Polymerizable polyol (allyl carbonate) compositions

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a divalent residue of a poly(C2-C4 alkylene glycol), R1 is an allyl group, and i is 2;
• and
• (b) a minor amount of a radically polymerizable second monomer represented by the following general formula,
• 4
• wherein R2 is a divalent linking group that is free of urethane linkages;
• R3 is a residue of a material having a single hydroxy group and at least one allyl group, R3 being free of urethane linkages;
• and j is 2.

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a polyvalent residue of a polyol having at least two hydroxy groups, R1 is an allyl group, and i is a whole number from 2 to 4;
• and
• (b) a radically polymerizable second monomer present in said composition in an amount of from 0.1 percent by weight to 10 percent by weight based on the total weight of said polymerizable composition, such that a polymerizate of said composition is substantially free of tinting defects, said radically polymerizable second monomer represented by the following general formula,
• 5
• wherein R2 is a residue of a cycloaliphatic diisocyanate selected from the group consisting of isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(is6cyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, and mixtures thereof;
• and the material of which R3 is a residue is selected from the group consisting of aromatic alcohols, aliphatic alcohols, cycloaliphatic alcohols, poly(alkylene glycols)having a single hydroxy group, each having at least one allyl group, and mixtures thereof, R3 being free of urethane linkages;
• and j is 2.

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a polyvalent residue of a polyol having at least two hydroxy groups, R1 is an allyl group, and i is a whole number from 2 to 4;
• and
• (b) a radically polymerizable second monomer present in said composition in an amount of from 0.1 percent by weight to 10 percent by weight based on the total weight of said polymerizable composition, such that a polymerizate of said composition is substantially free of tinting defects, said radically polymerizable second monomer represented by the following general formula,
• 6
• wherein R2 is a residue of a cycloaliphatic diisocyanate selected from the group consisting of isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, and mixtures thereof;
• and the material of which R3 is a residue is selected from the group consisting of C2-C4 alkylene glycol allyl ether, poly(C2-C4 alkylene glycol) allyl ether, trimethylol propane di(allyl ether), trimethylol ethane di(allyl ether), pentaerythritol tri(allyl ether), di-trimethylolpropane tri(allyl ether) and mixtures thereof, R3 being free of urethane linkages;
• and j is 2.

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a polyvalent residue of a polyol having at least two hydroxy groups, R1 is an allyl group, and i is a whole number from 2 to 4;
• and
• (b) a radically polymerizable second monomer present in said composition in an amount of from 0.1 percent by weight to 10 percent by weight based on the total weight of said polymerizable composition, such that a polymerizate of said composition is substantially free of tinting defects, said radically polymerizable second monomer represented by the following general formula,
• 7
• wherein R2 is a residue of a cycloaliphatic diisocyanate selected from the group consisting of isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, and mixtures thereof;
• and the material of which R3 is a residue is selected from the group consisting of poly(ethylene glycol)allyl ether, poly(1,2-propylene glycol)allyl ether and mixtures thereof, R3 being free of urethane linkages;
• and j is 2.

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a divalent residue of a poly(C2-C4 alkylene glycol), R1 is an allyl group, and i is 2;
• and
• (b) a radically polymerizable second monomer present in said composition in an amount at least sufficient such that a polymerizate of said composition is substantially free of tinting defects, said radically polymerizable second monomer represented by the following general formula,
• 8
• wherein R2 is a residue of a cycloaliphatic diisocyanate selected from isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, and mixtures thereof, R2 being free of urethane linkages;
• R3 is a residue of a material having a single hydroxy group and at least one allyl group, R3 being free of urethane linkages;
• and j is 2.

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a divalent residue of a poly(C2-C4 alkylene glycol), R1 is an allyl group, and i is 2;
• and
• (b) a radically polymerizable second monomer present in said composition in an amount at least sufficient such that a polymerizate of said composition is substantially free of tinting defects, said radically polymerizable second monomer represented by the following general formula,
• 9
• wherein R2 is a residue of a cycloaliphatic diisocyanate selected from isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, and mixtures thereof, R2 being free of urethane linkages;
• R3 is a residue of a material chosen from poly(C2-C4 alkylene glycol) allyl ether, trimethylol propane di(allyl ether), trimethylol ethane di(allyl ether) and mixtures thereof, R3 being free of urethane linkages;
• and j is 2.

A polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a residue of diethylene glycol, R1 is an allyl group, and i is 2;
• and
• (b) a radically polymerizable second monomer present in said composition in an amount at least sufficient such that a polymerizate of said composition is substantially free of tinting defects, said radically polymerizable second monomer represented by the following general formula,
• 10
• wherein R2 is a residue of a cycloaliphatic diisocyanate selected from isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, and mixtures thereof, R2 being free of urethane linkages;
• R3 is a residue of poly(1,2-propylene glycol) allyl ether, R3 being free of urethane linkages;
• and j is 2.

A photochromic article comprising a polymerizate of a polymerizable composition comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a polyvalent residue of a polyol having at least two hydroxy groups, R1 is an allyl group, and i is a whole number from 2 to 4;
• and
• (b) a minor amount of a radically polymerizable second monomer represented by the following general formula,
• 11
• wherein R2 is a polyvalent linking group that is free of urethane linkages;
• R3 is a residue of a material having a single hydroxy group and at least one allyl group, R3 being free of urethane linkages;
• and j is a number from 2 to 4.

A photochromic article adapted to be free of tinting defects comprising at least a photochromic amount of a photochromic substance, a tinting defect inhibiting additive, and an at least partially cured substrate comprising:

• (a) a major amount of a radically polymerizable first monomer represented by the following general formula,
• R—[—O—C(O)—O—R1]i
• wherein R is a polyvalent residue of a polyol having at least two hydroxy groups, R1 is an allyl group, and i is a whole number from 2 to 4;
• and
• (b) a minor amount of a radically polymerizable second monomer represented by the following general formula,
• 12
• wherein R2 is a polyvalent linking group that is free of urethane linkages;
• R3 is a residue of a material having a single hydroxy group and at least one allyl group, R3 being free of urethane linkages;
• and j is a number from 2 to 4.