Heat activated ethylenically unsaturated-polythiol compositions
AssigneeW. R. Grace & Co.
InventorCharles Robert Morgan
Life of this patent
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Abstract
This invention is directed to heat-activated compositions comprising ethylenically unsaturated compounds, e.g., monomers and/or prepolymers in combination with a polythiol and a catalytic amount of substituted or unsubstituted pinacol. The resulting heat-activated product can be utilized as coatings, gaskets, sealants, resists and the like.
Claims11
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.sub.1 and R.sub.3 are members independently selected from the group consisting of a substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.degree.-250.degree. 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.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.degree.-250.degree. 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.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.degree.-250.degree. C for a time sufficient to obtain a cured polythioether.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.degree.-250.degree. C for a time sufficient to increase the viscosity of the composition to a pregellation stage.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.degree.-250.degree. C for a time sufficient to obtain a cured polythioether coating.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.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.sup.2 in the 250-400 nanometer region and, thereafter, heating the composition to a temperature in the range 50.degree.-250.degree. C for a time sufficient to obtain a cured polythioether.
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.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsbustituted aromatic radicals, R.sub.2 and R.sub.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.degree.-250.degree. C and, thereafter, exposing said composition to U.V. radiation having an intensity in the range 0.0004 to 60.0 watts/cm.sup.2 in the 250-400 nanometer region for a time sufficient to obtain a cured polythioether.
Dependencies are inferred from the claim text.