Carbonate and hydroxy carbamate functionalized silicones

A silicone composition consisting essentially of a hydroxy carbamate functionalized silicone having the formula:

• M.sub.a M'.sub.b D.sub.c D'.sub.d T.sub.e T'.sub.f Q.sub.g where
• M=R.sub.3 SiO.sub.1/2,
• M'=R.sub.3-i R'.sub.i SiO.sub.1/2,
• D=R.sub.2 SiO.sub.2/2,
• D'=R.sub.2-j R'.sub.j SiO.sub.2/2,
• T=RSiO.sub.3/2,
• T'=R'SiO.sub.3/2, and
• Q=SiO.sub.4/2
• where the subscript i varies from 1 to 3, the subscript j is either 1 or 2 and the subscripts a, b, c, d, e, f, and g are zero or positive subject to the limitation that the sum of b+d+f is at least one, and b, c, or e is one or greater, and the sum of a+c+e+g is zero or positive, with R being an independently selected monovalent hydrocarbon radical for each M, D, and T and ranging from 1 to about 40 carbon atoms with R' defined as:
• --CH.sub.2 --CH.sub.2 --R"--CH(OH)--CH.sub.2 O.sub.2 CNR.sup.1 R.sup.2,
• --CH.sub.2 --CH.sub.2 --R"--CH(O.sub.2 CNR.sup.1 R.sup.2)--CH.sub.2 --OH or mixtures thereof
• where R" is a divalent radical having from one to about forty carbon atoms and R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen and one to forty carbon atom monovalent hydrocarbon radicals.

A silicone composition comprising a carbonate functionalized silicone having the formula:

• M.sub.a M".sub.b D.sub.c D".sub.d T.sub.e T".sub.f Q.sub.g where
• M=R.sub.3 SiO.sub.1/2,
• M"=R.sub.3-i R'".sub.i SiO.sub.1/2,
• D=R.sub.2 SiO.sub.2/2,
• D"=R.sub.2-j R'".sub.j SiO.sub.2/2,
• T=RSiO.sub.3/2,
• T"=R'"SiO.sub.3/2, and
• Q=SiO.sub.4/2
• where the subscript i varies from 1 to 3, the subscript j is 1 or 2 and the subscripts a, b, c, d, e, f, and g are zero or positive subject to the limitations that the sum of b+d+f is at least one, and b, c, or e is one or greater, and the sum of a+c+e+g is zero or positive, with R being an independently selected monovalent hydrocarbon radical for each M, D, and T and ranging from 1 to about 40 carbon atoms with R'" defined as:
• ##STR11## where is a divalent radical having from one to about forty carbon atoms.

A process for making a silicone comprising a hydroxy carbamate functionalized silicone comprising:

• (a) reacting a hydrogen siloxane having the formula:
• M.sub.z M.sup.H.sub.y D.sub.x D.sup.H.sub.w T.sup.v T.sup.H.sub.u Q.sub.t where
• M=R.sub.3 SiO.sub.1/2,
• M.sup.H =R.sub.3-k H.sub.k SiO.sub.1/2,
• D=R.sub.2 SiO.sub.2/2,
• D.sup.H =R.sub.2-m H.sub.m SiO.sub.2/2,
• T=RSiO.sub.3/2,
• T.sup.H =HSiO.sub.3/2, and
• Q=SiO.sub.4/2
• where the subscript k varies from 1 to 3, the subscript m is either 1 or 2 and the subscripts t, u, v, w, x, y, and z are zero or positive subject to the limitations that the sum of u+w+y is greater than zero, that one of y, x or v is one or greater and that the sum of t+v+x+z is zero or positive, with R being an independently selected monovalent hydrocarbon radical for each M, D, and T and ranging from 1 to about 40 carbon atoms,
• with an unsaturated cyclic carbonate ester having the formula:
• ##STR12## where R" is a divalent radical having from one to about forty carbon atoms in the presence of a hydrosilylation catalyst;
• (b) producing thereby a carbonate functionalized silicone having the formula:
• M.sub.a M".sub.b D.sub.c D".sub.d T.sub.e T".sub.f Q.sub.g where
• M=R.sub.3 SiO.sub.1/2,
• M"=R.sub.3-i R'".sub.i SiO.sub.1/2,
• D=R.sub.2 SiO.sub.2/2,
• D"=R.sub.2-j R'".sub.j SiO.sub.2/2,
• T=RSiO.sub.3/2,
• T"=R'"SiO.sub.3/2, and
• Q=SiO.sub.4/2
• where the subscript i varies from 1 to 3, the subscript j is 1 or 2 and the subscripts a, b, c, d, e, f, and g are zero or positive subject to the limitation that the sum of b+d+f is at least one, and b, c, or e is one or greater, and the sum of a+c+e+g is zero or positive, with R being an independently selected monovalent hydrocarbon radical for each M, D, and T and ranging from 1 to about 40 carbon atoms with R'" defined as:
• ##STR13## where is a divalent radical having from one to about forty carbon atoms;
• (c) reacting said carbonate ester functionalized silicone in the presence of an amine having the formula:
• HNR.sup.1 R.sup.2
• where R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen and one to forty carbon atom monovalent hydrocarbon radicals;
• and
• (d) producing thereby a hydroxy carbamate functionalized silicone having the formula:
• M.sub.a M'.sub.b D.sub.c D'.sub.d T.sub.e T'.sub.f Q.sub.g where
• M=R.sub.3 SiO.sub.1/2,
• M'=R.sub.3-i R'.sub.i SiO.sub.1/2,
• D=R.sub.2 SiO.sub.2/2,
• D'=R.sub.2-j R'.sub.j SiO.sub.2/2,
• T=RSiO.sub.3/2,
• T'=R'SiO.sub.3/2, and
• Q=SiO.sub.4/2
• where the subscript i varies from 1 to 3, the subscript j is either 1 or 2 and the subscripts a, b, c, d, e, f, and g are zero or positive subject to the limitation that the sum of b+d+f is at least one, and b, c, or e is one or greater, and the sum of a+c+e+g is zero or positive, with R being an independently selected monovalent hydrocarbon radical for each M, D, and T and ranging from 1 to about 40 carbon atoms with R' defined as:
• --CH.sub.2 --CH.sub.2 --R"--CH(OH)--CH.sub.2 O.sub.2 CNR.sup.1 R.sup.2,
• --CH.sub.2 --CH.sub.2 --R"--CH(O.sub.2 CNR.sup.1 R.sup.2)--CH.sub.2 --OH or mixtures thereof
• where R" is a divalent radical having from one to about forty carbon atoms and R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen and one to forty carbon atom monovalent hydrocarbon radicals.