Patent US4376068A successfully refreshed from Google Patents.
US4376068A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Use of isomeric farnesene product-by-process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles
Assignee: International Flavors and Fragrances Inc
•
Filing: 1981-08-13
•
Granted: 1983-03-08
•
Expires: 2001-08-13
Abstract
Abstract Described are isomeric mixtures of farnesene prepared by dehydrating nerolidol using potassium bisulfate or paratoluene sulfonic acid and then distilling the resultant product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing waxy, white-flowery (magnolia-like, tuberose, gardenia-like) aromas with citrusy (lemon/lime), pettitgrain-like undertones and green top notes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, cosmetic powders and the like).
Inventors
- 👤 Braja D. Mookherjee
- 👤 Robert W. Trenkle
- 👤 Bernard J. Chant
- 👤 Anton van Ouwerkerk
- 👤 Venkatesh Kamath
- 👤 Cynthia J. Mussinan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 09:32
CPC Classifications
C; C11; C11B; C11B9/00; C11B9/0007; C07; C07C; C07C1/00; C07C1/20; C07C1/24; C07C2527/00; C07C2527/02; C07C2527/053; C07C2527/055
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
225 words
A process for augmenting or enhancing the wet petal, white flower aroma of a consumable material selected from the group consisting of (a) perfume compositions, (b) colognes and (c) perfumed polymers comprising the step of intimately admixing with a perfume composition base, a cologne base or a polymer, an aroma augmenting or enhancing quantity of a farnesene isomer mixture produced according to the process of dehydrating a nerolidol isomer mixture containing nerolidol isomers defined according to the structures: ##STR54## in the presence of a catalyst selected from the group consisting of potassium acid sulfate and paratoluene sulfonic acid at a temperature in the range of from 110° C. up to 200° C. and at a pressure in the range of from 1 mm/Hg pressure up to 200 atmospheres pressure, absolute during the reaction, simultaneously removing water of reaction from the reaction mass, and then distilling the resulting product at a temperature in the range of from 51° up to 103° C. and a pressure in the range of from 0.7 up to 2.0 mm/Hg, with the proviso that when a potassium acid sulfate catalyst is used, the temperature of reaction is in the range of 180°-200° C.; and with the further proviso that when using a paratoluene sulfonic acid catalyst, the reaction temperature is in the range of from 115° C. up to 200° C.
Claim 2
Dependent Claim
225 words
A process for augmenting or enhancing the wet petal, white flower aroma of a consumable material selected from the group consisting of (a) perfume compositions, (b) colognes and (c) perfumed polymers comprising the step of intimately admixing with a perfume composition base, a cologne base or a polymer, an aroma augmenting or enhancing quantity of a farnesene isomer mixture produced according to the process of dehydrating a nerolidol isomer mixture containing nerolidol isomers defined according to the structures: ##STR54## in the presence of a catalyst selected from the group consisting of potassium acid sulfate and paratoluene sulfonic acid at a temperature in the range of from 110° C. up to 200° C. and at a pressure in the range of from 1 mm/Hg pressure up to 200 atmospheres pressure, absolute during the reaction, simultaneously removing water of reaction from the reaction mass, and then distilling the resulting product at a temperature in the range of from 51° up to 103° C. and a pressure in the range of from 0.7 up to 2.0 mm/Hg, with the proviso that when a potassium acid sulfate catalyst is used, the temperature of reaction is in the range of 180°-200° C.; and with the further proviso that when using a paratoluene sulfonic acid catalyst, the reaction temperature is in the range of from 115° C. up to 200° C.
Claim 3
Dependent Claim
14 words
The process of claim 1 wherein the consumable material is a perfumed microporous polymer.
Claim 4
Dependent Claim
19 words
The process of claim 1 wherein the consumable material is a cologne and the cologne comprises ethanol and water.
Claim 5
Dependent Claim
192 words
A perfume composition having an intense wet petal, white flower aroma nuance comprising a perfume base and intimately admixed therewith in an organoleptic property modifying, augmenting or enhancing quantity a product containing farnesene isomers produced according to the process of dehydrating a mixture of nerolidol isomers having the structures: ##STR55## using a dehydrating agent selected from the group consisting of potassium acid sulfate and paratoluene sulfonic acid at a temperature in the range of from 110° C. up to 200° C. and at a pressure in the range of from 1 mm/Hg pressure up to 200 atmospheres during the reaction, simultaneously removing water of reaction from the reaction mass, and then distilling the resulting product at a temperature in the range of from 51° up to 103° C. and a pressure in the range of from 0.7 up to 2.0 mm/Hg, with the proviso that when a potassium acid sulfate catalyst is used, the temperature of reaction is in the range of 180°-200° C.; and with the further proviso that when using a paratoluene sulfonic acid catalyst, the reaction temperature is in the range of from 115° C. up to 200° C.
Claim 6
Dependent Claim
192 words
A perfume composition having an intense wet petal, white flower aroma nuance comprising a perfume base and intimately admixed therewith in an organoleptic property modifying, augmenting or enhancing quantity a product containing farnesene isomers produced according to the process of dehydrating a mixture of nerolidol isomers having the structures: ##STR55## using a dehydrating agent selected from the group consisting of potassium acid sulfate and paratoluene sulfonic acid at a temperature in the range of from 110° C. up to 200° C. and at a pressure in the range of from 1 mm/Hg pressure up to 200 atmospheres during the reaction, simultaneously removing water of reaction from the reaction mass, and then distilling the resulting product at a temperature in the range of from 51° up to 103° C. and a pressure in the range of from 0.7 up to 2.0 mm/Hg, with the proviso that when a potassium acid sulfate catalyst is used, the temperature of reaction is in the range of 180°-200° C.; and with the further proviso that when using a paratoluene sulfonic acid catalyst, the reaction temperature is in the range of from 115° C. up to 200° C.
Claim 7
Dependent Claim
115 words
The process of claim 1 wherein in the dehydrating process, the dehydration agent is potassium acid sulfate, the process is carried out in the presence of a hydrocarbon mineral oil solvent and the process is carried out at a temperature in the range of from 180° up to 200° C. at from 1 mm/Hg pressure up to 25 mm/Hg pressure, simultaneously removing water of reaction from the reaction mass during the reaction, and then distilling the resulting product at a temperature in the range of from 51° up to 73° C. and a pressure in the range of from 0.7 up to 2.0 mm/Hg, said product having a GLC profile defined according to FIG. 2.
Claim 8
Dependent Claim
14 words
The process of claim 5 wherein the consumable material is a perfumed microporous polymer.
Claim 9
Dependent Claim
24 words
The process of claim 5 wherein the consumable material is a microporous polymer which is selected from the group consisting of polyethylene and polypropylene.
Claim 10
Dependent Claim
108 words
The process of claim 1 wherein in the dehydrating process, the dehydrating agent is paratoluene sulfonic acid and the reaction temperature ranges from 115° C. at atmospheric pressure, at reflux, up to 200° C. at reflux and the reaction takes place in the presence of a solvent selected from the group consisting of toluene, xylene and a heavy hydrocarbon mineral oil, simultaneously removing water of reaction during the reaction and then fractionally distilling the resulting mixture at a temperature in the range of from 89° up to 92° C. and at a pressure of 1.8 mm/Hg, said product being defined according to the GLC profile of FIG. 16L.
Claim 11
Dependent Claim
14 words
The process of claim 8 wherein the consumable material is a perfumed microporous polymer.
Claim 12
Dependent Claim
15 words
The process of claim 8 wherein the consumable material is a perfume composition or cologne.
Claim 13
Dependent Claim
19 words
The process of claim 8 wherein the consumable material is a cologne and the cologne comprises ethanol and water.
References Cited (Backward Citations)
US3553296A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-03-07 | 1986-09-06 | 1987-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-03-07 | 1990-09-06 | 1991-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-03-07 | 1994-09-06 | 1995-03-08 | $7700.00 | Window Closed / Lapsed |