US4675394A
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Polysaccharide derivatives containing aldehyde groups, their preparation from the corresponding acetals and use as paper additives
Assignee: Ingredion Inc
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Filing: 1985-07-24
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Granted: 1987-06-23
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Expires: 2005-07-24
Abstract
Abstract Polysaccharide aldehydes having the general structure ##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. R is (CH 2 ) n or a divalent aromatic group and n is 0 or greater; R 1 , R 6 , and R 7 are hydrogen or an organic group; R 2 , R 5 , and R 8 are (CH 2 ) m with m being 1-6; R 3 and R 4 are hydrogen or a lower alkyl; Y 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 11 , 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.
Inventors
- 👤 Daniel B. Solarek
- 👤 Patrick G. Jobe
- 👤 Martin M. Tessler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:43
CPC Classifications
C; C08; C08B; C08B11/00; C08B11/02; C08B11/04; C08B11/14; C08B31/00; C08B31/08; C08B31/12; C08B31/125; C08B37/00; C08B37/006; C08B37/0087; C08B37/0096; D; D21; D21H; D21H17/00; D21H17/20; D21H17/21; D21H17/24; D21H17/25; D21H17/28; D21H17/31
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
97 words
An aldehyde-containing polysaccharide derivative having the general structure ##STR70## wherein Sacch--O represents a polysaccharide molecule; R is (CH 2 ) n , with n being 0 or greater; or a divalent aromatic group, R 1 , R 6 , and R 7 are independently hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; R 2 , R 5 and R 8 are independently (CH 2 ) m with m being 1-6; R 3 is hydrogen or a lower alkyl group; R 4 is hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; and Y is an anion.
Claim 2
Dependent Claim
97 words
An aldehyde-containing polysaccharide derivative having the general structure ##STR70## wherein Sacch--O represents a polysaccharide molecule; R is (CH 2 ) n , with n being 0 or greater; or a divalent aromatic group, R 1 , R 6 , and R 7 are independently hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; R 2 , R 5 and R 8 are independently (CH 2 ) m with m being 1-6; R 3 is hydrogen or a lower alkyl group; R 4 is hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; and Y is an anion.
Claim 3
Dependent Claim
134 words
A acetal-containing polysaccharide derivative having the general structure ##STR71## wherein Sacch--O represents a polysaccharide molecule; R 9 is (CH 2 ) 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 1 , R 6 , and R 7 are independently hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; R 2 , R 5 , and R 8 are independently (CH 2 ) m with m being 1-6; R 3 is hydrogen or a lower alkyl; and R 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.
Claim 4
Dependent Claim
134 words
A acetal-containing polysaccharide derivative having the general structure ##STR71## wherein Sacch--O represents a polysaccharide molecule; R 9 is (CH 2 ) 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 1 , R 6 , and R 7 are independently hydrogen or an alkyl, aryl, aralkyl, or alkaryl group; R 2 , R 5 , and R 8 are independently (CH 2 ) m with m being 1-6; R 3 is hydrogen or a lower alkyl; and R 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.
Claim 5
Dependent Claim
13 words
The derivative of claim 1 or 2, wherein the polysaccharide is a starch.
Claim 6
Dependent Claim
13 words
The derivative of claim 1 or 2, wherein the polysaccharide is a gum.
Claim 7
Dependent Claim
13 words
The derivative of claim 1 or 2, wherein the polysaccharide is a cellulose.
Claim 8
Dependent Claim
58 words
The derivative of claim 3, wherein the starch is a waxy maize, corn, high amylose corn, potato, rice, sweet potato, or tapioca starch; R 1 , R 6 , and R 7 are indepedently hydrogen or a methyl group m is 1; R 3 and R 4 are hydrogen; and Y is a chloride, sulfate, or nitrate anion.
Claim 9
Dependent Claim
18 words
The derivative of claim 6, wherein the starch contains one or more cationic, anionic, nonionic or zwitterionic group.
Claim 10
Dependent Claim
34 words
The derivative of claim 7, wherein n is 1; and m is 1; R 1 is hydrogen or methyl; R 3 and R 4 are hydrogen; and R 6 and R 7 are methyl.
Claim 11
Dependent Claim
129 words
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 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.
Claim 12
Dependent Claim
36 words
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.
Claim 13
Dependent Claim
41 words
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.
Claim 14
Dependent Claim
11 words
The derivative of claim 3, wherein n is 0 or 1.
Claim 15
Dependent Claim
11 words
The derivative of claim 4, wherein n is 0 or 1.
Claim 16
Dependent Claim
11 words
The derivative of claim 5, wherein n is 0 or 1.
Claim 17
Dependent Claim
81 words
The method of claim 10, wherein in the acetal-containing derivatizing reagent Z--R 11 -- is ##STR73## R 9 is (CH 2 ) n with n being 0 or 1; R 1 , R 6 , and R 7 are hydrogen or methyl; R 2 , R 5 , and R 8 are independently (CH 2 ) m with m being 1 or 2; R 3 and R 4 are hydrogen; X is chlorine, bromine, or iodine; and Y is an anion.
Claim 18
Dependent Claim
33 words
The method of claim 15, wherein n is 1; m is 1; R 1 is hydrogen or methyl; R 3 and R 4 are hydrogen; and R 6 and R 7 are methyl.
Claim 19
Dependent Claim
11 words
The method of claim 16, wherein the polysaccharide is a gum.
Claim 20
Dependent Claim
11 words
The method of claim 16, wherein the polysaccharide is a cellulose.
Claim 21
Dependent Claim
58 words
The method of claim 11, wherein the starch is a waxy maize, corn, high amylose corn, potato, rice, sweet potato, or tapioca starch R 1 , R 6 , and R 7 are independently hydrogen or a methyl; group m is 1; R 3 and R 4 are hydrogen; and Y is a chooride, sulfate, or nitrate anion.
Claim 22
Dependent Claim
18 words
The method of claim 19, wherein the starch contains one or more cationic, anionic, nonionic or zwitterionic group.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-06-22 | 1990-12-22 | 1991-06-23 | $2000.00 | Window Closed / Lapsed |
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