Air curing polymer compositions

• US 5,559,192 A
• Filed: 06/06/1995
• Issued: 09/24/1996
• Est. Priority Date: 12/21/1990
• Status: Expired due to Term

• Current Assignee: Rohm and Haas Company (Dow, Inc.)
• Original Assignee: Rohm and Haas Company (Dow, Inc.)
• Inventors: Bors, Daniel A., Lavoie, Alvin C., Emmons, William D.
• Primary Examiner(s): REDDICK, MARIE L
• Application Number:
  US08/467,347
• Time in Patent Office: 476 Days
• Field of Search: 524/398, 524/435, 524/502, 524/517, 524/525, 524/529, 524/531, 524/534, 524/523, 524/533, 525/206, 525/208, 525/193, 525/195, 525/196, 525/298, 525/300, 525/312, 525/313, 525/327.3, 525/328.6, 525/370, 525/371, 525/378, 525/379, 525/380, 525/231, 525/303 , 525/220, 525/245, 525/328.9, 525/223, 523/400, 523/437
• US Class Current: 525/300
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08F 220/1804 C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
• CPC Class Codes: C08F 220/283 and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
• CPC Class Codes: C08F 246/00 Copolymers in which the nature of only the monomers in minority is defined
• CPC Class Codes: C08F 2810/20 leading to a crosslinking, either explicitly or inherently
• CPC Class Codes: C08F 2810/30 leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
• CPC Class Codes: C08F 2810/50 wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
• CPC Class Codes: C08F 8/02 Alkylation
• CPC Class Codes: C08F 8/06 Oxidation
• CPC Class Codes: C08F 8/32 by reaction with amines
• CPC Class Codes: C08F 8/44 Preparation of metal salts or ammonium salts
• CPC Class Codes: C08J 7/12 Chemical modification

Abstract

An air curing polymer composition is disclosed which contains acetoacetate functional polymer and an autoxidizable material. The composition cures on exposure to oxygen. One pack stable ambient curing compositions and a method of stabilizing acetoacetate functional groups to prevent hydrolysis are also disclosed.

Claims

1. A self-crosslinking film-forming composition consisting essentially of a vinyl polymer containing pendant acetoacetate functionality and a polyunsaturated aerobic radical source which generates a free radical flux on exposure of the composition to oxygen, wherein said aerobic radical source is selected from the group consisting of allyl and polyallyl ethers, provided that said composition contains substantially no conventional polymerization initiator.

2. A film-forming composition according to claim 1 which further comprises a metal drier.

3. A film-forming composition according to claim 1 or 2 wherein said vinyl polymer containing pendant acetoacetate functionality is soluble in water or water-co-solvent mixtures.

4. A film-forming composition according to claim 1 or 2 wherein said vinyl polymer containing pendant acetoacetate functionality is prepared by emulsion or dispersion polymerization.

5. A film-forming composition according to claim 3 in which the pendant acetoacetate functionality has been converted to pendant enamine functionality by reaction with a molar excess of ammonia or a primary amine capable of enamine formation.

6. A composition according to claim 5 wherein the primary amine is selected from the group consisting of ethanolamine, methyl amine, isopropyl amine and mixtures thereof.

7. A film-forming composition according to claim 4 in which the pendant acetoacetate functionality has been converted to pendant enamine functionality by reaction with a molar excess of ammonia or a primary amine capable of enamine formation.

8. A composition according to claim 7 wherein the primary amine is selected from the group consisting of ethanolamine, methyl amine, isopropyl amine and mixtures thereof.

9. A composition according to claim 1 or 2 wherein the pendant acetoacetate functionality is incorporated in the vinyl polymer by polymerization of a monomer selected from the group consisting of allyl acetoacetate, acetoacetoxyethyl methacrylate, acetoacetoxypropyl methacrylate, and acetoacetoxybutyl methacrylate.

10. A composition according to claim 9 wherein the vinyl polymer contains from 0.5 to 100 percent of the acetoacetate monomer by weight.

11. A composition according to claim 9 wherein the vinyl polymer contains from 1 to 40 percent of the acetoacetate monomer by weight.

12. A film-forming composition according to claim 1 or 2 wherein said vinyl polymer containing pendant acetoacetate functionality is a solution polymer in non-aqueous organic solvent.

13. A composition according to claim 1 or claim 2 wherein the polyunsaturated aerobic radical source is from 0.5 to 6 wt % of the composition.

14. A composition according to claim 1 or 2 where the vinyl polymer is a homopolymer or copolymer of acetoacetoxyethyl methacrylate or acrylate.

15. A composition according to claim 2 wherein the metal drier is incorporated at 0.01 to 1% metal content by weight.

16. A composition according to claim 15 wherein the metal drier is a cobalt salt.