Uv-absorbing compounds with at least one reactive hydrogen

Abstract

UV-absorbing compounds are provided that have at least one reactive hydrogen. These compounds have structures: wherein the generic notations have meanings as described herein. Also provided are formulations comprising a UV-absorbing compounds.

We claim: 
     
         1 . A compound having the structure: 
       
         
           
           
               
               
           
         
         wherein 
         each R 1  and R 2  is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms; 
         each R 31 , R 32 , R 33 , R 34  and R 35  is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms with the proviso that at least one of said R 31 , R 33 , and R 35  has a structure —X-Q-A; 
         each R 41 , R 42 , R 43 , R 44  and R 45  is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms with the proviso that at least one of said R 41 , R 42 , R 43 , R 44  and R 45  is non-hydrogen; 
         each X is independently selected from the group consisting of O, NR 1 , and S; 
         each Q is independently selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; and 
         each A is independently selected from the group consisting of OH, NHR 1 , and SH. 
       
     
     
         2 . The compound according to  claim 1  having the structure: 
       
         
           
           
               
               
           
         
         wherein 
         X is selected from the group consisting of O, NR 1 , and S; 
         Q is selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; 
         A is selected from the group consisting of OH, NHR 1 , and SH; 
         each R 1  is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl; and 
         R 43  is a functionalized or unfunctionalized alkyl. 
       
     
     
         3 . The compound according to  claim 2  wherein said Q is a residue of a compound selected from the group consisting of: diols, diamines, thio alcohols, amino alcohols, polyols, polyether polyols, polyacetal polyethers, polyalkylene polyamines, polyetheramines, polyalkylene imines, polysaccharides, and combinations thereof. 
     
     
         4 . The compound according to  claim 3  having a structure selected from the group consisting of: 
       
         
           
           
               
               
           
         
         and    
       
     
     
         5 . A compound having the structure: 
       
         
           
           
               
               
           
         
         wherein 
         each R 1 , R 2 , R 3 , R 4  and R 5  is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms with the proviso that at least one of said R 1 , R 2 , R 3 , R 4  and R 5  has a structure 
       
       
         
           
           
               
               
           
         
         X is selected from the group consisting of O, NR 7 , and S; 
         Q is selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; 
         A is selected from the group consisting of OH, NHR 7 , and SH; 
         each R 6  and R′ 6  are the same or different and independently selected from the group consisting of functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms; and 
         each R 7  is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms. 
       
     
     
         6 . The compound according to  claim 5  having the structure: 
       
         
           
           
               
               
           
         
         wherein: 
         X is selected from the group consisting of O, NR 7 , and S; 
         Q is selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; 
         A is selected from the group consisting of OH, NHR 7 , and SH; 
         R 6  and R′ 6  are the same and selected from the group consisting of functionalized and unfunctionalized alkyl; and 
         each R 7  is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl optionally having one or more heteroatoms. 
       
     
     
         7 . The compound according to  claim 6  wherein said Q is a residue of a compound selected from the group consisting of: diols, diamines, thio alcohols, amino alcohols, polyols, polyether polyols, polyacetal polyethers, polyalkylene polyamines, polyetheramines, polyethylene imines, polysaccharides, and combinations thereof. 
     
     
         8 . The compound according to  claim 7  having a structure selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . A compound having the structure: 
       
         
           
           
               
               
           
         
         wherein 
         each R 11 , R 12 , R 13 , R 14  and R 15  is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms with the proviso that at least one of said R 12  and R 14  has a structure 
       
       
         
           
           
               
               
           
         
       
       and at least two of said R 11 , R 13 , and R 15  is selected from the group consisting of hydroxyl, alkoxyl, and combinations thereof;
 each R 21 , R 22 , R 23 , R 24  and R 25  is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms; 
 each X is independently selected from the group consisting of O and NR 16 ; 
 each Q is independently selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; 
 each A is independently selected from the group consisting of OH, NHR 16 , and SH; and 
 each R 16  is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms. 
 
     
     
         10 . The compound according to  claim 9  having the structure: 
       
         
           
           
               
               
           
         
         wherein 
         X is selected from the group consisting of O and NR 16 ; 
         Q is selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; 
         A is selected from the group consisting of OH, NHR 16 , and SH; 
         R 23  is selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl; and 
         each R 16  is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl. 
       
     
     
         11 . The compound according to  claim 10  wherein said Q is a residue of a compound selected from the group consisting of: diols, amino alcohols, polyols, polyether polyols, polyacetal polyethers, polyalkylene polyamines, polyetheramines, polyethylene imines, polysaccharides, and combinations thereof. 
     
     
         12 . The compound according to  claim 11  having a structure selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         13 . A formulation comprising at least one compound of  claim 1 . 
     
     
         14 . The formulation according to  claim 13  that is a personal care formulation, pharmaceutical, food, adhesive, coating, electronic, ink, paper, paint, polish, printing, construction, energy, oilfield, lubricant, industrial, biocide, preservative, agrochemical, or wood-care formulation. 
     
     
         15 . The formulation according to  claim 14  wherein said personal care formulation is a skin lotion, skin crème, skin ointment, skin salve, anti-aging crème, moisturizer, deodorant, tanning agent, sun block, sunscreen, foundation, concealer, eyebrow pencil, eye shadow, eye liner, mascara, rouge, finishing powder, lipstick, lip gloss, nail polish, make-up remover, nail polish remover, shampoo, rinse-off conditioner, leave-on conditioner, hair styling gel, hair mousse, hair spray, styling aide, hair color, or hair color remover. 
     
     
         16 . The formulation according to  claim 13  that further comprises at least one additional ingredient selected from the group consisting of: propellants, lower molecular weight alcohols, UV absorbers, and combinations thereof. 
     
     
         17 . The formulation according to  claim 16  wherein said UV active is selected from the group consisting of: 2,4-bis-(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-s-triazine, aminobenzoic acid; 2-aminobenzophenone; amyl dimethyl PABA; bemotrizinol; benzophenone-3; benzophenone-4; benzophenone-9; 2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol; 2-(2H-benzotriazole-2-yl)-4-methylphenol; 2-(2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol; bis-benzoxazoyl phenyl ethylhexyl amino triazine; 3-benzylidene camphor sulfonic acid; CAS number 152261-33-1; N,N′-bisformyl-N,N′-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-hexamethylendiamine; bisoctrizole; 2-[(p-(tert-butylamido)-anilino]-4,6,-bis[(p-(2′-ethylhexyl-1′-oxycarbonyl)-anilino]-1,3,5-triazine; 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol; 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol; camphor benzalkonium methosulfate; diethanolamine p-methoxycinnamate; diethylaminohydroxybenzoylhexylbenzoate; diethylhexyl butamido triazone; digalloyl trioleate; dioxybenzone; disodium phenyl dibenzimidazole tetrasulfonate; drometrizole trisiloxane; ecamsule; ensulizole; ethyl 4-bis(hydroxypropyl)aminobenzoate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; ethylhexyl triazone; beta-2-glucopyranoxypropylhydroxybenzophenone; glyceryl aminobenzoate; homomenthyl salicylate; [2-hydroxy-4-(octyloxy)phenyl](phenyl)methanone; 2-[bis(2-hydroxyethyl)amino]ethyl salicylate; (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; lawsone with dihydroxyacetone; meradimate; methoxycinnamido propyl hydroxy sultaine menthyl anthranilate; meradimate; methyl-2-aminobenzoate; oxybenzone; 2-phenylbenzimidazole-5-sulfonic acid (and its potassium, sodium and triethanolamine salts); sulisobenzone; bis-(2,2,6,6-tetramethyl-4-piperidyl)-sebacate; sterically hindered oligomeric amine, triethanolamine salicylate, and blends thereof. 
     
     
         18 . The formulation according to  claim 16  wherein said propellant is selected from the group consisting of: dimethyl ether, hydrofluorocarbon 152A, n-butane, iso-butane, n-propane, iso-pentane, compressed air, liquified nitrogen, nitrous oxide, liquified carbon dioxide, and combinations thereof. 
     
     
         19 . The formulation according to  claim 16  wherein said lower molecular weight alcohol is selected from the group consisting of: methanol, ethanol, 1-propanol, 2-propanol, n-butanol, sec-butanol, tert-butanol, and combinations thereof.