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

Patent metadata

Field	Value
Publication number	US-10294389-B2
Application number	US-6767306-A
Country	US
Kind code	B2
Filing date	Sep 21, 2006
Priority date	Sep 22, 2005
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

Disclosed herein is a thermally curable mixture, comprising 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); and at least one compound (B) which can be reacted by transesterification, transamidation, self-condensation of N-hydroxyalkylamino groups, self-condensation of N-alkoxyalkylamino groups, transacctalization of N-alkoxyalkylamino groups, acctalization of N-hydroxyalkylamino groups, or a combination thereof. Also disclosed is a process for making the thermally curable mixture, and a cured material comprising the product of thermally curing the mixture.

First claim

What is claimed is:

1. A thermally curable, liquid 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 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-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 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.

2. The thermally curable, liquid mixture of claim 1 , wherein the at least one phosphonic diester (A) is selected from the group consisting of acyclic phosphonic diesters and cyclic phosphonic diesters, and wherein the at least one diphosphonic diester (A) is selected from the group consisting of acyclic diphosphonic diesters and cyclic diphosphonic diesters.

3. The thermally curable, liquid mixture of claim 2 , comprising at least one acyclic phosphonic diester having the general formula I:

wherein R 1 and R 2 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 R 1 or R 2 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 R 1 and R 2 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.

4. The thermally curable, liquid mixture of claim 1 , further comprising at least one additive (D).

5. A cured material, comprising the product of thermally curing a mixture according to claim 1 .

6. The cured material of claim 5 , comprising moldings, sheets, coatings, adhesive layers, seals, or a combination thereof.

7. The thermally curable, liquid mixture of claim 3 , wherein R 1 and R 2 are identical or different from one another and are selected from the group consisting of phenyl, methyl, and ethyl.

8. The thermally curable, liquid mixture of claim 7 , wherein R 1 and R 2 are phenyl.

9. The thermally curable, liquid mixture of claim 1 , wherein at least one additive (D) is present as the separate component (II).

10. The thermally curable, liquid mixture of claim 4 , wherein the 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) is present in component (II).

11. The thermally curable, liquid mixture of claim 1 , wherein the at least one first compound (B) is a (co)polymer of olefinically unsaturated monomers.

12. The thermally curable, liquid mixture of claim 1 , wherein the 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) is present in component (I).

13. 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.

14. The thermally curable, liquid mixture of claim 3 , wherein at least one acyclic phosphonic diester having the general formula I and R 1 and R 2 are identical or different from one another 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 R 1 or R 2 and the oxygen atom of the O—P group.

15. The process of claim 13 , further comprising mixing at least one additive (D).

16. The process of claim 13 , further comprising:
mixing the at l

Assignees

• Poppe Andreas
• Westhoff Elke
• Gebauer Beate
• Mayenfels Peter
• Basf Coatings Gmbh

Inventors

• Poppe Andreas
• Westhoff Elke
• Gebauer Beate
• Mayenfels Peter

Classifications

• C09D175/04 Primary

  Polyurethanes · CPC title

• C08K5/524

  Esters of phosphorous acids, e.g. of H3PO3 · CPC title

• C09D167/00

  Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers · CPC title

• C08L61/00

  Compositions of condensation polymers of aldehydes or ketones (with polyalcohols C08L59/00; with polynitriles C08L77/00); Compositions of derivatives of such polymers · CPC title

• C08K5/527

  Cyclic esters · CPC title