US4387221A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alkyl- and alkenyl-sulfosuccinate starchhalf-esters, a method for the preparation thereof
Assignee: Ingredion Inc
•
Filing: 1982-04-01
•
Granted: 1983-06-07
•
Expires: 2002-04-01
Abstract
Abstract Novel C 1 -C 22 alkyl- and C 3 -C 22 alkenyl-sulfosuccinate starch half-esters are prepared by reacting a starch base or a modified starch base containing anionic, cationic, and/or nonionic substituent groups with about 0.1 to 100% by weight of the corresponding alkyl- or alkenyl-sulfosuccinic anhydride. The reaction is carried out at pH 5-9 and at 5°-90° C. for 0.5-20 hours or at pH 9-11 at 5°-30° C. for about 0.5-3 hours. This one-step method may also be used to prepare sulfosuccinate half-esters. The long chain derivatives (e.g. octyl-, octadecyl-, octenyl-, and dodecenyl-sulfosuccinate half-esters) are hydrophobic.
Inventors
- 👤 Martin M. Tessler
- 👤 Otto B. Wurzburg
- 👤 Teresa A. Dirscherl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 11:54
CPC Classifications
C; C08; C08B; C08B31/00; C08B31/02; C08B31/04; D; D21; D21H; D21H17/00; D21H17/20; D21H17/21; D21H17/24; D21H17/28; D21H17/29
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
79 words
A starch derivative, comprising a starch ester of the general structure: ##STR4## or mixtures of (i) and (ii); wherein St--O-- represents a starch molecule or modified starch molecule; R is a C 1 -C 22 straight or branched chain alkyl group or mixtures thereof, a C 3 -C 22 straight or branched chain alkenyl group or mixtures thereof, or a mixture of said alkyl and alkenyl groups; M is a cation; and n is the valence number of M.
Claim 2
Dependent Claim
79 words
A starch derivative, comprising a starch ester of the general structure: ##STR4## or mixtures of (i) and (ii); wherein St--O-- represents a starch molecule or modified starch molecule; R is a C 1 -C 22 straight or branched chain alkyl group or mixtures thereof, a C 3 -C 22 straight or branched chain alkenyl group or mixtures thereof, or a mixture of said alkyl and alkenyl groups; M is a cation; and n is the valence number of M.
Claim 3
Dependent Claim
22 words
The derivative of claim 1, wherein M is hydrogen, ammonium, an alkali or an alkaline earth metal, or a protonated tertiary amine.
Claim 4
Dependent Claim
14 words
The derivative of claim 2, wherein M is sodium, potassium, calcium, or protonated triethylamine.
Claim 5
Dependent Claim
17 words
The derivative of claim 1, wherein said modified starch molecule contains cationic, anionic, or nonionic substituent groups.
Claim 6
Dependent Claim
33 words
The derivative of claim 4, where said cationic groups are diethylaminoethyl ether groups or 3-(trimethylammonium chloride)-2-hydroxypropyl ether groups; said anionic groups are 2-sulfo-2-carboxyethyl ether groups; and said nonionic groups are hydroxypropyl ether groups.
Claim 7
Dependent Claim
74 words
The derivative of claim 1, wherein said straight chain alkenyl group has the formula --CH 2 --CH═CH(--CH 2 ) n --CH 3 , where n is 0-18, and said branched alkenyl group has the formula --CH(--CH 2 --R 1 )--CH═CH--R 2 or --CH 2 --C(═CH--R 2 )--CH 2 --R 1 , where R 1 and R 2 are hydrogen or one or more alkyl groups containing a total of up to 18 carbon atoms.
Claim 8
Dependent Claim
29 words
The derivative of claim 6, where said alkyl groups are octyl or octadecyl groups and said alkenyl groups are octenyl, dodecenyl, or C 15 -C 20 mixed, branched alkenyl.
Claim 9
Dependent Claim
92 words
A starch derivative, which comprises a starch ester or mixture of starch esters prepared by reacting a starch base or modified starch base with about 0.1 to 100% by weight, based on dry starch, of a sulfonated alkyl- or alkenyl-succinic anhydride reagent and isolating the resulting starch ester(s), said sulfonated anhydride reagent being prepared by reacting a C 1 -C 22 straight or branched chain alkyl succinic anhydride, or a C 3 -C 22 straight or branched chain alkenyl succinic anhydride, or mixtures thereof with liquid sulfur trioxide in an organic solvent.
Claim 10
Dependent Claim
92 words
A starch derivative, which comprises a starch ester or mixture of starch esters prepared by reacting a starch base or modified starch base with about 0.1 to 100% by weight, based on dry starch, of a sulfonated alkyl- or alkenyl-succinic anhydride reagent and isolating the resulting starch ester(s), said sulfonated anhydride reagent being prepared by reacting a C 1 -C 22 straight or branched chain alkyl succinic anhydride, or a C 3 -C 22 straight or branched chain alkenyl succinic anhydride, or mixtures thereof with liquid sulfur trioxide in an organic solvent.
Claim 11
Independent Claim
138 words
A method for preparing a starch ester derivative of the general structure: ##STR5## or mixtures of (i) and (ii); wherein St--O-- represents a starch molecule or a modified starch molecule; R' is hydrogen, a C 1 -C 22 straight or branched chain alkyl group or mixtures thereof, a C 3 -C 22 straight or branched chain alkenyl group or mixtures thereof, or a mixture of said alkyl and alkenyl groups; M is a cation; and n is the valence of number of M, which comprises the steps of: (a) reacting a starch base or modified starch base with about 0.1 to 100% by weight, based on dry starch, of an anhydride reagent having the general formula ##STR6## where M' is hydrogen or a tertiary amine and R' is as defined above; and (b) isolating the resulting starch ester.
Claim 12
Independent Claim
138 words
A method for preparing a starch ester derivative of the general structure: ##STR5## or mixtures of (i) and (ii); wherein St--O-- represents a starch molecule or a modified starch molecule; R' is hydrogen, a C 1 -C 22 straight or branched chain alkyl group or mixtures thereof, a C 3 -C 22 straight or branched chain alkenyl group or mixtures thereof, or a mixture of said alkyl and alkenyl groups; M is a cation; and n is the valence of number of M, which comprises the steps of: (a) reacting a starch base or modified starch base with about 0.1 to 100% by weight, based on dry starch, of an anhydride reagent having the general formula ##STR6## where M' is hydrogen or a tertiary amine and R' is as defined above; and (b) isolating the resulting starch ester.
Claim 13
Dependent Claim
51 words
The method of claim 9, wherein said reaction is carried out in an aqueous medium at a pH of about 5-9 and at a temperature of about 5°-90° C. for 0.5-20 hours or at a pH of about 9-11 and at a temperature of about 5°-30° C. for about 0.5-3 hours.
Claim 14
Dependent Claim
29 words
The method of claim 9, wherein said reaction is carried out at about pH 6-9 and about 20°-45° C. for about 1-6 hours with about 1-20% of said anhydride.
Claim 15
Dependent Claim
24 words
The method of claim 9, wherein said modified starch base is prepared by reacting a starch base with a cationic, anionic, or nonionic reagent.
Claim 16
Dependent Claim
30 words
The method of claim 12, wherein said cationic reagent is 2-diethylaminoethyl chloride hydrochloride or 3-chloro-2-hydroxypropyl trimethylammonium chloride; said anionic reagent is 3-chloro-2-sulfopropionic acid; and said nonionic reagent is propylene oxide.
References Cited (Backward Citations)
US2884412A
Cited
US2825727A
Cited
US2961440A
Cited
US2891947A
Cited
US2989520A
Cited
US3077469A
Cited
US3459632A
Cited
US3706771A
Cited
US3910880A
Cited
US3987043A
Cited
US3756966A
Cited
US3791838A
Cited
US3904601A
Cited
US4029544A
Cited
US4139699A
Cited
US4061610A
Cited
US4239592A
Cited
US4119487A
Cited
US4243479A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-06-06 | 1986-12-06 | 1987-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-06-06 | 1990-12-06 | 1991-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-06-06 | 1994-12-06 | 1995-06-07 | $7700.00 | Window Closed / Lapsed |