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(12) United States Patent (10) Patent No.: US 9,587,086 B2 Lu Et Al

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(12) United States Patent (10) Patent No.: US 9,587,086 B2 Lu Et Al USOO9587086B2 (12) United States Patent (10) Patent No.: US 9,587,086 B2 Lu et al. (45) Date of Patent: Mar. 7, 2017 (54) POLY(VINYLACETAL) RESIN 2008/026827O A1 10, 2008 Chen et al. 2008/0286542 A1 11/2008 Hayes et al. COMPOSITIONS, LAYERS, AND 2012/0133764 A1 5, 2012 Hurlbut INTERLAYERS HAVING ENHANCED 2013/0022824 A1 1/2013 Meise et al. OPTICAL PROPERTIES 2013/O137789 A1 5, 2013 Olsen et al. 2013, O139520 A1 6, 2013 Masse et al. (71) Applicant: Solutia Inc., St. Louis, MO (US) 2013,0236693 A1 9, 2013 Lu 2014/0363651 A1 12/2014 Lu et al. 2014/0363652 All 12/2014 Lu et al. (72) Inventors: Jun Lu, East Longmeadow, MA (US); 2014/0364549 A1 12/2014 Lu et al. Wenjie Chen, Amherst, MA (US); 2014/0364550 A1 12/2014 Lu Curtis Schilling, III, Kingsport, TN 2016. O159051 A1 6, 2016 Lu (US); John Joseph D'Errico, Glastonbury, CT (US); Pinguan Zheng, FOREIGN PATENT DOCUMENTS Kingsport, TN (US) DE 10343 385 A1 4/2005 DE 102O11111624 2/2013 ............. CO8K 5,103 (73) Assignee: EASTMAN CHEMICAL COMPANY., JP H1180421 * 3, 1999 ............... CO8K 5, 12 Kingsport, TN (US) JP 3124441 B2 1, 2001 JP 2002-104878 4/2002 (*) Notice: Subject to any disclaimer, the term of this JP 3377848 B2 2, 2003 patent is extended or adjusted under 35 WO WO 2010.108975 A1 9, 2010 U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS (21) Appl. No.: 14/587,692 English translation of JPH1 180421, dated Mar. 1999, pp. 1-12.* (22) Filed: Dec. 31, 2014 English translation of DE 102011111624, dated Feb. 2013, pp. 1-29. (65) Prior Publication Data Wade, Bruce; “Vinyl Acetal Polymers'; Encyclopedia of Polymer US 2016/O16OOO5 A1 Jun. 9, 2016 Science & Technology, 3 ed., vol. 8, pp. 38.1-399 (2003). ASTM D1396; Standard Test Methods for Chemical Analysis of Poly(Vinyl Butryal); Published Jul. 1992. Related U.S. Application Data ASTM D542; “Standard Test Method for Index of Refraction of Transparent Organic Plastics': Published Mar. 2014. (60) Provisional application No. 62/088,957, filed on Dec. ASTM D1003: “Standard Test Method for Haze and Luminous 8, 2014. Transmittance of Transparent Plastics': Published Nov. 2013. ASTM D2240; “Standard Test Method for Rubber Property– (51) Int. Cl. Durometer Hardness'; Published Apr. 2010. CSK 5/103 (2006.01) ASTM E90; "Standard Test Method for Laboratory Measurement of CSK 5/12 (2006.01) Airborne Sound Transmission Loss of Building Partitions and CSK 5/539 (2006.01) Elements”; Published Aug. 2009. Co-pending U.S. Appl. No. 14299,945, filed Jun. 9, 2014; Lu et al. (52) U.S. Cl. Co-pending U.S. Appl. No. 14299,975, filed Jun. 9, 2014; Lu et al. CPC ................ C08K 5/103 (2013.01); C08K 5/12 Co-pending U.S. Appl. No. 14299,996, filed Jun. 9, 2014; Lu et al. (2013.01); C08K 5/1539 (2013.01) Co-pending U.S. Appl. No. 14/300.612, filed Jun. 10, 2014; Jun Lu. (58) Field of Classification Search Notification of Transmittal of the International Search Report and CPC .................................. C08K 5/103; C08K 5/12 the Written Opinion of the International Searching Authority, or the See application file for complete search history. Declaration; International Application No. PCT/US2014/041698 with a mailing date of Aug. 29, 2014. (56) References Cited (Continued) U.S. PATENT DOCUMENTS Primary Examiner — Paul A Zucker 2,282,026 A 5, 1942 Bren et al. 2,282,057 A 5/1942 Hopkins et al. Assistant Examiner — Mark Luderer 2,823, 192 A 2f1958 Elwell et al. (74) Attorney, Agent, or Firm — Steven A. Owen 3,644,594 A 2f1972 Mont et al. 4,287,307 A 9, 1981 Hostettler 4,361,625. A 11, 1982 Beckmann et al. (57) ABSTRACT 4.675.434 A * 6/1987 Uhm ....................... CO7C 67/08 556.106 Resin compositions, layers, and interlayers comprising two 4,874,814 A 10, 1989 Cartier et al. 5,137,954. A 8/1992 DasGupta et al. or more thermoplastic polymers and at least one RI balanc 5,169,897 A 12, 1992 Walls ing agent for adjusting the refractive index of at least one of 5, 190,826 A 3, 1993 Asahina et al. the resins or layers is provided. Such compositions, layers, 5,340,654 A 8, 1994 Ueda et al. and interlayers exhibit enhanced optical properties while 5,728,472 A 3, 1998 D’Errico 6,984,679 B2 1/2006 Papenfuhs retaining other properties, such as impact resistance and 7,510,771 B2 3, 2009 Lu acoustic performance. 2004/0065229 A1 4/2004 Papenfuhs et al. 2007, 0037926 A1* 2, 2007 Olsen ....................... CO8K5/12 524,569 10 Claims, No Drawings US 9,587,086 B2 Page 2 (56) References Cited Office Action dated Apr. 15, 2015 received in co-pending U.S. Appl. No. 14299,996. Office Action dated Jul. 6, 2015 received in co-pending U.S. Appl. OTHER PUBLICATIONS No. 14/299,975 Office Action dated Dec. 17, 2015 received in co-pending U.S. Co-pending U.S. Appl. No. 14/505,191, filed Oct. 2, 2014; Jun Lu. Appl. No. 14/587,702. Notification of Transmittal of the International Search Report and Co-pending U.S. Appl. No. 14/505.247, filed Oct. 2, 2014; Jun Lu. the Written Opinion of the International Searching Authority, or the Co-pending U.S. Appl. No. 14/514,641, filed Oct. 15, 2014; Jun Lu. Declaration; International Application No. PCT/US2015/063874 Co-pending U.S. Appl. No. 14/563,622, filed Dec. 8, 2014; Lu et al. with a mailing date of Mar. 29, 2016. Co-pending U.S. Appl. No. 14/563,719, filed Dec. 8, 2014; Lu et al. Office Action dated Jul. 11, 2016 received in co-pending U.S. Appl. Co-pending U.S. Appl. No. 14/563,347, filed Dec. 8, 2014; Lu et al. No. 14/587,702. Co-pending U.S. Appl. No. 14/563,352, filed Dec. 8, 2014; Liet al. Dupont. Untitled discloses comparisons between PVB and SGP Co-pending U.S. Appl. No. 14/563,359, filed Dec. 8, 2014; Lu et al. interlayers used in Safety glass, accessed on Sep. 12, 2016. Dupont. Co-pending U.S. Appl. No. 14/563,364, filed Dec. 8, 2014; Lu et al. com, obtained from http://www2.dupont.com/Building CN/assets/ Co-pending U.S. Appl. No. 14/563,372, filed Dec. 8, 2014; Lu et al. downloads/SGPintro E.pdf. Co-pending U.S. Appl. No. 14/563,077, filed Dec. 8, 2014; Ukidwe PubChem. Glutaraldehyde, accessed on Sep. 12, 2016, NIH.gov, et al. obtained from https://pubchem.ncbi.nlm.nih.gov/compound/ Co-pending U.S. Appl. No. 14/563,373, filed Dec. 8, 2014; Lu et al. glotaraldehydefisection=Top. Co-pending U.S. Appl. No. 14/563,378, filed Dec. 8, 2014; Lu et al. Sigma-Aldrich, Tri(ethylene glycol) bis(2-ethylhexanoate), Co-pending U.S. Appl. No. 14/563,381, filed Dec. 8, 2014; Lu et al. accessed on Sep. 12, 2016, Sigmaaldrich.com, obtained from http:// Co-pending U.S. Appl. No. 14/563,011, filed Dec. 8, 2014; Jun Lu. www.sigmaaldrich.com/catalog/product/aldrich/525103?lang-en& Co-pending U.S. Appl. No. 14/587,675, filed Dec. 31, 2014; Lu et region=US. al. AZOM, Indium Tin Oxide (ITO)—Properties and Applications, Jan. Co-pending U.S. Appl. No. 14/587,702, filed Dec. 31, 2014; Lu et 23, 2004, Azo Materials, obtained from http://www.azom.com/ al. article.aspx?AtricleID=2349. Office Action dated Apr. 6, 2015 received in co-pending U.S. Appl. No. 14/300.612. * cited by examiner US 9,587,086 B2 1. 2 POLY(VINYLACETAL) RESIN different refractive indices. Clarity is another important COMPOSITIONS, LAYERS, AND optical property that is determined by measuring the level of INTERLAYERS HAVING ENHANCED haze within the interlayer or panel. High haze typically OPTICAL PROPERTIES occurs when different types of optically incompatible poly mers and/or plasticizers are blended or mixed together. In CROSS-REFERENCE TO RELATED Such mixtures, light passing through the blend is scattered as APPLICATION it encounters regions of different polymer materials, and the result is a hazy, visually unclear appearance. High clarity This application claims priority to U.S. Provisional Appli polymers and interlayers are those having very low haZe cation Ser. No. 62/088,957 filed Dec. 8, 2014, the disclosure 10 values. of which is incorporated herein by reference in its entirety. Thus, a need exists for polymer resins, resin layers, and interlayers that exhibit desirable optical properties, such as BACKGROUND reduced haze and mottle and improved clarity, without sacrificing other properties, including impact resistance and 1. Field of the Invention 15 acoustic performance. Such interlayers could be monolithic This disclosure relates to polymer resins and, in particular, or multilayered and should be usable in a wide variety of to polymer resins Suitable for use in polymer interlayers, applications, including safety glass and polymer laminates. including those utilized in multiple layer panels. 2. Description of Related Art SUMMARY Poly(vinyl butyral) (PVB) is often used in the manufac ture of polymer sheets that can be used as interlayers in In a first aspect, the present invention provides a plasti multiple layer panels, including, for example, light-trans cizer comprising at least one of following: (i) a terephthalate mitting laminates Such as safety glass or polymeric lami comprising one of the following compounds: bis-(2-ethyl nates. PVB is also used in photovoltaic solar panels to hexyloxyethoxyethoxyethyl) terephthalate, bis-(2-ethyl encapsulate the panels which are used to generate and 25 hexyloxyethoxyethyl) terephthalate, bis-(2-ethylhexyloxy Supply electricity for commercial and residential applica ethyl) terephthalate, bis-(dodecyl) terephthalate, bis tions.
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