Polymer compositions and coatings for food and beverage packaging

• US 10,266,719 B2
• Filed: 05/12/2014
• Issued: 04/23/2019
• Est. Priority Date: 05/16/2013
• Status: Active Grant

• Current Assignee: The Coca-Cola Company
• Original Assignee: The Coca-Cola Company
• Inventors: You, Xiaorong, Shi, Yu, Liu, Linda Hsiao-hua
• Primary Examiner(s): Higgins, Gerard
• Assistant Examiner(s): Ortman, Jr., Kevin C
• Application Number:
  US14/891,613
• Publication Number:
  US 20160122581A1
• Time in Patent Office: 1,807 Days
• Field of Search: 428 357, 428 358, 428480, 428413, 4284111, 428461, 428412, 428458, 428500, 428447, 4284744, 428522, 428336, 428 341, 428 366, 42840221, 428414, 428416, 428418, 4284231, 428426, 428457, 4281951, 428220, 428327, 428328, 428339, 428354, 428 3691, 428451, 428463, 428483, 428516, 428520, 428523, 428 644, 428688, 428116, 428141, 428142, 428196, 428201, 4282111, 428219, 4283171, 4283184, 428 3238, 428 3239, 428332, 428334, 428 348, 428355 AC, 428 355, 428 359, 428 364, 428 3, 523400, 523100, 523402, 523122, 523456, 523200, 523351, 523410, 523435, 523115, 523116, 523124, 523216, 523334, 523406, 523408, 523412, 523414, 523425, 523427, 523428, 523434, 523437, 523439, 523440, 523443, 523458, 523461, 523466, 523523, 4273855, 427386, 427256, 427384, 427402, 427327, 4273722, 4274071, 427487, 427236, 427287, 427288, 427331, 4273882, 4274274, 4274301, 427180, 427195, 427282, 427 21, 427 224, 427379, 427409, 42742801, 427429, 427458, 427496, 427508, 427 79, 4271262, 427162, 427177, 4272071, 4272084, 427239, 427272, 427289, 427299, 427 23, 427302, 427318, 427333, 427337, 4273744, 427387, 4273881, 427397, 4274276, 427439, 427485, 427486, 427504, 427510, 427511, 427512, 427533, 427539, 558156, 558 87, 558158, 558397, 558406, 558430, 558443, 252500, 25218311, 252397, 252403, 252407, 25218214, 25218215, 25218228, 25218229, 25218231, 25218828, 252189, 25230135, 2524002, 25240024, 252405, 252600
• 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 283/10 on to polymers containing more than one epoxy radical per molecule C08F283/004 takes precedence
• CPC Class Codes: C08L 2312/00 Crosslinking
• CPC Class Codes: C09D 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09D 151/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 5/002 Priming paints C09D5/08 takes precedence

Abstract

The present disclosure relates to coatings and coating compositions that are substantially free of bisphenol A (BPA) and similar compounds, which help reduce or minimize flavor loss associated with foods or beverages stored in contact with the coating compositions. In one aspect, the composition can include the reaction products of an intimate mixture of cyclic ether resins and acrylate resins, which provides a unique cross-linked and interpenetrating network of polymers.

Claims

1. A coating composition for use in food and beverage packaging, comprising a polymeric reaction product formed from a mixture of:

a) at least one cyclic ether monomer selected from the group consisting of isosorbide diglycidyl ether, ethylene oxide and vinyl oxirane in a 5;

1 ratio by weight, propylene oxide and vinyl oxirane in a 10;

1 ratio by weight, and 1,4-cyclohexanedimethanol diglycidyl ether,

b) at least one polyacrylate monomer selected from the group consisting of dipentaerythritol pentaacrylate, diacryloyl methane, tripropylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, and trimethylolpropane triacrylate,

c) a free radical initiator,

d) at least one surfactant, and

e) a carrier liquid, wherein;

from 5% to 25% of skeletal bonds in the polymeric reaction product are network-forming bonds; and

the coating composition is substantially free of BPA, BPF, BADGE and BFDGE.

2. The coating composition according to claim 1, wherein the polymeric reaction product constitutes at least 20% of the coating composition as measured by dry weight.

3. The coating composition according to claim 1, wherein the mixture further comprises a cross-linker in an amount from about 0.1% to about 10% by weight.

4. The coating composition according to claim 1, wherein the mixture further comprises a condensation-type cross-linking resin selected from methylated and butylated melamines, alkylated and imino mixed ether melamines, alkylated ureas, formaldehyde-free modified ureas, benzoguanamine, glycoluril, and combinations thereof.

5. The coating composition according to claim 1, wherein the mixture further comprises a catalyst selected from a tetraalkyl ammonium halide, a tetraalkyl phosphonium iodide or acetate, a tetraaryl phosphonium iodide or acetate, tin octoate, zinc octoate, triphenylphosphine, or any combination thereof.

6. The coating composition according to claim 1, wherein:

a) the at least one cyclic ether monomer is 1,4-cyclohexanedimethanol diglycidyl ether; and

b) the at least one polyacrylate monomer is tripropylene glycol diacrylate, trimethylolpropane triacrylate, propoxylated neopentyl glycol diacrylate, or any combination thereof.

7. The coating composition according to claim 1, wherein the at least one acrylate monomer is from about 4.7 wt % to about 9.4 wt % of the mixture.

8. The coating composition according to claim 1, wherein the at least one cyclic ether monomer is about 9.5 wt % of the mixture.

9. The coating composition according to claim 1, wherein the free-radical initiator comprises t-butylperoxybenzoate.

10. The coating composition according to claim 1, wherein the at least one surfactant comprises 2,4,6-tris(dimethylamino)phenol and/or sodium bis(2-ethylhexyl) sulfosuccinate.

11. A food and beverage container comprising:

a) a metal selected from aluminum, aluminum alloys, steel, steel alloys, tin, tin alloys, zinc, zinc alloys, chrome or chrome alloys; and

b) a coating formed from the coating composition according to claim 1 at least partially coating a surface of the metal.

12. The food and beverage container according to claim 11, wherein the coating is from 0.1 to 20 microns thick and has a contact angle with water of at least 70 degrees.

13. The food and beverage container according to claim 11, wherein the coating remains intact after the coating has been in contact with an aqueous solution having a pH between 2.4 and 2.5 for a period of 12 months at a temperature between 20°

C. and 25°

C.

14. The food and beverage container according to claim 11, wherein the coating remains intact after the side of the metal opposite the coating receives an impact by an object uniformly over a 10 cm² surface area having a momentum of 25 μ

N/s, and wherein the coating is exposed to a carbonated or uncarbonated aqueous solution during a period from at least 24 hours prior to the impact to at least 24 hours following the impact.

15. The food and beverage container according to claim 11, wherein:

a) the at least one cyclic ether monomer is 1,4-cyclohexanedimethanol diglycidyl ether; and

b) the at least one acrylate monomer is tripropylene glycol diacrylate, trimethylolpropane triacrylate, propoxylated neopentyl glycol diacrylate, or any combination thereof.