Use of phosphonic acid diesters and diphosphonic acid diesters and thermally curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters

A process for preparing a thermally curable, liquid mixture, comprising:

• mixing:
• compounds (A) in an amount of 0.1 to 20 wt. %, wherein (A) comprises:
• at least one phosphonic diester (A), at least one diphosphonic diester (A), or at least one phosphonic diester and at least one diphosphonic diester (A),
• at least one first compound (B) comprising at least two reactive functional groups comprising hydroxyl groups, which is selected from the group consisting of addition resins, condensation resins, and (co)polymers of olefinically unsaturated monomers;
• and
• at least one second compound (B) comprising N-hydroxyalkyamino groups, N-alkoxyalkylamino groups, or a combination thereof, which is an amino resin and can be reacted by transesterification, transamidation, self-condensation of N-hydroxyalkylamino groups, self-condensation of N-alkoxyalkylamino groups, transacetalization of N-alkoxyalkylamino groups, acetalization of N-hydroxyalkylamino groups, or a combination thereof;
• and
• at least one polyisocyanate (C) comprising at least two free isocyanate groups;
• and
• homogenizing the resultant mixture,
• wherein the thermally curable, liquid mixture is a two-component or multi-component coating system, the two-component or multi-component coating system comprising the at least one first compound (B) comprising at least two reactive functional groups as a separate component (I) and the at least one polyisocyanate (C) as a separate component (II);
• wherein a proportion of (B):(C) is in the range of 0.01 to 100, wherein (B) includes the total of the at least one first compound (B) comprising at least two reactive functional groups and the at least one second compound (B) comprising N-hydroxyalkylamino groups, N-alkoxyalkylamino groups, or a combination thereof;
• and
• wherein the two-component or multi-component coating system is substantially water-free.

A thermally curable mixture, comprising:

• compounds (A) in an amount of 0.1 to 20 wt. %, wherein (A) comprises:
• at least one phosphonic diester (A), at least one diphosphonic diester (A), or at least one phosphonic diester and at least one diphosphonic diester (A);
• at least one first compound (B) comprising hydroxyl groups, which is selected from the group consisting of addition resins, condensation resins, and (co)polymers of olefinically unsaturated monomers;
• and at least one second compound (B) comprising N-hydroxyalkylamino groups, N-alkoxyalkylamino groups, or a combination thereof, which is an amino resin and can be reacted by transesterification, transamidation, self-condensation of N-hydroxyalkylamino groups, self-condensation of N-alkoxyalkylamino groups, transacetalization of N-alkoxyalkylamino groups, acetalization of N-hydroxyalkylamino groups, or a combination thereof;
• and
• at least one polyisocyanate (C) comprising at least two free isocyanate groups;
• wherein the at least one phosphonic diester is a cyclic phosphonic diester having the general formula II:
• the at least one diphosphonic diester is an acyclic diphosphonic diester having the general formula III:
• (R1—O)(O)PH—O—PH(O)(O—R2) (III);
• or
• a cyclic diphosphonic diester having the general formula IV:
• wherein R1 and R2 are identical or different from one another and are selected from the group consisting of:
• substituted and unsubstituted alkyl- having 1 to 20 carbon atoms, cycloalkyl- having 3 to 20 carbon atoms, and aryl- having 5 to 20 carbon atoms, the hyphen symbolizing in each case the covalent bond between a carbon atom of the radical R1 or R2 and the oxygen atom of the O—P group;
• substituted and unsubstituted alkylaryl-, arylalkyl-, alkylcycloalkyl-, cycloalkylalkyl-, arylcycloalkyl-, cycloalkylaryl-, alkylcycloalkylaryl-, alkylarylcycloalkyl-, arylcycloalkylalkyl-, arylalkylcycloalkyl-, cycloalkylalkylaryl-, and cycloalkylarylalkyl-, the alkyl, cycloalkyl-, and aryl groups therein each containing the above-recited number of carbon atoms and the hyphen symbolizing in each case the covalent bond between a carbon atom of the radical R1 and R2 and the oxygen atom of the O—P group;
• and
• substituted and unsubstituted radical- of the above-recited kind, containing at least one heteroatom selected from the group consisting of oxygen atom, sulfur atom, nitrogen atom, phosphorus atom, and silicon atom, the hyphen symbolizing the covalent bond between a carbon atom of the radical and the oxygen atom of the O—P group;
• and
• wherein R3 and R4 are identical or different from one another and are selected from the group consisting of:
• substituted and unsubstituted, divalent alkyl- having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, and aryl- having 5 to 20 carbon atoms, the hyphen symbolizing in each case the covalent bond between a carbon atom of the radical R3 or R4 and the oxygen atom of the O—P group;
• substituted and unsubstituted, divalent alkylaryl-, arylalkyl-, alkylcycloalkyl-, cycloalkylalkyl-, arylcycloalkyl-, cycloalkylaryl-, alkylcycloalkylaryl-, alkylarylcycloalkyl-, arylcycloalkylalkyl-, arylalkylcycloalkyl-, cycloalkylalkylaryl-, and cycloalkylarylalkyl-, the alkyl, cycloalkyl-, and aryl groups therein each containing the above-recited number of carbon atoms and the hyphen symbolizing in each case the covalent bond between a carbon atom of the radical R3 and R4 and the oxygen atom of the O—P group;
• and
• substituted and unsubstituted, divalent radical- of the above-recited kind, containing at least one heteroatom selected from the group consisting of oxygen atom, sulfur atom, nitrogen atom, phosphorus atom, and silicon atom, the hyphen symbolizing the covalent bond between a carbon atom of the radical and the oxygen atom of the O—P group;
• and
• wherein Z is a covalent bond between an atom of the radical R3 and an atom of the radical R4 or is a divalent linking group selected from the group consisting of oxygen atom, substituted and unsubstituted sulfur atom, substituted nitrogen atom, substituted phosphorus atom, substituted silicon atom, substituted and unsubstituted alkyl having 1 to 10 carbon atoms,
• cycloalkyl having 3 to 10 carbon atoms, and aryl having 5 to 10 carbon atoms, said alkyl, cycloalkyl, and aryl being free from heteroatoms or containing at least one heteroatom selected from the group consisting of oxygen atom, sulfur atom, nitrogen atom, phosphorus atom, and silicon atom,
• wherein the thermally curable, liquid mixture is a two-component or multi-component coating system, the two-component or multi-component coating system comprising the at least one compound (B) as a separate component (I) and the at least one polyisocyanate (C) as a separate component (II);
• wherein a proportion of (B):(C) is in the range of 0.1:100 to 1:10, wherein (B) includes the total of the at least one first compound (B) comprising at least two reactive functional groups and the at least one second compound (B) comprising N-hydroxyalkylamino groups, N-alkoxyalkylamino groups, or a combination thereof;
• and
• wherein the two-component or multi-component coating system is substantially water-free.

A thermally curable, liquid mixture, comprising:

• compound (A) in an amount of 0.1 to 20 wt. %, wherein compound (A) comprises:
• at least one acyclic phosphonic diester having the general formula I:
• wherein R1 and R2 are identical or different from one another and are selected from the group consisting of:
• substituted and unsubstituted alkyl- having 1 to 20 carbon atoms, cycloalkyl- having 3 to 20 carbon atoms, and aryl- having 5 to 20 carbon atoms, the hyphen symbolizing in each case the covalent bond between a carbon atom of the radical R1 or R2 and the oxygen atom of the O—P group;
• at least one first compound (B) comprising a hydroxyl-functional (co)polymer of olefinically unsaturated monomers;
• at least one second compound (B) comprising an amino resin;
• at least one polyisocyanate (C) comprising at least two free isocyanate groups;
• wherein the thermally curable, liquid mixture is a two-component or multi-component coating system, the two-component or multi-component coating system comprising the at least one first compound (B) as a separate component (I) and the at least one polyisocyanate (C) as a separate component (II);
• a proportion of (B):(C) is in the range of 0.01 to 100, wherein (B) includes the total of the at least one first compound (B) and the at least one second compound (B);
• the at least one acyclic phosphonic diester compound (A) is present in component (II);
• and
• the two-component or multi-component coating system is substantially water-free.