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(12) United States Patent (10) Patent No.: US 8,242.228 B2 Cox Et Al

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(12) United States Patent (10) Patent No.: US 8,242.228 B2 Cox Et Al USOO8242228B2 (12) United States Patent (10) Patent No.: US 8,242.228 B2 Cox et al. (45) Date of Patent: Aug. 14, 2012 (54) LOW HAZE THERMOPLASTIC (58) Field of Classification Search .................... 528/44, POLYURETHANE USING MIXTURE OF 528/59, 65, 66,80, 81, 85; 252/182.2, 182.21, CHAIN EXTENDERS INCLUDING 1.3- AND 252/182,22, 182.25, 182.28 1,4-CYCLOHEXANEDIMETHANOL See application file for complete search history. (56) References Cited (76) Inventors: John M. Cox, Lake Jackson, TX (US); Francisco Lerma, Lake Jackson, TX U.S. PATENT DOCUMENTS (US); Mark F. Sonnenschein, Midland, 4.245,081 A * 1/1981 Quiring et al. .................. 528.65 MI (US) 6,187,968 B1 2/2001 Itoh et al. 6,521,164 B1* 2/2003 Plummer et al. ......... 264,328.17 Subject to any disclaimer, the term of this 2002/O1236O1 A1 9/2002 Sonnenschein et al. (*) Notice: 2009.01.04449 A1 4/2009 Farah et al. ................ 428/422.8 patent is extended or adjusted under 35 2009,0198O14 A1* 8, 2009 Baikerikar et al. ........... 524,849 U.S.C. 154(b) by 137 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 12/593,377 EP O781792 A 7/1997 OTHER PUBLICATIONS (22) PCT Filed: Dec. 3, 2007 Paint & Coatings Industry, UNOXOL Diol: A new liquid (86). PCT No.: PCT/US2007/024.753 cycloaliphatic diol for coating applications. Jun. 2006. Presented by Argyropoulus, John et al. S371 (c)(1), A new liquid cycloaliphatic diol for coating Applications. (2), (4) Date: Sep. 28, 2009 Argyropoulos, John et al. Presented at the International Waterborne, High-Solids, and Powder Coatings Symposium, Feb. 26-28, 2003, (87) PCT Pub. No.: WO2008/121133 New Orleans, LA, USA. p. 1-8.* PCT Pub. Date: Oct. 9, 2008 * cited by examiner (65) Prior Publication Data Primary Examiner — Ling Choi Assistant Examiner — Michael L. Leonard US 2010/01 13733 A1 May 6, 2010 (74) Attorney, Agent, or Firm — Christopher P. Demas: Related U.S. Application Data Thoburn T. Dunlap (57) ABSTRACT (60) Provisional application No. 60/920,642, filed on Mar. The present invention is a low haze thermoplastic polyure 29, 2007. thane (TPU) prepared from a chain extender mixture that (51) Int. Cl. includes an acyclic diol and a mixture of 1.3- and 1.4-cyclo COSG 18/00 (2006.01) hexanedimethanol. The TPU elastomers exhibit good optical (52) U.S. Cl. ................ 528/65:528/44; 528/59; 528/66; clarity, particularly when formed into relatively thick injec 528/80; 528/81: 528/85; 252/1822; 252/182.21; tion molded parts. 252/182.22: 252/182.25; 252/182.28 18 Claims, No Drawings US 8,242,228 B2 1. 2 LOW HAZE THERMOPLASTC As used herein, the term “thermoplastic polyurethane' or POLYURETHANE USING MIXTURE OF “TPU” in intended as a shorthand to include materials having CHAIN EXTENDERS INCLUDING 1.3- AND urethane groups (as are formed in the reaction of hydroxyl 1,4-CYCLOHEXANEDIMETHANOL containing compounds with isocyanate-containing com pounds) as well as materials having both urethane and urea This application claims priority from PCT Application groups (as are formed in the reaction of isocyanate-contain Serial No. PCT/US2007/24753 filed on Dec. 3, 2007, which ing compounds with both hydroxyl-containing compounds claims the benefit of U.S. Provisional Application No. and compounds that contain primary or secondary amino 60/920,642 filed Mar. 29, 2007. groups). 10 In another embodiment, the invention is a TPU elastomer This invention relates to thermoplastic polyurethanes. which is a polymer of (1) at least one high equivalent weight Thermoplastic polyurethane (“TPU) elastomers are used poly(caprolactone) diol or mixture thereof with one or more in a variety of applications such as gears, bearings, joints for other high equivalent weight diols, (2) a chain extender mix precision machinery, parts for electronic instruments, soles, ture that includes at least 60 mole-% of 1,4-butanediol and at bladders and uppers for athletic shoes and ski boots, automo 15 least 8 mole-% of a mixture of cyclohexanedimethanol iso tive parts, seals, gaskets and packings for hydraulic fluid mers, and (3) at least one diisocyanate, wherein the mixture of systems, as well as other applications. TPU elastomers are cyclohexanedimethanol isomers includes at least 40 weight typically the reaction product of one or more diisocyanate percent each of 1.3-cyclohexanedimethanol and 1.4-cyclo compounds, one or more high equivalent weight diols and one hexanedimethanol. or more chain extenders. The TPU elastomers of the invention often have better It is sometimes desirable that the TPU elastomer exhibits optical clarity, particularly when molded into thicker parts, good optical clarity, for functional or aesthetic reasons, or than similar TPU elastomers that use only 1,4-butanediol as both. An example of this is footwear applications, in which the chain extender. uppers, air or gel bladders, and elements of soles (such as The chain extender mixture used in the present invention is cleats, for example) are sometimes desired to be clear for 25 a mixture containing at least two components. The first com reasons of appearance. In addition to being clear, the TPU ponent is an acyclic diol or diamine, which has a molecular elastomer must meet other performance criteria for the par weight of up to about 400 and preferably up to about 250. Diol ticular application. In footwear applications, abrasion resis chain extenders are preferred. The acyclic diol or diamine tance and permeability to moisture are important attributes. chain extender constitutes at least 60 mole percent of the The TPU elastomer must also exhibit a hardness that is suit 30 chain extender mixture. In preferred embodiments, the acy able for the intended application. clic diolor diamine chain extender constitutes at least 80 mole A wide variety of polyols, chain extenders and polyisocy percent of the chain extender mixture and it may constitute up anate have been proposed for use in TPU elastomer applica to 92 mole-% of the chain extender mixture. A mixture of tions. See, e.g., U.S. Pat. Nos. 3,214,411, 4,371,684, 4,980, acyclic diols and diamines may be used as the first component 445, 5,013,811, 5,648.447, 6,521,164 and 7,045,650, among 35 of the chain extender mixture. many others. In some cases, it has been proposed to use Examples of acyclic diol chain extenders include, for mixtures of polyols and/or chain extenders to make TPU example, ethylene glycol, diethylene glycol, 1,3-pro elastomers. For example, U.S. Pat. Nos. 4.371,684 and 6,521, panediol, dipropylene glycol, tripropylene glycol, 1,4-bu 164 each describes the use of particular chain extender mix tanediol, 1.6-hexanediol, 1.5-heptanediol and the like. tures in manufacturing TPU elastomers. 40 Examples of acyclic diamine chain extenders include ethyl Many commercially-used soft- to moderately hard (Shore ene diamine, 2-methyl-1,5-pentanediamine, 1.6-hexanedi Adurometer hardness of 60 to a Shore D durometerhardness amine, and the like. 1,4-butanediol is most preferred among of about 75) TPU elastomer formulations are based on 1,4- these. butanediol as the chain extender. 1,4-butanediol-based sys The second component of the chain extender mixture is a tems often provide a good balance of properties at reasonable 45 mixture of 1.3-cyclohexanedimethanol and 1,4-cyclohex cost, compared to systems that are based on other chain anedimethanol. The ratio of 1.3-cyclohexanedimethanol to extenders. One problem with some 1,4-butanediol-based sys 1,4-cyclohexanedimethanol units can vary from about 20:80 tems is that they tend to exhibit a significant amount of haze, to 80:20. A preferred ratio of these is from about 65:35 to or loss of optical clarity. The problem with haze is particularly 35:65 by weight. A more preferred ratio is from about 60:40 severe in thicker parts. As the part becomes thicker, the loss of 50 to about 40:60 by weight. The 1.3-cyclohexanedimethanol optical clarity is often greater than would be expected due to and 1.4-cyclohexanedimethanol each can be the cis-isomer, the mere increase in the part thickness. It would be desirable the trans-isomer, or a mixture of both cis- and trans-isomers. to provide a TPU elastomer that is economical, has good The most preferred cyclohexanedimethanol mixture contains mechanical properties and exhibits good optical clarity. The all four of cis-1,3-cyclohexanedimethanol, trans-13-cyclo hardness of the TPU elastomer suitably is between a Shore A 55 hexanedimethanol, cis-1,4-cyclohexandimethanol and trans durometer hardness of 60 and a Shore D durometer hardness 1,4-cyclohexane dimethanol, and in which the 1.3-isomers of 75. constitute from 40 to 60% by weight of the mixture and the This invention is a thermoplastic polyurethane (TPU) elas 1,4-isomers constitute from about 60 to 40% by weight of the tomer which is a polymer of (1) at least one high equivalent mixture. weight, difunctional compound, (2) a chain extender mixture 60 The cyclohexanedimethanol mixture constitutes at least 8 and (3) at least one diisocyanate, wherein the chain extender mole percent of the chain extender mixture. It may constitute mixture includes at least 60 mole-% of an acyclic diol or up to 40 mole percent of the chain extender mixture. It pref diamine having a molecular weight of up to about 400 and at erably constitutes from 8 to 30 mole percent of the chain least 8 mole-% of a mixture of cyclohexanedimethanol extender mixture and even more preferably from 10 to 25 (CHDM) isomers, the mixture of cyclohexanedimethanol 65 mole percent of the chain extender mixture.
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