US4703116A
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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: 1986-02-14
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Granted: 1987-10-27
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Expires: 2006-02-14
Abstract
Abstract Polysaccharide aldehydes having the formula Sacch-O-CH2-CH=CH-CHO, SaachOCH2CCCHO, <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> +TR <IMAGE> 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 <IMAGE> and then hydrolyzing the acetal by adjusting the pH to less than 7, preferably 2-4. In the formulas, n is 1-3; R11 and R12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R11 or R12 is one of the groups when n is 2, or R11 and R12 are not present when n is 3; R13 is an alkyl group, optionally containing an ether linkage, or an aralkyl group; R14 and R15 are individually a hydrogen or a methyl group; R16, R17, and R18 are individually an alkyl group; 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; R19, if present, is a divalent organic group containing no reactive substituents; and A and A'0 are lower alkyls or together form at least a 5-membered cyclic acetal.
Inventors
- 👤 Daniel B. Solarek
- 👤 Patrick G. Jobe
- 👤 Martin M. Tessler
- 👤 Robert L. Billmers
- 👤 Diane J. Lamb
- 👤 John J. Tsai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:46
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: 37
Claim 1
Independent Claim
118 words
An aldehyde-containing polysaccharide derivative, which is prepared by hydrolyzing, at a pH of less than 7 an acetal-containing polysaccharide which is prepared by a non-oxidative process which consists of reacting a polysaccharide, at a pH of 10 or above, with an acetal-containing reagent having the general structure ##STR50## where Z is an organic group capable of reacting with a polysaccharide molecule to form an ether derivative and is selected from the group consisting of an epoxide, a halohydrin, an ethylenically unsaturated group, and a halogen; R 19 is a divalent organic group containing no starch-reactive substituents; and A and A' are independently a lower alkyl group or A and A' together form at least a 5-membered cyclic acetal.
Claim 2
Dependent Claim
118 words
An aldehyde-containing polysaccharide derivative, which is prepared by hydrolyzing, at a pH of less than 7 an acetal-containing polysaccharide which is prepared by a non-oxidative process which consists of reacting a polysaccharide, at a pH of 10 or above, with an acetal-containing reagent having the general structure ##STR50## where Z is an organic group capable of reacting with a polysaccharide molecule to form an ether derivative and is selected from the group consisting of an epoxide, a halohydrin, an ethylenically unsaturated group, and a halogen; R 19 is a divalent organic group containing no starch-reactive substituents; and A and A' are independently a lower alkyl group or A and A' together form at least a 5-membered cyclic acetal.
Claim 3
Dependent Claim
142 words
An aldehye-containing polysaccharide derivative which has a structure selected from the group consisting of ##STR51## wherein Sacch--O-- represents a polysaccharide molecule; n is 1 to 3; R 11 and R 12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R 11 or R 12 is one of the groups when n is 2, or R 11 and R 12 are not present when n is 3; R 13 is an alkyl group which can contain an ether linkage or an aralkyl group; R 14 and R 15 individually are hydrogen or a methyl group; R 16 , R 17 , and R 18 individually are an alkyl group; A, A', A", and A"' are independently a lower alkyl group or A and A' together form at least a 5-membered cyclic acetal; and Y - is an anion.
Claim 4
Dependent Claim
142 words
An aldehye-containing polysaccharide derivative which has a structure selected from the group consisting of ##STR51## wherein Sacch--O-- represents a polysaccharide molecule; n is 1 to 3; R 11 and R 12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R 11 or R 12 is one of the groups when n is 2, or R 11 and R 12 are not present when n is 3; R 13 is an alkyl group which can contain an ether linkage or an aralkyl group; R 14 and R 15 individually are hydrogen or a methyl group; R 16 , R 17 , and R 18 individually are an alkyl group; A, A', A", and A"' are independently a lower alkyl group or A and A' together form at least a 5-membered cyclic acetal; and Y - is an anion.
Claim 5
Dependent Claim
12 words
The derivative of claim 2, which has the structure Sacch--O--CH 2 --CH═CH--CHO.
Claim 6
Dependent Claim
12 words
The derivative of claim 2, which has the structure Sacch--O--CH 2 --C.tbd.C--CHO.
Claim 7
Dependent Claim
10 words
The derivative of claim 2, which has the structure ##STR52##
Claim 8
Dependent Claim
10 words
The derivative of claim 2, which has the structure ##STR53##
Claim 9
Dependent Claim
10 words
The derivative of claim 2, which has the structure ##STR54##
Claim 10
Dependent Claim
13 words
The derivative of claim 2, which has the structure ##STR55## or mixtures thereof.
Claim 11
Dependent Claim
10 words
The derivative of claim 2, which has the structure ##STR56##
Claim 12
Dependent Claim
10 words
The derivative of claim 2, which has the structure ##STR57##
Claim 13
Dependent Claim
141 words
An acetal-containing polysaccharide derivative which has a structure selected from the group consisting of ##STR58## wherein Sacch--O-- represents a polysaccharide molecule; n is 1 to 3; R 11 and R 12 independently are an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R 11 or R 12 is one of the groups when n is 2, or R 11 and R 12 are not present when n is 3; R 13 is an alkyl group which can contain an ether linkage or an aralkyl group; R 14 and R 15 are individually a hydrogen or a methyl group; R 16 R 17 , and R 18 are individually an alkyl group; A, A', A" and A"' are independently an alkyl group or A and A' together form at least a five-membered cyclic acetal; and Y - is an anion.
Claim 14
Dependent Claim
141 words
An acetal-containing polysaccharide derivative which has a structure selected from the group consisting of ##STR58## wherein Sacch--O-- represents a polysaccharide molecule; n is 1 to 3; R 11 and R 12 independently are an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R 11 or R 12 is one of the groups when n is 2, or R 11 and R 12 are not present when n is 3; R 13 is an alkyl group which can contain an ether linkage or an aralkyl group; R 14 and R 15 are individually a hydrogen or a methyl group; R 16 R 17 , and R 18 are individually an alkyl group; A, A', A" and A"' are independently an alkyl group or A and A' together form at least a five-membered cyclic acetal; and Y - is an anion.
Claim 15
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR59##
Claim 16
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR60##
Claim 17
Dependent Claim
13 words
A derivative of claim 11, which has the structure ##STR61## Y - .
Claim 18
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR62##
Claim 19
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR63##
Claim 20
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR64##
Claim 21
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR65##
Claim 22
Dependent Claim
10 words
The derivative of claim 11, which has the structure ##STR66##
Claim 23
Dependent Claim
23 words
The derivative of claim 5 or 14, wherein R 11 and R 12 are --CH 3 groups and wherein the polysaccharide is starch.
Claim 24
Dependent Claim
17 words
The derivative of claim 6 or 15, wherein R 13 is ##STR67## and the polysaccharide is starch.
Claim 25
Dependent Claim
32 words
The derivative of claim 7 or 16, wherein R 14 and R 15 are H or wherein R 14 is --CH 3 and R 15 is H and the polysaccharde is starch.
Claim 26
Dependent Claim
19 words
The derivative of claim 8 or 17, wherein R 16 is --CH 2 -- and the polysaccharide is starch.
Claim 27
Dependent Claim
19 words
The derivative of claim 9 or 18, wherein R 17 is --CH 2 -- and the polysaccharide is starch.
Claim 28
Dependent Claim
19 words
The derivative of claim 10 or 19, wherein R 18 is --CH 2 -- and the polysaccharide is starch.
Claim 29
Dependent Claim
18 words
The derivative of claim 2 or 11 wherein the polysaccharide is a starch, a gum, or a cellulose.
Claim 30
Dependent Claim
11 words
The derivative of claim 26, wherein the polysaccharide is the starch.
Claim 31
Dependent Claim
23 words
The derivative of claim 27, wherein the starch is a waxy maize, corn, high amylose corn, potato, rice, sweet potato, or tapioca starch.
Claim 32
Dependent Claim
11 words
The derivative of claim 28, wherein the starch is corn starch.
Claim 33
Dependent Claim
18 words
The derivative of claim 28, wherein the starch contains one or more cationic, anionic, nonionic or zwitterionic groups.
Claim 34
Dependent Claim
12 words
The derivative of claim 29, wherein the starch contains diethylaminoethyl ether groups.
Claim 35
Dependent Claim
11 words
The derivative of claim 26, wherein the polysaccharide is a gum.
Claim 36
Dependent Claim
11 words
The derivative of claim 32, wherein the gum is guar gum.
Claim 37
Dependent Claim
14 words
The derivative of claim 26, wherein the polysaccharide is cellulose or a cellulose derivative.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1990-10-26 | 1991-04-27 | 1991-10-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-10-26 | 1995-04-27 | 1995-10-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-10-26 | 1999-04-27 | 1999-10-27 | $7700.00 | Window Closed / Lapsed |