US3956352A
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Heterocyclic aluminum compounds and process for their preparation
Assignee: L'Oréal SA
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Filing: 1973-12-28
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Granted: 1976-05-11
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Expires: 1993-12-28
Abstract
Abstract A heterocyclic aluminum compound of the formula (CH2)n--O Z ANGLE ANGLE Al-Cl (CH2)n--O wherein n is 1 or 2. When n is 1, Z is -CH=CH-. When n is 2, Z is either -(CH2)m wherein m is 0-6, or a heteroatom selected from -O-, -S-, >SO, >SO2 or >N-COR' where R' is an aliphatic hydrocarbon of 1-17 carbon atoms, -(CH2)q-C6H5 where q is 0 or 1, styryl, diphenyl methyl or phenyl optionally substituted by chlorine, fluorine, methyl and alkoxy having 1-4 carbon atoms. The compound can be prepared by reacting isopropyl aluminate with an omega -diol of the formula (CH2)n-OH Z ANGLE (CH2)n-OH wherein Z has the meaning given above and then reacting the resulting product with dry HCl or an acyl chloride of the formula R'-COCl wherein R' has the meaning given above. The heterocyclic aluminum compound exhibits antiperspirant activity. It can be used in cosmetic antiperspirant compositions comprising a cosmetic vehicle and about 0.2-30 weight percent thereof based on the weight of said composition.
Inventors
- 👤 Claude Bouillon
- 👤 Pierre Dufaure
- 👤 Georges Rosenbaum
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 12:30
CPC Classifications
C; C07; C07F; C07F5/00; C07F5/06; C07F5/069; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/58; A61Q; A61Q1/00; A61Q1/12; A61Q15/00
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
128 words
A compound of the formula ##EQU6## wherein: n is 1 or 2, and a. when n = 1, Z is --CH=CH-; and b. when n = 2, Z is selected from the group consisting of i. --(CH 2 ) m wherein m is 0-6, and ii. a heteroatom, optionally substituted, selected from the group consisting of --O--, --S--, >SO, >SO 2 and >N-COR' wherein R' is selected from the group consisting of aliphatic hydrocarbon, saturated or unsaturated, branched or straight chain, having 1 to 17 carbon atoms, --(CH 2 ) q --C 6 H 5 wherein q is 0 or 1, styryl, diphenyl methyl and phenyl optionally substituted by a member selected from the group consisting of chlorine, fluorine, methyl and alkoxy having 1 to 4 carbon atoms.
Claim 2
Dependent Claim
128 words
A compound of the formula ##EQU6## wherein: n is 1 or 2, and a. when n = 1, Z is --CH=CH-; and b. when n = 2, Z is selected from the group consisting of i. --(CH 2 ) m wherein m is 0-6, and ii. a heteroatom, optionally substituted, selected from the group consisting of --O--, --S--, >SO, >SO 2 and >N-COR' wherein R' is selected from the group consisting of aliphatic hydrocarbon, saturated or unsaturated, branched or straight chain, having 1 to 17 carbon atoms, --(CH 2 ) q --C 6 H 5 wherein q is 0 or 1, styryl, diphenyl methyl and phenyl optionally substituted by a member selected from the group consisting of chlorine, fluorine, methyl and alkoxy having 1 to 4 carbon atoms.
Claim 3
Dependent Claim
20 words
A compound of claim 1, selected from the group consisting of 1. 2-chloro-4,7-dihydro-1,3,2-dioxalumepine, 2. 2-chloro-1,3,2-dioxalumepane, 3. 2-chloro-1,3,2-dioxalumonane, 4. 2-aluma-1,3-dioxacyclotridecane chloride,
Claim 4
Dependent Claim
32 words
2-chloro-1,3,6,2-trioxalumocane, 6. 2-chloro-1,3,6,2-dioxathialumocane, 7. 2-chloro-6-dodecanoyl-1,3,6,2-dioxazalumocane, 8. 6-benzoyl-2-chloro-1,3,6,2-dioxazalumocane, 9. 2-chloro-1,3,6,2-S,S-dioxathialumocane dioxide, 10. 2-chloro-6-pivaloyl-1,3,6,2-dioxazalumocane, 11. 6-p-butoxybenzoyl-2-chloro-1,3,6,2-dioxazalumocane, 12. 2-chloro-6-o-methoxybenzoyl-1,3,6,2-dioxazalumocane, 13. 2-chloro-1,3,6,2-S-dioxathialumocane oxide, 14. 2-chloro-6-diphenylacetyl-1,3,6,2-dioxazalumocane, 15. 2-chloro-6-(propene-2-oyl)-1,3,6,2-dioxazalumocane, 16. 2-chloro-6-(undecene-9-oyl)-1,3,6,2-dioxazalumocane, 17. 2-chloro-6-cinnamoyl-1,3,6,2-dioxazalumocane, 18. 2-chloro-6-m-chlorobenzoyl-1,3,6,2-dioxazalumocane and 19. 2-chloro-6-o-toluoyl-1,3,6,2-dioxazalumocane.
Claim 5
Dependent Claim
32 words
2-chloro-1,3,6,2-trioxalumocane, 6. 2-chloro-1,3,6,2-dioxathialumocane, 7. 2-chloro-6-dodecanoyl-1,3,6,2-dioxazalumocane, 8. 6-benzoyl-2-chloro-1,3,6,2-dioxazalumocane, 9. 2-chloro-1,3,6,2-S,S-dioxathialumocane dioxide, 10. 2-chloro-6-pivaloyl-1,3,6,2-dioxazalumocane, 11. 6-p-butoxybenzoyl-2-chloro-1,3,6,2-dioxazalumocane, 12. 2-chloro-6-o-methoxybenzoyl-1,3,6,2-dioxazalumocane, 13. 2-chloro-1,3,6,2-S-dioxathialumocane oxide, 14. 2-chloro-6-diphenylacetyl-1,3,6,2-dioxazalumocane, 15. 2-chloro-6-(propene-2-oyl)-1,3,6,2-dioxazalumocane, 16. 2-chloro-6-(undecene-9-oyl)-1,3,6,2-dioxazalumocane, 17. 2-chloro-6-cinnamoyl-1,3,6,2-dioxazalumocane, 18. 2-chloro-6-m-chlorobenzoyl-1,3,6,2-dioxazalumocane and 19. 2-chloro-6-o-toluoyl-1,3,6,2-dioxazalumocane.
Claim 6
Dependent Claim
135 words
A process for the preparation of the compound of claim 1, comprising reacting in an anhydrous solvent and in essentially equimolar amounts (i) an ω-diol of the formula: ##EQU7## wherein n is 1 or 2 and (a) when n = 1, Z represents --CH=CH-- and (b) when n = 2, Z is selected from the group consisting of --(CH 2 ) m wherein m = 0-6 and a hetero atom selected from the group consisting of --O--, --S--, >SO, >SO 2 and >NH, with (ii) aluminum isopropylate, and reacting the product resulting from the reaction with a member selected from the group consisting of (1) dry hydrochloric acid when Z is other than >NH and (2) acyl halide of the formula R'--COCl when Z is >NH, wherein R' has the meaning given in claim 1.
Claim 7
Dependent Claim
25 words
The process of claim 3 wherein said anhydrous solvent is selected from the group consisting of aromatic hydrocarbon, chlorinated hydrocarbon, alcohol, ether and mixtures thereof.
Claim 8
Dependent Claim
6 words
2-chloro-1,3,6,2-dioxathialumocane, as claimed in claim 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) | 1979-05-11 | 1979-11-10 | 1980-05-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-11 | 1983-11-10 | 1984-05-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-11 | 1987-11-10 | 1988-05-11 | $7700.00 | Window Closed / Lapsed |