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(12) Patent Application Publication (10) Pub. No.: US 2004/0158031A1 Yoshimura Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0158031A1 Yoshimura Et Al US 2004O158031A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0158031A1 Yoshimura et al. (43) Pub. Date: Aug. 12, 2004 (54) ALICYCLIC COMPOUND FOR OPTICAL (30) Foreign Application Priority Data MATERIAL Jun. 19, 2001 (JP)...................................... 2001-185491 (76) Inventors: Yuichi Yoshimura, Mie (JP); Motoharu Takeuchi, Tokyo (JP) Publication Classification Correspondence Address: (51) Int. Cl. ............................................. C08G 75/00 Antonelli Terry (52) U.S. Cl. .............................................................. 528/377 Stout & Kraus Suite 1800 (57) ABSTRACT 1300 North Seventeenth Street Arlington, VA 22209 (US) The alicyclic compound of the present invention has a five or more membered ring Structure having an epithioethylene (21) Appl. No.: 10/474,704 linkage and/or an epidithioethylene linkage, and has tow or more Sulfur atoms in its molecule. Optical materials pro (22) PCT Filed: Jun. 11, 2002 duced by curing the alicyclic compound or a composition containing the alicyclic compound by polymerization Show (86) PCT No.: PCT/JP02/05800 high refractive index. US 2004/0158031 A1 Aug. 12, 2004 ALCYCLIC COMPOUND FOR OPTICAL more of the alicyclic compounds. To achieve a high refrac MATERIAL tive indeX efficiently, the composition for optical materials contains the alicyclic compound in an amount preferably 5 TECHNICAL FIELD to 100% by weight, more preferably 10 to 100% by weight 0001. The present invention relates to optical materials based on the total amount thereof. Suitable for producing plastic lenses, prisms, optical fibers, information recording media, and filters, particularly, Suit 0007. The composition for optical materials referred to able for producing plastic spectacle lenses. herein may include a mixture comprising at least one type of the alicyclic compound as only one essential component and BACKGROUND ART a mixture comprising at least one type of the alicyclic compound and a compound capable of reacting with the 0002 Plastic materials have been widely used in various optical applications, particularly in manufacturing spectacle alicyclic compound (hereinafter referred to as “reactive lenses, because of their lightweight, toughness and easineSS compound”) as the essential components. The reactive com of dyeing. Optical materials, particularly Spectacle lenses are pound is not specifically limited as long as it provides a required to have, in addition to a low Specific gravity, a high transparent resin usable as optical materials upon curing by clearness, a low yellowneSS, and optical properties Such as polymerization with the alicyclic compound. a high refractive indeX and a large Abbe's number. Since a 0008 Examples of the alicyclic compound of the present large refractive indeX reduces the thickness of a lens, many invention include, but not limited to, 1,2-epidithiocyclopen Studies have been made thereon to date and many novel compounds have been proposed. Recently, many organic tane, 1,2-epidithiocyclohexane, 1,2:3,4-diepithiocyclopen compounds having Sulfur atom and/or Selenium atom have tane, 1,2:3,4-diepithiocyclohexane, 1,2:4,5-diepithiocyclo been proposed to achieve a high refractive indeX and a high hexane, 1,2:34:5,6-triepithiocyclohexane, 1,2:2,3:3,4:4,5:5, Abbe’s number. Of Such compounds, Some polyepisulfide 6:1,6-hexaepithiocyclohexane, 1,2-epithio-4- compounds have been found to be well balanced in refrac epithioethylcyclopentane, 1,2-epithio-3- tive index and Abbe’s number. For example, Japanese Patent epithioethylcyclohexane, 1,2-epithio-4- Application Laid-Open No. 9-110979 proposes a straight epithioethylcyclohexane, 1,2-epithio-3-thiacyclopentane, chain polyepisulfide compound, Japanese Patent Applica 1,2-epithio-4-thiacyclopentane, 1,2-epithio-3-thiacyclohex tion Laid-Open No. 9-71580 proposes a branched poly ane, 1,2-epithio-4-thiacyclohexane, 1,2:4,5-diepithio-3-thia episulfide compound, Japanese Patent Application Laid cyclohexane, 1,2:4,5-diepithio-3,6-dithiacyclohexane, Open No. 9-255781 proposes a polyepisulfide compound 1,2:4,5-diepidithio-3,6-dithiacyclohexane, 1,2:4,5-diepi having a cyclic Structure, and Japanese Patent Application thio-3,6,7-trithiacycloheptane, 1,2:5,6-diepithio-3,4,7,8- Laid-Open No. 11-140046 proposes a polyepisulfide com tetrathiacyclooctane, 1,2:5,6-diepidithio-3,4,7,8-tetrathiacy pound having Selenium atom. However, the refractive index clooctane, 1,2:14:4,5-triepithio-3,6-dithiacyclohexane, of materials obtained from these polyepisulfide are limited 1,2:14:25:4,5-tetraepithio-3,6-dithiacyclohexane, and to 1.73 at most. 1,2:14:25:4,5-tetraepidithio-3,6-dithiacyclohexane. DISCLOSURE OF INVENTION 0009. Of the above exemplified compounds, preferred are 0003. An object of the present invention is to provide an alicyclic compounds having at least one Sulfide linkage in optical material which enables to attain a refractive indeX addition to the epi(di)thioethylene linkage in its ring struc ture or in its side chain, Such as 1,2-epithio-4-epithioethyl higher than attained by known materials. cyclopentane, 1,2-epithio-3-epithioethylcyclohexane, 1,2- 0004. As a result of extensive study for achieving the epithio-4-epithioethylcyclohexane, 1,2-epithio-3- above object, the inventors have found that a five- or more thiacyclopentane, 1,2-epithio-4-thiacyclopentane, 1,2- membered alicyclic compound having an epithioethylene epithio-3-thiacyclohexane, 1,2-epithio-4-thiacyclohexane, linkage and/or an epidithioethylene linkage in its ring Struc 1,2:4,5-diepithio-3-thiacyclohexane, 1,2:4,5-diepithio-3,6- ture and tow or more Sulfur atoms in its molecule, or a composition containing the alicyclic compound provides an dithiacyclohexane, 1,2:4,5-diepidithio-3,6-dithiacyclohex optical material having a high refractive index upon curing ane, 1,2:4,5-diepithio-3,6,7-trithiacycloheptane, 1,2:5,6- by polymerization. diepithio-3,4,7,8-tetrathiacyclooctane, 1,2:5,6-diepidithio-3, 4,7,8-tetrathiacyclooctane, 1,2:14:4,5-triepithio-3,6- BEST MODE FOR CARRYING OUT THE dithiacyclohexane, 1,2:14:25:4,5-tetraepithio-3,6- INVENTION dithiacyclohexane, and 1.2:14:2,5:4,5-tetraepidithio-3,6- dithiacyclohexane. 0005 The alicyclic compound for use in the present invention has a five- or more membered ring Structure which 0010 More preferred are alicyclic compounds having has at least one epithioethylene linkage and/or an epidithio two or more epi(di)thioethylene linkages, Such as 1,2:4,5- ethylene linkage (hereinafter referred to collectively as diepithio-3-thiacyclohexane, 1,2:4,5-diepithio-3,6-dithiacy “epi(di)thioethylene linkage'). The alicyclic compound has clohexane, 1,2:4,5-diepidithio-3,6-dithiacyclohexane, 1,2:4, two or more Sulfur atoms including the Sulfur atom in the 5-diepithio-3,6,7-trithiacycloheptane, 1,2:5,6-diepithio-3,4, epi(di)thioethylene linkage. 7,8-tetrathiacyclooctane, 1,2:5,6-diepidithio-3,4,7,8- 0006 The optical material obtained by curing the alicy tetrathiacyclooctane, 1,2:14:4,5-triepithio-3,6- clic compound or a composition containing the alicyclic dithiacyclohexane, 1,2:14:25:4,5-tetraepithio-3,6- compound by polymerization exhibits a high refractive dithiacyclohexane, and 1.2:14:2,5:4,5-tetraepidithio-3,6- indeX. The composition may contain only one type or two or dithiacyclohexane. US 2004/0158031 A1 Aug. 12, 2004 0.011 Still more preferred are alicyclic compounds rep 0022. As described above, the composition for optical resented by the following formula 1: materials of the present invention may contain the reactive compound in addition to the alicyclic compound. The reac tive compound is preferably an episulfide compound having (1) a functional group that is easily reacted with the alicyclic R1 compound, for example, an epithioethyl group and/or an epidithioethyl group represented by the following formula 2: a Sw-C-S,Y Y-R V / V (2) S-C-S, CH2 -CH-S 0012 wherein S is sulfur atom; w and X are each inde pendently 1 or 2, y and Z are each independently integer 0023 wherein S is Sulfur atom and v is 1 or 2. from 0 to 2; R', R, R and R" are each independently 0024 Examples of the episulfide compounds are shown hydrogen or hydrocarbon group having 1 to 5 carbon atoms, below. excluding y and Z being Simultaneously Zero. Examples of the alicyclic compounds represented by the formula 1 0025 (1) Episulfide Compounds Having Aliphatic Chain include 1,2:4,5-diepithio-3-thiacyclohexane, 1,2:4,5-diepi Skeleton thio-3,6-dithiacyclohexane, 1,2:4,5-diepidithio-3,6-dithia 0026 1,1-Bis(epithioethyl)methane, 1-(epithioethyl)-1- cyclohexane, 1,2:4,5-diepithio-3,6,7-trithiacycloheptane, (3-epithiopropyl)methane, 1,1-bis(B-epithiopropyl 12:5,6-diepithio-3,4,7,8-tetrathiacyclooctane, and 1,2:5,6- )methane, 1-(epithioethyl)-1-(B-epithiopropyl)ethane, 1,2- diepidithio-3,4,7,8-tetrathiacyclooctane. bis(B-epithiopropyl)ethane. 1-(epithioethyl)-3-(B- epithiopropyl)butane, 1,3-bis(B-epithiopropyl)propane, 0013 The alicyclic compounds may be synthesized 1-(epithioethyl)-4-(3-epithiopropyl)pentane, 1,4-bis(B-epi mainly from corresponding olefins, epoxy compounds, diha thiopropyl)butane, 1-(epithioethyl)-5-(B-epithiopropyl)hex logenated compounds and dithiols by the following method: ane, 1-(epithioethyl)-2-(B-epithiobutylthio)ethane, 1-(epith 0014 (1) a method in which a cyclic olefin is reacted ioethyl)-2-2-(B-epithiobutylthio)ethylthioethane, with a thiosulfenyl halide or disulfur dichloride, fol tetrakis(3-epithiopropyl)methane, 1,1,1-tris(3-epithiopropy lowed by ring closure with alkali treatment to produce l)propane,
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