Coating composition comprising an acetal-functional binder

• US 7,045,579 B2
• Filed: 03/07/2003
• Issued: 05/16/2006
• Est. Priority Date: 03/07/2002
• Status: Expired due to Fees

• Current Assignee: Akzo Nobel N.V. (Nouryon BV)
• Original Assignee: Akzo Nobel N.V. (Nouryon BV)
• Inventors: Van Oorschot, Josephus Christiaan, Van Den Berg, Keimpe Jan, Hobel, Klaus, Mensink, Marcel Johannes Antonius, Hulsbos, Edith, Raghosing, Kenny Abdoel Nassier
• Primary Examiner(s): Wu, David W.
• Assistant Examiner(s): Lee, Rip A.
• Application Number:
  US10/383,600
• Publication Number:
  US 20030207104A1
• Time in Patent Office: 1,166 Days
• Field of Search: 525/350, 524/874, 524/355.R, 524/355.N, 524/355.EN
• US Class Current: 525/350
• CPC Class Codes: C07C 237/08 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 271/16 to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• CPC Class Codes: C08G 18/0866 the dispersing or dispersed phase being an aqueous medium
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/3271 Hydroxyamines
• CPC Class Codes: C08G 18/3819 having nitrogen
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/4036 Mixtures of compounds of group C08G18/56 with other macromolecular compounds
• CPC Class Codes: C08G 18/423 containing cycloaliphatic groups
• CPC Class Codes: C08G 18/8108 having only one isocyanate or isothiocyanate group
• CPC Class Codes: C08G 18/834 by compounds containing a thiol group
• CPC Class Codes: C08K 5/37 Thiols
• CPC Class Codes: C08K 5/372 Sulfides , e.g. R-(S)x-R'
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• CPC Class Codes: C08L 31/02 Homopolymers or copolymers of esters of monocarboxylic acids
• CPC Class Codes: C08L 57/04 Copolymers in which only the monomer in minority is defined
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 75/10 from polyacetals
• CPC Class Codes: C09D 129/14 : Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
• CPC Class Codes: C09D 175/04 : Polyurethanes
• CPC Class Codes: C09D 175/10 : from polyacetals
• CPC Class Codes: Y10T 428/28 : Web or sheet containing structurally defined element or component and having an adhesive outermost layer

Abstract

The invention relates to a coating composition comprising an acetal-functional binder and a thiol-functional cross-linker, wherein the acetal-functional binder is represented by the following formula

wherein P is a binder backbone, K is a divalent and/or trivalent organic moiety having 1 to 30 carbon atoms and having one or two links to the binder backbone, A is selected from oxygen, sulphur, and NR^VII, wherein R^VII is hydrogen or an alkyl group with 1 to 4 carbon atoms, m is an integer from 1 to 50, n is an integer from 1 to 10, and R and R′ may be the same or different and represent alkyl groups with 1 to 4 carbon atoms. In a further aspect, the invention relates to acetal-functional binders, acetal-functional monomers, a process for the preparation of said monomers, coating compositions comprising said acetal-functional binders, and to a process for the preparation of a coating composition comprising an acetal-functional polyurethane dispersion and a thiol-functional cross-linker.

Claims

1. A coating composition comprising:

a) an acetal-functional binder, and

b) a thiol-functional cross-linker,

wherein the acetal-functional binder is represented by formula II

2. The coating composition according to claim 1 wherein K is

3. The coating composition according to claim 1 wherein K is a divalent organic moiety comprising an —

O-bond linked to the binder backbone and the individual moieties of K may be the same or different and are the moieties represented by (i) the structure of formula IIIa or (ii) the structure of formula IIIb,

4. The coating composition according to claim 1 wherein the binder is an acetal-functional polyurethane and wherein the individual moieties of K in formula II comprise di- and trivalent moieties, and the individual moieties of K are linked to the binder backbone via —

O-bonds and are the moieties represented by (i) the structure of formula IIIa, (ii) the structure of formula IIIb, (iii) the structure of formula Via or (iv) the structure of formula VIb

5. The coating composition according to claim 1 wherein the binder is an acetal-functional polyaddition polymer and wherein K is divalent and linked to the binder backbone via an —

O-bond, and the individual moieties of K may be the same or different and are the moieties represented by (i) the structure of formula IXa or (ii) the structure of formula IXb,

6. The coating composition according to claim 2 wherein the acetal-functional binder is obtained obtained by amidation of esters with aminoacetals of formula Ia

7. The coating composition according to claim 6 wherein the acetal-functional binder is a compound represented by formula X

8. The coating composition according to claim 1 wherein the cross-linker is a thiol-functional polyurethane or esterification reaction product of a polyol and a mercapto carboxylic acid.

9. The coating composition according to claim 1 wherein the molar ratio of acetal-functional groups to thiol-functional groups is in the range between 1.0:

0.1 and 1.0;

3.5.

10. The coating composition according to claim 1 wherein the acetal-functional binder is a polyurethane or polyaddition polymer.

11. The coating composition according to claim 1 wherein the coating composition is solvent borne.

12. The coating composition according to claim 11 wherein the coating composition contains at most 10 weight-% of added organic solvent and which is liquid.

13. The coating composition according claim 1 wherein the coating composition is water borne.

14. A coated substrate, which has been coated with a composition according to claim 1.

15. A method of coating which comprises applying the coating composition according to claim 1 to a substrate, wherein the substrate is an automobile or a large transportation vehicle.

16. An adhesive composition comprising:

a) an acetal-functional binder, and

b) a thiol-functional cross-linker,

wherein the acetal-functional binder is represented by formula II