US 6,306,923 B1 · Ultraviolet or visible light polymerizable and/or crosslinkable maleimide-functional coating compositions

Abstract

These compositions comprise at least one compound (A) and at least one compound (B) containing electron enriched or depleted olefinic double bonds, respectively. The compound(s) (A) are prepolymers consisting in the reaction products of at least one maleic anhydride of formula (I); of at least one compound (II) having at least one —NH2 function and at least another function F selected among —OH, —NH2,—NH—, —COOH, —COOR3 or —OOCR3; of at least one compound (III) capable of forming the chain of the prepolymers by polycondensation and/or polyaddition, compound(s) (II) having first reacted with anhydride(s) (I) opening the maleic anhydride rings with formation of maleamic acid functions (f′), the latter having then been at least partially closed again into maleimides N-substituted by groups functionalized by a function F, the functionalities and proportions of compounds (II) and (III) having been selected in order to exclude any gelation of the reaction medium. R1, R2=H, C1-C12 alkyl or halogen, R3=C1-C5 alkyl.

Compositions polymerizable and/or crosslinkable by ultraviolet or visible light, comprising at least one compound (A) containing electron depleted olefinic double bonds;

and at least one compound (B) containing electron enriched olefinic double bonds, wherein said at least one compound (A) is selected from the group consisting of prepolymers having maleimide functional groups (f):
wherein each of Rand R2 represents independently H, a C1-C12 alkyl group, or a halogen,
being prepared by reacting:
at least one maleic anhydride represented by formula (I):
at least one amino functional compound (II) having at least one —NH2 functional group and at least one other functional group F selected from the group consisting of —OH, —NH2, —NH—, —COOH,
wherein
R3 is a C1-C5 alkyl group;
at least one compound (III) to form the chain of the prepolymers by polycondensation and/or polyaddition, said compounds (III) being defined as:
when the N-substituted maleimide has a functional group F which is —OH, NH2 or —NH—, said compound (III) comprises
(a) at least one compound selected from the group consisting of a polyacid, a cyclic anhydride;
and mixtures thereof;
(b) at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyamine, and a polyisocyanate;
or
(c) at least one polyisocyanate;
or at least one polyisocyanate and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyacid, a cyclic anhydride, and a polyamine;
when the N-substituted maleimide has a functional group F which is —COOH, said compound (III) comprises
(a) at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, and a polyamine;
or
(b) at least one compound selected from a polyol a mono- or a polyfunctional epoxy and a polyamine;
and at least one compound selected from a polyacid, a cyclic anhydride and a polyisocyanate;
or
(c) of at least one polyisocyanate;
or
(d) at least one polyisocyanate and at least one compound selected from a polyol, a mono-or polyfunctional epoxy, a polyacid, a cyclic anhydride and a polyamine;
when the N-substituted maleimide has a functional group F which is —C(O)—O—R3 said compound (III) comprises
(a) at least one compound allowing transesterification, having a functional group —OH and at least one other functional group selected from the group consisting of —OH, —NH— and —COOH;
wherein when said other functional group is —OH or —NH—, the compounds (III) are
(i) at least one compound selected from the group consisting of a polyacid and a cyclic anhydride and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyamine, and a polyisocyanate;
or
(ii) at least one polyisocyanate;
or
(iii) at least one polyisocyanate and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyacid, a cyclic anhydride and a polyamine;
and
wherein when said other functional group is —COOH, the compounds (III) comprise
(i) at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy and a polyamine;
or
(ii) at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy and a polyamine;
and at least one compound selected from a polyacid, a cyclic anyhydride and a polyisocyanate;
or
(iii) at least one polyisocyanate;
or
(iv) a polyisocyanate and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyacid, a cyclic anhydride and a polyamine.
when the N-substituted maleimide has a functional group F which is —O—C(O)—R3, the compounds (III) comprise
(a) at least one compound allowing transesterification, having an acid functional group and at least one other functional group selected from the group consisting of —OH, —NH— and —COOH;
wherein
when said another functional group is —OH or —NH, the compounds (III) comprise
(i) at least one compound selected from the group consisting of a polyacid and cyclic anhydride;
and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyamine, and a polyisocyanate;
or
(ii) at least one polyisocyanate;
or
(iii) a polyisocyanate and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy a polyacid, a cyclic anhydride and a polyamine;
when said other functional group is —COOH, the compounds (III) comprise
(i) at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, and a polyamine;
or
(ii) at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy and a polyamine;
and at least one compound selected from the group consisting of a polyacid, a cyclic anhydride and a polyisocyanate;
or
(iii) at least one polyisocyanate;
or
(iv) at least one polyisocyanate and at least one compound selected from the group consisting of a polyol, a mono- or polyfunctional epoxy, a polyacid, a cyclic anhydride and a polyamine;
said compounds (II) having first reacted with said maleic anhydrides (I) in order to open the maleic anhydride rings to form F functional compounds having groups of the formula (f′):
heating to form maleimides N-substituted by groups having a functional group F;
and
reacting said maleimides N-substituted by groups having a functional group F with at least one polyfunctional compound III, said compound III having functional groups reactive with said functional group F, without gelation of the reaction medium.

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Ultraviolet or visible light polymerizable and/or crosslinkable maleimide-functional coating compositions

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Ultraviolet or visible light polymerizable and/or crosslinkable maleimide-functional coating compositions

Life of this patent

Abstract

Claims27