Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1998-12-23
2000-05-02
Carr, Deborah D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554 51, 554 42, 554 66, 554 68, 554 69, 510119, 510123, 510125, 510135, C07C23350
Patent
active
06057464&
DESCRIPTION:
BRIEF SUMMARY
The invention relates to high-foaming sulfates of fatty acid polyhydroxyalkylamides, compositions comprising these sulfates, a process for the preparation of the sulfates and of the compositions and their use.
Organic sulfates which contain long hydrophobic alkyl groups, such as, for example, fatty alcohol sulfates or sulfated fatty alcohol alkoxylates, are active anionic surfactants which have diverse uses.
U.S. Pat. No. 2,717,894 and WO-A 94/12472 describe sulfates of fatty acid polyhydroxyalkylamides. These compounds are prepared by reaction of fatty acid polyhydroxyalkylamides with typical sulfating reagents, such as oleum, gaseous sulfur trioxide, SO.sub.3 /pyridine complex or chlorosulfonic acid. As stated in U.S. Pat. No. 2,717,894, the sulfated products have a significantly increased foaming power, compared with the neutral amides on which they are based.
It has now been found, surprisingly, that sulfates of amino-functionalized fatty acid polyhydroxyalkylamides which, in the non-neutralized form, are predominantly in the zwitterionic structure (see example) also foam to a considerably greater degree, compared with the nonionic starting amides, and are additionally distinguished by an improved skin tolerance. These novel active compounds are prepared with the aid of the sulfating reagents already mentioned.
The surfactants according to the invention correspond to the following formulae (I) and (II) ##STR1## in which CO--R is an aliphatic acyl radical having 6 to 22 carbon atoms, polyhydroxyhydrocarbon radical having 4 to 12 carbon atoms in the radical Z, where X is a hydrogen atom or an SO.sub.3 H group or an SO.sub.3 M group, in which M is one alkali metal or half an alkaline earth metal equivalent or ammonium, with the proviso that X is not hydrogen in one to (b-2) cases.
The sulfates of the formulae (I) and (II) according to the invention, for example the compound 2 described in the example, give very good values in the Ross-Miles foam height test and in the whipped foam volume test in 0.1% strength concentration in water at pH 7. The sulfates according to the formulae (I) and (II) can be combined as desired with cationic, nonionic, amphoteric or anionic surfactants, for example with ether-sulfates based on glycol monoalkyl ethers or alkyl sulfates or alkyl-sulfonates. The sulfates according to the formulae (I) and (II) can also advantageously be used in combination with fatty acid polyhydroxylamides, in particular with the N,N-dialkylaminoalkyl-sugar amides used for their preparation. The surfactants according to the invention dissolve in water, lower alcohols, lower glycols or a mixture of these solvents. The same applies to compositions of the sulfates according to the formulae (I) and (II) with suitable cosurfactants.
The preparation of a suitable dialkylaminopropyl-glucamide according to a process which is already known is first described below. Novel sulfates according to the formulae (I) and (II) are prepared from this precursor in the example.
Preparation of fatty acid polyhydroxyalkylamide C.sub.12/14 -dimethylaminopropyl-glucamide (DMAP-GA):
304.5 g of a 41% strength by weight aqueous solution of a technical grade N-(3-dimethylamino)-propylglucamine (prepared according to U.S. Pat. No. 4,021,539, Example F), called DMAP-G in the following, having a DMAP-G content of 96% by weight, based on the solid substance (i.e. 0.45 mol of DMAP-G), are dewatered with the aid of a customary stripping apparatus. For this purpose, the solution is heated to about 100.degree. C. and initially dewatered under normal pressure up to a residual water content of about 5% by weight. The solution is now heated to 130.degree. C., for further dewatering, and kept at this temperature, a vacuum of up to 25 mbar being applied stepwise. Dewatering is carried out down to a residual water content of 0.2% by weight. 104.1 g (0.473 mol) of C.sub.12/14 -fatty acid methyl ester (molecular weight 220 g/mol, according to the hydrolysis number) are added at 130.degree. C. with stirring to the melt thus obtained. The mixture
REFERENCES:
patent: 2717894 (1955-09-01), Schwartz
patent: 5312934 (1994-05-01), Letton
Carr Deborah D.
Clariant GmbH
Dearth Miles B.
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