US4299737A
Expired / Lapsed
US
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Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils
Assignee: Henkel AG and Co KGaA
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Filing: 1980-03-17
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Granted: 1981-11-10
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Expires: 2000-03-17
Abstract
Abstract This invention relates to clear, stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils which contain hydroxyalkylether alkoxylates as solubilizers. Said solubilizers are prepared by reacting epoxyalkanes with mono- or polyfunctional alcohols and then reacting the reaction product thereof successively with propylene oxide and ethylene oxide.
Inventors
- 👤 Alfred Meffert
- 👤 Fanny Scheuermann
- 👤 Achim Werdehausen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:47
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/39; A61Q; A61Q13/00; C; C11; C11D; C11D1/00; C11D1/66; C11D1/722
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
282 words
A clear, stable, aqueous or aqueous-alcoholic solution of a fat-soluble perfume oil, which comprises (a) from about 0.1 to 20% by weight, based on the total weight of the solution, of a hydroxyalkylether alkoxylate prepared by reacting an epoxyalkane of the formula ##STR3## wherein R 1 and R 2 , which may be the same or different, each represent hydrogen or an alkyl radical having from about 1 to 24 carbon atoms, with the proviso that the sum of the carbon atoms in R 1 and R 2 is from about 2 to 26, or a mixture thereof, with monohydric or polyhydric aliphatic alcohols having from 1 to 10 carbon atoms and from 1 to 4 hydroxyls groups in molar ratio of epoxyalkane to alcohol of from 1:1.1 to 1:10 in the absence of solvents and in the presence of from about 0.25 to 10 g per mol of epoxyalkane of sulfuric acid or aromatic sulfonic acid not having more than 8 carbon atoms at from about 50° to 130° C., to form an ether alcohol, and then, after neutralization of the acid and distillation of unreacted alcohol, reacting the ether alcohol obtained first with from about 0.5 to 10 mols of propylene oxide per mol of ether alcohol and then with from about 4 to 20 mols of ethylene oxide per mol of ether alcohol, the molar ratio of the ethylene oxide employed to the propylene oxide employed being from about 4:1 to 12:1; (b) from about 0.1 to 1.0% by weight, based on the total weight of the solution, of a fat-soluble perfume oil; and (c) the remainder to 100% by weight of water or water and a water-miscible alcohol.
Claim 2
Dependent Claim
282 words
A clear, stable, aqueous or aqueous-alcoholic solution of a fat-soluble perfume oil, which comprises (a) from about 0.1 to 20% by weight, based on the total weight of the solution, of a hydroxyalkylether alkoxylate prepared by reacting an epoxyalkane of the formula ##STR3## wherein R 1 and R 2 , which may be the same or different, each represent hydrogen or an alkyl radical having from about 1 to 24 carbon atoms, with the proviso that the sum of the carbon atoms in R 1 and R 2 is from about 2 to 26, or a mixture thereof, with monohydric or polyhydric aliphatic alcohols having from 1 to 10 carbon atoms and from 1 to 4 hydroxyls groups in molar ratio of epoxyalkane to alcohol of from 1:1.1 to 1:10 in the absence of solvents and in the presence of from about 0.25 to 10 g per mol of epoxyalkane of sulfuric acid or aromatic sulfonic acid not having more than 8 carbon atoms at from about 50° to 130° C., to form an ether alcohol, and then, after neutralization of the acid and distillation of unreacted alcohol, reacting the ether alcohol obtained first with from about 0.5 to 10 mols of propylene oxide per mol of ether alcohol and then with from about 4 to 20 mols of ethylene oxide per mol of ether alcohol, the molar ratio of the ethylene oxide employed to the propylene oxide employed being from about 4:1 to 12:1; (b) from about 0.1 to 1.0% by weight, based on the total weight of the solution, of a fat-soluble perfume oil; and (c) the remainder to 100% by weight of water or water and a water-miscible alcohol.
Claim 3
Dependent Claim
24 words
The solution of claim 1 wherein the sum of the carbon atoms of R 1 and R 2 is from about 6 to 20.
Claim 4
Dependent Claim
19 words
The solution of claim 1 wherein the molar ratio of epoxyalkane to alcohol is from about 1:2 to 1:6.
Claim 5
Dependent Claim
26 words
The solution of claim 1 wherein the ether alcohol is reacte with from about 0.5 to 4 mols of propylene oxide per mol of ether alcohol.
Claim 6
Dependent Claim
26 words
The solution of claim 1 wherein the ether alcohol is reacted with from about 7 to 14 mols of ethylene oxide per mol of ether alcohol.
Claim 7
Dependent Claim
70 words
The solution of claim 1 wherein the epoxyalkane is reacted with ethylene glycol in a molar ratio of epoxyalkane to ethylene glycol of from about 1:2 to 1:6 to form an ether alcohol, and then the ether alcohol is reacted with from about 0.5 to 4 mols of propylene oxide per mol of ether alcohol and from about 7 to 14 mols of ethylene oxide per mol of ether alcohol.
Claim 8
Dependent Claim
20 words
The solution of claim 1 which contains other conventional substances present in aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils.
Claim 9
Dependent Claim
54 words
The solution of claim 1, wherein the epoxyalkane is 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, a mixture comprising about 70% by weight of C 12 -1,2-epoxyalkane and about 30% by weight of C 14 -1,2-epoxyalkane, or a mixture comprising about 40% by weight of C 16 -1,2-epoxyalkane and about 60% by weight of C 18 -1,2-epoxyalkane.
Claim 10
Dependent Claim
88 words
The solution of claim 1, wherein the epoxyalkane is a mixture of non-terminal epoxyalkanes comprising a mixture of about 22% by weight of C 11 -epoxyalkane, about 30% by weight of C 12 -epoxyalkane, about 26% by weight of C 13 -epoxyalkane, and about 22% by weight of C 14 -epoxyalkane or a mixture of about 26% by weight of C 15 -epoxylalkane, about 35% by weight of C 16 -epoxyalkane, about 32% by weight of C 17 -epoxyalkane, and about 7% by weight of C 18 -epoxyalkane.
Claim 11
Dependent Claim
67 words
The solution of claim 1, wherein the hydroxyalkylether alkoxylate (a) is the product of reaction from a member selected from the group consisting of: α-C 14/16 -epoxide+ethylene glycol+1 PO+9 EO; α-C 12/18 -epoxide+ethylene glycol+1.2 PO+9 EO; α-C 12/14 -epoxide+ethylene glycol+1 PO+10 EO; α-C 16/18 -epoxide+ethylene glycol+1 PO+11 EO; α-C 14/16 -epoxide+ethylene glycol+1.2 PO+9 EO; i-C 15/18 -epoxide+ethylene glycol+1 PO+9 EO; and i-C 15/18 -epoxide+ethylene glycol+1.2 PO+9 EO.
Claim 12
Dependent Claim
20 words
The solution of claim 1, wherein the ratio of component (a) to component (b) is from about 2:1 to 4:1.
Claim 13
Dependent Claim
25 words
The solution of claim 1 which comprises from about 0.5 to 5% by weight, based on the total weight of the solution, of hydroxyalkylether alkoxylate.
Claim 14
Independent Claim
245 words
A method of solubilizing a fat-soluble perfume oil in a clear, stable, aqueous or aqueous-alcoholic solution comprising adding water or an alcohol-water mixture to a concentrate of said perfume oil and a hydroxyalkylether alkoxylate prepared by reacting an epoxyalkane of the formula ##STR4## wherein R 1 and R 2 , which may be the same or different, each represent hydrogen or an alkyl radical having from about 1 to 24 carbon atoms, with the proviso that the sum of the carbon atoms in R 1 and R 2 is from about 2 to 26, or a mixture thereof, with monohydric or polyhdyric aliphatic alcohols having from about1 to 10 carbon atoms and from 1 to 4 hydroxyl groups in molar ratio of epoxyalkane to alcohol of from 1:1.1 to 1:10 in the absence of solvents and in the presence of from about 0.25 to 10 g per mol of epoxyalkane of sulfuric acid or aromatic sulfonic acid not having more than 8 carbon atoms at from about 50° to 130° C., to form an ether alcohol, and then, after neutralization of the acid and distillation of unreacted alcohol, reacting the ether alcohol obtained first with from about 0.5 to 10 mols of propylene oxide per mol of ether alcohol and then with from about 4 to 20 mols of ethylene oxide per mol of ether alcohol, the molar ratio of the ethylene oxide employed to the propylene oxide employed being from about 4:1 to 12:1.
Claim 15
Independent Claim
245 words
A method of solubilizing a fat-soluble perfume oil in a clear, stable, aqueous or aqueous-alcoholic solution comprising adding water or an alcohol-water mixture to a concentrate of said perfume oil and a hydroxyalkylether alkoxylate prepared by reacting an epoxyalkane of the formula ##STR4## wherein R 1 and R 2 , which may be the same or different, each represent hydrogen or an alkyl radical having from about 1 to 24 carbon atoms, with the proviso that the sum of the carbon atoms in R 1 and R 2 is from about 2 to 26, or a mixture thereof, with monohydric or polyhdyric aliphatic alcohols having from about1 to 10 carbon atoms and from 1 to 4 hydroxyl groups in molar ratio of epoxyalkane to alcohol of from 1:1.1 to 1:10 in the absence of solvents and in the presence of from about 0.25 to 10 g per mol of epoxyalkane of sulfuric acid or aromatic sulfonic acid not having more than 8 carbon atoms at from about 50° to 130° C., to form an ether alcohol, and then, after neutralization of the acid and distillation of unreacted alcohol, reacting the ether alcohol obtained first with from about 0.5 to 10 mols of propylene oxide per mol of ether alcohol and then with from about 4 to 20 mols of ethylene oxide per mol of ether alcohol, the molar ratio of the ethylene oxide employed to the propylene oxide employed being from about 4:1 to 12:1.
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) | 1984-11-09 | 1985-05-11 | 1985-11-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-09 | 1989-05-11 | 1989-11-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-09 | 1993-05-11 | 1993-11-10 | $7700.00 | Window Closed / Lapsed |