POLYMERS CONTAINING CYCLOBUTANEDIOL AND 2,2 BIS(HYDROXYMETHYL) AlKYLCARBOXYLIC ACID

Abstract

Disclosed is a polyester composition comprising a polyester further comprising (a) at least one cyclobutanediol; (b) at least one 2,2-bis(hydroxymethyl)alkylcarboxylic acid and/or a derivative thereof; and (c) at least one polycarboxylic acid and/or a derivative thereof. This polyester composition can be useful in several areas including but not limited to thermoplastic polyesters, curable polyesters, inks, paints, composites, coating compositions, for example, waterborne coatings, water-dispersible coatings, solvent-borne coatings, and powder coatings.

1 . A polyester for use in a coating composition comprising a residues of:
 (a) at least one 2,2,4,4-tetraalkylcyclobutane-1,3-diol defined by the following formula:   
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , and R 4  are each independently a C 1  to C 8  alkyl radical, wherein each of said alkyl radicals is selected from the group consisting of a linear alkyl radical, a branched alkyl radical, and a linear and branched alkyl radical; 
         (b) at least one 2,2-bis(hydroxymethyl)alkylcarboxylic acid and/or a derivative thereof; and 
         (c) at least one polycarboxylic acid, different from (b), and/or a derivative thereof. 
       
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . The polyester of  claim 1  wherein said 2,2,4,4-tetraalkylcyclobutane-1,3-diol is 2,2,4,4-tetramethylcyclobutane-1,3-diol. 
     
     
         5 . The polyester of  claim 1  wherein said 2,2-bis(hydroxymethyl)alkylcarboxylic acid is selected from at least one of 2,2-bis(hydroxymethyl)propionic acid, 2,2-bis(hydroxymethyl)butanoic acid, 2,2-bis(hydroxymethyl)pentanoic acid, and 2,2-bis(hydroxymethyl)hexanoic acid. 
     
     
         6 . The polyester of  claim 1  wherein said 2,2-bis(hydroxymethyl)alkylcarboxylic acid is 2,2-bis(hydroxymethyl)propionic acid. 
     
     
         7 . The polyester of  claim 1  wherein said 2,2,4,4-tetraalkylcyclobutane-1,3-diol is 2,2,4,4-tetramethylcyclobutane-1,3-diol and said 2,2-bis(hydroxymethyl)alkylcarboxylic acid is 2,2-bis(hydroxymethyl)propionic acid. 
     
     
         8 . The polyester of  claim 1  wherein at least one said polycarboxylic acid or derivative thereof (c) comprises naphthalenedicarboxylic, 1,2-cyclohexanedicarboxylic, 1,3-cyclohexanedicarboxylic, 1,4-cyclohexanedicarboxylic, phthalic, terephthalic, isophthalic, fumaric, succinic, adipic, glutaric, azelaic, sebacic, resorcinol diacetic, diglycolic, 4,4′-oxybis(benzoic), biphenyldicarboxylic, 4,4′-methylenedibenzoic, trans-4,4′-stilbenedicarboxylic, or sulfoisophthalic acids. 
     
     
         9 . The polyester of  claim 1  further comprising at least one additional polyhydroxyl component. 
     
     
         10 . The polyester of  claim 9  wherein the polyester comprises at least one additional polyhydroxyl component in an amount in the range of from 0.01 to 80 mole percent, based on the total moles of diols equaling 100 mole %. 
     
     
         11 . The polyester of  claim 10  wherein said at least one polyhydroxyl component is selected from 2,2-dimethyl-1,3-propanediol, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, 2,2,4-trimethyl-1,3-pentanediol, hydroxypivalyl hydroxypivalate, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2,4,4-tetramethyl-1,6-hexanediol, 1,10-decanediol, 1,4-benzenedimethanol, hydrogenated bisphenol A, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, 1,1,1-trimethylol propane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof. 
     
     
         12 . (canceled) 
     
     
         13 . The polyester of  claim 1  or  7  wherein said polyester has an acid number in the range of from about 10 to about 100 mg KOH/g and a hydroxyl number in the range of from about 0.10 to about 200 mg KOH/g. 
     
     
         14 . The polyester of  claim 1  or  7  wherein said polyester has an acid number in the range of from about 10 to about 100 mg KOH/g and a hydroxyl number in the range of from about 5 to about 200 mg KOH/g. 
     
     
         15 . The polyester of  claim 1  or  7  further comprising a crosslinking agent. 
     
     
         16 . The polyester of  claim 15  wherein said crosslinking agent is selected from the group consisting of amino resins, phenolic resins, isocyanate resins, epoxy resins, blocked isocyanate resins, β-hydroxy alkylamides, and epoxidized phenolic resins. 
     
     
         17 . The polyester of  claim 1  or  7  having a number average molecular weight of from 500 to 15,000. 
     
     
         18 . The polyester of  claim 1  or  7  having a number average molecular weight of from 750 to 7,500. 
     
     
         19 . The polyester of  claim 1  or  7  having a number average molecular weight of from 1000 to 5000. 
     
     
         20 . The polyester of  claim 1  or  7  further comprising an organic cosolvent. 
     
     
         21 .- 28 . (canceled) 
     
     
         29 . A polyester comprising:
 (a) residues of at least one 2,2,4,4-tetraalkylcyclobutane-1,3-diol in an amount in the range of from about 5 to about 95 mole percent;   (b) residues of 2,2-bis(hydroxymethyl)propionic in an amount in the range of from about 1 to about 50 mole percent;   (c) optionally, residues of at least one additional polyhydroxyl component in an amount in the range of from 0 to 65 mole percent, and   (d) residues of at least one polycarboxylic acid different than (b) and/or a derivative thereof,   wherein the total moles of diols in the polyester equal 100 mole %; and the total moles of acids in the polyester equal 100 mole %; and   wherein said polyester has an acid number in the range of from about 10 to about 100 mg KOH/g and a hydroxyl number in the range of from about 0.10 to about 200 mg KOH/g.   
     
     
         30 . A polyester for use in a coating composition comprising:
 (a) residues of at least one 2,2,4,4-tetraalkylcyclobutane-1,3-diol in an amount in the range of from about 30 to about 95 mole percent;   (b) residues of 2,2-bis(hydroxymethyl)propionic acid in an amount in the range of from about 5 to about 30 mole percent;   (c) optionally, residues of at least one additional polyhydroxyl component in an amount in the range of from 0 to 65 mole percent;   (d) residues of at least one polycarboxylic acid and/or a derivative thereof,   wherein the total moles of diols in the polyester equal 100 mole %; and the total moles of acids in the polyester equal 100 mole %; and   wherein said polyester has an acid number in the range of from about 10 to about 100 mg KOH/g and a hydroxyl number in the range of from about 5 to about 200 mg KOH/g.   
     
     
         31 . A coating composition comprising:
 (a) at least one polyester comprising residues of—
 (i) at least one 2,2,4,4-tetraalkylcyclobutane-1,3-diol; 
 (ii) 2,2-bis(hydroxymethyl)dimethylolpropionic acid; and 
 (iii) at least one polycarboxylic acid and/or a derivative thereof; and 
   (b) at least one crosslinking agent or at least one neutralizing agent, or combinations thereof;   wherein, if present, said crosslinking agent is selected from the group consisting of amino resins, phenolic resins, isocyanate resins, epoxy resins, blocked isocyanate resins, β-hydroxy alkylamides, and epoxidized phenolic resins and wherein if present said neutralizing agent is selected from the group consisting of ammonia, trimethylamine, diethylamine, monoethanolamine, monoisopropanolamine, morpholine, ethanolamine, diethanolamine, triethanolamine, 2-amino-2-methyl-1-propanol, N,N-dimethylethanolamine, N, N-diethylethanolamine, N-methyldiethanolamine, sodium oxide, potassium oxide, magnesium oxide, calcium oxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, calcium carbonate, magnesium bicarbonate, alkali metal borate compounds and their hydrates, sodium phosphate, potassium biphosphate, and sodium pyrophosphate.