Formulations comprising hydroxy methionine analog and having low levels of sulfate ions and bisulfate salts, processes for preparing the formulations, compositions comprising the formulations, and methods of using the formulations.

Formulations comprising hydroxy methionine analog and having low levels of sulfate ions and bisulfate salts, processes for preparing the formulations, compositions comprising the formulations, and methods of using the formulations.

A thiol group-containing polymer represented by:
HS(RS.sub.r).sub.nRSH
wherein R is an organic group including a OCH.sub.2O bond and a branched alkylene group, n is an integer of from 1 to 200, r is an integer of from 1 to 5, an average value of r is 1.1 or more and lower than 1.8, and the thiol group-containing polymer is a liquid at room temperature and has a specific gravity at 23 C. of 1.20 to 1.27.

A thiol group-containing polymer represented by:
HS(RS.sub.r).sub.nRSH
wherein R is an organic group including a OCH.sub.2O bond and a branched alkylene group, n is an integer of from 1 to 200, r is an integer of from 1 to 5, an average value of r is 1.1 or more and lower than 1.8, and the thiol group-containing polymer is a liquid at room temperature and has a specific gravity at 23 C. of 1.20 to 1.27.

Formulations comprising hydroxy methionine analog and having low levels of sulfate ions and bisulfate salts, processes for preparing the formulations, compositions comprising the formulations, and methods of using the formulations.

Formulations comprising hydroxy methionine analog and having low levels of sulfate ions and bisulfate salts, processes for preparing the formulations, compositions comprising the formulations, and methods of using the formulations.

Polythioether polymers, sealants containing polythioether polymers, and compounds useful as stabilizing monomers in the manufacture of polythioether polymers are provided. In many embodiments the polymers and sealants demonstrate reduced risk of spoilage that may be caused by low temperature storage of the polymer or uncured sealant. Compounds useful as stabilizing monomers include compounds according to formula I: CH.sub.2CR.sup.1CHR.sup.2SR.sup.3SCHR.sup.4CR.sup.5CH.sub.2 [I] wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are independently selected from H, CH.sub.3 or C.sub.2H.sub.5, and wherein R.sup.3 is selected from divalent groups comprising 2-12 carbon atoms, 0-5 ether oxygen atoms and 0-5 thioether sulfur atoms, which may be straight, branched or cyclic.

Polythioether polymers, sealants containing polythioether polymers, and compounds useful as stabilizing monomers in the manufacture of polythioether polymers are provided. In many embodiments the polymers and sealants demonstrate reduced risk of spoilage that may be caused by low temperature storage of the polymer or uncured sealant. Compounds useful as stabilizing monomers include compounds according to formula I: CH.sub.2CR.sup.1CHR.sup.2SR.sup.3SCHR.sup.4CR.sup.5CH.sub.2 [I] wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are independently selected from H, CH.sub.3 or C.sub.2H.sub.5, and wherein R.sup.3 is selected from divalent groups comprising 2-12 carbon atoms, 0-5 ether oxygen atoms and 0-5 thioether sulfur atoms, which may be straight, branched or cyclic.

A method of producing a thiol group-containing polymer includes reacting bis(2-chloroethyl) formal with sodium hydrosulfide, wherein the thiol group-containing polymer is represented by general formula:
HS(RS.sub.r).sub.nRSH
where R is an organic group including a C.sub.2H.sub.4OCH.sub.2OC.sub.2H.sub.4 structure, n is an integer of from 1 to 200, r is an integer of from 1 to 5, and the average value of r is 1.1 or more and lower than 1.8, and wherein the thiol group-containing polymer is a liquid polymer.

A method of producing a thiol group-containing polymer includes reacting bis(2-chloroethyl) formal with sodium hydrosulfide, wherein the thiol group-containing polymer is represented by general formula:
HS(RS.sub.r).sub.nRSH
where R is an organic group including a C.sub.2H.sub.4OCH.sub.2OC.sub.2H.sub.4 structure, n is an integer of from 1 to 200, r is an integer of from 1 to 5, and the average value of r is 1.1 or more and lower than 1.8, and wherein the thiol group-containing polymer is a liquid polymer.