Ketal compounds and uses thereof

Abstract

Various esterified alkyl ketal ester or hydroxyalkyl ketal ester products are useful as components of organic polymer compositions. The ketal esters are produced in certain transesterifications between alkyl ketal esters and/or hydroxyalkyl ketal esters and polyols, aminoalcohols, polyamines and/or polycarboxylic acids. The products are excellent plasticizers for a variety of organic polymers, notable poly(vinyl chloride) plastisols. The products are also very good lubricants for many lubrication applications.

1 . A compound having a structure corresponding to structure I 
       
         
           
           
               
               
           
         
       
       wherein
 a is from 0 to 12; 
 b is 0 or 1; 
 each R 1  is independently hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group; 
 each R 2 , R 3 , and R 4  are independently methylene, alkylmethylene, or dialkylmethylene; 
 x is at least 1, y is 0 or a positive number and x+y is at least 2; 
 R 6  is a hydrocarbyl group or a substituted hydrocarbyl group; and 
 each Z is independently —O—, —NH— or —NR— where R is a hydrocarbyl group or a substituted hydrocarbyl group. 
 
     
     
         2 . The compound of  claim 1 , wherein each Z is —O—. 
     
     
         3 . The compound of  claim 1 , where y is from 0 to 2, x is at least 2. 
     
     
         4 . The compound of  claim 1 , wherein all a are 2, and all R 1  are methyl. 
     
     
         5 . The compound of  claim 4 , where y is 0 and x is 2. 
     
     
         6 . The compound of  claim 4 , wherein y is 1 and x is 1. 
     
     
         7 . A compound of  claim 1  which has the structure 
       
         
           
           
               
               
           
         
       
     
     
         8 . A compound of  claim 1  which has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         9 . A compound of  claim 1 , wherein R 6  contains one or more ether or ester groups. 
     
     
         10 . A compound of  claim 1 , wherein R 6  is C 2 -C 6  alkyl. 
     
     
         11 . A mixture comprising two or more compounds of  claim 1 . 
     
     
         12 . A composition comprising the compound of  claim 1  and an organic polymer. 
     
     
         13 . A composition comprising a mixture of  claim 11  and a polymer. 
     
     
         14 . The composition of  claim 12 , which has a glass transition temperature at least 5° C. lower than a glass transition temperature of the polymer. 
     
     
         15 . The composition of  claim 12 , which has a glass transition temperature at least 30° C. lower than a glass transition temperature of the polymer. 
     
     
         16 . The composition of  claim 12 , wherein the compound or mixture constitutes from 0.1 to 90% of the combined weight of the compound or mixture and the polymer. 
     
     
         17 . The composition of  claim 12 , wherein the polymer is a thermoplastic. 
     
     
         18 . The composition of  claim 12 , wherein the polymer is a thermoset. 
     
     
         19 . The composition of  claim 12 , wherein the polymer comprises a poly(vinyl chloride), polyhydroxyalkanoate, a poly(lactic acid), a polystyrene, a polyurethane, a polyurea, a polyurea-urethane, a polycarbonate, an acrylic polymer, a styrene-acrylic polymer, a vinyl-acrylic polymer, an ethylene-vinyl acetate polymer, a polyester, a polyamide, a polyether, a polybutadiene, an acrylonitrile-butadiene-styrene copolymer, a styrene-butadiene-styrene copolymer, a polyvinyl acetate, an elastomer, or homopolymers thereof, or random, graft, or block copolymers thereof, or blends or mixtures thereof. 
     
     
         20 . The composition of  claim 12 , wherein the composition forms a dispersed phase in a latex, a dispersion, or an emulsion. 
     
     
         21 . The composition of  claim 12 , wherein the compound is melt blended or solution blended with the polymer. 
     
     
         22 . The composition of  claim 12 , wherein the composition is a plastisol. 
     
     
         23 . The composition of  claim 22 , wherein at least a portion of the compound is in a liquid phase of the plastisol. 
     
     
         24 . The composition of  claim 12 , further comprising one or more crosslinkers, adjuvants, colorants, antifouling agents, tougheners, solvents, fillers, metal particulates, odor scavenging agents, lubricants, thermal stabilizers, light stabilizers including UV stabilizers, flame retardant additives, pigments, blowing agents, processing aids, impact modifiers, coalescing solvents, antioxidant or a combination of any two or more thereof. 
     
     
         25 . The composition of  claim 12 , further comprising one or more additives selected from the group consisting of dialkyl phthalates, trimethyl pentanyl diisobutyrate, dialkyl isophthalates, dialkyl terephthalates, alkyl benzyl phthalates, dialkyl adipates, trialkyl trimellitates, alkylyl trialkyl citrates, dialkyl azelates, dialkyl glutarates, dialkyl sebacates, dialkyl cyclohexanedicarboxylates, esters of pentaerythritol, esters of glycerol, fatty acid triglycerides, esters of fatty acids, glycol dibenzoates, epoxidized soybean oil, and mixtures thereof. 
     
     
         26 . An article comprising the composition of  claim 12 . 
     
     
         27 . A process for plasticizing a polymer comprising melt or solution blending a polymer and a plasticizing amount of at least one compound of  claim 1 . 
     
     
         28 . The process of  claim 27 , wherein compound constitutes from 0.1 to 90% of the combined weights of the compound and the polymer. 
     
     
         29 . A method for making an ester or amide compound according to  claim 1  comprising:
 a. contacting reagents comprising (A) one or more alkylketal esters having the structure 
 
       
         
           
           
               
               
           
         
         
           (B) a catalyst and (C) a polyol having the structure R 6 (OH) t  or a polyamine having the structure R 6 (NRH) t  or R 6 (NH 2 ) t  where R is a hydrocarbyl or substituted hydrocarbyl group and 
         
         b. effecting a reaction to form an alcohol and a compound of  claim 1 , wherein t=x+y and R 20  is a hydrocarbyl group or substituted hydrocarbyl group having up to 36 carbon atoms. 
       
     
     
         30 . The method of  claim 29 , wherein reagent (C) is a polyol having the structure R 6 (OH) t . 
     
     
         31 . The method of  claim 30 , wherein t is 2 and the mole ratio of the alkyl ketal ester to the polyol is in a range of 2:1 to 10:1. 
     
     
         32 . A method of making a compound of  claim 1  comprising:
 a. reacting a compound comprising a structure corresponding to 
 
       
         
           
           
               
               
           
         
       
       with a polyol comprising a structure corresponding to R 6 (OH) t  to form water and a compound comprising a structure corresponding to 
       
         
           
           
               
               
           
         
         b. adding a compound comprising a structure corresponding to 
       
       
         
           
           
               
               
           
         
       
       and
 c. effecting a reaction to form water and a compound having a structure corresponding to  claim 1 , wherein a, b, R 1 , R 2 , R 3 , R 4  and R 6  are as defined in  claim 1 , x is at least 1, y is zero or a positive number and t=x+y. 
 
     
     
         33 . A lubricant composition comprising an antioxidant and at least one compound of  claim 1 . 
     
     
         34 . A method of lubricating at least two contacting surfaces, the method comprising introducing the lubricant composition of  claim 33  between the two contacting surfaces.