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WO 2019/055177 Al 21 March 2019 (21.03.2019) W 1P O PCT

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WO 2019/055177 Al 21 March 2019 (21.03.2019) W 1P O PCT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2019/055177 Al 21 March 2019 (21.03.2019) W 1P O PCT (51) International Patent Classification: Declarations under Rule 4.17: C08G 65/02 (2006.01) C08G 18/32 (2006.01) — as to applicant's entitlement to apply for and be granted a C08G 65/26 (2006.01) patent (Rule 4.17(H)) (21) International Application Number: — as to the applicant's entitlement to claim the priority of the PCT/US20 18/047252 earlier application (Rule 4.17(Hi)) (22) International Filing Date: Published: 2 1 August 2018 (21.08.2018) — with international search report (Art. 21(3)) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 62/559,109 15 September 2017 (15.09.2017) US (71) Applicant: DOW GLOBAL TECHNOLOGIES LLC [US/US]; 2040 Dow Center, Midland, Michigan 48674 (US). (72) Inventors: MASY, Jean-Paul; Herbert H . Dowweg 5, 4542 NM Hoek, Postbus 48, 4530AA Terneuzen (NL). BABB, David A.; 230 1N . Brazosport Boulevard, Freeport, Texas 77541 (US). (74) Agent: Gary C Cohn PLLC; 325 7th Avenue, #203, San Diego, California 92101 (US). (81) Designated States (unless otherwise indicated, for every kind of national protection available) : AE, AG, AL, AM, 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, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available) : AR PO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, 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, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). © (54) Title: CONTINUOUS PROCESS FOR MAKING POLYETHER POLYOLS (57) Abstract: An alkylene oxide mixture containing greater than 50% by weight ethylene oxide is continuously polymerized in the o presence of a double metal cyanide polymerization catalyst and an alkoxylated initiator having a hydroxyl equivalent weight of up to 200. The catalyst remains active, producing a polyol having an equivalent weight of up to 700 with a high oxyethylene content continuously at fast reaction rates. CONTINUOUS PROCESS FOR MAKING POLYETHER POLYOLS This invention relates to a process for continuously copolymerizing an alkylene oxide mixture containing predominantly ethylene oxide in the presence of a double metal cyanide (DMC) polymerization catalyst. DMC complexes are effective catalysts for polymerizing propylene oxide to form poly(propylene oxide) polyols. The poly(propylene oxide) polyols are useful as a raw material for making polyurethanes. Mixtures of propylene oxide and ethylene oxide have also been polymerized using DMC catalysts. In general, these mixtures have contained mostly propylene oxide and a minor amount of ethylene oxide. In some cases, DMC catalysts have been described for polymerizing mixtures containing predominantly ethylene oxide. However, these polymerizations have been mainly limited to end-capping a poly(propylene oxide) in an attempt to introduce primary hydroxyl groups. For example, US Patent No. 6,884,826 describes a process in which propylene oxide is polymerized using a DMC catalyst. As the polymerization proceeds, ethylene oxide is fed along with the propylene oxide, in gradually increasing proportions. During the last 15% or so of the polymerization, the ethylene oxide concentration in the monomer mixture being fed to the reaction increases above 50% by weight. The process of US Patent No. 6,884,826 has significant shortcomings. It is inherently a batch or semi-batch process, and is not adaptable to continuous polyol production. Additionally, although the DMC catalyst remains active for the relatively short periods during which ethylene oxide is the predominant monomer present, it nonetheless deactivates after only a short time, particularly when product equivalent weight is low. This again restricts the process of US Patent No. 6,884,826 to batch or semi-batch operation. A random copolymer of predominantly ethylene oxide and a minor amount of propylene oxide is useful in some polyurethane applications. These polyols have found use as, for example, for making viscoelastic foam. They are also useful as cell openers in flexible polyurethane foam. These polyols can be made in batch or semi-batch processes using potassium hydroxide or other basic catalysts, but no commercially acceptable method has been found for making these polyols using a DMC catalyst, because of the problem of catalyst deactivation in the presence of high concentrations of ethylene oxide in the monomer feed. Because of the potential advantages DMC catalysis offers, it would be desirable to provide a continuous process for making these random copolymers. WO 2016/209677 describes a continuous process for making such random copolymers using a DMC catalyst. A promoter compound is required to prevent deactivation of the catalyst. This invention is a continuous process for producing a polyether product having a hydroxyl equivalent weight of 200 to 2000, comprising: a) forming in a continuous reactor a mixture of A) a double metal cyanide catalyst, B) an alkylene oxide mixture containing propylene oxide and at least 60% by weight ethylene oxide based on the weight of the alkylene oxide, C) at least one alkoxylated initiator compound having at least one hydroxyl group and a hydroxyl equivalent weight of 70 to 200 but lower than that of the polyether product, and D) a polymerizate consisting of alkoxylated species having molecular weights greater than the initiator compound and up to and including molecular weight of the polyether product, and b) continuously adding additional catalyst, additional alkylene oxide mixture containing propylene oxide and at least 60% by weight ethylene oxide based on the weight of the alkylene oxide, and additional initiator compound to the continuous reactor under polymerization conditions and continuously withdrawing a product stream containing the polyether product from the continuous reactor, wherein: i) steps a) and b) are performed in the substantial absence of a magnesium, Group 3 - Group 15 metal or lanthanide series metal bonded to at least one alkoxide, aryloxy, carboxylate, acyl, pyrophosphate, phosphate, thiophosphate, dithiophosphate, phosphate ester, thiophosphate ester, amide, siloxide, hydride, carbamate or hydrocarbon anion and which is devoid of halide anions, and ii) the polyether product contains 50 to 90% by weight polymerized ethylene oxide. Surprisingly, the process operates continuously at high polymerization rates and without deactivation, permitting sustained continuous operation despite the absence of the magnesium, Group 3 - Group 15 or lanthanide series metal compound. The alkylene oxide mixture polymerized in this invention contains greater than 60% by weight ethylene oxide, based on the weight of the oxide mixture. It may contain, for example, at least 70% or at least 75% by weight ethylene oxide, and may contain as much a s 95%, as much as 90% or a s much as 85% ethylene oxide, by weight in each case. The alkylene oxide mixture contains at most 40% by weight 1,2-propylene oxide. It may contain up to 30%, up to 25%, up to 15%, up to 10%, or up to 5% by weight 1,2-propylene oxide. The alkylene oxide mixture may contain a small amount, such a s up to 25% by weight, up to 10% by weight or up to 5% by weight, of one or more other alkylene oxides, but such other alkylene oxides may be omitted. The initiator compound is an alkoxylated organic compound that is to be further alkoxylated in the polymerization reaction. It contains 1 or more hydroxyl groups, preferably 2 or more hydroxyl groups. It may contain 12 or more hydroxyl groups. Preferred initiators contain 2 to 8 hydroxyl groups per molecule. Mixtures of initiator compounds can be used. The initiator compound has a hydroxyl equivalent weight of 70 to 200 but lower than that of the polyether product. In some embodiments the hydroxyl equivalent weight is 70 to 150 or 70 to 125. Suitable initiators include but are not limited to alkoxylates of one or more of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,4-butane diol, 1,6-hexane diol, 1,8-octane diol, cyclohexane dimethanol, glycerin, trimethylolpropane, trimethylolethane, pentaerythritol, sorbitol, sucrose, phenol, a Ci-24 alkanol, and a polyphenolic initiator such a s bisphenol A or 1, 1, 1- tris(hydroxyphenyl)ethane and the like. The alkoxylate may be an ethoxylate and/or a propoxylate. The initiator may be neutralized with or contain a small amount of an acid, particularly if the initiator is produced in the presence of a base. If an acid is present, it may be present in an amount of about 10 to 100 ppm, based on the weight of the initiator, as described in USP 6,077,978. Alternatively, the acid may be used in somewhat larger amounts, such a s 100 to 1000 ppm, again based on the weight of the initiator, as described in US Published Patent Application No.
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