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(12) United States Patent (10) Patent No.: US 9,668,472 B2 Meredith Et Al

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(12) United States Patent (10) Patent No.: US 9,668,472 B2 Meredith Et Al USOO9668472B2 (12) United States Patent (10) Patent No.: US 9,668,472 B2 Meredith et al. (45) Date of Patent: Jun. 6, 2017 (54) POLYAMIDE AND POLYIMIDE STICKER (58) Field of Classification Search ADUVANTS CPC ...... A01N 25/24: A01N 43/54: A01N 43/653; C08G 69/40; C08G 73/10; C08G 2310/00 (71) Applicant: Huntsman Petrochemical LLC. The See application file for complete search history. Woodlands, TX (US) (56) References Cited (72) Inventors: Matthew T. Meredith, Spring, TX (US); Alan J Stern, Magnolia, TX U.S. PATENT DOCUMENTS (US); Dilek Saylik, Meadow Heights (AU) 3,806,456 A * 4/1974 Vogel ................... BO1D 17,047 252/77 3.812,082 A * 5/1974 Jones ................... CO8G 18,346 (73) Assignee: Huntsman Petrochemical LLC. The OS 528,125 Woodlands, TX (US) 4,151,173 A 4/1979 Vogel 4,374,741 A 2f1983 Rieder (*) Notice: Subject to any disclaimer, the term of this 4,789,721 A ck 12/1988 Waddill et al. patent is extended or adjusted under 35 5,053,484 A * 10/1991 Speranza ............... Cosge U.S.C. 154(b) by 11 days. 5,093,382 A 3/1992 Speranza et al. 6,399,713 B1 6/2002 MacQueen et al. (21) Appl. No.: 14/.420,916 6,423.304 B1* 7/2002 Shah ...................... A61K 8,042 424/400 (22) PCT Filed: Nov. 6, 2013 8,247.459 B2 8/2012 Kostansek 2004/0186263 A1 9, 2004 Pavlin (86). PCT No.: PCT/US2013/065175 2007/0244216 A1 10, 2007 Stern 2009.0035380 A1 2/2009 Kostansek S 371 (c)(1), 2011/0105333 A1 5, 2011 Israels et al. (2) Date: Feb. 11, 2015 2012/0108431 A1 5/2012 Williams et al. (87) PCT Pub. No.: WO2014/070451 FOREIGN PATENT DOCUMENTS PCT Pub. Date: May 8, 2014 EP 2020.177 A 2, 2009 JP 2001-172104 A 6, 2001 O O WO O2/O59181 A 8, 2002 (65) Prior Publication Data WO 2006/080917 A 8, 2006 US 2015/0230456 A1 Aug. 20, 2015 WO 2007/109051. A 9, 2007 * cited by examiner Related U.S. Application Data (60) Provisional application No. 61/721,152, filed on Nov. Pr.imary Examiner — Paul A Zucker 1, 2012, provisional application No. 61/826,711, filed Assistant Examiner — Mark Luderer on May 23, 2013. (74) Attorney, Agent, or Firm — Huntsman International LLC (51) Int. Cl. C08G 69/40 (2006.01) (57) ABSTRACT C08G 73/10 (2006.01) A Sticker adjuvant that may be used in agrochemical com AOIN 43/54 (2006.01) positions is disclosed. The Sticker adjuvant is a polyether AOIN 43/653 (2006.01) amide or a polyether imide formed by the reaction of a AOIN 25/24 (2006.01) polyether polyamine with a polyfunctional monomer. The (52) U.S. Cl. polyfunctional monomer may be a polyacid, a di-functional CPC ............. A0IN 25/24 (2013.01); A0IN 43/54 acyl halide, an acid anhydride, a poly(acid anhydride) and a (2013.01); A0IN 43/653 (2013.01); C08G mixture thereof. 69/40 (2013.01); C08G 73/10 (2013.01); C08G 2310/00 (2013.01) 22 Claims, 2 Drawing Sheets U.S. Patent US 9,668,472 B2 NNI POAD-PAN U.S. Patent Jun. 6, 2017 Sheet 2 of 2 US 9,668,472 B2 N POAR DIMER ACID+JEFFAMINE(R) S ED-900 POLYETHERAMINE 3 NOSTICKER FIG 2 == © # of ©|*dips///////////////|- in Water 2@*////////////////|- FIG. 3 US 9,668,472 B2 1. 2 POLYAMIDE AND POLYMIDE STICKER FIG. 1B is a graph showing percent mass retention versus ADUVANTS Sticker adjuvant type and formulation type for the Sticker formulations of FIG. 1 after 200 dips in water. CROSS-REFERENCE TO RELATED FIG. 2 is a graph showing percent mass retention of APPLICATIONS different tebuconazole fungicide formulations versus num ber of dips in water. This application is the National Phase of International FIG. 3 is a graph showing percent mass retention of Application PCT/US2013/065175 filed Nov. 6, 2013 which designated the U.S. and which claims priority to U.S. App. different AZOxystrobin fungicide formulations versus num Ser. No. 61/826,711 filed May 23, 2013 and U.S. App. Ser. ber of dips in water. No. 61/721,152 filed Nov. 1, 2012. The noted applications 10 are incorporated herein by reference. DETAILED DESCRIPTION FIELD The articles “a” and “an are used herein to refer to one or to more than one (i.e. to at least one) of the grammatical Embodiments described herein are generally related to 15 object of the article. By way of example, “a polyether agricultural adjuvants. More specifically, a novel type of polyamine” means polyether polyamine or more than one Sticker adjuvant is described. polyether polyamine. Sticker adjuvants are agricultural adjuvants that promote BACKGROUND adhesion of active ingredients to plant Surfaces. Embodi A wide range of chemicals are applied to plants to ments of the present invention disclose a sticker adjuvant encourage growth, discourage growth, and/or discourage that is a polyether amide or a polyether imide formed from pests. Many of these chemicals are active by contact with reacting a polyether polyamine with a polyfunctional mono plant leaves. Usually, contact for some minimum amount of mer selected from the group consisting of a polyacid, a time is necessary for full activity. Sticker adjuvants are di-functional acyl halide, an acid anhydride, a poly(acid widely used to slow or prevent the active ingredient from 25 anhydride) and a mixture thereof. Such sticker adjuvants, washing off the plant Surface during rain or irrigation. when applied to test materials that mimic Surfaces of leaves Older, simpler sticker adjuvants used included fatty acids and their salts, mineral oils and drying oils (such as tung oil and fruits, show favorable resistance to water wash-off and and linseed oil). More recent sticker adjuvants include latex are expected to provide favorable Sticking for active ingre polymers, polymeric terpenes, alkylphenol alkoxylates dients. (such as nonylphenol ethoxylate condensate polymers), fatty 30 Embodiments of the present invention include a sticker acid derivatives, gums and polysaccharides. adjuvant formed by the reaction of a polyether polyamine However, these currently used sticker adjuvants have with a polyfunctional monomer. The polyether polyamine limited formulation abilities and the alkylphenol alkoxy may be polyether diamine. Useful polyether diamines lates. Such as the popular Sticker adjuvant is based on include polyoxyalkylene diamines Such as polyethylene nonylphenol ethoxylate condensate polymers, have been 35 oxide-polypropylene oxide copolymers that are co-termi restricted in the various regions. nated by amine groups. Such polyether diamines may have the formula: H.N(PO),(EO), (PO)NH, wherein x=0 to 10, SUMMARY y=0 to 40 and Z=0 to 10, EO-ethylene oxide and Embodiments of the present invention disclose a sticker PO propylene oxide. The polyether polyamines may also be adjuvant that is a polyether amide or a polyether imide 40 other polyethylene oxide or polypropylene oxide polymers formed by the reaction of a polyether polyamine with a co-terminated by amine groups. Representative polyether polyfunctional monomer. The polyfunctional monomer may diamines use ethylene oxide (EO) and propylene oxide (PO) be a polyacid, a di-functional acyl halide, an acid anhydride, include: a poly(acid anhydride) and a mixture thereof. HN NH2 Embodiments of the present invention further disclose a 45 spreader-Sticker adjuvant that includes a sticker adjuvant N-11-r and a spreader adjuvant. The Sticker adjuvant is a polyether EO only amide or a polyether imide formed by the reaction of a HN NH2 polyether polyamine with a polyfunctional monomer Such as a polyacid, a di-functional acyl halide, an acid anhydride, a 50 poly(acid anhydride) and a mixture thereof. The spreader rtr adjuvant may be a nonionic or anionic Surfactant. The PO only spreader-Sticker adjuvant may further include a solvent. HN O NH2 Embodiments of the present invention further disclose an agrochemical composition that includes a sticker adjuvant, 55 rt irr an active ingredient, a spreader adjuvant and a solvent. The PO and EO Sticker adjuvant is a polyether amide or a polyether imide formed by the reaction of a polyether polyamine with a Other types of polyether polyamines or ether oligomers polyfunctional monomer Such as a polyacid, a di-functional may be used. A diamine of polytetrahydrofuran, alone or acyl halide, an acid anhydride, a poly(acid anhydride) and a copolymerized with other alkylene oxide or olefinic mono mixture thereof. The agrochemical composition may be an 60 mers, may be used. Any primary polyamine having a hydro emulsifiable concentrate or a suspension concentrate. carbon chain with Some ether oxygen atoms included may be used. The oxygen atoms may be spaced at regular BRIEF DESCRIPTION OF THE DRAWINGS intervals, so that the polyether polyamine has a single repeating monomer unit, or the oxygen atoms may be spaced FIG. 1A is a graph showing percent mass retention versus 65 at differing intervals, which may be random or distributed Sticker adjuvant type and formulation type for several Sticker according to a repeating pattern. Thus, the polyether formulations after 100 dips in water. polyamine may be a diamine of an ether copolymer, which US 9,668,472 B2 3 4 may be random, block, repeating, or alternating, or of an n=-37.3. ELASTAMINER HE-1000 is an amine of ether multipolymer having three or more different ether approximately 1000 average molecular weight, based on a monomer units. PEG poly(ethylene glycol). It is a mixture of diamine and The oxygen atoms of the polyether component of the triamine, and it contains a significant amount of secondary polyether polyamine may be replaced, altogether or in part, amine as well as primary amine.
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