2,4,4-irisubstituted tetrahydro pyranyl esters and organoleptic uses thereof

• US 4,963,285 A
• Filed: 02/09/1989
• Issued: 10/16/1990
• Est. Priority Date: 02/09/1989
• Status: Expired due to Fees

• Current Assignee: International Flavors & Fragrances Incorporated
• Original Assignee: International Flavors & Fragrances Incorporated
• Inventors: Greene, Roger E., Sprecker, Mark A.
• Primary Examiner(s): Lieberman, Paul
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/308,182
• Time in Patent Office: 614 Days
• Field of Search: 252/174.11, 252/89.1, 252/187.25, 252/187.26
• US Class Current: 252/187.25
• CPC Class Codes: C07D 309/10 Oxygen atoms
• CPC Class Codes: C07D 309/12 only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
• CPC Class Codes: C11B 9/008 the hetero rings containing six atoms

Abstract

Described are 2,4,4-trisubstituted tetrahydro pyranyl esters defined according to the structure: ##STR1## wherein R₁ represents methyl or ethyl and R₂ represents C₂ -C₄ straight chain or branched chain alkyl or alkenyl and organoleptic used 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.

Claims

1. A 2,4,4-trisubstituted tetrahydro pyranyl ester defined according to the structure:

##STR209## wherein R₁ represents methyl or ethyl and R₂ represents C₂ -C₄ straight chain or branched chain alkyl or alkenyl.

2. The compound of claim 1 having the structure:

##STR210##

3. The compound of claim 1 having the structure:

##STR211##

4. The compound of claim 1 having the structure:

##STR212##

5. The compound of claim 1 having the structure:

##STR213##

6. The compound of claim 1 having the structure:

##STR214##

7. The compound of claim 1 having the structure:

##STR215##

8. The compound of claim 1 having the structure:

##STR216##

9. The compound of claim 1 having the structure:

##STR217##

10. The compound of claim 1 having the structure:

##STR218##

11. The compound of claim 1 having the structure:

##STR219##

12. The compound of claim 1 having the structure:

##STR220##

13. The compound of claim 1 having the structure:

##STR221##

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 1.

15. 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.

16. 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.

17. 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.

18. 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.

19. 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.

20. 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 7.

21. 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 8.

22. 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 9.

23. A process for augmenting or enhancing the aroma of a consumable material selected form 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 10.

24. 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 11.

25. 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 12.

26. A process for augmenting of 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 13.

27. 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.

28. A process for producing a stable single phase aqueous alkaline metal hypochlorite solution having a pleasant fragrance consisting, in sequential 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;

##STR222## wherein at least one of R₁ and R₂ is C₁₀ -C₁₂ straight chain or branched chain alkyl and M.sub.α and

M.sub.β

are the same or different and each represents lithium, potassium or sodium; and

(ii) a mixture of at least one compound having the structure;

##STR223## and a compound having the structure;

##STR224## 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.

29. 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:

##STR225## 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.sub.α and

M.sub.β

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

##STR226## and intimately admixed therewith (i) a substance having the structure;

##STR227## 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, (ii) up to 0.2% of one or more compatible perfume oils, and (iii) an aroma augmenting or enhancing quantity of at least one compound defined according to claim 1, such hypochlorite solution having a pH of from 11 up to 14.0.

30. The composition of matter of claim 29 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.

31. The composition of claim 29 wherein the compound having the structure:

##STR228## is selected from the group of materials having the structures;

##STR229##

32. The process of claim 35 wherein the composition of matter admixed in step (b) also includes diisoamylene epoxide.