Ethyl norbornyl alkyl ethers, organoleptic uses thereof and process for preparing same

• US 4,772,411 A
• Filed: 01/28/1988
• Issued: 09/20/1988
• Est. Priority Date: 01/28/1988
• Status: Expired due to Term

• Current Assignee: International Flavors & Fragrances Incorporated
• Original Assignee: International Flavors & Fragrances Incorporated
• Inventors: Sprecker, Mark A., Hanna, Marie R., Androulakis, Margo
• Primary Examiner(s): Lieberman, Paul
• Assistant Examiner(s): Le, Hoa Van
• Application Number:
  US07/149,676
• Time in Patent Office: 236 Days
• Field of Search: 568/665, 252/95, 252/94, 252/102, 252/547, 252/558, 252/174.11, 252/DIG. 14, 252/522 R, 252/187.25, 252/187.23, 512/15, 524/367
• US Class Current: 252/187.25
• CPC Class Codes: C07C 43/18 having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C11B 9/0042 compounds containing condensed hydrocarbon rings
• CPC Class Codes: C11B 9/0046 containing only two condensed rings
• CPC Class Codes: C11D 3/3956 Liquid compositions
• CPC Class Codes: C11D 3/50 Perfumes

Abstract

Described are ethyl norbornyl alkyl ethers of our invention defined according to the generic structure: ##STR1## wherein R represents C₁ -C₄ lower alkyl and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations. Also described is a process for preparing such ethyl norbornyl alkyl ethers of our invention by means of reaction of compounds defined according to the structure: ##STR2## and/or compounds defined according to the structure: ##STR3## in admixture with compounds having the structure: ##STR4## with hydrogen in the presence of a hydrogenation catalyst.

Claims

1. A mixture of compounds defined according to the structure:

##STR153## wherein R represents C₁ -C₄ lower alkyl.

3. The mixture of claim 1 wherein R is isopropyl.

5. The mixture of claim 1 wherein R is methyl.

9. A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, perfumed articles and perfumed polymers comprising the step of intimately admixing with said consumable material an aroma augmenting or enhancing quantity of at least one compound defined according to claim 1.

11. A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, perfumed articles and perfumed polymers comprising the step of intimately admixing with said consumable material an aroma augmenting or enhancing quantity of at least one compound defined according to claim 3.

13. A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, perfumed articles and perfumed polymers comprising the step of intimately admixing with said consumable material an aroma augmenting or enhancing quantity of at least one compound defined according to claim 5.

15. A chlorine-containing bleach composition comprising:

(a) a chlorine bleach base; and

(b) intimately admixed therewith at least one compound defined according to claim 1.

16. A perfumed aqueous alkali metal hypochlorite solution comprising as a sole detergent a composition of matter selected from the group consisting of (1) at least one substance defined according to the structure:

##STR159## wherein at least one of R₁ and R₂ is C₁₀ -C₁₂ straight chain or branched chain alkyl;

when one of R₁ or R₂ is C₁₀ -C₁₂ straight chain or branched chain alkyl and the other of R₁ or R₂ is hydrogen;

wherein M and M are the same or different and each represents alkali metal selected from the group consisting of sodium, potassium and lithium and (2) a mixture comprising a material having the structure;

##STR160## and intimately admixed therewith a substance having the structure;

##STR161## wherein R₃ '"'"'" is straight chain alkyl;

wherein more than 55% of the R₃ '"'"'" moieties consist of straight chain alkyl having from 11 up to 13 carbon atoms and wherein "A" and "B" are each separately methyl up to 0.2% of one or more compatible perfume oils, such hypochlorite solution having a pH of 11 up to 14.0 and an aroma augmenting or enhancing quantity of at least one compound defined according to claim 1.

17. The composition of matter of claim 16 which is thickened using a thickening quantity of C₁₀ -C₂₀ alkanoic acid salt thickener in a concentration such that the viscosity of the composition is 20-60 centipoises at a temperature of 20°

-40°

C.

18. The composition of claim 16 wherein the compound having the structure:

##STR162## is selected from the group of materials having the structures;

##STR163##

19. A process for producing a stable single phase aqueous alkaline metal hypochlorite solution having a pleasant fragrance consisting, in seqential order, of the steps of (a) adjusting the pH of an aqueous alkali metal hypochlorite solution to the range of 11-14.0;

(b) admixing a composition of matter selected from the group consisting of;

(i) a chemical compound having the structure;

##STR164## wherein at least one of R₁ and R₂ is C₁₀ -C₁₂ straight chain or branched chain alkyl and M and M are the same or different and each represents lithium, potassium or sodium and (ii) a mixture of at least one compound having the structure;

##STR165## and a compound having the structure;

##STR166## wherein R₃ '"'"'" is straight chain alkyl;

wherein more than 55% of the R₃ '"'"'" moieties consist of straight chain alkyl having from 11 to 13 carbon atoms and wherein "A" and "B" are each separately methyl or taken together complete a morpholine ring with at least one compound defined according to claim 1 and (c) adding said premix to the pH adjusted hypochlorite solution.

20. The process of claim 19 wherein the perfuming material in addition to being at least one compound defined according to claim 1 also includes diisoamylene epoxide.

2. A mixture of compounds having the structures:

##STR154## wherein R is C₁ -C₄ lower alkyl.

4. The mixture of claim 2 wherein R is isopropyl

6. The mixture of claim 2 wherein R is methyl.

10. A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, perfumed articles and perfumed polymers comprising the step of intimately admixing with said consumable material an aroma augmenting or enhancing quantity of at least one compound defined according to claim 2.

12. A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, perfumed articles and perfumed polymers comprising the step of intimately admixing with said consumable material an aroma augmenting or enhancing quantity of at least one compound defined according to claim 4.

14. A process for augmenting or enhancing the aroma of a consumable material selected from the group consisting of perfume compositions, perfumed articles and perfumed polymers comprising the step of intimately admixing with said consumable material an aroma augmenting or enhancing quantity of at least one compound defined according to claim 6.

7. A mixture of compounds containing compounds having the structure:

##STR155## wherein R is C₁ -C₄ alkyl produced according to the process of reacting with hydrogen over a hydrogenation catalyst the mixture of compounds defined according to the structure;

##STR156##

8. A mixture of compounds containing the compounds having the structures:

##STR157## wherein R is C₁ -C₄ lower alkyl produced according to the process of reacting with hydrogen over a hydrogenation catalyst the mixture of compounds having the structures;

##STR158##