Oligomeric amino-containing aminolysis products of polymethacrylates or polyacrylates, and epoxy resin coating compositions containing such aminolysis products as curing agents

Claim 2

A solid product of aminolysis by an alkylene polyamine of the formula: ##STR8## wherein R 1 is an alkylene group having 2 to 6 carbon atoms, R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4, of an alkyl methacrylate ester oligomer having a number average molecular weight from about 600 to 10,000, selected from the group consisting of: (1) homopolymers of a (C 1 -C 4 ) alkyl methacrylate and (2) copolymers exclusively of at least two alkyl methacrylates in which a (C 1 -C 4 ) alkyl methacrylate is the major component, the product having N-amino-substituted methacrylamide units of the formula: ##STR9## wherein R 1 , R, and n are as defined hereinabove, in the oligomer chain.

Claim 3

A solid product according to claim 1 having 0.5 to 10 milliequivalents of amine per gram thereof.

Claim 4

A solid product of aminolysis, by a polyamine of formula I as defined in claim 1, of a vinyl oligomer having a number average molecular weight from about 600 to about 10,000 selected from the group consisting of: (1) homopolymers of a (C 1 -C 4 ) alkyl methacrylate, (2) copolymers of at least two alkyl methacrylates in which a (C 1 -C 4 ) alkyl methacrylate is the major component, (3) homopolymers of a (C 1 -C 4 ) alkyl acrylate, (4) copolymers exclusively of at least two alkyl acrylates in which a (C 1 -C 4 ) alkyl acrylate is the major component, (5) copolymers of an alkyl acrylate with an alkyl methacrylate containing at least 35 mole percent of at least one (C 1 -C 6 ) alkyl acrylate or methacrylate, and (6) copolymers of (a) at least one monomer selected from alkyl acrylates and alkyl methacrylates with (b) at least one monomer selected from acrylic acid, methacrylic acid, styrene, and vinyltoluene, such copolymers containing at least 35 mole percent of at least one (C 1 -C 6 ) alkyl acrylate or methacrylate, the product having N-amide-substituted amide units of the formula: ##STR10## wherein R o is H or CH 3 , R 1 is an alkylene group having 2 to 6 carbon atoms, and R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4 and also having carboxylic units selected from methacrylic acid and acrylic acid units in the oligomer chain, the product having 0.5 to 10 milliequivalents of amine per gram and 0.25 to 5 milliequivalents of carboxylic acid per gram, at least some of the carboxylic acid units being in the form of an internal salt of amino groups on the amide units.

Claim 5

A solid product according to claim 3 in which a substantial portion of the oligomer chain consists of hydrophobic units of styrene or vinyltoluene inert to hydrolysis or aminolysis.

Claim 6

A coating composition having a binder consisting essentially of (a) a product of aminolysis by an alkylene polyamine of the formula ##STR11## wherein R 1 is an alkylene group having 2 to 6 carbon atoms, R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4, of a vinyl oligomer having a number average molecular weight from about 600 to about 10,000 selected from the group consisting of (1) homopolymers of a (C 1 -C 4 ) alkyl methacrylate, (2) copolymers of at least two alkyl methacrylates in which a (C 1 -C 4 ) alkyl methacrylate is the major component, (3) homopolymers of a (C 1 -C 4 ) alkyl acrylate, (4) copolymers exclusively of at least two alkyl acrylates in which a (C 1 -C 4 ) alkyl acrylate is the major component, (5) copolymers of an alkyl acrlate with an alkyl methacrylate containing at least 35 mole percent of at least one (C 1 -C 6 ) alkyl acrylate or methacrylate, and (6) copolymers of (a) at least one monomer selected from alkyl acrylates and alkyl methacrylates with (b) at least one monomer selected from acrylic acid, methacrylic acid, styrene, and vinyltoluene, such copolymers containing at least 35 mole percent of at least one (C 1 -C 6 ) alkyl acrylate or methacrylate, the product having N-amine-substituted amide units of the formula ##STR12## wherein R o is H or CH 3 , R 1 is an alkylene group having 2 to 6 carbon atoms, and R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4 and also having carboxylic units selected from methacrylic acid and acrylic acid units in the oligomer chain, the product having 0.5 to 10 milliequivalents of amine per gram and 0.25 to 5 milliequivalents of carboxylic acid per gram, at least some of the carboxylic acid units being in the form of an internal salt of amine groups on the amide units and (b) a resin-forming polyepoxide, the proportion of aminolysis product used in the composition providing from 25 to 75 equivalents of amine with respect to 75 to 25 equivalents of epoxide groups provided in the polyepoxide.

Claim 7

A coating composition having a binder consisting essentially of (a) a product of aminolysis by an alkylene polyamine of the formula ##STR11## wherein R 1 is an alkylene group having 2 to 6 carbon atoms, R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4, of a vinyl oligomer having a number average molecular weight from about 600 to about 10,000 selected from the group consisting of (1) homopolymers of a (C 1 -C 4 ) alkyl methacrylate, (2) copolymers of at least two alkyl methacrylates in which a (C 1 -C 4 ) alkyl methacrylate is the major component, (3) homopolymers of a (C 1 -C 4 ) alkyl acrylate, (4) copolymers exclusively of at least two alkyl acrylates in which a (C 1 -C 4 ) alkyl acrylate is the major component, (5) copolymers of an alkyl acrlate with an alkyl methacrylate containing at least 35 mole percent of at least one (C 1 -C 6 ) alkyl acrylate or methacrylate, and (6) copolymers of (a) at least one monomer selected from alkyl acrylates and alkyl methacrylates with (b) at least one monomer selected from acrylic acid, methacrylic acid, styrene, and vinyltoluene, such copolymers containing at least 35 mole percent of at least one (C 1 -C 6 ) alkyl acrylate or methacrylate, the product having N-amine-substituted amide units of the formula ##STR12## wherein R o is H or CH 3 , R 1 is an alkylene group having 2 to 6 carbon atoms, and R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4 and also having carboxylic units selected from methacrylic acid and acrylic acid units in the oligomer chain, the product having 0.5 to 10 milliequivalents of amine per gram and 0.25 to 5 milliequivalents of carboxylic acid per gram, at least some of the carboxylic acid units being in the form of an internal salt of amine groups on the amide units and (b) a resin-forming polyepoxide, the proportion of aminolysis product used in the composition providing from 25 to 75 equivalents of amine with respect to 75 to 25 equivalents of epoxide groups provided in the polyepoxide.

Claim 8

A composition according to claim 5 adapted to preparation and distribution as a two-package system in which one package contains the aminolysis product and the other comprises the resin-forming polyepoxide.

Claim 9

A composition according to claim 5 comprising a water-immiscible solvent for the aminolysis product and the polyepoxide.

Claim 10

A composition according to claim 5 comprising a water-miscible solvent for the aminolysis product and the polyepoxide.

Claim 11

A composition according to claim 5 which contains a volatile aldehyde or ketone as at least part of the solvent thereof.

Claim 12

A composition according to claim 6 wherein the package containing the aminolysis product also contains a volatile ketone or aldehyde.

Claim 13

A solid product according to claim 2 wherein it also contains in the oligomer chain 0.25 to 5 milliequivalents of carboxyl per gram, at least some of the carboxyl being in the form of an internal salt of amine groups on the amide units.

Claim 14

A coating composition having a binder consisting essentially of a product of aminolysis by an alkylene polyamine of the formula ##STR13## wherein R 1 is an alkylene group having 2 to 6 carbon atoms, R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4, of an alkyl methacrylate ester oligomer having a number average molecular weight from about 600 to 10,000, selected from the group consisting of: (1) homopolymers of a (C 1 -C 4 ) alkyl methacrylate and (2) copolymers exclusively of at least two alkyl methacrylates in which a (C 1 -C 4 ) alkyl methacrylate is the major component, the product having N-amino-substituted methacrylamide units of the formula ##STR14## wherein R 1 , R, and n are as defined hereinabove, in the oligomer chain and (b) a resin-forming polyepoxide, the proportion of aminolysis product in the composition providing 25 to 75 equivalents of amine and the polyepoxide providing 75 to 25 equivalents of epoxide groups.

Claim 15

A coating composition having a binder consisting essentially of a product of aminolysis by an alkylene polyamine of the formula ##STR13## wherein R 1 is an alkylene group having 2 to 6 carbon atoms, R is H or R 1 NH 2 , and n is 0 or an integer from 1 to 4, of an alkyl methacrylate ester oligomer having a number average molecular weight from about 600 to 10,000, selected from the group consisting of: (1) homopolymers of a (C 1 -C 4 ) alkyl methacrylate and (2) copolymers exclusively of at least two alkyl methacrylates in which a (C 1 -C 4 ) alkyl methacrylate is the major component, the product having N-amino-substituted methacrylamide units of the formula ##STR14## wherein R 1 , R, and n are as defined hereinabove, in the oligomer chain and (b) a resin-forming polyepoxide, the proportion of aminolysis product in the composition providing 25 to 75 equivalents of amine and the polyepoxide providing 75 to 25 equivalents of epoxide groups.

Claim 16

A coating composition according to claim 12 in which the product of aminolysis has 0.5 to 10 milliequivalents of amine per gram thereof.

Claim 17

A coating composition according to claim 5 in which a substituted portion of the oligomer chain consists of hydrophobic units of styrene or vinyltoluene inert to hydrolysis or aminolysis.

Claim 18

A coating composition according to claim 13 in which the product of aminolysis contains 0.25 to 5 milliequivalents of carboxyl per gram, at least some of the carboxyl being in the form of an internal salt of amine groups on the amide units.

Claim 19

An aqueous coating composition according to claim 13 adapted to be used as an adhesive or as a protective coating in which the aminolysis product is water-dispersible and the polyepoxide is a water-dispersible resin-forming polyepoxide containing at least two vic-epoxy groups and having an epoxy equivalency of about 100 to 1025.

Claim 20

An aqueous coating composition according to claim 14 adapted to be used as an adhesive or as a protective coating in which the aminolysis product is water-dispersible and the polyepoxide is a water-dispersible resin-forming polyepoxide containing at least two vic-epoxy groups and having an epoxy equivalency of about 100 to 1025.

Claim 21

An aqueous coating composition according to claim 5 adapted to be used as an adhesive or as a protective coating in which the aminolysis product is water-dispersible and the polyepoxide is a water-dispersible resin-forming polyepoxide containing at least two vic-epoxy groups and having an epoxy equivalency of about 100 to 1025.