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WO 2017/079437 Al 11 May 2017 (11.05.2017) P O P C T

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WO 2017/079437 Al 11 May 2017 (11.05.2017) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/079437 Al 11 May 2017 (11.05.2017) P O P C T (51) International Patent Classification: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, C08G 59/18 (2006.01) C08L 63/00 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, C08G 59/62 (2006.01) KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/US2016/060332 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 3 November 20 16 (03 .11.20 16) ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (30) Priority Data: TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, 62/250,217 3 November 2015 (03. 11.2015) US TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (71) Applicant: VALSPAR SOURCING, INC. [US/US]; PO LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Box 1461, Minneapolis, MN 55440 (US). SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). (72) Inventors: EVANS, Richard, H.; 1801 St. James Place, Wexford, PA 15090 (US). WEBSTER, Benjamin, J.; Declarations under Rule 4.17 : 1627 Durbin Street, Pittsburgh, PA 15205 (US). O'BRI¬ — as to applicant's entitlement to apply for and be granted a EN, Robert, M.; 163 Ridge Road, Monongahela, PA patent (Rule 4.1 7(H)) 15063 (US). NIEDERST, Jeffrey; 596 Sunrise Drive, Leechburg, PA 15656 (US). — as to the applicant's entitlement to claim the priority of the earlier application (Rule 4.1 7(in)) (74) Agent: DEMASTER, Andrew, A.; Valspar Sourcing, Inc., PO Box 1461, Minneapolis, MN 55440 (US). — of inventorship (Rule 4.17(iv)) (81) Designated States (unless otherwise indicated, for every Published: kind of national protection available): AE, AG, AL, AM, — with international search report (Art. 21(3)) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, o o (54) Title: LIQUID EPOXY RESIN COMPOSITION USEFUL FOR MAKING POLYMERS (57) Abstract: A liquid epoxy resin composition is provided. In preferred embodiments, the liquid epoxy resin composition is free of bisphenol A, bisphenol F, and bisphenol S, including epoxides thereof, and is useful in preparing a polyether polymer having util - ity in coating compositions, including, e.g., coating compositions for use on food or beverage containers. LIQUID EPOXY RESIN COMPOSITION USEFUL FOR MAKING POLYMERS CROSS-REFERENCE TO RELATED APPLICATION(S) [001] This application claims the benefit of U.S. Provisional Application No. 62/250,217 filed on November 3, 2015 and entitled "Liquid Epoxy Resin Composition Useful For Making Polymers," which is incorporated herein by reference in its entirety. BACKGROUND OF THE INVENTION [002] Various polymers are conventionally made using diepoxide reactants reacted with extender compounds to build molecular weight. For example, epoxy polymers made by reacting bisphenol A ("BPA") with the diglycidyl ether of BPA ("BADGE") are used in a variety of polymer end use applications, including in coating compositions for use in preventing or inhibiting the corrosion of metals. SUMMARY [003] The present invention provides a liquid epoxy resin composition that is preferably useful in making a polymer such as an aromatic polyether polymer. In some embodiments, such polymers are useful for formulating food or beverage container coatings, including food-contact food or beverage container coatings. The liquid epoxy resin composition is preferably storage stable under ambient conditions for at least 1 month, more preferably for at least 3 months, and even more preferably for at least 6 months or even a year or more. In preferred embodiments, the liquid epoxy resin composition is preferably substantially free, more preferably completely free, of materials having estrogenic activity greater or equal to that of bisphenol S ("BPS"). [004] In one embodiment, a liquid epoxy resin composition is provided that is preferably substantially free of bisphenol A ("BPA"), bisphenol F ("BPF"), and BPS, including any epoxides thereof, and is derived from reactants including an epihalohydrin (more preferably epichlorohydrin) and a diphenol (more preferably a substituted diphenol, and even more preferably an ortho-substituted diphenol). The liquid epoxy resin composition preferably comprises less than 80 weight percent, if any, of n=0 diepoxide compounds derived from a diphenol, based on the total weight of any unreacted diphenol and any compounds including at least one structural unit derived from a diphenol. [005] In another embodiment, a liquid epoxy resin composition is provided that is preferably substantially free of BPA, BPF, BPS, including any epoxides thereof, and is derived from reactants including epichlorohydrin and tetramethyl bisphenol F ("TMBPF"). The liquid epoxy resin composition preferably comprises at least 85 weight percent of n=0 and n=l TMBPF-containing diepoxide resins, based on the total weight of any compounds present including at least one structural unit derived from TMBPF and any unreacted TMBPF that may be present. The liquid epoxy resin composition also preferably includes less than 80 weight percent of n= 0 TMBPF-containing diepoxide resins, based on the total weight of compounds present including at least one structural unit derived from TMBPF and any unreacted TMBPF that may be present. Preferably, liquid epoxy resin composition includes less than 5 weight percent, if any, of TMBPF-containing mono-epoxide resins. [006] In yet another embodiment, a polyether polymer is provided that is a reaction product of ingredients including the liquid epoxy resin composition of the present invention. In a preferred such embodiment, the polyether polymer is an aromatic polyether polymer preferably having a number average molecular weight (Mn) of at least 2,000, or at least 4,000 and a glass transition temperature (Tg) of at least 60°C, or at least 70°C. [007] In yet another embodiment, a process is provided that includes reacting an epihalohydrin (preferably epichlorohydrin) and a diphenol (preferably a substituted diphenol, more preferably an ortho-substituted diphenol, and even more preferably tetramethyl bisphenol F) in a molar ratio (epichlorohydrimdiphenol) of from about 7 :1 to about 1:1, more preferably from about 6:1 to about 1.01:1, and even more preferably from about 5:1 to about 3:1 to provide a liquid epoxy resin composition of the present invention. [008] The above summary of the present invention is not intended to describe each disclosed embodiment or every implementation of the present invention. The description that follows more particularly exemplifies illustrative embodiments. In several places throughout the application, guidance is provided through lists of examples, which can be used in various combinations. In each instance, the recited list serves only as a representative group and should not be interpreted as an exclusive list. [009] The details of one or more embodiments of the invention are set for in the description below. Other features, objects, and advantages of the invention will be apparent from the description and from the claims. SELECTED DEFINITIONS [010] Unless otherwise specified, the following terms as used herein have the meanings as provided below. [Oil] The term "substantially free" of a particular compound means that the compositions of the present invention contain less than 1,000 parts per million (ppm) of the recited compound. The term "essentially free" of a particular compound means that the compositions of the present invention contain less than 100 parts per million (ppm) of the recited compound. The term "completely free" of a particular compound means that the compositions of the present invention contain less than 20 parts per billion (ppb) of the recited compound. In the context of the aforementioned phrases, the compositions of the present invention contain less than the aforementioned amount of the compound whether the compound itself is present in unreacted form or has been reacted with one or more other materials. [012] Unless otherwise indicated, the term "polymer" includes both homopolymers and copolymers (i.e., polymers of two or more different monomers). [013] The term "comprises" and variations thereof do not have a limiting meaning where these terms appear in the description and claims. [014] The terms "preferred" and "preferably" refer to embodiments of the invention that may afford certain benefits, under certain circumstances. However, other embodiments may also be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, and is not intended to exclude other embodiments from the scope of the invention. [015] As used herein, "a," "an," "the," "at least one," and "one or more" are used interchangeably. Thus, for example, a coating composition that comprises "an" additive can be interpreted to mean that the coating composition includes "one or more" additives. [016] Also herein, the recitations of numerical ranges by endpoints include all numbers subsumed within that range (e.g., 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, 5, etc.).
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