Resins based on ketones and aldehydes, having improved solubility properties and low color numbers

Abstract

A resin is based on ketones and aldehydes and is prepared in methanol or ethanol in the presence of a phase transfer catalyst. The resin features a very broad solubility and low intrinsic color.

1 . A resin comprising reacted units of one or more cycloaliphatic ketones and at least one of an aliphatic or aromatic aldehyde, wherein the ketone and the aldehyde are reacted in the presence of a phase transfer catalyst of formula (A)  
       
         
           
           
               
               
           
         
       
       where 
 X is a nitrogen atom or a phosphorus atom,  
 R 1  is a phenyl radical or a benzyl radical,  
 R 2 , R 3 , and R 4  are identical or different and are each an alkyl radical having 1 to 22 carbon atoms in the carbon chain, a phenyl radical, or a benzyl radical, and  
 Y is the anion of an organic acid, inorganic acid or a hydroxide ion that is soluble in ethanol and has a Gardner color number of less than 4 measured on a 50% solution in ethyl acetate.  
 
     
     
         2 . The resin as claimed in  claim 1 , wherein the phase transfer catalyst is present in an amount of from 0.01 to 15% by mass based on the total weight of the ketone.  
     
     
         3 . The resin as claimed in  claim 1 , wherein the phase transfer catalyst is present in an amount of from 0.1 to 10% by mass based on the total weight of the ketone.  
     
     
         4 . The resin as claimed in  claim 1 , wherein the phase transfer catalyst is present in an amount of from 0.1 to 5% by mass based on the total weight of the ketone.  
     
     
         5 . The resin as claimed in  claim 1 , wherein the phase transfer catalyst is at least one selected from the group consisting of cetyldimethylbenzylammonium chloride, tributylbenzylammonium chloride, trimethylbenzylammonium chloride, trimethylbenzylammonium iodide, triethylbenzylammonium chloride, triethylbenzylammonium iodide, triphenylbenzylphosphonium chloride, triphenylbenzylphosphonium iodide and a mixture thereof.  
     
     
         6 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of cyclohexanone and at least one alkyl-substituted cyclohexanone having one or more C 1 -C 8  alkyl radicals.  
     
     
         7 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of at least one selected from the group consisting of 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone, and 3,3,5-trimethylcyclohexanone, and cyclohexanone.  
     
     
         8 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of cyclohexanone, 4-tert-butylcyclohexanone, and 3,3,5-trimethylcyclohexanone.  
     
     
         9 . The resin as claimed in  claim 1 , wherein the resin further comprises reacted units of one or more ketones selected from the group consisting of acetone, acetophenone, methyl ethyl ketone, 2-heptanone, 3-pentanone, methyl isobutyl ketone, cyclopentanone, picacolone, cyclododecanone, a mixture of 2,2,4-and 2,4,4-trimethylcyclopentanone, cycloheptanone, and cyclooctanone.  
     
     
         10 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of one or more branched or unbranched aldehyde.  
     
     
         11 . The resin as claimed in  claim 1 , wherein the aldehyde is selected from the group consisting of formaldehyde, acetaldehyde, n-butyraldehyde, iso-butyraldehyde, dodecanal and benzaldehyde.  
     
     
         12 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of at least formaldehyde.  
     
     
         13 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of one or more further monomers in a minor amount.  
     
     
         14 . The resin as claimed in  claim 13 , wherein the further monomer is at least one selected from the group consisting of phenol, urea and derivatives thereof.  
     
     
         15 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of substituted and unsubstituted cyclohexanone in a molar ratio of from 0.1:0.9 to 0.9:0.1.  
     
     
         16 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of substituted and unsubstituted cyclohexanone in a molar ratio from 0.2:0.8 to 0.8:0.2.  
     
     
         17 . The resin as claimed in  claim 1 , wherein the resin comprises reacted units of substituted and unsubstituted cyclohexanone in a molar ratio from 0.3:0.7 to 0.7:0.3.  
     
     
         18 . The resin as claimed in  claim 1 , wherein a ratio between the ketone component and the aldehyde component is from 1:0.9 to 1:4.  
     
     
         19 . The resin as claimed in  claim 1 , wherein a ratio between the ketone component and the aldehyde component is from 1:1 to 1:2.  
     
     
         20 . The resin as claimed in  claim 1 , having a Gardner color number of less than 4.  
     
     
         21 . The resin as claimed in  claim 1 , having a Gardner color number of less than 2.  
     
     
         22 . The resin as claimed in  claim 1 , having a Gardner color number of less than 1.5.  
     
     
         23 . The resin as claimed in  claim 1 , having a melting range between 30 and 150° C.  
     
     
         24 . The resin as claimed in  claim 1 , having a melting range between 40 and 100° C.  
     
     
         25 . The resin as claimed in  claim 1 , having a melting range between 50 and 100° C.  
     
     
         26 . The resin as claimed in  claim 1 , having an OH number of from 0 to 200 mg KOH/g.  
     
     
         27 . The resin as claimed in  claim 1 , having an OH number of from 0 to 150 mg KOH/g.  
     
     
         28 . The resin as claimed in  claim 1 , having an OH number of from 0 to 100 mg KOH/g.  
     
     
         29 . The resin as claimed in  claim 1 , wherein the resin is completely soluble as a 10% strength or 50% strength by weight solution in ethanol and white spirit to give a clear solution.  
     
     
         30 . A process for preparing the resin claimed in  claim 1 , which comprises 
 reacting the ketone and the aldehyde in methanol or ethanol as auxiliary solvent in the presence of a phase transfer catalyst .    
     
     
         31 . The process as claimed in  claim 30 , wherein the phase transfer catalyst is a compound of the formula (A)  
       
         
           
           
               
               
           
         
       
       where 
 X is a nitrogen atom or a phosphorus atom,  
 R 1  is a phenyl radical or a benzyl radical,  
 R 2 , R 3 , and R 4  are identical or different and are each an alkyl radical having 1 to 22 carbon atoms in the carbon chain, a phenyl radical, or a benzyl radical, and  
 Y is the anion of an organic acid, inorganic acid or a hydroxide ion.  
 
     
     
         32 . The process for preparing a resin based on ketones and aldehydes as claimed in  claim 30 , wherein the phase transfer catalyst is present in an amount of from 0.01 to 15% by mass, based on the total weight of the resin.  
     
     
         33 . A composition comprising the resin as claimed in  claim 1 .  
     
     
         34 . The composition of  claim 33 , selected from the group consisting of a coating composition, a printing ink, a pigment paste, a tinting paste, a ball point paste, a graphic ink, a polish, an adhesive, a sealant and an insulating material.