Fragrance Compositions Comprising Ionic Liquids

Abstract

The present invention relates to a fragrance composition comprising ionic liquids for enhanced evaporation of the perfume raw materials. The invention also relates to methods of use of the fragrance compositions for perfuming suitable substrates, particularly skin and hair.

What is claimed is: 
     
         1 . A fragrance composition comprising:
 (a) from 0.001% to 99.9% by weight of the total fragrance composition of a perfume raw material other than dimethyl benzyl carbonyl butyrate, wherein the perfume raw material displays a positive deviation from Raoult's Law; and   (b) from 0.01% to 99% by weight of the total fragrance composition of at least one ionic liquid comprising:
 (i) an anion; and 
 (ii) a cation; 
   wherein the ionic liquid is a liquid at temperatures lower than 100° C., preferably at ambient temperature.   
     
     
         2 . The fragrance composition according to  claim 1 , wherein the positive deviation from Raoult's Law is determined by the D2879:2010 Standard Test Method (“ASTM D2879 Isoteniscope Method”) or the Infrared Gas-Phase Spectroscopy as described herein. 
     
     
         3 . The fragrance composition according to  claim 1 , wherein the perfume raw material displays the positive deviation from Raoult's Law having an activity coefficient (γ) greater than 1 at a mole fraction between 0.05 to 0.8 of the perfume raw material, preferably at the mole fraction between 0.05 to 0.2, or preferably at the mole fraction between 0.2 to 0.4, or preferably at the mole fraction between 0.4 to 0.6, or preferably at the mole fraction between 0.6 to 0.8 of the perfume raw material. 
     
     
         4 . The fragrance composition according to  claim 1 , wherein the cation and anion are essentially free of the following chemical elements: antimony, barium, beryllium, bromine, cobalt, chromium, fluorine, iodine, lead, nickel, selenium, and thallium. 
     
     
         5 . The fragrance composition according to  claim 1 , wherein the perfume raw material comprises at least one low volatility perfume raw material having a vapour pressure less than 0.003 Torr (<0.00040 kPa) at 25° C.; and the low volatility perfume raw material is present in an amount from 0.001 wt % to 99.9 wt %, preferably from 0.01 wt % to 99 wt %, wherein the wt % is relative to the total weight of the perfume raw material. 
     
     
         6 . The fragrance composition according to  claim 5 , wherein the low volatility perfume raw material comprises an alcohol moiety, a phenol moiety or combination thereof. 
     
     
         7 . The fragrance composition according to  claim 5 , wherein the perfume raw material comprises at least 2, 3, 4, 5, 6 or more low volatility perfume raw materials. 
     
     
         8 . The fragrance composition according to  claim 1 , wherein the low volatility perfume raw material is selected from the group consisting of Table 1 Low Volatility Perfume Raw Materials and combinations thereof. 
     
     
         9 . The fragrance composition according to  claim 8 , wherein the low volatility perfume raw material is selected from the group consisting of: 2-methyl-1-phenylpropan-2-yl butanoate; 4-penten-2-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; 1-propanol, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methyl-, 1-propanoate; and benzeneacetonitrile, α-cyclohexylidene-. 
     
     
         10 . The fragrance composition according to  claim 5 , wherein the perfume raw material further comprises at least one, two, three, four or more highly volatile perfume raw materials having a vapour pressure greater than 0.003 Torr (>0.00040 kPa) at 25° C., and the highly volatile perfume raw material is present in an amount from 0.001 wt % to 99.9 wt %, wherein the wt % is relative to the total weight of the perfume raw material. 
     
     
         11 . The fragrance composition according to  claim 1 , wherein the anion has the formula (I):
   [R 1 —O—C(O)—CH(SO 3 )—R 3 —C(O)—P—R 2 ] −   (I)
   wherein:
 R 1  and R 2  are independently selected from the group consisting of alkyl, mono or oligo-alkoxyalkyl and alkenyl; and 
 R 3  is alkylene, heteroarylene, arylene, or cycloalkylene. 
   
     
     
         12 . The fragrance composition according to  claim 11 , wherein:
 R 1  and R 2  are independently selected from alkyl having 5 or more carbon atoms, preferably 6 to 18 carbon atoms; and   R 3  is —(CH 2 ) n — wherein n is an integer of from 1 to 12.   
     
     
         13 . The fragrance composition according to  claim 12 , wherein the anion is 1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate. 
     
     
         14 . The fragrance composition according to  claim 1 , wherein the anion has the formula (II): 
       
         
           
           
               
               
           
         
         wherein:
 R 4  is selected from the group consisting of hydrogen, cyano, alkyl, alkoxy and alkoxyalkyl. 
 
       
     
     
         15 . The fragrance composition according to  claim 14 , wherein the anion is 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide. 
     
     
         16 . The fragrance composition according to  claim 1 , wherein the anion has the formula (III): 
       
         
           
           
               
               
           
         
         wherein:
 R 5  is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclyalkyl, heteroaryl and heteroarylalkyl. 
 
       
     
     
         17 . The fragrance composition according to  claim 16 , wherein the anion is methyl sulfonate. 
     
     
         18 . The fragrance composition according to  claim 1 , wherein the anion is independently selected from the group consisting of:
   [R 1 —O—C(O)—CH(SO 3 )—R 3 —C(O)—O—R 2 ] −   (I)
   (a)   wherein:
 R 1  and R 2  are independently selected from the group consisting of alkyl or alkenyl, provided that the alkyl is not substituted with nitro, azido or halide; and 
 R 3  is alkylene, heteroarylene, arylene, or cycloalkylene; 
   
       
         
           
           
               
               
           
         
         (b) 
         wherein:
 R 4  is selected from the group consisting of hydrogen, cyano, alkyl, alkoxy and alkoxyalkyl; 
 
       
       
         
           
           
               
               
           
         
         (c) 
         wherein:
 R 5  is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclyalkyl, heteroaryl and heteroarylalkyl; and 
 
         (d) combinations thereof. 
       
     
     
         19 . The fragrance composition according to  claim 18 , further comprising the anion independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       and combinations thereof;
 wherein:
 each R 5  and R 6  are independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclyalkyl, heteroaryl and heteroarylalkyl. 
 
 
     
     
         20 . The fragrance composition according to  claim 1 , wherein the cation is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       and combinations thereof;
 wherein:
 X is CH 2  or O; 
 each R 1a , R 3a , and R 4a  are independently selected from hydrogen, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 alkoxy, C 1 -C 20 alkoxyC 1 -C 20 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkylC 1 -C 4 alkyl, C 2 -C 20 heterocyclyl, C 6 -C 10 aryl, C 6 -C 10 arylC 1 -C 10 alkyl, C 1 -C 10 heteroaryl, halo, haloC 1 -C 20 alkyl, hydroxyl, hydroxylC 1 -C 20 alkyl or —N(R 6a ) 2 ; 
 each R 2a  is independently selected from hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, or C 1 -C 20 alkynyl; 
 each R 5a  is independently selected from hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20  alkynyl, —R 7a —OR 8a , or —R 7a —OR 7a —OR 8a ; 
 each R 6a  is independently selected from hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclyalkyl, heteroaryl, or heteroarylalkyl; 
 each R 7a  is independently selected from a direct bond, or alkylene chain, or alkenylene chain, or alkynylene chain; and 
 each R 8a  is independently selected from a hydrogen, alkyl, alkenyl or alkynyl. 
 
 
     
     
         21 . The ionic liquid according to  claim 20 , wherein the cation is independently selected from the group consisting of: 1-butyl-3-methylimidazolium; (N-ethyl-2-(2-methoxyethoxy)-N,N-dimethylethanaminium); 2-(2-ethoxyethoxy)-N-ethyl-N,N-dimethylethanaminium; N-benzyl-N,N-dimethyloctan-1-aminium; N-benzyl-N,N-dimethylnonan-1-aminium and combinations thereof. 
     
     
         22 . The fragrance composition according to  claim 1  further comprising:
 (c) from about 10 wt % to about 80 wt % by weight of the total fragrance composition of a volatile solvent; and 
 (d) from about 0.1 wt % to about 50 wt % by weight of the total fragrance composition of a low volatility co-solvent or a mixture of low volatility co-solvents. 
 
     
     
         23 . A product comprising a fragrance composition according to  claim 1 , wherein the product is selected from the group consisting of a perfume, deodorant, an eau de toilette, an eau de parfum, a cologne, an after shave, a body splash and a body spray.