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Patent US5049634A successfully refreshed from Google Patents.
US5049634A
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Derivatized and/or crosslinked products from acetal- and aldehyde-containing polysaccharide graft polymers
Assignee: Ingredion Inc
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Filing: 1989-09-22
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Granted: 1991-09-17
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Expires: 2009-09-22
Abstract
Abstract A derivatized graft polymer of a polysaccharide, a crosslinked graft polymer of a polysaccharide, and a derivatized and crosslinked graft polymer of a polysaccharide are prepared. The derivatized polymer has the structure Sacch-g-[(M--CH═N--Y) x -g-[(M) q ]; the crosslinked polymer has the structure Sacch-g-[(M--CH═N) z -P] w -g-[(M) q ] or Sacch-g-[(M--CH═C) z -P] w -g-[(M) q ]; the derivatized and crosslinked polymer has the structure Sacch-g-[(M--CH═N--Y) x ]-g-[(M--CH═N)-P]-g-[(M) q ] or Sacch-g-[(M--CH═N--Y) x ]-g-[(M--CH═C) z -P] w -g-[(M) q ]. Sacch represents a polysaccharide such as starch, gum, or cellulose; g-represents a graft; M represents one or more ethylenically or allylically unsaturated monomers, at least one of which contains an acetal or aldehyde; P represents a multivalen residue from a reagent containing more than one primary amine group or ketone group; --N═ represents the group formed when one primary amine group of P reacts with the acetal or aldehyde group of the monomer repecting unit M; 13 CH═ represents the group formed when one of the ketone groups of P reacts with the acetal or aldehyde group of the monomer repeating unit M; x is at least 1; z is at least 2; w is at least 1; and q is 0 or greater.
Inventors
- 👤 John J. Tsai
- 👤 Patrick G. Jobe
- 👤 Robert L. Billmers
- 👤 Rama S. Chandran
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:00
CPC Classifications
C; C08; C08F; C08F251/00; C08F251/02
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
149 words
A derivatized graft polymer of a polysaccharide having the structure Sacch-g-[(M--CH═N--Y) x ]-g-[(M) q ], where Sacch represents a polysaccharide; g represents a graft; M represents a repeating unit derived from one or more ethylenically or allylically unsaturated monomers, at least one of which contains an aldehyde or acetal group; Y represents (a) a monovalent group derived from a water-soluble substituted or unsubstituted aromatic compound containing only one primary amine group, or (b) a monovalent group derived from a water-soluble substituted or unsubstituted aliphatic or cycloaliphatic compound containing only one primary amine group, or (c) a multivalent group derived from a water-soluble protein containing more than one primary amine group; --CH═N--Y is the group formed by the reaction of the aldehyde or acetal group of the monomer repeating unit M with the free primary amine group of Y; x is at least 1; and q is 0 or greater.
Claim 2
Dependent Claim
149 words
A derivatized graft polymer of a polysaccharide having the structure Sacch-g-[(M--CH═N--Y) x ]-g-[(M) q ], where Sacch represents a polysaccharide; g represents a graft; M represents a repeating unit derived from one or more ethylenically or allylically unsaturated monomers, at least one of which contains an aldehyde or acetal group; Y represents (a) a monovalent group derived from a water-soluble substituted or unsubstituted aromatic compound containing only one primary amine group, or (b) a monovalent group derived from a water-soluble substituted or unsubstituted aliphatic or cycloaliphatic compound containing only one primary amine group, or (c) a multivalent group derived from a water-soluble protein containing more than one primary amine group; --CH═N--Y is the group formed by the reaction of the aldehyde or acetal group of the monomer repeating unit M with the free primary amine group of Y; x is at least 1; and q is 0 or greater.
Claim 3
Dependent Claim
16 words
The polymer of claim 1, wherein the polysaccharide is a starch, a gum, or a cellulose.
Claim 4
Dependent Claim
52 words
The polymer of claim 1, wherein the polysaccharide is a starch; wherein at least one of the monomer repeating units M is from an aromatic acetal- or aldehyde-containing monomer and wherein, after reaction of the acetal or aldehyde group with the amine group of Y, the (M--CH═N--Y) group has the structure: ##STR37##
Claim 5
Dependent Claim
52 words
The polymer of claim 1, wherein the polysaccharide is a starch; wherein at least one of the monomer repeating units M is from an aromatic acetal- or aldehyde-containing monomer and wherein, after reaction of the acetal or aldehyde group with the amine group of Y, the (M--CH═N--Y) group has the structure: ##STR38##
Claim 6
Dependent Claim
52 words
The polymer of claim 1 wherein the polysaccharide is a starch; wherein at least one of the monomer repeating units M is from an aliphatic acetal- or aldehyde-containing monomer and wherein, after reaction of the acetal or aldehyde group with the amine group of Y, the (M--CH═N--Y) group has the structure: ##STR39##
Claim 7
Dependent Claim
56 words
The graft polymer of claim 1, wherein the polysaccharide is a starch and wherein Y is derived from 3-aminopropyltriethoxysilane and has the structure --CH 2 --CH 2 --CH 2 --Si(OC 2 H 5 ) 3 or derived from polyethyleneglycol monoamine and has the structure ##STR40## where R is H and CH 3 in a 2:3 ratio.
Claim 8
Dependent Claim
44 words
The polymer of claim 1 which is prepared by reacting a derivatizing reagent Y--NH 2 containing only one primary amine group with a polysaccharide graft polymer having the structure Sacch-g-(M) x , where Sacch, M, Y, and x are as defined in claim 1.
Claim 9
Dependent Claim
141 words
The polymer of claim 7, wherein, the polysaccharide is a starch and wherein one of the repeating units M is derived from an acetal-containing monomer selected from the group consisting of 2[2-(1,3-dioxolan-2-yl)ethoxy] ethyl methacrylate; 2[2-(1,3-dioxolan-2-yl)-1-methylethoxy]ethyl methacrylate; N-methyl, N-(2,2-dimethoxy)ethyl, N,N-diallylammonium bromide; 2-(5,5-dimethyl-1,3-dioxan-2-yl)ethoxyethyl acrylate; 2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl acrylate; N-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl acrylamide; 1-(5,5-dimethyl-1,3-dioxan-2-yl)-2-propyl acrylate; 3-N-methyl, N-2,2-dimethoxyethyl)amino-2-hydroxypropyl methacrylate; N,N-dimethyl, N-[3-(2-dioxolan-2-yl)ethoxyethoxy-2-hydroxypropyl methacrylamidopropylammonium chloride; 5-(N,N-di[propyl-1-en-]aminomethyl)-2-dimethoxymethyl furan; phenyl (4-dimethoxymethyl) acrylate; phenyl (4-dimethoxymethyl) acrylate; 2-(2-dimethoxymethyl phenoxy)ethyl acrylate; 2-[2- 2-(1,3-dioxalano) phenoxy]ethyl acrylate; 2-hydroxy-3-(4-dimethoxymethyl phenoxy) propyl, 2-methyl propenoate; and 2-hydroxy-3-(2-dimethoxymethyl phenoxy propyl 2-methyl propenoate; or wherein one of the repeating units M is derived from an aldehyde-containing monomer is selected from the group consisting of 5-(dimethoxymethyl)furfur-2-yl]methylacrylate and 5-(N,N-di-[propyl-1-en-3-]-aminomethyl)-2-furan carboxaldehyde; and wherein the derivatizing reagent Y--NH 2 containing at least one primary amine group is selected from the group consisting of polyethyleneglycol monoaime, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, cyclohexylamine, ethanol amine, benzyl amine, isopropyl amine, and amino acids.
Claim 10
Dependent Claim
28 words
The polymer of claim 4, wherein the polysaccharide is a starch selected from the group consisting of corn, waxy maize, high amylose corn, tapioca, rice, and potato starch.
Claim 11
Dependent Claim
28 words
The polymer of claim 5, wherein the polysaccharide is a starch selected from the group consisting of corn, waxy maize, high amylose corn, tapioca, rice, and potato starch.
Claim 12
Dependent Claim
28 words
The polymer of claim 6, wherein the polysaccharide is a starch selected from the group consisting of corn, waxy maize, high amylose corn, tapioca, rice, and potato starch.
Claim 13
Dependent Claim
134 words
A crosslinked graft polymer of a polysaccharide having the structure Sacch-g-[(M--CH═N).sub.z -P].sub.w -g-[(M).sub.q ]or Sacch-g-[(M--CH═C).sub.z -P].sub.w -g-[(M).sub.q ] where Sacch represents a polysaccharide, M represents a repeating unit derived from one more ethylenically or allylically unsaturated monomers, at least one of which contains an acetal group or aldehyde group; P represents a multivalent residue from a reagent containing more than one primary amine group or ketone group; --N═ represents the group formed when one primary amine group of P reacts with the acetal or aldehyde group of the monomer repeating unit M; --CH═ represents the group formed when one of the ketone groups of P reacts with the acetal or aldehyde group of the monomer repeating unit M; z is at least 2; w is at least 1; and q is 0 or greater.
Claim 14
Dependent Claim
134 words
A crosslinked graft polymer of a polysaccharide having the structure Sacch-g-[(M--CH═N).sub.z -P].sub.w -g-[(M).sub.q ]or Sacch-g-[(M--CH═C).sub.z -P].sub.w -g-[(M).sub.q ] where Sacch represents a polysaccharide, M represents a repeating unit derived from one more ethylenically or allylically unsaturated monomers, at least one of which contains an acetal group or aldehyde group; P represents a multivalent residue from a reagent containing more than one primary amine group or ketone group; --N═ represents the group formed when one primary amine group of P reacts with the acetal or aldehyde group of the monomer repeating unit M; --CH═ represents the group formed when one of the ketone groups of P reacts with the acetal or aldehyde group of the monomer repeating unit M; z is at least 2; w is at least 1; and q is 0 or greater.
Claim 15
Dependent Claim
54 words
The polymer of claim 12 which is crosslinked through --CH═N-- linkages and which is prepared by reacting a polysaccharide graft polymer with a crosslinking reagent containing at least two primary amine groups, where the polysaccharide graft polymer has the structure Sacch-g(M) x , where Sacch, M, and x are as defined in claim 12.
Claim 16
Dependent Claim
50 words
The polymer of claim 12 crosslinked through --CH═H-- linkages which is prepared by reacting a polysaccharide graft polymer with a crosslinking reagent containing at least two ketone groups, where the polysaccharide graft polymer has the structure Sacch-g(M) x , where Sacch, M and x are as defined in claim 12.
Claim 17
Dependent Claim
16 words
The polymer of claim 12, wherein the polysaccharide is a starch, a gum, or a cellulose.
Claim 18
Dependent Claim
28 words
The polymer of claim 15, wherein the polysaccharide is a starch selected from the group consisting of corn, waxy maize, high amylose corn, tapioca, rice, and potato starch.
Claim 19
Dependent Claim
215 words
A derivatized and crosslinked graft polymer of a polysaccharide having the structure Sacch-g-[(M--CH═N--Y) x ]-g-[(M--CH═N) z --P] w -g-[(M) q ] or Sacch-g-[(M--CH═N--Y) x ]-g-[(M--CH═C) z --P] w -g-[(M) q ], where Sacch represents a polysaccharide; M represents a repeating unit derived from one more ethylenically or allylically unsaturated monomers, at least one of which contains an acetal group or an aldehyde group; Y represents (a) a monovalent group derived from a water-soluble substituted or unsubstituted aromatic compound containing only one primary amine group, or b) a monovalent group derived from a water-soluble substituted or unsubstituted aliphatic or cycloaliphatic compound containing only one primary amine group, or (c) a multivalent group derived from a water-soluble protein containing more than one primary amine group; P represents a multivalent residue from a reagent containing more than one primary amine group or ketone group; --N═ represents the group formed when one primary amine group of P reacts with the acetal or the aldehyde group of the monomer repeating unit M; --CH═ represents the group formed when one of the ketone groups of P reacts with the acetal or the aldehyde group of the monomer repeating unit M; x is at least 1; z is at least 2; w is at least 1; and q is 0 or greater.
Claim 20
Dependent Claim
215 words
A derivatized and crosslinked graft polymer of a polysaccharide having the structure Sacch-g-[(M--CH═N--Y) x ]-g-[(M--CH═N) z --P] w -g-[(M) q ] or Sacch-g-[(M--CH═N--Y) x ]-g-[(M--CH═C) z --P] w -g-[(M) q ], where Sacch represents a polysaccharide; M represents a repeating unit derived from one more ethylenically or allylically unsaturated monomers, at least one of which contains an acetal group or an aldehyde group; Y represents (a) a monovalent group derived from a water-soluble substituted or unsubstituted aromatic compound containing only one primary amine group, or b) a monovalent group derived from a water-soluble substituted or unsubstituted aliphatic or cycloaliphatic compound containing only one primary amine group, or (c) a multivalent group derived from a water-soluble protein containing more than one primary amine group; P represents a multivalent residue from a reagent containing more than one primary amine group or ketone group; --N═ represents the group formed when one primary amine group of P reacts with the acetal or the aldehyde group of the monomer repeating unit M; --CH═ represents the group formed when one of the ketone groups of P reacts with the acetal or the aldehyde group of the monomer repeating unit M; x is at least 1; z is at least 2; w is at least 1; and q is 0 or greater.
Claim 21
Dependent Claim
48 words
The polymer of claim 17 prepared by reacting a derivatized graft polymer of a polysaccharide with a crosslinking reagent containing more than one primary amine or ketone group or by reacting a crosslinked graft polymer of a polysaccharide with a derivatizing reagent containing only one primary amine group.
Claim 22
Dependent Claim
16 words
The polymer of claim 17, wherein the polysaccharide is a starch, a gum, or a cellulose.
Claim 23
Dependent Claim
28 words
The polymer of claim 18, wherein the polysaccharide is a starch selected from the group consisting of corn, waxy maize, high amylose corn, tapioca, rice, and potato starch.
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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) | 1994-09-16 | 1995-03-18 | 1995-09-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-09-16 | 1999-03-18 | 1999-09-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-09-16 | 2003-03-18 | 2003-09-17 | $7700.00 | Window Closed / Lapsed |