Methods and Materials for the Functionalization of Polymers and Coatings Including Functionalized Polymer

• US 20140076768A1
• Filed: 08/16/2013
• Published: 03/20/2014
• Est. Priority Date: 02/17/2012
• Status: Active Grant

• Current Assignee: Swimc, LLC (The Sherwin-Williams Company)
• Original Assignee: Valspar Sourcing, Inc. (Sherwin-Williams Company)
• Inventors: Skillman, Charles, Cavallin, Carl, Evans, Richard H.
• Granted Patent: US 9,650,176 B2
• Time in Patent Office: Days
• US Class Current: 206/524.3
• CPC Class Codes: B32B 15/08 of synthetic resin
• CPC Class Codes: B32B 15/082 comprising vinyl resins; comprising acrylic resins
• CPC Class Codes: B32B 15/085 comprising polyolefins
• CPC Class Codes: B32B 15/09 comprising polyesters
• CPC Class Codes: B32B 15/095 comprising polyurethanes
• CPC Class Codes: B32B 15/098 comprising condensation resins of aldehydes, e.g. with phenols, ureas or melamines
• CPC Class Codes: B65D 25/14 Linings or internal coatings of containers made by folding or erecting blanks made of paper B65D5/56 ; linings for domestic water storage heaters F24H1/183
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C
• CPC Class Codes: C08G 63/553 Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
• CPC Class Codes: C08G 63/918 Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C09D 133/04 Homopolymers or copolymers of esters C09D143/04 takes precedence
• CPC Class Codes: C09D 167/06 Unsaturated polyesters having carbon-to-carbon unsaturation
• CPC Class Codes: C09D 201/08 Carboxyl groups
• CPC Class Codes: Y10T 428/1355 Elemental metal containing [e.g., substrate, foil, film, coating, etc.]

Abstract

The disclosure provides a functionalized polymer for use in coating compositions and a method for making the functionalized polymer. In some embodiments, the functionalized polymer is a water-dispersible polymer, more preferably a water-dispersible polyester polymer, having one or more side groups including one or more salt groups. Packaging containers (e.g., food or beverage cans) comprising the functionalized polymer and methods of making such containers are also provided.

Claims

1-39. -39. (canceled)

40. An article comprising a food or beverage can, or a portion thereof, the article comprising:

a metal substrate; and

a coating disposed on at least a portion of the metal substrate, the coating formed from a coating composition comprising an aqueous dispersion of a water-dispersible polymer, wherein the polymer includes;

a backbone having at least one heteroatom; and

a side group that includes at least one salt group, wherein the side group comprises the reaction product of an unsaturated compound having at least one salt or salt-forming group that is attached to another portion of the polymer via reaction of the unsaturated compound with one or more double or triple bonds, with the proviso that the reaction of the unsaturated compound with the one or more double or triple bonds does not require the participation of a free-radical initiator.

41. The article of claim 40, wherein the side group is attached directly to the backbone.

42. The article of claim 40, wherein the side group is attached to another portion of the polymer via a carbon-carbon bond.

43. The article of claim 40, wherein the side group includes at least a portion of a cyclic group that links the side group to the backbone or another portion of the water-dispersible polymer that is attached to the backbone.

44. The article of claim 43, wherein the cyclic group has at least one carbon-carbon double bond present in a ring of the cyclic group.

45. The article of claim 40, wherein the reaction of the unsaturated compound with the one or more double or triple bonds comprises a pericyclic reaction.

46. The article of claim 45, wherein the reaction of the unsaturated compound with the one or more double or triple bonds comprises a cycloaddition reaction.

47. The article of claim 46, wherein the cycloaddition reaction is a Diels-Alder reaction.

48. The article of claim 40, wherein the reaction of the unsaturated compound with the one or more double or triple bonds comprises an Ene reaction.

49. The article of claim 40, wherein the at least one salt group of the side group comprise a neutralized acid or anhydride group.

50. The article of claim 40, wherein the unsaturated compound includes at least two conjugated carbon-carbon double bonds.

51. The article of claim 40, wherein the unsaturated compound comprises sorbic acid or neutralized sorbic acid.

52. The article of claim 40, wherein the side group is formed from a single molecule of the unsaturated compound having a molecular weight of less than 200.

53. The article of claim 40, wherein the side group is attached, via a carbon-carbon bond, to a structural unit derived from maleic anhydride.

54. The article of claim 40, wherein the water-dispersible polymer is a polyester polymer.

55. The article of claim 54, wherein the polyester polymer has a glass transition temperature of at least 25°

C. and a number average molecular weight of at least 2,000.

58. A method of making a polymer comprising:

providing an unsaturated precursor polymer having a number average molecular weight of at least 2,000 and one or more double or triple bonds; and

reacting in a Diels-Alder reaction, an Ene reaction, or a combination thereof;

(i) an unsaturated compound having one or more functional groups with

(ii) the unsaturated precursor polymer such that a covalent attachment is formed between the unsaturated compound and the unsaturated precursor polymer.

59. An aqueous coating composition including a water-dispersible polymer comprising:

a backbone having at least one heteroatom; and

a side group that includes at least one salt group, wherein the side group comprises the reaction product of an unsaturated compound having at least one salt or salt-forming group that is attached to another portion of the polymer via reaction of the unsaturated compound with one or more double or triple bonds, with the proviso that the reaction of the unsaturated compound with the one or more double or triple bonds does not require the participation of a free-radical initiator;

wherein the coating composition is suitable for use in forming a food-contact coating.