2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers, process for preparing same and perfumery uses thereof

• US 4,962,090 A
• Filed: 03/22/1990
• Issued: 10/09/1990
• Est. Priority Date: 03/22/1990
• Status: Expired due to Fees

• Current Assignee: International Flavors & Fragrances Incorporated
• Original Assignee: International Flavors & Fragrances Incorporated
• Inventors: Belko, Robert P., Sprecker, Mark A., Hanna, Marie R., Beck, Charles E. J., Brucato, Salvatore M.
• Primary Examiner(s): Reamer, James H.
• Application Number:
  US07/497,593
• Time in Patent Office: 201 Days
• Field of Search: 512/9, 512/12, 549/416, 252/174.11, 252/94, 252/108
• US Class Current: 252/187.25
• CPC Class Codes: C07D 309/10 Oxygen atoms
• CPC Class Codes: C07D 311/96 spiro-condensed with carbocyclic rings or ring systems
• CPC Class Codes: C11B 9/008 the hetero rings containing six atoms

Abstract

Described are 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers defined according to the generic structure: ##STR1## wherein R'"'"' represents methyl or ethyl; R₁ and R₂ taken alone are the same or different hydrogen, phenyl, C₁ -C₈ alkyl or C₂ -C₈ alkenyl (with the proviso that R₁ and R₂ are not both hydrogen) and R₁ and R₂ taken together represent C₅ -C₁₂ cycloalkyl or alkyl cycloalkyl, and reaction products containing said 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers taken alone or taken further together in admixture with compounds defined according to the generic structure: ##STR2## wherein in the compounds defined according to the structure: ##STR3## one of the dashed lines in the moiety: ##STR4## represents a carbon-carbon double bond and each of the other dashed lines represent carbon-carbon single bonds; and R₁ '"'"' and R₂ '"'"' taken alone or taken together are defined in the same manner that R₁ and R₂ are defined, supra; 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, perfume polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.

Claims

1. At least one 2,4-disubstituted or 2,2,4-trisubstituted tetrahydropyranyl-pyranyl-4-ether defined according to the structure:

##STR327## wherein R'"'"' is selected from the group consisting of methyl and ethyl and R₁ and R₂ taken alone are the same or different hydrogen, phenyl, C₁ -C₈ alkyl or C₂ -C₈ alkenyl, with the proviso that R₁ and R₂ are not both hydrogen, and R₁ and R₂ taken together represent a C₅ -C₁₂ cycloalkyl or alkyl cycloalkyl moiety.

2. A mixture of compounds comprising at least one compound defined according to claim 1 and a compound having the structure:

##STR328## wherein R₁ '"'"' and R₂ '"'"' taken alone are the same or different hydrogen, phenyl, C₁ -C₈ alkyl or C₂ -C₈ alkenyl, with the proviso that R₁ and R₂ are not both hydrogen and R₁ and R₂ taken together represent a C₅ -C₁₂ cycloalkyl or alkyl cycloalkyl moiety, and wherein the moiety;

##STR329## is indicative of a mixture of compounds wherein in the mixture one of the dashed lines in the moiety;

##STR330## is a carbon-carbon double bond and each of the other two of the dashed lines represent carbon-carbon single bonds.

3. A compound of claim 1 having the structure:

##STR331##

4. A compound of claim 1 having the structure:

##STR332##

5. A compound of claim 1 having the structure:

##STR333##

6. A compound of claim 1 having the structure:

##STR334##

7. A compound of claim 1 having the structure:

##STR335##

8. A compound of claim 1 having the structure:

##STR336##

9. A compound of claim 1 having the structure:

##STR337##

10. A compound of claim 1 having the structure:

##STR338##

11. A compound of claim 1 having the structure:

##STR339##

12. A compound of claim 1 having the structure:

##STR340##

13. A compound of claim 1 having the structure:

##STR341##

14. A compound of claim 1 having the structure:

##STR342##

15. A compound of claim 1 having the structure:

##STR343##

16. A compound of claim 1 having the structure:

##STR344##

17. A compound of claim 1 having the structure:

##STR345##

18. A compound of claim 1 having the structure:

##STR346##

19. A compound of claim 1 having the structure:

##STR347##

20. A compound of claim 1 having the structure:

##STR348##

21. A compound of claim 1 having the structure:

##STR349##

22. A compound of claim 1 having the structure:

##STR350##

23. 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.

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 composition of matter defined according to claim 2.

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 3.

26. A process for agumenting or enhancing the aroma of a consumable material selectedfrom 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.

27. 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 steps of intimately admixing with said consumable material, an aroma augmenting or enhancing quantity of at least one compound defined according to claim 5.

28. 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.

29. 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.

30. 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.

31. 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 intimtely admixing with said consumable material, an aroma augmenting or enhancing quantity of at least one compound defined according to claim 9.

32. 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 10.

33. 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.

34. 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.

35. 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 13.

36. 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 14.

37. 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 15.

38. 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 16.

39. 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 17.

40. 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 intimtely admixing with said consumable material, an aroma augmenting or enhancing quantity of at least one compound defined according to claim 18.

41. 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 19.

42. 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 20.

43. 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 21.

44. 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 22.

45. 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.

46. 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:

##STR351## 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 alkali metal selected from the group consisting of sodium, potassium and lithium and (2) a mixture comprising a material having the structure;

##STR352## and intimately admixed therewith a substance having the structure;

##STR353## 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.

47. The composition of matter of claim 46 which is thickened using a thickening quantity of C₁₀ 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.

48. The composition of claim 46 wherein the compound having the structure:

##STR354## is selected from the group of materials having the structures;

##STR355##

49. 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;

##STR356## wherein at least one of R₁ and R₂ is C₁₀ -C₁₂ straight chain or branched chain alkyl and M.sub.α and

Mβ

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

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

##STR357## and a compound having the structure;

##STR358## 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.

50. The process of claim 49 wherein the perfuming material in addition to being at least one compound defined according to claim 1 also includes diisoamylene epoxide.