# US 8,784,555 B2 · Surface active blocked isocyanates and coating compositions thereof

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- Number: US 8,784,555 B2
- Document ID: US8784555B2
- Status: Granted
- Kind: B2
- Application number: 13/054,828
- Filed: 2009-07-23
- Published: 2011-05-26
- Granted: 2014-07-22
- Earliest claimed: 2008-07-29
- Assignees: Axalta Coating Systems IP Co., LLC
- Applicants: Jun Lin
- Inventors: Jun Lin
- Web page: https://patentgrep.com/patent/US8784555B2

## CPC

- C09D 7/00: Features of coating compositions, not provided for in group C09D5/00 (driers C09F9/00); Processes for incorporating ingredients in coating compositions
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C07F 7/18: Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C08G 77/045: {containing less than 25 silicon atoms}
- C08G 77/26: nitrogen-containing groups
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D 183/04: Polysiloxanes
- C09J 183/04: Polysiloxanes
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

Disclosed herein is a surface active adhesion promoting agent and a coating composition comprising the surface active adhesion promoting agent. The adhesion promoting agent is a blocked isocyanate functional siloxane containing material. Addition of small amount of the adhesion promoting agent to a coating composition, especially clearcoat compositions, helps to provide adhesion to a variety of materials that may be subsequently applied to the coating composition.

## Claims

### Claim 1

A surface active adhesion promoting agent comprising at least a blocked isocyanate and a siloxane portion having at least two or more silicon atoms and a number average molecular weight in the range of from 500 to 4500, wherein said surface active adhesion promoting agent is of the formula;
A-Si(X)3-qRq
wherein q is 0, 1 or 2;
A is G-C(O)NH—R1 and is attached to the silicon atom through R1;
G is the residue of an isocyanate blocking agent;
each X is independently chosen from the group consisting of OR2, OY, OSi(X′)2A or a hydrolysable group; wherein at least one of X is OY or OSi(X′)2A;
Y is Si(Z)3-w(R3)w or Si(X′)2A;
each X′ is independently chosen from the group consisting of OR2, OY or a hydrolysable group;
each Z is independently chosen from the group consisting of OR4, OSi(X′)2A, OY, hydrolysable group or a silsesquioxane;
R1 is a divalent organic radical consisting of an alkyl group having from 3 to 4 carbon atoms;
each R, R2, R3 or R4 is independently chosen from the group consisting of C1 to C8 aliphatic group, C3 to C20 cycloaliphatic, alkylcycloaliphatic, cycloaliphaticalkyl group, C6 to C20 aryl group or a fluorine containing or perfluoro derivative thereof;
w is 0, 1 or 2; and
wherein A-Si(X)3-qRq has a molecular weight in the range of from 500 to 4500.

### Claim 2 (depends on 1)

The surface active adhesion promoting agent of claim 1 wherein each of R, R2, R3 or R4 is CH3.

### Claim 3 (depends on 1)

The surface active adhesion promoting agent of claim 1 wherein the blocking agent is a pyrazole.

### Claim 4

A coating composition comprising a surface active adhesion promoting agent wherein said surface active adhesion promoting agent comprises at least a blocked isocyanate and a siloxane portion having at least two or more silicon atoms and a number average molecular weight in the range of from 500 to 4500, wherein the surface active adhesion promoting agent is of the formula;
A-Si(X)3-qRq
wherein q is 0, 1 or 2;
A is G-C(O)NH—R1 and is attached to the silicon atom through R1;
G is the residue of an isocyanate blocking agent, wherein the blocking agent is chosen from the group selected from imidazole, 2-methyl imidazole, 4-methyl imidazole, pyrrole, pyrrolidine, morpholine, pyridine, piperidine, alkyl malonate, acetoacetic ester and cyanoacetic ester and a combination thereof;
each X is independently chosen from the group consisting of OR2, OY, OSi(X′)2A or a hydrolysable group; wherein at least one of X is OY or OSi(X′)2A;
Y is Si(Z)3-w(R3)w or Si(X′)2A;
each X′ is independently chosen from the group consisting of OR2, OY or a hydrolysable group;
each Z is independently chosen from the group consisting of OR4, OSi(X′)2A, OY, hydrolysable group or a silsesquioxane;
R1 is a divalent organic radical consisting of an alkyl group having from 3 to 4 carbon atoms;
each R, R2, R3 or R4 is independently chosen from the group consisting of C1 to C8 aliphatic group, C3 to C20 cycloaliphatic, alkylcycloaliphatic, cycloaliphaticalkyl group, C6 to C20 aryl group or a fluorine containing or perfluoro derivative thereof;
w is 0, 1 or 2; and
wherein A-Si(X)3-qRq has a molecular weight in the range of from 500 to 4500.

### Claim 5 (depends on 4)

The coating composition of claim 4, wherein said coating composition is substantially free from boron.

### Claim 6 (depends on 4)

The coating composition of claim 4 wherein each of R, R2, R3 or R4 is CH3.

### Claim 7 (depends on 4)

The coating composition of claim 4 wherein the isocyanate blocking agent is dimethylpyrazole.

### Claim 8 (depends on 4)

The coating composition of claim 4, wherein the surface active adhesion promoting agent is present in an amount of 0.5 to 7 percent by weight based on the total weight of the binder components of said coating composition.

### Claim 9 (depends on 4)

The coating composition of claim 4 wherein said coating composition is substantially free from boron.