Heat activated ethylenically unsaturated-polythiol compositions

Claim 2

A heat activatable composition comprising an ethylenically unsaturated compound, a polythiol, the mole ratio of the carbon-to-carbon double bonds in the ethylenically unsaturated compound to the thiol groups in the polythiol being in the range of 1:10 to 10:1 respectively, and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and polythiol of a pinacol of the general formula: ##STR9## wherein R 1 and R 3 are members independently selected from the group consisting of a substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy.

Claim 3

The composition of claim 1 containing in addition 0.0005 to 30% by weight of a photosensitizer based on the weight of the ethylenically unsaturated compound and the polythiol.

Claim 4

The composition according to claim 1 wherein the pinacol is benzopinacol.

Claim 5

The composition of claim 1 as a coating on a substrate.

Claim 6

The process of forming an adduct which comprises admixing a composition comprising a mono-ethylenically unsaturated compound with a polythiol containing at least two thiol groups, and 0.01-5% by weight based on the weight of the mono-ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR10## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to cause the unsaturated carbon-to-carbon bond in the mono-ethylenically unsaturated compound to react with a thiol group in the polythiol.

Claim 7

The process of forming an adduct which comprises admixing a composition comprising a mono-ethylenically unsaturated compound with a polythiol containing at least two thiol groups, and 0.01-5% by weight based on the weight of the mono-ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR10## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to cause the unsaturated carbon-to-carbon bond in the mono-ethylenically unsaturated compound to react with a thiol group in the polythiol.

Claim 8

The process of forming a chain-extended polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing two unsaturated carbon-to-carbon double bonds, a polythiol containing two SH groups per molecule, the mole ratio of the carbon-to-carbon double bonds in the ethylenically unsaturated compound to the thiol groups in the polythiol being 1:1 respectively, and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR11## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to cause the unsaturated carbon-to-carbon bonds in the ethylenically unsaturated compound to react with the thiol groups in the polythiol.

Claim 9

The process of forming a chain-extended polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing two unsaturated carbon-to-carbon double bonds, a polythiol containing two SH groups per molecule, the mole ratio of the carbon-to-carbon double bonds in the ethylenically unsaturated compound to the thiol groups in the polythiol being 1:1 respectively, and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR11## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to cause the unsaturated carbon-to-carbon bonds in the ethylenically unsaturated compound to react with the thiol groups in the polythiol.

Claim 10

The process of forming a cured polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR12## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to obtain a cured polythioether.

Claim 11

The process of forming a cured polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR12## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to obtain a cured polythioether.

Claim 12

The process of thickening a composition which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR13## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to increase the viscosity of the composition to a pregellation stage.

Claim 13

The process of thickening a composition which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR13## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; and, thereafter, heating said composition to a temperature in the range 50°-250° C for a time sufficient to increase the viscosity of the composition to a pregellation stage.

Claim 14

The process of forming a cured polythioether coating on a substrate which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR14## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy, applying said admixture to a substrate as a coating having a thickness in the range of 0.001 - 100 mils, and, thereafter, heating the composition to a temperature in the range of 50°-250° C for a time sufficient to obtain a cured polythioether coating.

Claim 15

The process of forming a cured polythioether coating on a substrate which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR14## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy, applying said admixture to a substrate as a coating having a thickness in the range of 0.001 - 100 mils, and, thereafter, heating the composition to a temperature in the range of 50°-250° C for a time sufficient to obtain a cured polythioether coating.

Claim 16

The process of forming a cured polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four, a photosensitizer, and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR15## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; exposing said composition to U.V. radiation having an intensity in the range 0.0004 to 60.0 watts/cm 2 in the 250-400 nanometer region and, thereafter, heating the composition to a temperature in the range 50°-250° C for a time sufficient to obtain a cured polythioether.

Claim 17

The process of forming a cured polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four, a photosensitizer, and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR15## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; exposing said composition to U.V. radiation having an intensity in the range 0.0004 to 60.0 watts/cm 2 in the 250-400 nanometer region and, thereafter, heating the composition to a temperature in the range 50°-250° C for a time sufficient to obtain a cured polythioether.

Claim 18

The process of forming a cured polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR16## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsbustituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; heating the composition to a temperature in the range 50°-250° C and, thereafter, exposing said composition to U.V. radiation having an intensity in the range 0.0004 to 60.0 watts/cm 2 in the 250-400 nanometer region for a time sufficient to obtain a cured polythioether.

Claim 19

The process of forming a cured polythioether which comprises admixing a composition comprising an ethylenically unsaturated compound containing at least two unsaturated carbon-to-carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total functionality of the unsaturated carbon-to-carbon bonds per molecule in the ethylenically unsaturated compound and the thiol groups per molecule in the polythiol being greater than four and 0.01-5% by weight based on the weight of the ethylenically unsaturated compound and the polythiol of a pinacol of the general formula: ##STR16## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsbustituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy; heating the composition to a temperature in the range 50°-250° C and, thereafter, exposing said composition to U.V. radiation having an intensity in the range 0.0004 to 60.0 watts/cm 2 in the 250-400 nanometer region for a time sufficient to obtain a cured polythioether.