Acetals useful for the preparation of polysaccharide derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D31906

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048047694

ABSTRACT:
Polysaccharide aldehydes having the formula Sacch-O-CH.sub.2 -CH.dbd.CH-CHO, Sacch-O-CH.sub.2 -C.tbd.C-CHO, ##STR1## such as starch, cellulose, and gum aldehydes, are useful for imparting wet, dry, or temporary wet strength to paper. They are prepared by a non-oxidative method which involves reacting the polysaccharide base, in the presence of alkali, with a derivatizing acetal reagent having the general structure ##STR2## and then hydrolyzing the acetal by adjusting the pH to less than 7, preferably 2-4. In the formulas, n is 1-3; R.sup.11 and R.sup.12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R.sup.11 or R.sup.12 is one of the groups when n is 2, or R.sup.11 and R.sup.12 are not present when n is 3; R.sup.13 is an alkyl group, optionally containing an ether linkage, or an aralkyl group; R.sup.14 and R.sup.15 are individually a hydrogen or a methyl group; R.sup.16, R.sup.17, and R.sup.18 are individually an alkyl group; Y.sup.- is an anion; Z is an organic group capable of reacting with the polysaccharide base to form an ether derivative and selected from the group consisting of an epoxide, ethylenically unsaturated group, halohydrin, and halogen; R.sup.19, if present, is a divalent organic group containing no reactive substiuents; and A and A' are lower alkyls or together form at least a 5-membered cyclic acetal.

REFERENCES:
patent: 2698937 (1955-01-01), Staerkle et al.
patent: 3519618 (1970-07-01), Parmerter
patent: 4048435 (1977-09-01), Rutenberg et al.
patent: 4276414 (1981-06-01), Tessler

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