Azlactone-functional compounds and curable compositions containing same

Claim 1

An azlactone-functional compound having the formula wherein R 1 is hydrogen, chlorine or a methyl group; R 2 is a single bond or a methylene or ethylene group, the last two of which can be substituted by alkyl groups having 1 to 6 carbon atoms or phenyl groups; R 3 and R 4 are independently an alkyl or cycloalkyl group having 1 to 12 carbon atoms, an aryl or aralkyl group having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; X is a nucleophilic group selected from in which R5 is a hydrocarbyl group selected from (1) an alkyl or cycloalkyl group having 1 to 18 carbon atoms optionally substituted by at least one cyano, halo, ether, ester, keto, silyl, or sulfide group having 1 to 10 carbon atoms, or (2) an aryl or aralkyl group having 6 to 12 carbon atoms, optionally substituted by at least one cyano, halo, ether, keto, ester, silyl, or sulfide group having 1 to 10 carbon atoms; R is a mono or polyvalent organic group that has a valence of n and is the residue of a nucleophilic group-substituted compound, (HX) n R, in which X is defined above, the residue having a molecular weight up to 20,000, R being selected from (1) an aliphatic group having 2 to 20 carbon atoms and an aryl group having up to 20 carbon atoms, these groups optionally having one to four catenary heteroatoms of oxygen, nitrogen or sulfur, (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and'(6) polysiloxane, all optionally including at least one non-nucleophilic or nucleophilic group; and n is an integer having a value of one to six.

Claim 6

A method for preparing an azlactone-functional compound according to Claims 1 to 4 comprising the steps: 1) admixing (a) one to n gram moles of at least one alkenyl azlactone having the formula: wherein R 1 is hydrogen, chlorine or a methyl group; R 2 is a single bond or a methylene or ethylene group, the last two of which can be substituted by alkyl groups having 1 to 6 carbon atoms or phenyl groups; R 3 and R 4 are independently an alkyl or cycloalkyl group having 1 to 12 carbon atoms, an aryl or aralkyl group having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; (b) one gram mole of at least one nucleophilic group-substituted compound having the formula: wherein X is a nucleophilic group selected from in which R 5 is a hydrocarbyl group selected from (1) an alkyl or cycloalkyl group having 1 to 18 carbon atoms, optionally substituted by at least Q ne cyano, halo, ether, keto, ester, silyl, or sulfide group having 1 to 10 carbon atoms or (2) an aryl or aralkyl group having 6 to 12 carbon atoms optionally substituted by at least one cyano, halo, ether, keto, ester, silyl, or sulfide group having 1 to 10 carbon atoms; R is an organic group that has a valence of n and is the residue of a nucleophilic group-substituted compound, (HX) n R, in which X is defined above, the residue having a molecular weight up to 20,000; and n is an integer having a value of one to six, with the proviso that when X is ―S―, then from 0.001 to 5 percent by weight based on total weight of alkenyl azlactone of an acid catalyst having a pK a less than 5.0 is added; 2) allowing the mixture to react at 0 to 100°C until the reaction is.complete.

Claim 7

A method for preparing a polyamide resin comprising the steps of: 1) admixing 0.8 to 1.2 equivalents of (a) an azlactone-functional compound according to Claims 1 to 4 with (b) one equivalent of at least one nucleophilic group-functional chain-extending or crosslinking agent wherein R 6 is an organic group that has a valence of m and is the residue of a nucleophilic group-substituted chain-extending or crosslinking agent R6(YH)m, R 6 being selected from a) mono- and polyvalent aliphatic and aromatic groups having 2 to 20 carbon atoms and optionally one to four catenary heteroatoms selected from oxygen, nitrogen, and sulfur, b) mono- and polyvalent groups selected from polyoxyalkylene, polyester, polyolefin, polyacrylate, and polysiloxane having a molecular weight up to 500,000, both a) and b) groups being optionally substituted by at least one non-nucleophilic group selected from cyano, halo, ester, ether, keto, nitro, silyl, and sulfide, wherein Y is in which R 7 is hydrogen or a lower alkyl group of one to four carbon atoms, and m is an integer having a value of 1 to 20,000; 2) allowing the mixture to react at 0°C to 300°C.