Spirotetrathiocarbamates and spirooxothiocarbamates

A method for manufacturing optical lenses comprising:

• polymerizing a compound of Formula I:
• or a compound of Formula II:
• wherein X1, X2, X3, X4, X5, X6, X7 and X8, are independently O or S;
• and in compound of formula I at least two and up to all four X1, X2, X3 and X4 are sulfur;
• Z is —CmR22m— wherein m=1-4;
• —C(R2)2SC(R2)2—, —C(R2)2SSC(R2)2—, or
• —C(R2)2OC(R2)2;
• n is 1 to 4 in compound of formula I and is from 0 to 4 in compound of formula II;
• and
• 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)2 phenyl, furan, thiophene, halogen, C3-C6 cycloalkyl, C3-C6 heretocyclics, thiol,
• wherein A is S, O or phenyl and x is 0 or 1;
• R1 is C1-C22 alkyl;
• and
• R2 is H or C1-C22 alkyl to form a polymer,
• forming all or part of the optical lens.

A (co)polymer comprising (co)polymerized monomers of Formula I:

• or Formula II:
• wherein X1, X2, X3, X4, X5, X6, X7, and X8, are independently O or S;
• and in compound of formula I at least two and up to all four X1, X2, X3 and X4 are sulfur,
• Z is —CmR22m— wherein m=1-4;
• —C(R2)2SC(R2)2—, —C(R2)2SSC(R2)2—, or
• —C(R2)2OC(R2)2;
• n is from 1 to 4 in compound of formula I and n is 0 to 4 in compound of formula II;
• and
• 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)2 phenyl, furan, thiophene, halogen, C3-C6 cycloalkyl, C3-C6 heretocyclics, thiol;
• wherein A is S, O or phenyl and x is 0 or 1;
• R1 is C1-C22 alkyl;
• and
• R2 is H or C1-C22 alkyl.

A method for preparing a bis-derivative of a spirotetrathiocarbonate or spirooxothiocarbonate, comprising using either one of the following reactions schemes:

• wherein X1, X2, X3, X4, X5, X6, X7, and X8 are independently O or S;
• n′ is independently 0, 1 or 2;
• n is 0 to 4,
• Z is —CmR22m— wherein m=1-4;
• —C(R2)2SC(R2)2—, —C(R2)2SSC(R2)2—, —C(R2)2OC(R2)2—;
• M is independently selected from CH2Cl, CH2SH, 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)2 phenyl, furan, thiophene, halogen, C3-C6 cycloalkyl, C3-C6 heretocyclics, thiol,
• wherein A is S, O or phenyl and x is 0 or 1;
• R1 is C1-C22 alkyl;
• and
• R2 is H or C1-C22 alkyl.