US5539129A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Nonionic amphiphilic compounds derived from glycerol, a process for preparing them, and corresponding intermediate compounds
Assignee: L'Oréal SA
•
Filing: 1994-07-22
•
Granted: 1996-07-23
•
Expires: 2014-07-22
Abstract
Abstract <IMAGE> (I) <IMAGE> (II) Non-ionic amphiphilic, glycerol-derived compounds having formula (I), where R is a radical selected from the group consisting of C4-28 branched or linear alkenyl or alkyl radicals or mixtures thereof, or is a -CH2A grouping in which A is -OR', -SR, (II) where R' is a saturated or unsaturated hydrocarbonated radical and n represents an average statistical value n greater than 1 and equal to or less than 6; and, when R' is a -CH2A radical, n is also 2. These compounds are surface-active agents and some may form vesicles.
Inventors
- 👤 Alexandre Zysman
- 👤 Henri Sebag
- 👤 Alain Ribier
- 👤 Guy Vanlerberghe
- 👤 Claude Mahieu
- 👤 Claude Berthelot
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:57
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/22; A; A61; A61K; A61K8/00; A61K8/02; A61K8/14; A61K8/18; A61K8/30; A61K8/33; A61K8/39; A61Q; A61Q19/00; C07C; C07C323/00; C07C323/10; C07C323/11; C07C323/12; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C07C43/10; C07C43/11; C07C43/13; C07C43/135; C07C43/14; C07C43/178; C07C43/20; C07C43/23; C07C69/00; C07C69/02; C07C69/22; C07C69/33; A61Q1/00; A61Q1/02; A61Q1/04; A61Q1/06; A61Q17/00; A61Q17/04; A61Q19/002; A61Q19/04; A61Q19/08; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10T; Y10T428/00; Y10T428/29; Y10T428/2982; Y10T428/2984
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
88 words
A nonionic amphiphilic compound having the formula ##STR29## wherein R represents a radical selected from the group consisting of (i) a linear or branched C 4 -C 28 alkyl or alkenyl, or a mixture thereof, and (ii) --CH 2 A wherein A represents --OR', --SR' or ##STR30## wherein R' represents a saturated or unsaturated hydrocarbon, and n represents an average statistical value n greater than 1 and equal to not more than 6 and, when R represents --CH 2 A, n also represents a value equal to 2.
Claim 2
Dependent Claim
88 words
A nonionic amphiphilic compound having the formula ##STR29## wherein R represents a radical selected from the group consisting of (i) a linear or branched C 4 -C 28 alkyl or alkenyl, or a mixture thereof, and (ii) --CH 2 A wherein A represents --OR', --SR' or ##STR30## wherein R' represents a saturated or unsaturated hydrocarbon, and n represents an average statistical value n greater than 1 and equal to not more than 6 and, when R represents --CH 2 A, n also represents a value equal to 2.
Claim 3
Dependent Claim
47 words
The compound of claim 1 wherein R' represents a member selected from the group consisting of linear C 8 -C 22 alkyl, branched C 8 -C 36 alkyl, C 18 alkenyl and alkylaryl wherein said alkyl moiety is a linear or branched C 8 -C 16 alkyl.
Claim 4
Dependent Claim
11 words
The compound of claim 2 wherein the aryl moiety is phenyl.
Claim 5
Dependent Claim
14 words
The compound of claim 2 wherein said C 18 alkenyl is 9-octadecenyl or 9,12-octadecanedienyl.
Claim 6
Dependent Claim
62 words
The compound of claim 1 wherein R represents linear C 14 -C 18 alkyl or --CH 2 A wherein A represents OR' wherein R' represents linear C 10 -C 18 alkyl, and n represents an average statistical value n greater than 1 and equal to not more than 3 and, when R represents --CH 2 A, n also is equal to 2.
Claim 7
Dependent Claim
180 words
A process for preparing a compound having a formula ##STR31## wherein R represents a radical selected from the group consisting of (i) a linear or branched C 4 -C 28 alkyl or alkenyl, or a mixture thereof, and (ii) --CH 2 A wherein A represents --OR', --SR' or ##STR32## wherein R' represents a saturated or unsaturated hydrocarbon, and n represents an average statistical value n greater than 1 and equal to not more than 6 and, when R represents --CH 2 A, n also represents a value equal to 2, said process comprising a two-stage process, said first stage comprising reacting an isopropylideneglycerol having the formula ##STR33## in the presence of a basic catalyst, with an epoxide of formula III ##STR34## wherein R and n have the meanings given above, so as to produce an intermediate product having the formula II ##STR35## wherein R and n have the meanings given above, and in a second stage hydrolyzing said intermediate product of formula II so as to produce said compound of formula I and separating therefrom said compound of formula I.
Claim 8
Dependent Claim
180 words
A process for preparing a compound having a formula ##STR31## wherein R represents a radical selected from the group consisting of (i) a linear or branched C 4 -C 28 alkyl or alkenyl, or a mixture thereof, and (ii) --CH 2 A wherein A represents --OR', --SR' or ##STR32## wherein R' represents a saturated or unsaturated hydrocarbon, and n represents an average statistical value n greater than 1 and equal to not more than 6 and, when R represents --CH 2 A, n also represents a value equal to 2, said process comprising a two-stage process, said first stage comprising reacting an isopropylideneglycerol having the formula ##STR33## in the presence of a basic catalyst, with an epoxide of formula III ##STR34## wherein R and n have the meanings given above, so as to produce an intermediate product having the formula II ##STR35## wherein R and n have the meanings given above, and in a second stage hydrolyzing said intermediate product of formula II so as to produce said compound of formula I and separating therefrom said compound of formula I.
Claim 9
Dependent Claim
40 words
The process of claim 6 wherein said basic catalyst in said first stage is selected from the group consisting of an alkali metal, an alkali metal hydride, an alkali metal hydroxide, an alkali metal alcoholate and an alkali metal fluoride.
Claim 10
Dependent Claim
12 words
The process of claim 7 wherein said basic catalyst is potassium tert.-butylate.
Claim 11
Dependent Claim
51 words
The process of claim 6 wherein, in said first stage, at least a portion of said isopropylideneglycerol of formula (IV) and said basic catalyst are mixed under an inert atmosphere, the resulting mixture being heated to a temperature ranging from 50° to 150° C. and adding said epoxide of formula III.
Claim 12
Dependent Claim
25 words
The process of claim 6 wherein, in said second stage, said intermediate product of formula II is hydrolyzed in the presence of an acid catalyst.
Claim 13
Dependent Claim
24 words
The process of claim 10 wherein, in said second stage, said intermediate product of formula II is hydrolyzed in the presence of a solvent.
Claim 14
Dependent Claim
87 words
A nonionic compound of formula II ##STR36## wherein R represents a radical selected from the group consisting of (i) a linear or branched C 4 -C 28 alkyl or alkenyl, or a mixture thereof, and (ii) --CH 2 A wherein A represents --OR', --SR' or ##STR37## wherein R' represents a saturated or unsaturated hydrocarbon, and n represents an average statistical value n greater than 1 and equal to not more than 6 and, when R represents --CH 2 A, n also represents a value equal to 2.
Claim 15
Dependent Claim
87 words
A nonionic compound of formula II ##STR36## wherein R represents a radical selected from the group consisting of (i) a linear or branched C 4 -C 28 alkyl or alkenyl, or a mixture thereof, and (ii) --CH 2 A wherein A represents --OR', --SR' or ##STR37## wherein R' represents a saturated or unsaturated hydrocarbon, and n represents an average statistical value n greater than 1 and equal to not more than 6 and, when R represents --CH 2 A, n also represents a value equal to 2.
References Cited (Backward Citations)
US3463745A
Cited
US3998948A
Cited
US3821372A
Cited
US3748276A
Cited
US4224311A
Cited
US4115314A
Cited
US4086279A
Cited
US4897308A
Cited
US4105580A
Cited
US4282387A
Cited
EP0066107A1
Cited
EP0071019A1
Cited
US4670185A
Cited
GB2144122A
Cited
US4657556A
Cited
US4703114A
Cited
US4830857A
Cited
US4677232A
Cited
US4954345A
Cited
US4832868A
Cited
US4963535A
Cited
EP0283165A2
Cited
US5227470A
Cited
US5213802A
Cited
US5362494A
Cited
US5243086A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-07-23 | 2000-01-22 | 2000-07-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-07-23 | 2004-01-22 | 2004-07-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-07-23 | 2008-01-22 | 2008-07-23 | $7700.00 | Window Closed / Lapsed |