a9) United States SS644AL ‘US 201002! cz) Patent Application Publication — co) Pub. No.: US 2010/0288644 A1 oy os) (@) (60) Brown et al. COATING FOR METAL CONTAL METALWORKING LUBRICANT COMPOSITIONS, COMPOSITIONS FOR ELECTROPLATING AND. TROWINNING, LAT COMPOSITIONS AND PROC ‘THEREFOR Inventors: David W. Brown, Ambler, PA (US); Kenneth Breindel, Lansdale, PA Broadbent, Horsham, PA (US); Shailesh Shab, Dresher, PA (US Comespondence Address FOX ROTHSCHILD LLP 997 Lenox Drive, Bldg, #3 Lawrenceville, NJ 08648 (US) Assignee: Cognls Corporation, Ambler, PA ws) Appl. Nos 12/803,263 Filed: Nov. 12, 2009 Related US. Application Data Division of application No, 10700,167, filed on No 3.2008, now abandoned. Provisional aplication No. 60/423,118, filed on Nov 1, 2002, provisional aplication No. 60/424,249, filed con Now. 6, 2002, provisional application No, 60/430, (43) Pub. Date: Not . 18, 2010 485, fled on Dec. 3,2002, provisional application No (601434,477, fled an Dee. 18, 202. Publication Classification G1) Ince. 25D a2 (2006.01) BIB 4802 (2006.01), (2) US.CL 205/80; 72/42 6 ABSTRACT Coatings for metal containers, metalworking lubricant com- positions, compasitions for clectoplating and electowin. fing, and latex componitions comprising a base-catalyzed reaction produ of (a) at Teast one eomponnd of formula 1 ‘wherein each X group is halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen ‘atom, which i attached to two adjacent earbon atoms in the RR group to form an epoxy group, and R'is an alkanetryl group containing from 30 10 carbon atoms; and (b) atleast ‘one Compound having the forma I wherein R? is a substiuted or unsubstituted, saturated oF ‘unsaturated organi group having from :36 carbon atoms; Xis—O—, Sor NR™ where R'is hydrogen or @ C,-C allyl group? each AO group is independently an eth- ylenceny, 1 2-qropylencoxy o 12-butyleneoxy group. 2 isa ‘number from 0 10 200; and Y is hydrogen, or Y can be @ ‘mercapio group oF a amino group oF a Cy-Cy alkylnino rou in place ofa terminal OH group, provided that when Y is meteapto or an amino group, or a C,-C, alkylamino soup, nist last 1; wherein the mole ratio‘of component a) fob) is fom 0.1: to 5:1; are deseribe.US 2010/0288644 AI (COATING FOR METAL CONTAINERS, ‘METALWORKING LUBRICANT. COMPOSITIONS, COMPOSITIONS FOR ELECTROPLATING AND ELECTROWINNING, LATEX COMPOSITIONS AND PROCESSES. ‘THEREFOR (CROSS-REFERENCE TO RELATED "APPLICATIONS, 10001] This application claims priority, under 35 USC. $119) of US. Provisional Patent Application Nos, 60/423, 118, 60/424,249, 60/430,485, and 601434477 fled on Nov. 1, 2002, Now. 6, 2002, Dee. 3, 2002 and Dec. 18, 2002, respectively, the entire contents of cach of which are hereby inconporated by relerenee. BACKGROUND OF THE INVENTION 10002} One ofthe last stages inthe manufacture of shumi- ‘hum cans and other metal containers such as Ferrous metal ‘containers is the application of one or more finishing coatings Tor decorative purposes andlor ideatifieation, [0003] Such finishing coatings include acrylic paints, phe- nolic coatings whichare used for baked can coatings, bitumen paints which are used for aluminum paints, coumarone-in ‘dene paints which are used to make aluminum paints, lc ‘quers (whichis termalso applied tothe baking nish applied to the interior of food and beverage cans), and enamels 10008] Lubricating oils are fuids whose function is the reduction of fietion and wear between solid surfaces, usually metals, in relative motion. Aside fom te primary function of {ition and wear eotrol, Inbrcating oils are offen called ‘upon to serve other purposes, such ss corosion prevention, ‘electrical insulation, power Gunsmission, and evoling. The ter is particularly important in metal euting ned grinding 10005] There are two Fundamental classes of lubricating ‘agents, natural and synthetic. These Tubricating agents include petroleum-derived oils, natwal fatty acid esters, hydrocarbons prepared by the polymerization of olefinic hydrocarbons, polyatkytene glycol oils, synthetic esters hich are primarily esters of dibasic acids br organic esters of Phosphor or silicic acid, silicone oils which are linear oF ‘ycli siloxane polymers, halogenated hydrocarbons, perf ‘orinated polyalkylene glycols, polypheny! esters, polygly ‘ols, and neopentyl polyol esters. 10006] In the precaction of metal by electrolysis of aque- ‘ous solutions, the eloctwinning of the metals is usually ‘arti out i tank cells, Developmens in the electeowinning ‘of metals ffom aqueous solutions have been direted toward improved anodes, improved additives, higher current dens ties, the use of ionexchange membranes, beter electrolyte ‘quality contol and computer modeling ofthe processes. [0007] Fleciroplating is te process of applying a metalic ‘outing toanaricleby passing an electric current trough aa ‘electrolyte in contact with the article, The ASTM axis some ‘quality restriction hy defining electroplating as electrodepo- Sition ofan adherent metalic coating on an electrode sich thats surface having properties or dimensions different Irom those of the basic metal is formed. 0008} _Progressin electroplating islinked to improvements Jnmaterialsof constriction, power supplies and otber plating ‘equipment, purer industrial chemicals and anodes, improved adkitives forthe plating baths, and improved analytical test Nov. 18, 2010 au conto methods, The quality of electroplating is depen ) atleast one compound having the formula IL RXADLY wo ‘wherein R? is a substituted or unsubstituted, sti ‘ated of unsaturated, organie group having from 1 to about 36 carbon atoms; X is -O—,—-S—, or —NR— where R° is hydrocarbom of Cy-C alkyl group: each AO group is indepen- dently anethyleneoxy, 1.2-propyleneoxy oF 1.2- butyleneoxy group, nisantimber from Oto about 200; and Y is hydrogen, or Y ean be a mereapto group or an amino group ora, -C, aly amino troup in place ofa terminal “OH group, pro- Vided that wen Y iemereapta or an amino group ora CC, alkyl amino group. nisat lest Ind, optionally 6) alycidyl ether andor a glycidy! amine; Wherein the mole ratio of the linking compound a) to b) is from about 0.1:1 1 about 5:1, and wherein the metalworking lubricant composition has reduced foaming properties i aqueous and non-aqueous metalworking formulations an ‘improved lubricating and extreme pressure properties and, ‘wherein, B® is optionally substituted with a member selected from the group consisting of mereaptan funetionlity, thio functionality, amine functionality, amide functionality, aleo- hol functionality, silicone functionality ether functionality, and combinations thereof, 4i) applying the lubricant composition toa metal object to ‘be worked: and. ill) subjecting the metal object ro a working step select, fiom cutting, machining, grinding, or other metal pro= cessing or metalworking, sherehy the composition ‘modifies the harmful effect of friction andor high tem- peratures caused by the working 14, The method of claim 13 wherein sad lubricant com- position comprises from about 0.001% to about 10% by ‘weight of the ration product B. 15, The method of claim 15 wherein sad Iubricantcom- position comprises fom about0.1%to about 3% by weight of the reaction product B. 16. The method of claim 18 wherein c) is present, and ‘comprises from about 1 to sbot 20 mole percent based onthe mmoles of) 17. The method of claim 13 wherein sai lubricant com- positon further comprises at least one ative selected from the group consisting of viscosity. improvers, pour-point ‘depressants, antioxidants, amine solvents, buffers, nonionic surfactants (other than B), corrosion inhibitors, and coupling gents 18. The method of elaim 13 wherein sai lubricant com- positon comprises Irom about 30% to about 90% by weight ofA, 19. A method of electroplating, comprising 3) providing an aqueous electroplating composition, com- prising Nov. 18, 2010 A) at Jeast one metal or metalloid and ions thereof; and B) at least one hase-estalyzed reaction product of: 8) at least one compound of formula T RY, o ‘wherein each X proup is a halogen tom or one X group isa halogen atom and two X groups rep- seit an epoxy oxygen atom, which isaoched totwo adjacent carbon atoms in the R" group 10 form an epoxy group, and R isan alkanetry] group containing from about 3 to about 10 cate bon atom b)at least one compound having the formula I ReXIAOY oy wherein R? is a sturated or unsaturated, organic srouphaving from I to about 36 carbon atoms; X js-O-, Sor —NR' where ishydro- gen or a C,-C;, alkyl group, each AO group is independently" ethyleneoxy. 1.2-propyle- ‘neoxy, or 2-butyleneoxy group, ns a number {rom 0 about 200; and ishiydrogen, oY ean be a mercapto group oF an amino group oF & Cy-G, alkylamino group in place of a terminal- (Off group, provided that shen Y is meteapio or anamino group, or aC,-C,alkylamino group. 2 ist least 1: and, optionally «)a glycidyl ether andlor glycids! amine; ‘wherein tle mole rato oP component a) to b) is from about 0.1: to about 5: and wherein the base catalyzed reaction product is not epoxy functional and. provides, improved brightening and reduced foaming and, wherein, R? is option- ally substituted with a member selected from the group com- sisting of mereaptan functionality, thio funetionality, amine Tunetionality, amide functionality, aleobol functional cone functionality, ether funetionality, and. combinations thereof and ii) using said composition asthe aqueous electrolyte soht- tion in an electroplating operation, 20. The method of claim 14 wherein said electroplating ‘composition comprises {rom about 0,001% to about 5% by ‘weight of the reation prot P, 121. The method of claim 20 wherein said electroplating composition comprises from about 0.1% ta about 3% by ‘weight of the reaetion product B. 22. The method of claim 19 wherein e) is present, and ‘comprises fom about I toabout 20mole percent hasedon the soles of b. 23, The method ofeaim 19, wherein said metal, metalloid, ‘and ions of the composition are selected from the eroup consisting of zine nickel, copper, chromium, manganese, iron, cobalt, gallium, germaninm, arsenic, sclenium, ruthe- ‘ium, thodum palladium silver, cadmium, indium, tn, lead, bismuth, mercury, antimony. gold, indium, platinum, brass, bronze, gold alloys, lea-tin, nickel iron, nickel cobalt, nickel-phosphons,tin-nickel,tn-zin, zine-nickel,zine-co- bal, zne-iron lead-indium,nickel-manganese, nckel-tung- sen, palladum alloys, silver alloys and zine-manganese.