Process for acrylamidoacylation of alcohols

Claim 2

A process comprising the steps of a) reacting an alkenyl azlactone, a hydroxy functional compound, and a catalytically effective amount of a bicyclic amidine or a trivalent phosphorus compound, and b) isolating the resulting acrylamide or methacrylamide functional monomer, oligomer, or polymer, and c) optionally, curing the resulting acrylamide or methacrylamide functional monomer oligomer, or polymer.

Claim 3

A process according to claim 1 for preparing an acrylamide functional compound having the formula R OH) n-p A p wherein R represents a monomeric, oligomeric, or polymeric organic group containing hydroxyl functionality, said group having a valence of n and a number average molecular weight of up to 5,000,000; n is a positive integer of at least one and represents the valence of R; p is a positive integer between 1 and n inclusively; and A is an acrylamide group having the formula wherein R¹ is hydrogen or methyl; R² is a single bond or R² is a methylene group which can be substituted by one or two alkyl groups having 1 to 6 carbon atoms or a phenyl group; and R³ and R⁴ are independently hydrogen, an alkyl group of 1 to 20 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, an aryl group of 5 to 12 ring atoms, or an arenyl group of 6 to 26 carbon and heteroatoms, or R³ and R⁴ taken together with the carbon atom to which they are joined form a carbocyclic ring of 4 to 12 ring atoms, said process comprising the steps of a) reacting a mixture comprising 1) a hydroxy functional compound having the formula R OH) n wherein R and n are as defined above, 2) one to n equivalents of an alkenyl azlactone of general Formula II: wherein n, R¹, R², R³, R⁴ are as defined above, and 3) an effective amount of a catalyst selected from the group consisting of a) bicyclic amidines and b) trivalent phosphorus compounds, each of which optionally can be bound to a polymer, to produce said acrylamide functional compound, 4) optionally, at least one of a) a nonreactive solvent or diluent, b) an effective amount of an antioxidant, and c) a free radical inhibitor, and b) isolating the resulting acrylamide or methacrylamide functional monomer, oligomer, or polymer.

Claim 4

The process according to claim 2 wherein R is derived from the group consisting of monomeric, oligomeric, and polymeric alcohols.

Claim 5

The process according to claims 2 and 3 wherein said alcohol is selected from the group consisting of polyether polyols, polyester polyols, polysiloxane polyols, polycarbonate polyols, hydroxy functional polyacrylic and polymethacrylic ester polymers, phenolic resins, polymers and copolymers of hydroxy functional vinyl monomers, polymers and copolymers of vinyl esters, cellulose and modified cellulose polymers, and phenoxy polymers.

Claim 6

The process according to claims 1 to 4 wherein said azlactone is selected from the group selected from 4,4-dimethyl-2-ethenyl-2-oxazolin-5-one, 4,4-dimethyl-2-isopropenyl-2-oxazolin-5-one, 2-ethenyl-4-methyl-4-phenyl-2-oxazolin-5-one, 2-ethenyl-4,4-pentamethylene-2-oxazolin-5-one, 4,4-diphenyl-2-isopropenyl-2-oxazolin-5-one, 2-ethenyl-4-ethyl-4-methyl-2-oxazolin-5-one, and 4,4-dimethyl-2-ethenyl-4,5-dihydro-1,3-oxazin-6-one.

Claim 7

The process according to claims 1 to 5 wherein said bicyclic amidine has the formula wherein R⁵ and R⁶ independently are alkylene groups of 2 to 12 carbon atoms, and optionally at least one of said R⁵ and R⁶ alkylene groups is substituted by at least one aryl group having 5 to 12 ring atoms containing up to 3 S, N, and O atoms, or by at least one alkyl group having 1 to 20 carbon atoms, R⁷ is an alkyl group of 1 to 20 carbon atoms or aryl group of 5 to 12 ring atoms containing up to 3 S, N, and O atoms wherein said R⁷ aryl group optionally is substituted by one to three atoms and groups selected from the group consisting of halogen atoms, lower alkyl groups, lower alkoxy groups, N,N-di (lower alkyl) amino, nitro, cyano, and lower alkyl carboxylic ester groups, wherein lower is C₁ to C₄, and m is 0 or 1.

Claim 8

The process according to claims 1 to 6 wherein said trivalent phosphorus compound has the formula R⁸R⁹R¹⁰P wherein R⁸, R⁹, and R¹⁰ independently are selected from the group consisting of H, an alkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 12 ring atoms and up to 3 S, N, and O heteroatoms, an arenyl group having 6 to 26 carbon atoms and up to 3 S, N, and O heteroatoms, a lower alkoxy group having 1 to 4 C atoms, and a lower dialkyl amino group having 2 to 8 C atoms.

Claim 9

The process according to claims 1 to 7 wherein said bicyclic amidine is selected from the group consisting of 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene.

Claim 10

The process according to claims 1 to 8 wherein said trivalent phosphorus compound is selected from the group consisting of trimethylphosphine, triethylphosphine, triethylphosphite, tributylphosphine, trioctylphosphine, dimethylphenylphosphine, diphenylmethylphosphine, diphenylphosphine, dipropylphosphine, tris(dimethylamino)phosphine, 1,2-bis(di-n-propylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, diethylmethoxyphosphine, and triphenylphosphine.

Claim 11

The process according to claims 1 to 9 wherein said catalyst is present in an amount in the range of 0.1 mole percent to 50 mole percent based on azlactone.

Claim 12

A composition of matter comprising a) acrylamide functional compound having the formula R OH) n-p A p wherein R, A, n, and p are as defined in claim 2, and b) a catalytically effective amount of a bicyclic amidine or a trivalent phosphorus compound, said composition of matter optionally being cured.