US3931148A
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Hydroxyalkylamino glycosides and process of preparation
Assignee: BASF Corp
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Filing: 1974-12-23
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Granted: 1976-01-06
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Expires: 1994-12-23
Abstract
Abstract Glycosides are prepared by reacting a monosaccharide or a compound hydrolyzable to a monosaccharide with 3-chloro-1,2-propanediol in the presence of an acid catalyst producing a 2-hydroxy-3-chloropropyl glycoside. The glycoside is then reacted with a base and an amine having at least one alkyl group that contains 8 to 30 carbon atoms to produce an alkali soluble surfactant.
Inventors
- 👤 William K. Langdon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 01:05
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; C08; C08B; C08B11/00; C08B11/02; C08B11/04; C08B11/14; C08B11/145; C08B31/00; C08B31/08; C08B31/12; C08B31/125; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/02; Y10S516/07
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
106 words
A compound having the formula ##EQU5## wherein M is selected from the group consisting of ##EQU6## wherein R is selected from the group consisting of hydrogen or hydrocarbon ranging from CH 3 -C 18 H 37 , R' is selected from the group consisting of hydrocarbon ranging from C 8 H 17 to C 18 H 37 , R" is selected from the group consisting of benzyl or hydrocarbon ranging from CH 3 to C 18 H 37 , the moieties C 6 H 11 O 5 and C 6 H 10 O 5 represent glycosyl units and m is a number from 0 to 20.
Claim 2
Dependent Claim
106 words
A compound having the formula ##EQU5## wherein M is selected from the group consisting of ##EQU6## wherein R is selected from the group consisting of hydrogen or hydrocarbon ranging from CH 3 -C 18 H 37 , R' is selected from the group consisting of hydrocarbon ranging from C 8 H 17 to C 18 H 37 , R" is selected from the group consisting of benzyl or hydrocarbon ranging from CH 3 to C 18 H 37 , the moieties C 6 H 11 O 5 and C 6 H 10 O 5 represent glycosyl units and m is a number from 0 to 20.
Claim 3
Dependent Claim
28 words
The compound of claim 1 wherein R' is selected from the group consisting of hydrocarbon radicals ranging from C 10 H 21 to C 18 H 37 .
Claim 4
Dependent Claim
27 words
The compound of claim 1 wherein the moieties (C 6 H 11 O 5 ) and (C 6 H 10 O 5 ) are derived from dextrose.
Claim 5
Dependent Claim
27 words
The compound of claim 1 wherein the moieties (C 6 H 11 O 5 ) and (C 6 H 10 O 5 ) are derived from starch.
Claim 6
Dependent Claim
116 words
A process for the preparation of 2-hydroxy-3 alkylaminopropyl glycoside which comprises reacting glucose or a polysaccharide that is hydrolyzable to glucose with from about 0.5 mole to about 1.2 mole of 3-chloro-1,2-propanediol per mole of anhydroglucose unit based on said glucose or said polysaccharide in the presence of an acid catalyst, followed by a reaction with a quantity of an alkali metal hydroxide or an alkaline earth metal hydroxide sufficient to react with the hydrochloric acid formed in the reaction and a quantity of amine selected from the group consisting of primary, secondary, tertiary, saturated, unsaturated, alicyclic, arylalkyl and aryl amines containing from about 8 to about 30 carbon atoms equivalent to the amount of 3-chloro-1,2-propanediol.
Claim 7
Dependent Claim
116 words
A process for the preparation of 2-hydroxy-3 alkylaminopropyl glycoside which comprises reacting glucose or a polysaccharide that is hydrolyzable to glucose with from about 0.5 mole to about 1.2 mole of 3-chloro-1,2-propanediol per mole of anhydroglucose unit based on said glucose or said polysaccharide in the presence of an acid catalyst, followed by a reaction with a quantity of an alkali metal hydroxide or an alkaline earth metal hydroxide sufficient to react with the hydrochloric acid formed in the reaction and a quantity of amine selected from the group consisting of primary, secondary, tertiary, saturated, unsaturated, alicyclic, arylalkyl and aryl amines containing from about 8 to about 30 carbon atoms equivalent to the amount of 3-chloro-1,2-propanediol.
Claim 8
Dependent Claim
12 words
The process of claim 5 wherein the acid catalyst is sulfuric acid.
Claim 9
Dependent Claim
13 words
The process of claim 5 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 10
Dependent Claim
20 words
The process of claim 5 wherein the reaction with said metal hydroxides occurs prior to the reaction with the amine.
Claim 11
Dependent Claim
20 words
The process of claim 5 wherein the reaction with the amine occurs prior to the reaction with said metal hydroxides.
Claim 12
Dependent Claim
17 words
The process of claim 5 wherein the reaction with said metal hydroxides and the amine occurs simultaneously.
Claim 13
Dependent Claim
29 words
The process of claim 5 wherein the concentration of the acid catalyst is from about 0.01 to about 1.0 weight percent based upon the total weight of the reactants.
Claim 14
Dependent Claim
27 words
The process of claim 5 wherein R' is selected from the group consisting of hydrocarbon ranging from C 10 H 21 to C 18 H 37 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-05 | 1979-07-07 | 1980-01-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-05 | 1983-07-07 | 1984-01-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-05 | 1987-07-07 | 1988-01-06 | $7700.00 | Window Closed / Lapsed |