Spirotetrathiocarbamates and spirooxothiocarbamates

US7732507B2 · kind B2 · utility

Assignee

• Essilor International (Compagnie Generale d'Optique) · FR

Inventors

• Aref Jallouli · Midland, US
• Martin Rickwood · Clarks Summit, US
• Kimberly Morgan · Moosic, US
• Sirisoma Wanigatunga · Bound Brook, US

Key dates

• Filing date: Dec 19, 2003
• Grant date: Jun 8, 2010
• Expiry date: Jul 19, 2026

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D495/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Spirotetrathiocarbamates (STOCs) or oxa substituted compounds (SOTOCs) of Formula I: Formula (I) or bisSTOC or bisSOTOC compounds of Formula II: Formula (II) wherein X1, X2, X3, X4, X5, X6, X7, and X8, are independently O or S; and preferably at least two and up to all four of X1, X2, X3 and X4, and at least two and up to all four of X5, X6, X7, and X8 are sulfur; Z is —CmR22m wherein m=1 to 4; —C(R2)2SC(R2)2—, C(R2)2SSC(R2)2—, or —C(R2)OC(R2)2; n is from 0 to 4; M is selected from CH2Cl, CH2SC(O)R1, CH2SC(S)R1, CH2S(CH2CH2S)qH wherein q is 0, 1 or 2; —CR2═CH2, —CH2OC(O)CR2═CH2, CH2N═C═S, CH2N═C═O, CH2NR2H, CH2OH, CH2SCH2CH2CR2═CH2, phenyl, C(R2)phenyl, furan, thiophene, halogen, C3-C6 cycloalkyl, C3-C6 heretocyclics, thiol, H, (III) or (IV) wherein A is S, O or phenyl; x is 0 or 1; R1 is C1-C22 alkyl; and R2 is H or C1-C22 alkyl have excellent optical properties. Methods for preparing these compositions and optical lenses prepared from the compounds are also provided.