrophobic.
From U.S. Pat. No. 4,988,806 (Gruning) it is known to esterify carboxymethyl cellulose (CMC) with alkyl chloride, and react the ester so obtained with a diamine, in order to form an aminamide of CMC, which is subsequently quaternized. The process is relatively complicated, and it would be desirable to avoid the use of alkyl chloride, which is an unpleasant and relatively expensive compound and, besides, winds up as a waste product. Further, the process is restricted to short-chain amines, and does not appear suitable for rendering CMC hydrophobic.
Generally it is very difficult to have hydrophilic materials such as carboxyl groups-containing polysaccharides (notably CMC) react with hydrophobic materials such as fatty amines. Nonetheless, hydrophobically derivatized polysaccharides are known in the art.
Thus U.S. Pat. No. 4,228,277 (Landoll I) discloses cellulose ethers which have a sufficient degree of nonionic (methyl, hydroxyethyl, hydroxypropyl) substitution to cause them to be water-soluble and further are substituted with a hydrocarbon radical having about 10-24 carbon atoms in an amount between about 0.2 wt % and the amount which renders said cellulose ethers less than 1% soluble in water. Attaching the hydrocarbon radical to the cellulose ether is achieved by reaction with a long chain modifier, which may be an alkyl halide, an epoxide, an isocyanate, an acid, or an acyl halide. The disclosed materials exhibit an improved viscosifying effect, and also some surface activity.
U.S. Pat. No. 4,243,802 (Landoll II) discloses similar cellulose ethers, wherein the amount of C.sub.10 -C.sub.24 hydrocarbon substitution is such as will render the cellulose ether water-insoluble. These materials are used to effect viscosity increases in solutions of surfactants, or as emulsifiers in aqueous systems.
Similar cellulose ethers, in which the C.sub.10 -C.sub.24 substituent is an alkylaryl group, are disclosed in U.S. Pat. No. 5,120,838 to Just et al.
Hydrophobe substituted, water-soluble cationic polysaccharides are known from EP 189 935. The quintessence of these materials is that they have a side chain which incorporates one or more quaternary ammonium groups. Next to the quaternary ammonium groups, the side chain may also incorporate a C.sub.12 -C.sub.18 hydrocarbon chain. The materials are substantially water-soluble and may provide aqueous solutions having enhanced viscosity, foaming, and surface properties. They are disclosed to be useful in personal care, emulsions, and cleansers.
EP 512 319 discloses urethane derivatives of polysaccharides prepared by reacting carbonate groups-containing polysaccharide with a protic nucleophile such as an amine. The carbonate-containing polysaccharide is ob
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Batelaan Jan Gerardus
Van Der Horst Peter Marten
Akzo Nobel nv
Fennelly Richard P.
Lee Howard C.
White Everett
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