Claims
- 1. An aldehyde-containing polysaccharide derivative having the general structure ##STR70## wherein Sacch--O represents a polysaccharide molecule; R is (CH.sub.2).sub.n, with n being 0 or greater; or a divalent aromatic group, R.sup.1, R.sup.6, and R.sup.7 are independently hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; R.sup.2, R.sup.5 and R.sup.8 are independently (CH.sub.2).sub.m with m being 1-6; R.sup.3 is hydrogen or a lower alkyl group; R.sub.4 is hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; and Y is an anion.
- 2. A acetal-containing polysaccharide derivative having the general structure ##STR71## wherein Sacch--O represents a polysaccharide molecule; R.sup.9 is (CH.sub.2).sub.n or an aromatic group, with n being 0 or greater, with the proviso that n is at least 1 when the polysaccharide molecule is a starch molecule, R.sup.1, R.sup.6, and R.sup.7 are independently hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; R.sup.2, R.sup.5, and R.sup.8 are independently (CH.sub.2).sub.m with m being 1-6; R.sup.3 is hydrogen or a lower alkyl; and R.sup.4 is hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; A and A' are independently a lower alkyl or A and A' together form at least a 5-membered cyclic acetal; and Y is an anion.
- 3. The derivative of claim 1 or 2, wherein the polysaccharide is a starch.
- 4. The derivative of claim 1 or 2, wherein the polysaccharide is a gum.
- 5. The derivative of claim 1 or 2, wherein the polysaccharide is a cellulose.
- 6. The derivative of claim 3, wherein the starch is a waxy maize, corn, high amylose corn, potato, rice, sweet potato, or tapioca starch; R.sup.1, R.sup.6, and R.sup.7 are indepedently hydrogen or a methyl group m is 1; R.sup.3 and R.sup.4 are hydrogen; and Y is a chloride, sulfate, or nitrate anion.
- 7. The derivative of claim 6, wherein the starch contains one or more cationic, anionic, nonionic or zwitterionic group.
- 8. The derivative of claim 7, wherein n is 1; and m is 1; R.sup.1 is hydrogen or methyl; R.sup.3 and R.sup.4 are hydrogen; and R.sup.6 and R.sup.7 are methyl.
- 9. The method for preparing the derivative of claim 1, which comprises the steps of:
- (a) reacting a polysaccharide molecule, in the presence of an alkali, with an acetal-containing derivatizing reagent having the general structure ##STR72## where Z is a terminal organic group capable of reacting with the polysaccharide molecule to form an ether derivative and is selected from the group consisting of an epoxide, an ethylenically unsaturated group, a halohydrin, and a halogen; R.sup.11, is a divalent organic group containing no polysaccharide-reactive substituents; and A and A' are independently a lower alkyl or A and A' together form at least a 5-membered cyclic acetal;
- (b) hydrolyzing the resulting acetal-containing polysaccharide derivative by adjusting the pH to less than 7; and
- (c) isolating the resulting aldehyde-containing polysaccharide derivative.
- 10. The method of claim 9, wherein the reagent is used in an amount of about 0.5 to 100% by weight, based on dry polysaccharide, and wherein the pH in step (b) is adjusted to about 2-4.
- 11. The method claim 9, wherein polysaccharide is starch and the reaction of step (a) is carried out in the presence of a catalyst selected from the group consisting of an alkali metal iodide, a quaternary ammonium iodide, and an amine iodide.
- 12. The derivative of claim 3, wherein n is 0 or 1.
- 13. The derivative of claim 4, wherein n is 0 or 1.
- 14. The derivative of claim 5, wherein n is 0 or 1.
- 15. The method of claim 10, wherein in the acetal-containing derivatizing reagent Z--R.sup.11 -- is ##STR73## R.sup.9 is (CH.sub.2).sub.n with n being 0 or 1; R.sup.1, R.sup.6, and R.sup.7 are hydrogen or methyl; R.sup.2, R.sup.5, and R.sup.8 are independently (CH.sub.2).sub.m with m being 1 or 2; R.sup.3 and R.sup.4 are hydrogen; X is chlorine, bromine, or iodine; and Y is an anion.
- 16. The method of claim 15, wherein n is 1; m is 1; R.sup.1 is hydrogen or methyl; R.sup.3 and R.sup.4 are hydrogen; and R.sup.6 and R.sup.7 are methyl.
- 17. The method of claim 16, wherein the polysaccharide is a gum.
- 18. The method of claim 16, wherein the polysaccharide is a cellulose.
- 19. The method of claim 11, wherein the starch is a waxy maize, corn, high amylose corn, potato, rice, sweet potato, or tapioca starch R.sup.1, R.sup.6, and R.sup.7 are independently hydrogen or a methyl; group m is 1; R.sup.3 and R.sup.4 are hydrogen; and Y is a chooride, sulfate, or nitrate anion.
- 20. The method of claim 19, wherein the starch contains one or more cationic, anionic, nonionic or zwitterionic group.
Parent Case Info
This application is a continuation-in-part of Serial No. 641,820 filed Aug. 17, 1984, now abandoned.
US Referenced Citations (25)
Foreign Referenced Citations (2)
Number |
Date |
Country |
0147380 |
Mar 1985 |
EPX |
944459 |
Dec 1963 |
GBX |
Non-Patent Literature Citations (1)
Entry |
Collect. Czech. Chem. Commun. 1984 49(4) 821-7 CA 101:112625t. |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
641820 |
Aug 1984 |
|