US4687843A
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Esterified propoxylated glucose compositions
Assignee: Lubrizol Corp
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Filing: 1986-02-26
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Granted: 1987-08-18
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Expires: 2006-02-26
Abstract
Abstract An esterified propoxylated methyl glucoside composition is prepared by reacting a propoxylated methyl glucoside with a fatty acid at an elevated temperature in the presence of an acid catalyst. The esterified propoxylated methyl glucoside compositions find use as skin moisturizers and emollients which are especially suitable in skin care formulations.
Inventors
- 👤 Martin Smolin
- 👤 Stuart B. Polovsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 19:18
CPC Classifications
A; A61; A61Q; A61Q19/00; A61Q19/007; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/39; A61K8/60; A61K8/608; A61Q1/00; A61Q1/02; A61Q1/10; A61Q1/12; C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H13/06; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
69 words
A fatty acid ester of propoxylated methyl glucoside represented by the structural formula: ##STR7## wherein: w+x+y+z is from about 5 to 50; and each R 1 , R 2 , R 3 and R 4 is individually hydrogen or ##STR8## wherein M is a C 11 -C 29 alkyl or alkenyl, provided that at least one R 1 , R 2 , R 3 or R 4 is ##STR9##
Claim 2
Dependent Claim
69 words
A fatty acid ester of propoxylated methyl glucoside represented by the structural formula: ##STR7## wherein: w+x+y+z is from about 5 to 50; and each R 1 , R 2 , R 3 and R 4 is individually hydrogen or ##STR8## wherein M is a C 11 -C 29 alkyl or alkenyl, provided that at least one R 1 , R 2 , R 3 or R 4 is ##STR9##
Claim 3
Dependent Claim
12 words
The compound of claim 1, wherein W+X+Y+Z equals about 10 to 20.
Claim 4
Dependent Claim
10 words
The compound of claim 2, wherein W+X+Y+Z equals about 20.
Claim 5
Dependent Claim
39 words
The compound of claim 1, wherein the fatty acid ester is the ester of a fatty acid selected from the group consisting of stearic acid, linoleic acid, oleic acid, lauric acid, palmitic acid, linolenic acid and linseed oil acid.
Claim 6
Dependent Claim
16 words
The compound of claim 4, wherein the fatty acid ester is the ester of stearic acid.
Claim 7
Dependent Claim
14 words
The compound of claim 5 wherein the degree of esterification averages about the diester.
Claim 8
Dependent Claim
23 words
The compound of claim 6, having a saponification value of about 58 to 72, and a hydroxyl value of about 50 to 70.
Claim 9
Dependent Claim
105 words
A process for preparing an esterified propoxylated methyl glucoside, comprising: reacting a propoxylated methyl glucoside having the formula: ##STR10## wherein A+B+C+D is about 5 to 50, with a fatty acid at a temperature of about 100°-120° C. to produce said esterified propoxylated methyl glucoside having the formula: ##STR11## wherein W+X+Y+Z varies from about 5 to 50, and wherein any one of R 1 , R 2 , R 3 and R 4 can be H or ##STR12## wherein M is C 11 -C 29 alkyl or alkenyl, and at least one of R 1 , R 2 , R 3 and R 4 is ##STR13##
Claim 10
Dependent Claim
105 words
A process for preparing an esterified propoxylated methyl glucoside, comprising: reacting a propoxylated methyl glucoside having the formula: ##STR10## wherein A+B+C+D is about 5 to 50, with a fatty acid at a temperature of about 100°-120° C. to produce said esterified propoxylated methyl glucoside having the formula: ##STR11## wherein W+X+Y+Z varies from about 5 to 50, and wherein any one of R 1 , R 2 , R 3 and R 4 can be H or ##STR12## wherein M is C 11 -C 29 alkyl or alkenyl, and at least one of R 1 , R 2 , R 3 and R 4 is ##STR13##
Claim 11
Dependent Claim
19 words
The process of claim 8, wherein A+B+C+D is about 10 to 20 and W+X+Y+Z is about 10 to 20.
Claim 12
Dependent Claim
37 words
The process of claim 8, wherein ##STR14## is derived from at least one fatty acid selected from the group consisting of stearic acid, linoleic acid, oleic acid, lauric acid, palmitic acid, linolenic acid, and linseed oil acid.
Claim 13
Dependent Claim
12 words
The process of claim 10, wherein said fatty acid is stearic acid.
Claim 14
Dependent Claim
28 words
The distearate product formed by the process of claim 11, having a saponification value of about 58 to 72 and a hydroxyl value of about 50 to 70.
Claim 15
Dependent Claim
44 words
The process of claim 11, wherein the reaction is conducted in the presence of an acid catalyst selected from the group consisting of toluene sulfonic acid, sulfuric acid, phosphoric acid, SO 2 , H 3 BO 3 , a Lewis acid, and oxalic acid.
Claim 16
Dependent Claim
13 words
The process of claim 13, wherein the acid catalyst is toluene sulfonic acid.
Claim 17
Dependent Claim
26 words
The process of claim 8, wherein the reaction is conducted in an inert atmosphere, selected from the group consisting of nitrogen, argon, helium, and mixtures thereof.
Claim 18
Dependent Claim
11 words
The process of claim 15, wherein the inert atmosphere comprises nitrogen.
Claim 19
Dependent Claim
29 words
The process of claim 8, wherein the reactants are initially contacted and heated to a temperature of about 50° to 90° C. until homogeneity of the reaction mixture occurs.
Claim 20
Dependent Claim
26 words
The process of claim 17, wherein heating is conducted at a temperature of 100° to 120° C. under vacuum, until the acid value is below 5.
Claim 21
Dependent Claim
34 words
The process of claim 18, wherein the reaction mixture is then cooled to a temperature of about 60° to 90° C. and the pH is adjusted to a range of about 4.5 to 8.
Claim 22
Dependent Claim
18 words
The process of claim 19, wherein the pH is adjusted to a range of about 5.5 to 6.5.
Claim 23
Dependent Claim
22 words
The process of claim 19, wherein the reaction mixture is dried under vacuum at a temperature of about 90° to 120° C.
Claim 24
Dependent Claim
20 words
The process of claim 21, wherein the reaction mixture is filtered at a temperature of about 70° to 85° C.
Claim 25
Dependent Claim
9 words
A compound produced by the process of claim 14.
Claim 26
Dependent Claim
90 words
A topical skin care composition having moisturizing and emollient properties comprising an effective amount of a fatty acid ester of propoxylated methyl glucoside represented by the structural formula: ##STR15## wherein: w+x+y+z is from about 5 to 50; and each R 1 , R 2 , R 3 and R 4 is individually hydrogen or ##STR16## wherein M is a C 11 -C 29 alkyl or alkenyl, provided that at least one R 1 , R 2 , R 3 or R 4 is ##STR17## in combination with cosmetically suitable ingredients.
Claim 27
Dependent Claim
90 words
A topical skin care composition having moisturizing and emollient properties comprising an effective amount of a fatty acid ester of propoxylated methyl glucoside represented by the structural formula: ##STR15## wherein: w+x+y+z is from about 5 to 50; and each R 1 , R 2 , R 3 and R 4 is individually hydrogen or ##STR16## wherein M is a C 11 -C 29 alkyl or alkenyl, provided that at least one R 1 , R 2 , R 3 or R 4 is ##STR17## in combination with cosmetically suitable ingredients.
Claim 28
Dependent Claim
17 words
The composition of claim 24, wherein the average mole ratio varies from about 10 to 20, respectively.
Claim 29
Dependent Claim
13 words
The composition of claim 25, wherein the average mole ratio is about 20.
Claim 30
Dependent Claim
39 words
The composition of claim 24, wherein the fatty acid ester is the ester of a fatty acid selected from the group consisting of stearic acid, linoleic acid, oleic acid, lauric acid, palmitic acid, linolenic acid and linseed oil acid.
Claim 31
Dependent Claim
16 words
The composition of claim 27, wherein the fatty acid ester is the ester of stearic acid.
Claim 32
Dependent Claim
14 words
The composition of claim 28, wherein the degree of esterification averages about the diester.
Claim 33
Dependent Claim
51 words
The composition of claim 24, including a minor oil phase portion of less than about 25% by weight of the composition, wherein said minor oil phase portion contains the fatty acid ester of propoxylated methyl glucoside in an amount varying from about 0.5 to 5% by weight of the total formulation.
Claim 34
Dependent Claim
13 words
The composition of claim 24, in the form of a dry skin cream.
Claim 35
Dependent Claim
14 words
The composition of claim 24, in the form of a pressed powder eye shadow.
Claim 36
Dependent Claim
13 words
The composition of claim 24, in the form of a soft cream makeup.
Claim 37
Dependent Claim
11 words
The composition of claim 24, in the form of a moisturizer.
Claim 38
Independent Claim
38 words
A method for reducing the transepidermal water loss from the stratum corneum of the skin comprising contacting the skin with an effective amount of a fatty acid ester of propoxylated methyl glucoside in combination with cosmetically acceptable ingredients.
Claim 39
Independent Claim
38 words
A method for reducing the transepidermal water loss from the stratum corneum of the skin comprising contacting the skin with an effective amount of a fatty acid ester of propoxylated methyl glucoside in combination with cosmetically acceptable ingredients.
Claim 40
Dependent Claim
39 words
The method of claim 35, wherein the fatty acid ester is the ester of a fatty acid selected from the group consisting of stearic acid, linoleic acid, oleic acid, lauric acid, palmitic acid, linolenic acid and linseed oil acid.
Claim 41
Dependent Claim
16 words
The method of claim 36, wherein the fatty acid ester is the ester of stearic acid.
Claim 42
Dependent Claim
14 words
The method of claim 37, wherein the degree of esterification averages about the diester.
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) | 1990-08-17 | 1991-02-16 | 1991-08-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-17 | 1995-02-16 | 1995-08-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-17 | 1999-02-16 | 1999-08-18 | $7700.00 | Window Closed / Lapsed |