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    © All Rights Reserved
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    4 views7 pages

    Proposal Template

    Uploaded by

    nano
    Astm List

    Copyright:

    © All Rights Reserved
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    of 7
    2) United States Patent (10) Patent No: US 8,716,429 B2 Spilman et al. (45) Date of Patent: May 6, 2014 (S8)_ POLYESTER COIL COATING ‘apse $206 iim eee went St Ga Me A canst (75) tent: Gary E. Spilman, Midland Mt (usy, 2MMOISTESE AL B20DK Feat Scot JB, Midland MI(US);Paul.—Shogeperit AL” {12008 Namrsaeyetal” Popa, Auburn, MI (US) 200910192286 AL* 7/2009 Argyropoulos et a $2807 Samora 82009 Aker (73) Assignee: Dow Global Technologies LLC () Notice: Subject to any disclaimer, dhe term ofthis patent is extended or adjusted under 35, US.C. 15400) by 725 days, (21) Appl.Nos 12982333 (22) PCT Filed: Jan, 29, 2008 (86) PCTNos — PCT/USz008/052296 $371), (2),(4) Date: Jul. 16, 2009 (87) PCT Pub. Nos WO2008/094898 PCT Pub. Date: Aug. 7,2008 (65) Prior Publication Data US 2010000761541 Mar. 25,2010 Related US. Application Data (6) Provisional application No, 6898 617 filed on Ja, 31,2007. (51) Incl. C086 6300 (2006.01) (2) Us.cL usec 528/307; 525/441; S28°271; 528/272 (58) Feld of Classification Search usec ‘524/601; 525/441; 8282271, 272, 274, 528307, 308 ‘See application file for complete serch history. (66) References Cited US. PATENT DOCUMENTS. AOTLSTE A WI97S Lasher UTIS A 121979 Ubersac ‘A "9198 Chong A+ 11/1985 taekson ea ‘A “1986 liskson Jr tal ‘A 71986 lickson Jr etal A 101988 Tapin ‘A S1991 Chang tal A S1991 Lapinet a A * $1996 laser ta A 61996 Beavers etal A 91196 Sublet A 171996 Oberst eal A (61098 Dicken eta A 1011999 lasenoret al ‘A + "62000 ‘Tacha amine sass 25221 BL 62001 Argyopoulos a {6255523 BL 72001 Panandiker et al (6706779 B23 2004 Bahar eta 58065314 B2 102004 Feam etal {6S07265 BD 52005 Algrim tal T2792 B2 72007 Agarwal tl 1109 0253585 AL 21H 9'0255855 AL 102009 Dinthenko eal 102009 Aryropouos eta FOREIGN PATENT DOCUMENTS cA 2sssoaa $2006, @ o7soims 111895 P Sean] |2:2005, wo Datos 904 wo os2%0 $2001 wo aoowoisigs 2004 wo ao0w039902 $2008, wo, oowosos2 $2008 (OTHER PUBLICATIONS Heinemann Seal, “Polyester for Production of Westher-Resisant Coatings by Coi-Coatng” DerventAbsinet DEI97S3990, Acces- sion No. 989.3388. Franamann, G ea. Macropoyols Based on Polyesorwith Fluo CConaining Components, weil ase. Main Commponat ia Costing Agents, Comprises Dicatoxsic Acid (eg. Cyeoaliphatic 12> sieatoxylc aid, and Alcobol (eg. Tiunctionlzed Alesha, Derwent Abstract DEI02004040070, Aesesion No, 2008-26077 Ying, ot al, “Stes on Crystallization Behaviors of L4- Celohexane Dimctanol Modified Polytylene Teepe” Polymer Materials Sconce and Egincering, fn 2000, ol 16, No 1p 20-123, Borman, Molecular Weigh-Viscsily Reaionhis for Poy(h¢- buslene Teepe), Journal of Applied Polymer Science, vol 2, 2119-2136 (197. Argyropoulos, ef al, “UNOXOL TM Dicky A New Liquid Celoaliphaie Diol for Coatings Appiations”, Paint Coatings Inds, hn. 2006, p 1 Sohn Argyropulous, al “A New LigidCyelosliphati Diol for Coatings ppliains", Proceedings of de 30h Intl Waterborne, igh-Sois, & Powder Costings Symposium, Feb. 26-28, 2003, [New Orleans LA. * cit by examiner Primary Examiner —Ling Choi Assistant Examiner — Wenven Cai (14) Attorney, Agent, or Firm —Paul D, Hayhurst 7) ABSTRACT Ina curable coil coating composition comprising a mixture of (a) curable polyester hat isa liquid at room temperature, () across-linking szent; and (@) solvent; he improvement ‘comprising preparing the polyester from a composition com prising a mixture of 1.- and 14-cyclobexane dimethanol ‘wherein the molar rato ofthe 1,3 isomer tothe 1,4 isomer is from about 60:40 10 about 5:95. Cured coil coatings prepared ‘om these compositions exhibit an excellent combination of Aexbility and andes 14 Claims, No Drawings US 8,716,429 B2 1 POLYESTER COIL COATING FORMULATION (CROSS REFERENCE TO RELATED "APPLICATIONS ‘This application is 0371 of PCT/US20081082296 file Jan 29, 2008, which claims the benefit of US. Provisional Apli- ‘calion Se. No. 60898617 filed Jan, 31, 2007, BACKGROUND OF THE INVENTION The invention relates to polyester-containing coil costing ‘compositions and process for preparing them. Col coatings are applied to coiled shest metal stock, such ‘4 ste! or aluminum, in an economical, high-speed process, ‘Coil eoating i @ continuous operation, with the end of one «oil ypcally being attached tothe beginning of the following ‘coi to be coated. Important properties for col coated metals include weatherability, water resistance, chemical resistance, Scratch resistance, gloss, hardness, lexiilty, and resistance 'o surface delamination or cracking upon bending of the substrate, The latter property is important since the coated metal typically is subjected to a fomning step during the preparation of end wse ariles “Many cil coating compositions are known those skilled in thoart, However, formulation of eil coating compositions involves a trade-off wherein improved flexibility is only ined at the expense of hardnes, and vice vers. U.S. Pat No.6,897,265 B2 showsat lastoneexampeofacoll coating ‘composition having a Pencil Hawdness of at least 2H and a ‘Tend tet value of OT. However, this results only oained by using a blend of branched polyester and linear ples- ter It would be desirable 10 have a simplified coil coating ‘composition that could be used to prepare coatings having an ‘excellent combination of harness and fexbii ‘SUMMARY OF THE INVENTION ‘Thecompositionof he inventions such acompositionand includes a mixture of {a)acurable polyester that isa liquid at oom temperature, (b) cross-linking agent: and (o)a solvent ‘wherein the polyester is prepared using a polyol compris ing a mixture of 1,3- and 14-cyelohexane dimethanol ‘wherein the rato of the 13 isomer fo the 1,4 isomers from bout 60:40 to about $95 In another aspect, the invention is process for preparing an improved polyester evil coating composition, wherein 4 polyester i prepared by a process wherein a monomer com prising a diols reacted with a monomer comprising a poly- fimetional acd, the process comprising employing asthe diol ‘composition comprising a mixture of 1,3- and 14-cyclo- hexane dimethanol wherein the ratio ofthe 13 isomer othe 14 isomer is fom about 60:40 to about 5:95, ‘Surprisingly, the eoil coating composition ofthe invention ‘exhibits a outstanding combination of flexibility and hard- nes. DETAILED DESCRIPTION OF THE INVENTION ‘The compesition ofthe iveation includes a curable poly ‘ster, erosslinking agent, anda solvent As used herein the tem “polyol” means a compound witk at leat 2 hydroxyl groups. As used herein, te tem “il means a compound with 2 hydroxyl groups. As used herein, Fa » s 2 the erm “polyacid” means compound with t east 2 car bonylic acid groups, and the team “seid” means 3 com- pound with 2 carboxylic acid groups Polymers comprising a polyester uit stall are propared fiom the condetsation of monomers comprising 2 diacid andra polyacd anda ol andor polyol. Plyesters which maybeemployed inthe coating formulations ofthis invention are polymeriz fama composition comprising a mixture of 1.3-and l,-eyeloherane dimethan! wherein the molt rato ofthe 13 isomer to the I isomer is from about 6:40 to shout $95, Prefered polyesters advantageously exhibit a aumber average molecular weight of teas about 1,000, preferably from aout 2,000 to about 10,000, and most preferably fom shout 2500 to about 7.500 none embodiment of the aven- tion, the number average molecular weight sat east about 4,000. The gas transition temperature, oT ofthe polyes- ter advantageously is fom about -20° Co about 100" C preferably i om about =10°C. wo about 90°C, and more preferably som about 0° Ct about AC. The preferred polyesters generally have Tof ess than about 55°C. The polyester preferably is @ viscous liguid at 25° C, For the purposes of the invention, Ta is measured hy dierential Scanning clorinety The hydroxyl numberof the polyester advantageously is Joss than about 150 mg KOH, Preferably the hydoxsl number of the polyester 8 from about 10 1 about 100 m8 KOHs. More prefembly, the hydroxy] number ofthe poly= esters from shout 20 to bout 70 mg KOHig. Most pre ably he hydrox oumber othe polyesters om about 300 about SOmg KOH. The polyester ofthe invention advan seously has no more than about 2 byron groups per mol- soul Preferably, the polyester is hydroxyl or earboxyteri- raed, Advantageously, cuted coating comprising the com- position incured formes penilhanlness fat est 2H and 8 T head valve of 0. ‘The amount of polyester employed in the coil cating composition ofthe invention advantageously som about 20 toabout 90 weight percent, based onthe weight of polyester, crosi-lnker and solvent in the composition, preferably is from about 25 to about 70 weight percent, and most prefer ably is from sbout 30 to about 6D weight percent. In oe embodiment ofthe invention, the polyester i substantially fev of rctve diet. ‘The polyol composition emplayed inthe invention com prises & mixture of 1.3- and I-beyeloherane dimethanol wherein the eatio of the 1.3 isomer tot 1 isomer fom shout 60:0 to about 5:98. Advantageously. the polyol com- positon compises teas about 10 weight percent ofthe 13- and 4-ycloexanedimetbanol mixture, an preferably isat Jeastabout 30 weight perecat ofthe 1.-and | cyclohexane dimethanol mixture, based onthe weight of polyols in the polyol composition, Inne embodiment ofthe invention the polyol compesition comprises at least about 90 Weight per Cent ofthe 13 and 1-beyelohexane dinethanl mixture In one embodiment of the invention, the polyol composition compeses fom about 30 to about 7 weight percent of the 1.3-and I yelohexane dimethano! mixture Mixtures of 1,3 and 1,-eyclobexane dimethanol are know inthe at and canbe prepared, according to the teachings of US. Pat No. 6 252,121. A mise of 13- and I.deyeloexane dimetbanl having varios ratios of cis to tans isomers canbe mde by distilling UNOXOL, brand il (@mixtureofes and tans 1 3-and1teyeloexane dimetba- no available fom The Dow Chemica Company) o produce a dsilled faction anda reside fraction US 8,716,429 B2 3 “The above-described polyol optionally can beemployedin ‘conjunction with oae or more additional polyols, In one ‘embodiment ofthe invention, the addtional polyol generally ‘contains more than 2, preferably 21o about 10 carbon atoms, more preferably about 2 to 8 carbon atoms, in addition tos having 2 abou 6, preferably 2to about 4, hydroxyl groups. Some preferred examples ofthe ational polyols are one or more of the following: neopentyl glycol; ethylene glycol propylene glycol; butanediol; hexamelhylenediol 1.2-cyclo- hexanedi-methanol; trimethylol propane; pentaerythritol; 10 neopenty glycol hydroxypivalate diethylene glycol tiethyl- ‘ene peo: tetrethivene glycol dipropylene glyco: polypro- pylene alyeok; hexylene glycol: 2-methy!2-thyl,3-pro- Panediol; — 2-ethyl-1-hexanediol; —1,S-pentanedio ‘hiodiglyeol; 13-propanesil; 1,3-butanediol; 2.-butane- diol | butanediol; 2.24-timetiy! 1 3-pentaneiol: 1 2-cy-

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