N-alkyl lactam ethers, and compositions and uses thereof

Abstract

Described is a class of symmetrical and asymmetrical N-alkyl lactam ethers. One preferred ether is bis-N-ethyl pyrrolidone ether. Preferred compositions and uses of the ethers are in performance chemicals, personal care, and pharmaceutical fields, where they function a variety of roles, including as a solvent, solubilizer, freezing point depressor, diluent, extracting agent, cleaning agent, degreaser, absorbent and/or dispersion agent.

1 . An ether represented by the structure: 
       
         
           
           
               
               
           
         
         wherein: 
         said A 1  and A 2  are independently selected alkyl groups having 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between said 
       
       
         
           
           
               
               
           
         
          group and said 
       
       
         
           
           
               
               
           
         
          group; 
         said Q 1  and Q 2  are independently selected from the group consisting of functionalized and unfunctionalized alkyl and cycloalkyl groups and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; and 
         each said R is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl and cycloalkyl groups, and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; 
         with the provision that said ether is not: 
       
       
         
           
           
               
               
           
         
       
     
     
         2 . The ether according to  claim 1  wherein said A 1  and A 2  are the same. 
     
     
         3 . The ether according to  claim 2  represented by the structures: 
       
         
           
           
               
               
           
         
         wherein: 
         said Q 1  and Q 2  are independently selected from the group consisting of functionalized and unfunctionalized alkyl and cycloalkyl groups and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; and 
         each said R is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl and cycloalkyl groups, and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; 
         with the provision that in structures (A), (B), and (C) said Q 1  and Q 2  are not both ethyl and every said R is not hydrogen. 
       
     
     
         4 . The ether according to  claim 3  selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         and combinations thereof. 
       
     
     
         5 . The ether according to  claim 1  wherein said A 1  and A 2  are not the same. 
     
     
         6 . The ether according to  claim 5  represented by the structure: 
       
         
           
           
               
               
           
         
         wherein: 
         said Q 1  and Q 2  are independently selected from the group consisting of functionalized and unfunctionalized alkyl and cycloalkyl groups and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; and 
         each said R is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl and cycloalkyl groups and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms. 
       
     
     
         7 . The ether according to  claim 6  selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         and combinations thereof. 
       
     
     
         8 . A composition comprising an ether represented by the structure: 
       
         
           
           
               
               
           
         
         wherein: 
         said A 1  and A 2  are independently selected alkyl groups having 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between said 
       
       
         
           
           
               
               
           
         
          group and said 
       
       
         
           
           
               
               
           
         
          group; 
         said Q 1  and Q 2  are independently selected from the group consisting of functionalized and unfunctionalized alkyl and cycloalkyl groups and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; and 
         each said R is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl and cycloalkyl groups, and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms. 
       
     
     
         9 . The composition comprising an ether according to  claim 8  that has a form selected from the group consisting of: solids, semi-solids, liquids, gels, powders, granules, lozenges, tablets, patches, capsules, ointments, lotions, creams, suppositories, aerosols, syrups, elixirs, emulsions, non-aqueous suspensions, and aqueous suspensions. 
     
     
         10 . The composition according to  claim 9  wherein said ether has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The composition comprising an ether according to  claim 8  that is a skin lotion, skin créme, skin ointment, skin salve, anti-aging créme, moisturizer, deodorant, tanning agent, sun care composition, 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. 
     
     
         12 . The composition according to  claim 11  wherein said sun care composition comprises one or more UV absorbers selected from the group consisting of: p-aminobenzoic acid (PABA), Padimate O, ensulizole, cinoxate, benzophenone-3, enzophenone-8, homosalate, meradimate, octocrylene, 2-ethylhexyl-p-methoxycinnamate, octyl salicylate, sulisobenzone, trolamine salicylate, avobenzone, ecamsule, titanium dioxide, zinc oxide, 4-methylbenzylidene, Tinosorb M, neo heliopan AP, mexoryl XL, benzophenone-9, Uvinul T150, Uvinul A Plus, Uvasorb HEB, Parsol SLX, isopentenyl-4-methoxycinnamate, and combinations thereof. 
     
     
         13 . The composition according to  claim 11  wherein said ether has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         14 . The composition comprising an ether according to  claim 8  that is an acaricide, battery, cleaning, coating, encapsulation, fragrance, imaging, ink, oilfield, laundry pre-wash/stain remover, bird repellant, insect repellent, insecticide, termite-control, herbicide, slimacide, fungicide, medical, membrane, molded part, polishing, adhesive, hose/tubing, packaging, printing, or wood-care composition. 
     
     
         15 . The composition according to  claim 14  wherein said ether has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         16 . The composition comprising an ether according to  claim 8  that is an anti-acne, pain reliever, fever reducer, fungicide, liceacide, or disinfecting composition. 
     
     
         17 . The composition according to  claim 16  wherein said ether has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         18 . The composition according to  claim 8  further comprising at least one additional ingredient selected from the group consisting of: active ingredients, pharmaceutical active ingredients, UV absorbers, emollients, liquid carriers, surfactants, emulsifiers, rheology modifiers, lubricants, diluents, gas hydrate inhibitors, anti-agglomerants, humectants, anti-oxidants, preservatives, cleaning agents, pigments, dyes, inks, solvents, freezing point depressors, salts, thickeners, peroxides, oils, polymers, surfactants, emulsifiers, and combinations thereof. 
     
     
         19 . The composition according to  claim 18  wherein said polymers comprises one or more units selected from the group consisting of acrylamides, acrylates, anhydrides, allyl alcohols, cinnamyls, epoxides, methacrylates, styrenes, triazoles, vinyl acetates, vinyl acrylamides, vinyl amides, vinyl carbonates, vinyl ethers, vinyl lactams, vinyl chlorides, vinyl imidazoles, vinyl pyridines, vinyl silanes, vinyl sulfones, maleimides, maleates, fumarates, and combinations thereof. 
     
     
         20 . A use of an ether represented by the structure: 
       
         
           
           
               
               
           
         
         wherein 
         said A 1  and A 2  are independently selected alkyl groups having 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between said 
       
       
         
           
           
               
               
           
         
          group and said 
       
       
         
           
           
               
               
           
         
          group; 
         said Q 1  and Q 2  are independently selected from the group consisting of functionalized and unfunctionalized alkyl and cycloalkyl groups and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms; and 
         each said R is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl and cycloalkyl groups, and combinations thereof, wherein any of the beforementioned groups may be with or without heteroatoms. 
       
     
     
         21 . The use of an ether according to  claim 20  as a: solvent, solubilizer, stabilizer, freezing point depressor, paint stripper, cleaning agent, degreaser, electronics processing aide, anti-agglomerant, gas hydrate inhibitor, diluent, welding solvent for plastics, plasticizer, extracting agent, reaction medium, penetration enhancer, and/or dispersion agent. 
     
     
         22 . The use according to  claim 21  wherein said ether has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         23 . The use according to  claim 21  wherein said freezing point depressor is used on aircraft, roads, windshields, windows, or crops. 
     
     
         24 . The use according to  claim 21  wherein said solvent partially or completely replaces at least one solvent selected from the group consisting of: N-methyl-2-pyrrolidone, 1,1,1-trichloroethane, trichloroethylene, 1,1-dichloro-2,2-difluoroethylene, tetrachloroethylene, methylene chloride, chlorobenzene, acetone, methyl ether ketone, toluene, benzene, derivatives thereof, and combinations thereof. 
     
     
         25 . The use according to  claim 21  wherein said electronics processing aide removes marker dyes, soldering flux residue, photoresists, coatings or cured urethanes; solubilizes polyvinylidene fluoride; and/or strips epoxy flash. 
     
     
         26 . The use according to  claim 21  wherein said paint stripper partially or completely removes paint or graffiti. 
     
     
         27 . The use according to  claim 21  wherein said cleaner cleans hard surfaces, metal, rubber, plastic parts, electronics, computer components, paint-spray booths, aircraft equipment, molds, reaction vessels, reaction conduits, kitchen appliances, kitchen equipment, tile, fruit, or vegetables. 
     
     
         28 . The use according to  claim 21  wherein said reaction medium is used for C—C linkage reactions and/or polymerizations.