1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes, organoleptic uses thereof and processes for preparing same

• US 4,990,494 A
• Filed: 02/02/1990
• Issued: 02/05/1991
• Est. Priority Date: 02/02/1990
• Status: Expired due to Term

• Current Assignee: International Flavors & Fragrances Incorporated
• Original Assignee: International Flavors & Fragrances Incorporated
• Inventors: Narula, Anubhav P. S., De Virgilio, John J., Fox, Eleanor
• Primary Examiner(s): Reamer, James H.
• Application Number:
  US07/474,545
• Time in Patent Office: 368 Days
• Field of Search: 512/6, 512/20, 558/388, 564/265, 252/174.11, 252/95, 252/102, 252/187.23, 252/187.25, 252/547, 252/588
• US Class Current: 512/6
• CPC Class Codes: C07C 251/40 to carbon atoms of an unsaturated carbon skeleton
• CPC Class Codes: C07C 255/33 with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
• CPC Class Codes: C11B 9/0061 compounds containing a six-membered aromatic ring not condensed with another ring
• CPC Class Codes: C11B 9/0065 Nitriles
• CPC Class Codes: C11D 3/3956 Liquid compositions
• CPC Class Codes: C11D 3/50 Perfumes

Abstract

Described are 1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes defined according to the generic structure: ##STR1## wherein R₁ is selected from the group consisting of: (i) cyanide having the structure: ##STR2## (ii) hydroxylamino methyl having the structure: ##STR3## and wherein R₂ is C₁ -C₅ lower alkyl, 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 are processes for preparing such 1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes by means of reacting an alkyl benzyl halide with isopropyl cyanide in the presence of a basic catalyst such as sodamide.

Claims

1. The mixture of nitriles having the structures:

##STR127##

2. The mixture of oximes having the structures:

##STR128##

3. 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 of enhancing quantity of at least one compound defined according to claim 1.

4. 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.

5. 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.

6. A chlorine-containing bleach composition comprising:

(a) a chlorine bleach; and

(b) intimately admixed therewith at least one compound defined according to claim 2.

7. 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:

##STR129## 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 Mα and

Mβ

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;

##STR130## and intimately admixed therewith a substance having the structure;

##STR131## 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, said 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.

8. 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:

##STR132## 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 Mα and

Mβ

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;

##STR133## and intimately admixed therewith a substance having the structure;

##STR134## 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, said 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 2.

9. The composition of claim 7 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 centipoise at a temperature of 20°

-40°

C.

10. The composition of claim 8 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.

11. The composition of claim 7 wherein the compound having the structure:

##STR135## is selected from the group of materials having the structures;

##STR136##

12. The composition of claim 8 wherein the compound having the structure:

##STR137## is selected from the group of materials having the structures;

##STR138##

13. 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 of at least one compound having the structure;

##STR139## wherein at least one of R₁ and R₂ is C_10-12 straight chain or branched chain alkyl and Mα 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 structures;

##STR140## and a compound having the structure;

##STR141## 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.

14. 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;

##STR142## wherein at least one of R₁ and R₂ is C₁₀ -C₁₂ straight chain or branched chain alkyl and Mα 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;

##STR143## and a compound having the structure;

##STR144## 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 2 and (c) adding said premix to the pH adjusted hypochlorite solution.

15. The process of claim 13 wherein in step (b) there is also admixed diisoamylene epoxide.

16. The process of claim 14 wherein the step (b) there is also admixed diisoamylene epoxide.