EP0071019A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
2,3-Dialkoxypropyl glyceryl ether and its preparation process as well as cosmetic composition containing same
Assignee: Kao Corp
•
Filing: 1982-06-24
•
Granted: —
•
Expires: 2002-06-24
Abstract
Abstract Disclosed herein is a novel 2,3-dialkoxypropyl glyceryl ether and the preparation process for it. The above diglycerin dialkyl ether is readily prepared with high yield and purity by reacting its corresponding glycidyl ether with a protected glycerin to form a 1,3-dioxolan compound, followed by etherifying the thus formed 1,3-dioxolan compound into a dialkyl ether dioxolan compound, and then hydrolyzing the resultant dialkyl ether dioxolan compound. This diglycerin dialkyl ether is useful as an emulsifier, cleaner etc., and is preferably used as a component of cosmetic compositions. A cosmetic composition comprising the above 2,3- dialkoxypropyl glyceryl ether is also disclosed.
Inventors
- 👤 Naotake Takaishi
- 👤 Yoshiaki Inamoto
- 👤 Kouichi Urata
- 👤 Junichi Kawano
- 👤 Hisao Tsutsumi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 13:00
CPC Classifications
A; A61; A61Q; A61Q19/00; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/34; A61K8/345; C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C29/149; C07C31/00; C07C31/02; C07C31/125; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C07C43/13; C07C43/135; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/22; C07D407/00; C07D407/02; C07D407/12; A61K2800/00; A61K2800/74; A61K2800/75; A61Q1/00; A61Q1/02; A61Q1/04; A61Q1/06; A61Q1/10; A61Q19/001
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
50 words
A 2,3-dialkoxypropyl glyceryl ether represented by the general formula (I): wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, and R' means a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms.
Claim 2
Dependent Claim
50 words
A 2,3-dialkoxypropyl glyceryl ether represented by the general formula (I): wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, and R' means a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms.
Claim 3
Dependent Claim
44 words
The 2,3-dialkoxypropyl glyceryl ether according to Claim 1, wherein, in the general formula (I), R' means a lower alkyl group containing 1 - 3 carbon atoms and R denotes a saturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 20 carbon atoms.
Claim 4
Dependent Claim
13 words
The 2,3-dialkoxypropyl glyceryl ether according to Claim 2, wherein R means octyl group.
Claim 5
Dependent Claim
14 words
. The 2,3-dialkoxypropyl glyceryl ether according to Claim 2, wherein R denotes dodecyl group.
Claim 6
Dependent Claim
65 words
The 2,3-dialkoxypropyl glyceryl ether according to Claim 2, wherein R denotes a methyl-branched isostearyl group represented by the following formula: wherein m stands for integers ranging from 4 to 10, n means integers ranging from 5 to 11, m + n ranges from 11 to 17, and the methyl-branched isostearyl group has a distribution with a peak at m = 7 and n = 8.
Claim 7
Dependent Claim
79 words
The 2,3-dialkoxypropyl glyceryl ether according to Claim 1, wherein, in the general formula (I), R denotes a methyl-branched isostearyl group represented by the following general formula: wherein m stands for integers ranging from 4 to 10, n means integers ranging from 5 to 11, m + n ranges from 11 to 17, and the methyl-branched isostearyl group has a distribution with a peak at m = 7 and n = 8, and R' contains 4 - 18 carbon atoms.
Claim 8
Dependent Claim
13 words
The 2,3-dialkoxypropyl glyceryl ether according to Claim 6, wherein R' means butyl group.
Claim 9
Dependent Claim
13 words
The 2,3-dialkoxypropyl glyceryl ether according to Claim 6, wherein R' means octyl group.
Claim 10
Dependent Claim
98 words
A process for preparing a 4-(2',3'-dialkoxy)-propoxymethyl-1,3-dioxolan represented by the general formula (IV): wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, R 1 and R 2 are individually a hydrogen atom or a lower alkyl or an aryl or aralkyl group, and R' is a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms, which process comprises etherifying a 4-(2'-hydroxy-3'-alkoxy)propoxymethyl-l,3-dioxolan represented by the general formula (II): wherein R, R l and R 2 have the same significance as defined above.
Claim 11
Dependent Claim
98 words
A process for preparing a 4-(2',3'-dialkoxy)-propoxymethyl-1,3-dioxolan represented by the general formula (IV): wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, R 1 and R 2 are individually a hydrogen atom or a lower alkyl or an aryl or aralkyl group, and R' is a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms, which process comprises etherifying a 4-(2'-hydroxy-3'-alkoxy)propoxymethyl-l,3-dioxolan represented by the general formula (II): wherein R, R l and R 2 have the same significance as defined above.
Claim 12
Dependent Claim
33 words
The process according to Claim 9, wherein, in the general formulas (IV) and (II), R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 20 carbon atoms.
Claim 13
Dependent Claim
125 words
A process for preparing a 2,3-dialkoxypropyl glyceryl ether represented by the general formula (I): wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, and R' means a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms, which process comprises etherifying a 4-(2'-hydroxy-3'-alkoxy)propoxymethyl-l,3-dioxolan represented by the general formula (II): wherein R has the same significance as defined above, and R 1 and R 2 are each a hydrogen atom or a lower alkyl or an aryl or aralkyl group to obtain a 4-(2',3'-dialkoxy)-propoxymethyl-1,3-dioxolan represented by the general formula (IV): wherein R, R 1 and R 2 have the same significance as defined above; and then hydrolyzing the 4-(2',3'-dialkoxy)-propoxymethyl-1,3-dioxolan.
Claim 14
Dependent Claim
125 words
A process for preparing a 2,3-dialkoxypropyl glyceryl ether represented by the general formula (I): wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, and R' means a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms, which process comprises etherifying a 4-(2'-hydroxy-3'-alkoxy)propoxymethyl-l,3-dioxolan represented by the general formula (II): wherein R has the same significance as defined above, and R 1 and R 2 are each a hydrogen atom or a lower alkyl or an aryl or aralkyl group to obtain a 4-(2',3'-dialkoxy)-propoxymethyl-1,3-dioxolan represented by the general formula (IV): wherein R, R 1 and R 2 have the same significance as defined above; and then hydrolyzing the 4-(2',3'-dialkoxy)-propoxymethyl-1,3-dioxolan.
Claim 15
Dependent Claim
20 words
The process according to Claim 11, wherein the hydrolysis is carried out in the presence of a protonic acid catalyst.
Claim 16
Dependent Claim
21 words
The process according to Claim 11, wherein the hydrolysis is carried out in water containing a water-soluble organic solvent added thereto.
Claim 17
Dependent Claim
16 words
The process according to Claim 11, wherein the etherification is carried out using an alkyl halide.
Claim 18
Dependent Claim
17 words
The process according to Claim 14, wherein the alkyl halide is an alkyl bromide or alkyl iodide.
Claim 19
Dependent Claim
19 words
The process according to Claim 11, wherein the etherification is carried out in the presence of an alkaline substance.
Claim 20
Dependent Claim
29 words
The process according to any one of Claims 11 to 16, wherein the etherification is carried out in the presence of a catalytic amount of a quaternary onium salt.
Claim 21
Dependent Claim
53 words
A cosmetic composition comprising a 2,3-dialkoxypropyl glyceryl ether represented by the general formula wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, and R' means a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms.
Claim 22
Dependent Claim
53 words
A cosmetic composition comprising a 2,3-dialkoxypropyl glyceryl ether represented by the general formula wherein R denotes a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 8 - 24 carbon atoms, and R' means a saturated or unsaturated, straight chain or branched, aliphatic hydrocarbon group containing 1 - 24 carbon atoms.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.