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(12) United States Patent (10) Patent No.: US 8,946,374 B2 Imada Et Al

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(12) United States Patent (10) Patent No.: US 8,946,374 B2 Imada Et Al USOO894.6374B2 (12) United States Patent (10) Patent No.: US 8,946,374 B2 Imada et al. (45) Date of Patent: Feb. 3, 2015 (54) POLYETHER ESTER COMPOSITION, C08G 18/48 (2006.01) POLYURETHANE RESIN COMPOSITION, CSG 18/50 (2006.01) AND OPTICAL MATERALUSING THE (52) U.S. Cl. SAME USPC .................................. 528/79; 528/28: 528/83 (58) Field of Classification Search (75) Inventors: Tomoyuki Imada, Osaka (JP): Kouji USPC ................................................ 528/28, 79, 83 Shiraishi, Osaka (JP) See application file for complete search history. (73) Assignee: DIC Corporation, Tokyo (JP) (56) References Cited (*) Notice: Subject to any disclaimer, the term of this U.S. PATENT DOCUMENTS patent is extended or adjusted under 35 4,128,532 A * 12/1978 Eimers et al. ................... 528/79 U.S.C. 154(b) by 151 days. 5,942,158 A * 8/1999 Okoroafor et al. 252/586 2002/001643.6 A1 2/2002 Ohmori et al. .................. 528,61 (21) Appl. No.: 13/394,920 FOREIGN PATENT DOCUMENTS (22) PCT Filed: Sep. 14, 2010 JP 8-208830 A 8, 1996 JP 11-2792.51 A 10, 1999 (86). PCT No.: PCT/UP2010/065777 WO 2009 107301 A1 9, 2009 S371 (c)(1), (2), (4) Date: Mar. 8, 2012 * cited by examiner Primary Examiner — Rabon Sergent (87) PCT Pub. No.: WO2011/034033 (74) Attorney, Agent, or Firm — McDermott Will & Emery PCT Pub. Date: Mar. 24, 2011 LLP (65) Prior Publication Data (57) ABSTRACT A polyurethane resin composition for optical applications can US 2012/O172567 A1 Jul. 5, 2012 contain, as essential components, a polyisocyanate and a polyester-ether polyol obtained by polycondensation of a (30) Foreign Application Priority Data glycol component containing an alkylene oxide adduct of a bisphenol and an aromatic carboxylic acid component and Sep. 18, 2009 (JP) ................................. 2009-217OOO particularly preferably having a glass transition temperature (51) Int. Cl. of 50° C. or lower. An optical material using the composition C08G 18/42 (2006.01) is also provided for. C08G 18/46 (2006.01) 14 Claims, No Drawings US 8,946,374 B2 1. 2 POLYETHER ESTER COMPOSITION, CITATION LIST POLYURETHANE RESIN COMPOSITION, AND OPTICAL MATERALUSING THE Patent Literature SAME 5 PTL 1: Japanese Unexamined Patent Application Publication CROSS REFERENCE TO PRIORAPPLICATIONS No. 11-279251 This application is a U.S. National Phase application under SUMMARY OF INVENTION 35 U.S.C. S371 of International Application No. PCT/ JP2010/065777, filed on Sep. 14, 2010 and claims benefit of 10 Technical Problem priority to Japanese Patent Application No. 2009-217000. filed on Sep. 18, 2009. The International Application was Accordingly, an object of the present invention is to pro published in Japanese on Mar. 24, 2011 as WO 2011/034033 vide a polyester polyol suitable for optical applications to Such an extent that there is no problem in terms of class A1 under PCT Article 21(2). The contents of the applications 15 transition temperature and solubility in solvents in practical are hereby incorporated by reference. use while having a high refractive index, and a urethane resin TECHNICAL FIELD composition derived from the polyester polyol. Solution to Problem The present invention relates to a polyether ester compo sition and a polyurethane resin composition that are particu As a result of intensive studies conducted in order to larly suitable for optical applications. More specifically, the achieve the above object, the inventors of the present inven present invention relates to a polyurethane film having a high tion found the following: light transmittance and a low dispersion property. (1) By lowering the symmetry of the molecular structure (by 25 introducing a bending portion), intermolecular interaction is BACKGROUND ART weakened. Consequently, crystallinity decreases, thereby lowering the glass transition temperature. Examples of typical plastics for optical applications (2) In urethane resins, in the case where a polyester-polyether include polymethyl methacrylate and polycarbonate. Polym polyol is used as a diol component, the glass transition tem ethyl methacrylate is advantageous in terms of transparency, 30 perature of the polyester-polyether polyol can be controlled weather resistance, low birefringence, and good moldability to below, and the glass transition temperature of the resulting and is used in optical lenses such as a CD pick-up lens, optical urethane resin can also be made low. films such as a retardation film, and optical disk Substrates, (3) By using an alkylene oxide adduct of a bisphenol as an and the like. However, polymethyl methacrylate has a serious alcohol component of the polyester-polyether polyol, the disadvantage of a high water absorption rate. In the case 35 glass transition temperature of the polyester-polyether polyol where the water absorption rate is high, in optical lenses, can be controlled to be low. degradation of light-focusing accuracy and a change in the (4) In the case where a bisphenol derivative is used as an alcohol component of the polyester-polyether polyol and an refractive index are caused by swelling and deformation of aromatic carboxylic acid is used as a carboxylic acid compo the lenses. Furthermore, in disk substrates, deformation and 40 nent thereof, a polyester-polyether polyol having a high curvature are caused by water absorption, resulting in read/ refractive index can be obtained. write errors. (5) A polyurethane resin derived from the polyester-polyether Polycarbonate is advantageous in terms of transparency, heat polyol also has a high refractive index. resistance, impact resistance, a low water absorption rate, etc. The present invention has been made on the basis of the and is considered to be an important optical material. How 45 above finding. ever, polycarbonate is disadvantageous in that the birefrin Specifically, the present invention provides a polyester gence, which is an important characteristic in the optical ether polyol composition for optical applications, the polyes system, is high. In the case where the birefringence is high, in ter-ether polyol composition containing a polycondensate of optical disks, the polarization direction of reflected light with a glycol component containing an alkylene oxide adduct of a respect to incident light deviates, resulting in an increase in 50 bisphenol and an aromatic carboxylic acid component con noise. taining, as essential components, a naphthalenedicarboxylic Accordingly, materials that can compensate for these dis acid derivative and a phthalic acid derivative. advantages have been desired. Furthermore, the present invention provides a polyure In general, polyurethanes are excellent in terms of oil resis thane resin composition containing, as essential components, tance and abrasion resistance, but have low heat resistance. 55 a polyisocyanate and a polyester-ether polyol obtained by However, since physical properties of polyurethanes signifi polycondensation of a glycol component containing an alky cantly vary depending on the type of raw materials, condi lene oxide adduct of a bisphenol and an aromatic carboxylic tions for cross-linking, etc., various physical properties that acid component, and an optical material using the composi cannot be exhibited by other homopolymers can be adjusted. tion. As a polyurethane that is applied to optical applications, for 60 example, a polyurethane obtained by using an alkylene oxide Advantageous Effects of Invention adduct of 4,4'-(9H-fluorene-9,9-diyl)bis(phenol) as a dial component has been proposed (for example, refer to Patent According to the present invention, a high refractive index Literature 1). However, although a resin having a high refrac is realized by forming a highly aromatic structure composed tive index can be obtained in this technology, the glass tran 65 of a glycol unit having a bisphenol skeleton and an aromatic sition temperature of the resin is also increased and thus the carboxylic acid unit, while the glass transition temperature is resin is poor in practical use. controlled by controlling the orientation of the molecule with US 8,946,374 B2 3 4 phthalic anhydride. Thus, a high-refractive-index material Among these, bisphenol S. bisphenol A, 4,4'-(3,3,5-trim can be obtained by a simple and relatively inexpensive ethyl-1,1-cyclohexanediyl)bis(phenol), 4,4'-(9H-fluorene-9, method without using a special material or without employ 9-diyl)bis(phenol), tricyclo[5.2.1.0 decane diphenol, etc. ing a special synthesis method. Furthermore, since this mate are preferable. rial has a glass transition temperature within a range of prac tical use in terms of urethanization, the material is also The alkylene oxide adduct in the alkylene oxide adduct of suitable for a urethane-acrylated. UV-curable optical mate the bisphenol is preferably an alkylene oxide having 2 to 4 rial. Thus, it is possible to provide a urethane resin with high carbon atoms. practical utility, the urethane resin exhibiting a high refractive Regarding the amount of addition of the alkylene oxide in index suitable for optical applications and having a relatively the alkylene oxide adduct of the bisphenol, a compound in low glass transition temperature. 10 which 2 to 10 moles of an alkylene oxide is added per equiva lent of hydroxyl groups of a bisphenol is preferable from the DESCRIPTION OF EMBODIMENTS standpoint of controlling the glass transition temperature of the resulting urethane resin, crystallinity of the resin, and A polyurethane resin composition of the present invention solubility of the resin in solvents. contains, as an essential component, a polyester-ether polyol 15 In addition, other diol components may also be incorpo obtained by polycondensation of an alkylene oxide adduct of rated, as required. Examples of the other diol components a bisphenol serving as a glycol component and an aromatic include alkylene glycols such as ethylene glycol, propylene carboxylic acid serving as an acid component. glycol, 1,4-butane diol. 1,3-butane diol. 1.2-butylene glycol, The alkylene oxide adduct of the bisphenol is preferably, trimethylene glycol, neopentyl glycol, diethylene glycol, for example, a compound represented by general formula (1) 2-methyl-1,3-propylene glycol, triethylene glycol, octameth below.
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