Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-06-06
1998-07-07
Nutter, Nathan M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
5361231, C08B 3718, C02F 510
Patent
active
057770905
DESCRIPTION:
BRIEF SUMMARY
The invention relates to carboxymethyl inulin and a process for its preparation. Carboxymethyl inulin is known per se from an article of Chien et al in the Journal of Immunological Methods, 1979, 1, 39-46. The product disclosed therein has a degree of substitution (DS) of 0.11. It was prepared by conversion of inulin (74 mmoles monosaccharide units) with 450 mmoles sodium chloroacetate in 90 ml 10N NaOH. Accordingly, the efficiency of this reaction was 0.11/(450/74).times..times.100%=1,8%, i.e. an efficiency that is unacceptable for application on an industrial scale. Moreover, the known process appears to be unsuitable for obtaining higher DS values.
Carboxymethylation is a known process for the derivation of mono-, oligo- and polysaccharides, the primary and/or secondary alcohol groups of which are etherified with carboxymethyl groups. The derivatives thus obtained are (poly)-carboxylates, which find use in a great many applications, especially in detergent formulations, in the paper industry and in oil winning.
A further advantage of carboxymethylation is that the process can be carried out in a simple manner. The loss of chemicals is small and the products are biodegradable.
Known examples of carboxymethylated products are carboxymethyl cellulose (CMC) and carboxymethyl sucrose (CMSU).
The former product finds application in detergent compositions as an anti-redeposition agent and as a cobuilder to prevent calcium carbonate scale formation which occurs during the washing of laundry (also referred to as incrustation). According to U.S. Pat. No. 3,634,932, carboxymethylated sucrose is useful as a sequestering agent and also as a detergency builder for organic water-soluble synthetic detergents.
Though both products, CMSU and CMC, are biodegradable and therefore highly attractive to replace the well-established group of builders, such as organic phosphonates, nitrilotriacetate, inorganic triphosphate, and zeolites, or the group of cobuilders, such as polyacrylate, copolymers of acrylate and maleate, and polystyrene sulphonate, the properties of both CMC and CMSU detract from the performance in several respects.
A disadvantage of CMC is its relatively high viscosity, which allows only a limited amount to be incorporated in detergent compositions. CMSU, on the contrary, is readily soluble in water. Moreover, it has very good sequestering properties. However, it possesses no or hardly any crystallization inhibiting properties.
Consequently, there is a need for a biodegradable inhibitor selected from the group of carboxymethylated mono-, oligo- and polysaccharides which lacks the above-mentioned drawbacks.
Accordingly, the invention provides carboxymethyl inulin having a degree of substitution (DS) ranging from 0.15 to 2.5, preferably from 0.5 to 1.5.
Surprisingly, it was found that the addition of very small amounts (5 ppm-200 ppm) of CMI has--like CMSU--no or hardly any viscosity-increasing effect but--unlike CMSU--influences the crystallization rate and the crystal morphology of the precipitated calcium carbonate to a considerable extent.
It should be added that WO-A-91/17189 discloses that the oxidation product of inulin, a polycarboxysaccharide, possesses excellent calcium complexing properties. As it is readily soluble in water with no or hardly any viscosity increasing effect, it would appear to be a perfect candidate to take the place of the known non-biodegradable and/or viscous inhibitors of the crystallization of calcium carbonate in detergent compositions. Despite this, it was found by the inventors of the present application that crystal growth inhibition by the use of polycarboxyinulin was rather minimal.
The invention further relates to a process of preparing CMI having a DS ranging from 0.15 to 2.5, leading to much higher yields and efficiencies than may be obtained with the known process disclosed by Chien et al.
Said process is characterized in that in the known process where inulin is reacted at elevated temperature with an aqueous alkaline solution of monochloroacetic acid, followed by wor
REFERENCES:
patent: 3596766 (1971-08-01), Johnston et al.
patent: 3634392 (1972-01-01), Lyness et al.
patent: 4986980 (1991-01-01), Jacobsen
patent: 5122598 (1992-06-01), della Valle et al.
Journal of Immunological Methods, vol. 26, No. 1, 1979, pp. 39-46.
Chemical Abstracts, 90/256413/34, JP 2178-229-A, Jul. 11, 1990.
International Search Report, PCT/EP94/04097, dated Apr. 4, 1995.
Batelaan Jan Gerardus
Peters Johannes Andreas
van Bekkum Herman
Verraest Dorine Lisa
Akzo Nobel nv
Mancini Ralph J.
Morris Louis A.
Nutter Nathan M.
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