US4020272A
Expired / Lapsed
US
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Preparation of starch esters
Assignee: Ingredion Inc
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Filing: 1975-12-22
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Granted: 1977-04-26
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Expires: 1995-12-22
Abstract
Abstract Aqueous slurries or dispersions of starch are reacted with N,N'-disubstituted imidazolium salts under controlled conditions to yield starch esters. The starch ester derivatives can also be prepared by a reaction in non-aqueous solvents.
Inventors
- 👤 Martin M. Tessler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 03:54
CPC Classifications
C; C08; C08B; C08B31/00; C08B31/02
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
197 words
A process for preparing esters of a starch having free reactive hydroxyl groups comprising the steps of: a. reacting said starch with a N,N'-disubstituted imidazolium salt selected from the group consisting of ##STR3## wherein R is selected from the group consisting of lower alkyl (C 1 -C 4 ) and lower alkenyl (C 2 -C 4 ); R 1 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, cycloalkyl, aryl, substituted aryl, and arylalkyl; R 2 is selected from the group consisting of alkylene, substituted alkylene, bisalkylene ether, cycloalkylene, arylene and substituted arylene; and R 3 is selected from the group consisting of lower alkyl or H; R 1 and R 2 may each contain between 1 and 20 carbons; and X is Br - or Cl -; wherein the reaction with the starch is conducted in an aqueous medium at a pH level of from about 5.0 to 12.5 at temperatures of from 5° to 55° C. for a period of from about 10 minutes to 20 hours, employing the N,N'-disubstituted imidazolium salt in an amount of 0.10 to 100 percent on the weight of dry starch; and b. isolating the resultant starch derivative.
Claim 2
Dependent Claim
197 words
A process for preparing esters of a starch having free reactive hydroxyl groups comprising the steps of: a. reacting said starch with a N,N'-disubstituted imidazolium salt selected from the group consisting of ##STR3## wherein R is selected from the group consisting of lower alkyl (C 1 -C 4 ) and lower alkenyl (C 2 -C 4 ); R 1 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, cycloalkyl, aryl, substituted aryl, and arylalkyl; R 2 is selected from the group consisting of alkylene, substituted alkylene, bisalkylene ether, cycloalkylene, arylene and substituted arylene; and R 3 is selected from the group consisting of lower alkyl or H; R 1 and R 2 may each contain between 1 and 20 carbons; and X is Br - or Cl -; wherein the reaction with the starch is conducted in an aqueous medium at a pH level of from about 5.0 to 12.5 at temperatures of from 5° to 55° C. for a period of from about 10 minutes to 20 hours, employing the N,N'-disubstituted imidazolium salt in an amount of 0.10 to 100 percent on the weight of dry starch; and b. isolating the resultant starch derivative.
Claim 3
Dependent Claim
22 words
A process according to claim 1 wherein said starch is selected from the group consisting of corn, waxy maize, and potato starch.
Claim 4
Dependent Claim
37 words
A process according to claim 1 wherein the amount of N,N'-disubstituted imidazolium salt is from 5 to 30 percent on the weight of the dry starch and the pH level is maintained at from 7 to 9.
Claim 5
Dependent Claim
29 words
A process according to claim 1 wherein said N,N'-disubstituted imidazolium salt is selected from the group consisting of N-(p-toluenesulfonyl)-N'-methylimidazolium chloride, N-benzoyl-N'-methylimidazolium chloride, N-oleoyl-N'-methylimidazolium chloride, N-stearoyl-N'-methylimidazolium chloride, and N-palmitoyl-N'-methylimidazolium chloride.
Claim 6
Dependent Claim
186 words
A process for preparing esters of a starch having free reactive hydroxy groups comprising the steps of: a. reacting said starch with a N,N'-disubstituted imidazolium salt selected from the group consisting of ##STR4## wherein R is selected from the group consisting of lower alkyl (C 1 -C 4 ) and lower alkenyl (C 2 -C 4 ); R 1 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, cycloalkyl, aryl, substituted aryl, and arylalkyl; R 2 is selected from the group consisting of alkylene, substituted alkylene, bisalkylene ether, cycloalkylene, arylene and substituted arylene; and R 3 is selected from the group consisting of lower alkyl or H; R 1 and R 2 may each contain between 1 and 20 carbons; and X is Br - or Cl -; wherein the reaction is carried out in a non-aqueous liquid medium, at temperatures of from 20° to 150° C. for a period of from about 1 to 12 hours, employing the N,N'-disubstituted imidazolium salt in an amount of from 0.10 to 100 percent on the weight of dry starch; and b. isolating the resultant starch derivative.
Claim 7
Dependent Claim
186 words
A process for preparing esters of a starch having free reactive hydroxy groups comprising the steps of: a. reacting said starch with a N,N'-disubstituted imidazolium salt selected from the group consisting of ##STR4## wherein R is selected from the group consisting of lower alkyl (C 1 -C 4 ) and lower alkenyl (C 2 -C 4 ); R 1 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, cycloalkyl, aryl, substituted aryl, and arylalkyl; R 2 is selected from the group consisting of alkylene, substituted alkylene, bisalkylene ether, cycloalkylene, arylene and substituted arylene; and R 3 is selected from the group consisting of lower alkyl or H; R 1 and R 2 may each contain between 1 and 20 carbons; and X is Br - or Cl -; wherein the reaction is carried out in a non-aqueous liquid medium, at temperatures of from 20° to 150° C. for a period of from about 1 to 12 hours, employing the N,N'-disubstituted imidazolium salt in an amount of from 0.10 to 100 percent on the weight of dry starch; and b. isolating the resultant starch derivative.
Claim 8
Dependent Claim
22 words
A process according to claim 5 wherein said starch is selected from the group consisting of corn, waxy maize, and potato starch.
Claim 9
Dependent Claim
29 words
A process according to claim 5 wherein said N,N'-disubstituted imidazolium salt is selected from the group consisting of N-(p-toluenesulfonyl)-N'-methylimidazolium chloride, N-benzoyl-N'-methylimidazolium chloride, N-oleolyl-N'-methylimidazolium chloride, N-stearoyl-N'-methylimidazolium chloride, and N-palmitoyl-N'-methylimidazolium chloride.
References Cited (Backward Citations)
US3720663A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-25 | 1980-10-25 | 1981-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-25 | 1984-10-25 | 1985-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-25 | 1988-10-25 | 1989-04-26 | $7700.00 | Window Closed / Lapsed |