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US4788280A
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Polysaccharide derivatives containing aldehyde groups on an aromatic ring, their preparation from the corresponding acetals and use in paper
Assignee: Syracuse University
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Filing: 1987-09-08
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Granted: 1988-11-29
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Expires: 2007-09-08
Abstract
Abstract Polysaccharide aldehydes having the formula ##STR1## or Sacch--O--CH 2 --Ar--CHO (II) such as starch, cellulose, and gum aldehydes, are useful as paper additives for imparting strength and as the granular or gelatinized portion of a corrugating adhesive. Those having formula I are prepared by a nonoxidative 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 formula Ar is an aryl group, optionally containing an ether linkage, or an alkaryl group and A and A' are lower alkyls or together form at least a 5-membered cyclic acetal. The polysaccharide aldehydes are crosslinked by the addition of selected polyfunctional crosslinkers such as an aliphatic primary polyamine or polyketone.
Inventors
- 👤 Robert L. Billmers
- 👤 Martin M. Tessler
- 👤 David M. Del Giudice
- 👤 Craig Leake
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:23
CPC Classifications
D; D21; D21H; D21H17/00; D21H17/20; D21H17/21; D21H17/24; C; C08; C08B; C08B11/00; C08B11/02; C08B11/04; C08B31/00; C08B31/08; C08B31/12; C08B37/00; C08B37/006; C08B37/0087; D21H21/00; D21H21/14; D21H21/18
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
46 words
An aldehyde-containing polysaccharide derivative having the formula ##STR53## or Sacch-O--CH 2 --Ar--CHO (II), wherein Sacch-O-- represents a polysaccharide molecule and Ar in formula I is a divalent aryl group or an alkaryl group and Ar in formula II is a conjugated heterocyclic aryl or alkaryl group.
Claim 2
Dependent Claim
46 words
An aldehyde-containing polysaccharide derivative having the formula ##STR53## or Sacch-O--CH 2 --Ar--CHO (II), wherein Sacch-O-- represents a polysaccharide molecule and Ar in formula I is a divalent aryl group or an alkaryl group and Ar in formula II is a conjugated heterocyclic aryl or alkaryl group.
Claim 3
Dependent Claim
23 words
An aldehyde-containing polysaccharide having the formula ##STR54## where Ar has the structure ##STR55## or Sacch-O--CH 2 --Ar--CHO where Ar has the structure ##STR56##
Claim 4
Dependent Claim
23 words
An aldehyde-containing polysaccharide having the formula ##STR54## where Ar has the structure ##STR55## or Sacch-O--CH 2 --Ar--CHO where Ar has the structure ##STR56##
Claim 5
Dependent Claim
52 words
An acetal-containing polysaccharide derivative which has the structure ##STR57## wherein Sacch-O-- represents a polysaccharide molecule; Ar is a divalent aryl group which can contain an ether linkage or an alkaryl group; and A and A' are independently an alkyl group or A and A' together form at least a five-membered cyclic acetal.
Claim 6
Dependent Claim
52 words
An acetal-containing polysaccharide derivative which has the structure ##STR57## wherein Sacch-O-- represents a polysaccharide molecule; Ar is a divalent aryl group which can contain an ether linkage or an alkaryl group; and A and A' are independently an alkyl group or A and A' together form at least a five-membered cyclic acetal.
Claim 7
Dependent Claim
19 words
The derivative of claim 3, wherein Ar has the structure ##STR58## and A and A' are CH 3 .
Claim 8
Dependent Claim
18 words
The derivative of claim 1 or 3, wherein the polysaccharide is a starch in granular or dispersed form.
Claim 9
Dependent Claim
23 words
The derivative of claim 5, wherein the starch is a waxy maize, corn, high amylose corn, potato, rice, sweet potato, or tapioca starch.
Claim 10
Dependent Claim
11 words
The derivative of claim 6, wherein the starch is waxy maize.
Claim 11
Dependent Claim
18 words
The derivative of claim 7, wherein the starch contains one or more cationic, anionic, nonionic or zwitterionic groups.
Claim 12
Dependent Claim
11 words
The derivative of claim 8, wherein the starch contains cationic groups.
Claim 13
Dependent Claim
13 words
The derivative of claim 9, wherein the cationic groups are diethylaminoethyl ether groups.
Claim 14
Dependent Claim
13 words
The derivative of claim 1 or 3, wherein the polysaccharide is a gum.
Claim 15
Dependent Claim
11 words
The derivative of claim 11, wherein the gum is guar gum.
Claim 16
Dependent Claim
16 words
The derivative of claim 1 or 3, wherein the polysaccharide is a cellulose or cellulose derivative.
Claim 17
Dependent Claim
28 words
A crosslinked product having the structure ##STR59## wherein Sacch-O-- represents a polysaccharide molecule, P represents a divalent group, and Ar represents a divalent aryl group or alkaryl group.
Claim 18
Dependent Claim
28 words
A crosslinked product having the structure ##STR59## wherein Sacch-O-- represents a polysaccharide molecule, P represents a divalent group, and Ar represents a divalent aryl group or alkaryl group.
Claim 19
Dependent Claim
43 words
The crosslinked product of claim 14, wherein the polysaccharide is a starch; Ar is ##STR60## with R being a substituent on the aromatic ring; and P is --CH 2 --CH 2 --(NH--CH 2 --CH 2 ) x with x being 0 or greater.
Claim 20
Dependent Claim
63 words
The crosslinked product of claim 14, prepared by dispersing an aldehyde-containing polysaccharide derivative having the formula ##STR61## or Sacch-O--CH 2 --Ar--CHO in water and reacting the dispersed polysaccharide with an effective amount of a multifunctional crosslinker selected from the group consisting of an aliphatic polyamine containing at least two primary amine groups, a polyhydrazine, a polyhydrazide, a polysemicarbazide, a polythiol, and a polyketone.
Claim 21
Dependent Claim
18 words
The crosslinked product of claim 16, wherein the reaction is carried out at a pH below about 13.
Claim 22
Dependent Claim
25 words
The crosslinked product of claim 17, wherein the crosslinker is the polyamine or the polyhydrazide and the pH is about 2.5 to below about 13.
Claim 23
Dependent Claim
28 words
The crosslinked product of claim 18, wherein the polyamine is diethylene triamine or a polyethyleneimine having a molecular weight of about 12,000-100,000, and the polyhydrazide is adipic dihydrazide.
Claim 24
Dependent Claim
47 words
The crosslinked product of claim 14, prepared by dispersing an aldehyde-containing polysaccharide derivative having the formula ##STR62## or Sacch-O--CH 2 --Ar--CHO in water and reacting the dispersed polysaccharide with an effective amount of a cyclic or noncyclic polyketone as a crosslinker at a pH of above 11.
Claim 25
Dependent Claim
47 words
The crosslinked product of claim 14, prepared by dispersing an acetal-containing polysaccharide derivative having the formula ##STR63## in water and reacting the dispersed polysaccharide with an effective amount of an aliphatic polyamine as a crosslinker containing at least two primary amine groups at a pH about 9.
Claim 26
Dependent Claim
19 words
The crosslinked product of claim 21, wherein the crosslinker is a polyethylenimine and the pH is above about 2.
Claim 27
Dependent Claim
50 words
In a method for making paper having dry strength, wet strength, temporary wet strength, or combinations thereof, the step which comprises adding, as a strength aid, to the stock at any stage prior to forming a web, an effective amount of the aldehyde-containing polysaccharide derivative of claim 1 or 3.
Claim 28
Dependent Claim
9 words
The paper containing the strength aid of claim 23.
Claim 29
Dependent Claim
76 words
An improved water-resistant, alkaline-curing corrugating adhesive composition comprising an ungelatinized starch, a gelatinized starch, an alkali, and water, wherein the improvement comprised the presence of the aldehyde-containing starch derivative of claim 5 as at least a part of the ungelatinized starch in combination with an effective amount of a multifunctional crosslinker selected from the group consisting of an aliphatic primary polyamine a cyclic or noncyclic, a polyketone, a polyhydrazine, a polyhydrazide, a polysemicarbazides and a polythiol.
Claim 30
Dependent Claim
41 words
An improved water-resistant, alkaline-curing corrugating adhesive composition comprising an ungelatinized starch, a gelatinized starch, an alkali, and water, wherein the improvement comprises the presence of the aldehyde-containing starch derivative of claim 5 as at least a part of the gelatinized starch.
Claim 31
Dependent Claim
96 words
An improved water-resistant, alkaline-curing corrugating adhesive composition comprising an ungelatinized starch, a gelatinized starch, an alkali, and water, wherein the improvement comprises the presence of the aldehyde-containing starch derivative of claim 5 as at least a part of the ungelatinized starch in combination with an effective amount of a multifunctional crosslinker selected from the group consisting of an aliphatic primary polyamine a cyclic or noncyclic, a polyketone, a polyhydrazine, a polyhydrazide, a polysemicarbazides and a polythiol and the presence of the aldehyde-containing starch derivative of claim 5 as at least a part of the gelatinized starch.
Claim 32
Dependent Claim
43 words
The improved water-resistant, alkaline-curing corrugating adhesive or claim 25, 26, or 27 wherein the aldehyde-containing starch is the entire part of the ungelatinized starch, or the entire part of the gelatinized starch, or entire part of both the ungelatinized starch and gelatinized starch.
Claim 33
Dependent Claim
11 words
The crosslinked product of claim 20, wherein the polyketone is 2,5-hexanedione.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-11-29 | 1992-05-30 | 1992-11-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-29 | 1996-05-30 | 1996-11-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-29 | 2000-05-30 | 2000-11-29 | $7700.00 | Window Closed / Lapsed |