Photo-labile pro-fragrance conjugates

Abstract

The present invention relates to photo-labile pro-fragrance conjugates comprising: a) a photo-labile unit which upon exposure to electromagnetic radiation is capable of releasing a pro-fragrance unit; and b) a pro-fragrance unit, which when so released is either i) a pro-fragrance compound capable of releasing a fragrance raw material; or ii) a fragrance raw material. The present invention relates to systems for delivering fragrances to a situs, and to laundry detergent compositions, fine fragrances, personal care and hair care compositions comprising said systems.

1 . A photo-activated pro-fragrance conjugate comprising:
 a) a photo-labile unit which upon exposure to electromagnetic radiation is capable of releasing a pro-fragrance unit; and   b) a pro-fragrance unit comprising at least one nitrogen atom, and an optional linking moiety, said at least one nitrogen atom being bound directly to said photo-labile unit, or indirectly to said photo-labile unit by said linking moiety, via a chemical bond capable of being broken when said conjugate is exposed to electromagnetic radiation.   
     
     
         2 . A conjugate according to  claim 1  wherein said pro-fragrance unit has the formula: 
       
         
           
           
               
               
           
         
         wherein each R 3  is independently selected from hydrogen, substituted or unsubstituted C 1 -C 30  hydrocarbyl, and mixtures thereof. 
       
     
     
         3 . A conjugate according to  claim 1  comprising said optional linking moiety. 
     
     
         4 . A conjugate according to  claim 2  comprising said optional linking moiety. 
     
     
         5 . A conjugate according to  claim 1  having Formula I or II: 
       
         
           
           
               
               
           
         
         wherein each R 1  is independently hydrogen, a unit which can substitute for hydrogen selected from the group consisting of:
 a) —NHCOR 30 ; 
 b) —COR 30 ; 
 c) —COOR 30 ; 
 d) —COCH═CH 2 ; 
 e) —C(═NH)NH 2 ; 
 f) —N(R 30 ) 2 ; 
 g) —NHC 6 H 5 ; 
 h) —CON(R 30 ) 2 ; 
 i) —CONHNH 2 ; 
 j) —NHCN; 
 k) —OCN; 
 l) —CN; 
 m) F, Cl, Br, I, and mixtures thereof; 
 n) —OR 30 ; 
 o) —NHCHO; 
 p) —OH; 
 q) —NHN(R 30 ) 2 ; 
 r) —NHOR 30 ; 
 s) —CNO; 
 t) —NCS; 
 u) —SO 3 M; 
 v) —OSO 3 M; 
 w) —SCN; 
 x) —P(O)H 2 ; 
 y) —PO 2 ; 
 z) —P(O)(OH) 2 ; 
 aa) —SO 2 NH 2 ; 
 ab) —SO 2 R 30 ; 
 ac) —NO 2 ; 
 ad) —CF 3 , —CCl 3 , —CBr 3 ; 
 ae) and mixtures thereof, 
 
         or a C 1 -C 12  substituted or unsubstituted hydrocarbyl unit, R 30  is hydrogen, C 1 -C 20  linear or branched alkyl, C 6 -C 20  aryl, C 7 -C 20  alkylenearyl, and mixtures thereof; M is hydrogen, or a salt forming cation; 
         each R 2  is independently hydrogen, a C 1 -C 12  substituted or unsubstituted hydrocarbyl unit, and mixtures thereof; 
         X is —OH or —NHR 12 ; and R 12  is H, C 1 -C 12  substituted or unsubstituted alkyl, and mixtures thereof. 
       
     
     
         6 . A conjugate according to  claim 5  wherein said pro-fragrance unit has the formula: 
       
         
           
           
               
               
           
         
         wherein each R 3  is independently selected from hydrogen, substituted or unsubstituted C 1 -C 30  hydrocarbyl, and mixtures thereof. 
       
     
     
         7 . A conjugate according to  claim 6  comprising said optional linking moiety. 
     
     
         8 . A conjugate according to  claim 2  wherein said pro-fragrance unit has the formula: 
       
         
           
           
               
               
           
         
         wherein each R 4  is independently selected from the group consisting of:
 a) hydrogen; 
 b) C 1 -C 22  substituted or unsubstituted, branched or unbranched alkyl; 
 c) C 2 -C 22  substituted or unsubstituted, branched or unbranched alkenyl; 
 d) C 2 -C 20  substituted or unsubstituted, branched or unbranched hydroxyalkyl; 
 e) C 7 -C 20  substituted or unsubstituted alkylenearyl; 
 f) C 3 -C 20  substituted or unsubstituted cycloalkyl; 
 g) C 6 -C 20  aryl; 
 h) C 5 -C 20  heteroaryl units comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof; 
 i) and mixtures thereof; 
 
         any two R 4  units may optionally covalently bind together, when said any two R 4  units optionally covalently bind together said any two R 4  units form a moiety selected from the group consisting of aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof; and 
         G 1  and G 2  are each independently hydrogen, C 1 -C 20  linear or branched hydrocarbyl, —Y, —C(O)Y, and mixtures thereof; Y is C 6 -C 10  substituted or unsubstituted cyclic alkyl. 
       
     
     
         9 . A conjugate according to  claim 2  wherein said pro-fragrance unit has the formula: 
       
         
           
           
               
               
           
         
         wherein Z is oxygen or sulfur; and the index m is 1, 2 or 3. 
         R 5  is a substituted or unsubstituted hydrocarbyl unit which comprises:
 a) a C 6 -C 22  substituted or unsubstituted, linear or branched alkyl or alkenyl; 
 b) a C 6 -C 22  substituted or unsubstituted: cycloalkyl, branched cycloalkyl, cycloalkenyl, branched cycloalkenyl, aryl, heterocyclicalkyl, or heterocyclicalkenyl 
 c) and mixtures thereof; 
 
         R 6  comprises:
 a) hydrogen; 
 b) a C 1 -C 10  substituted or unsubstituted linear alkyl; 
 c) a C 3 -C 10  substituted or unsubstituted branched alkyl; 
 d) a C 2 -C 10  substituted or unsubstituted linear alkenyl; 
 e) a C 3 -C 10  substituted or unsubstituted branched alkenyl; 
 f) a C 3 -C 15  substituted or unsubstituted cycloalkyl; 
 g) a C 4 -C 15  substituted or unsubstituted branched cycloalkyl; 
 h) a C 4 -C 15  substituted or unsubstituted cycloalkenyl; 
 i) a C 5 -C 15  substituted or unsubstituted branched cycloalkenyl; 
 j) a C 6 -C 15  substituted or unsubstituted aryl; 
 k) a C 6 -C 22  substituted or unsubstituted heterocyclicalkyl; 
 l) a C 6 -C 22  substituted or unsubstituted heterocyclicalkenyl; 
 m) and mixtures thereof; 
 
         said R 5  and R 6  units may optionally, when taken together, form a substituted or unsubstituted ring comprising a ring moiety, said ring moiety comprising from 3 to 10 carbon atoms; 
         each R 7  is independently a substituted or unsubstituted hydrocarbyl unit; when taken together, any two geminal R 7  units form a carbonyl moiety, or when any two R 7  units covalently bind together, said R 7  units form a moiety selected from the group consisting of:
 i) a C 3 -C 6  spiroannulated ring; 
 ii) a heterocyclic aromatic ring comprising from 5 to 7 atoms; 
 iii) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms; 
 iv) a heterocyclic ring comprising from 5 to 7 atoms; 
 v) a non-heterocyclic ring comprising from 5 to 7 atoms; 
 vi) or mixtures thereof; and 
 
         the index m is an integer from 1 to 3. 
       
     
     
         10 . A composition comprising:
 a photo-activated pro-fragrance conjugate according to  claim 1 ; and   b) the balance carriers and adjunct ingredients.   
     
     
         11 . A photo-labile pro-fragrance conjugate delivery system comprising:
 a) from about 0.001% by weight, of a photo-activated pro-fragrance conjugate according to  claim 1 ; and   b) the balance carriers and adjunct ingredients.   
     
     
         12 . A laundry detergent comprising:
 a) from about 0.001% by weight, of a photo-activated pro-fragrance conjugate according to  claim 1 ;   b) from about 10% by weight, of a detersive surfactant; and   c) the balance carriers and adjunct ingredients.   
     
     
         13 . Perfume or fine fragrance comprising:
 a) from about 0.001% by weight, of a photo-activated pro-fragrance conjugate according to  claim 1 ;   b) from about 0.01% to about 99% by weight, of an admixture of fragrance raw materials; and   c) the balance carriers and adjunct ingredients.   
     
     
         14 . A hair shampoo or conditioner comprising:
 a) from about 0.001% by weight, of a photo-activated pro-fragrance conjugate according to  claim 1 ;   b) from about 0.01% to about 5% by weight, of an admixture of fragrance raw materials; and   c) the balance carriers and adjunct ingredients.