Segmented silicone polymers and methods of making and using the same
Segmented silicone polymers incorporating segments formed from medium-chain fatty acids are generally disclosed herein. Methods of using such compounds, for example, as surfactants, are also disclosed herein, as well as methods of making such compounds, for example, from medium-chain fatty acids derived from natural oils.
1 . A siloxane polymer comprising:
(a) one or more segments of formula (1):
and
(b) one or more segments of formula (II):
wherein:
each R 1 , R 2 , R 3 , and R 4 is independently a hydrogen atom, a C 1-14 hydrocarbyl group, or a C 1-14 hydrocarbyloxy group, wherein at least one of R 1 , R 2 , R 3 , and R 4 is a hydrogen atom;
each X 1 and X 2 is independently an oxygen atom, a sulfur atom, >NH, or >N(C 1-6 alkyl);
each G 1 and G 2 is independently a C 1-14 hydrocarbylene group;
each G 3 is independently a C 1-14 hydrocarbylene group, which is optionally substituted one or more times by substituents selected from the group consisting of —OH and —O(C 1-6 alkyl); and
each k is independently an integer ranging from 5 to 5000,
wherein the segments of formula (I) and the segments of formula (II) together make up at least 60% by weight of the siloxane polymer; and
wherein the numerical ratio of segments of formula (I) to segments of formula (II) in the siloxane polymer ranges from 1:5 to 5:1.
2 . The siloxane polymer of claim 1 , wherein G 1 and G 2 are independently selected from the group consisting of —(CH 2 ) 9 —, —(CH 2 ) 10 —, and —(CH 2 ) 11 —.
3 . The siloxane polymer of claim 1 , wherein each G 3 is independently selected from the group consisting of a C 1-14 alkylene group, a C 1-5 alkylene group, —(CH 2 ) 1-6 —, and —(CH 2 ) 2 —.
4 . The siloxane polymer of claim 1 , wherein each X 1 is an oxygen atom.
5 . The siloxane polymer of claim 1 , wherein each X 2 is an oxygen atom.
6 . The siloxane polymer of claim 1 , wherein each R 1 , R 2 , R 3 , and R 4 is independently a hydrogen atom, a C 1-14 hydrocarbyl group, or C 1-8 alkyl group.
7 . The siloxane polymer of claim 6 , wherein each R 1 , R 2 , R 3 , and R 4 is independently a C 1-14 hydrocarbyl group.
8 . The siloxane polymer of claim 6 , wherein each R 1 , R 2 , R 3 , and R 4 is independently a C 1-8 alkyl group.
9 . The siloxane polymer of claim 8 , wherein each R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl.
10 . The siloxane polymer of claim 1 , wherein the siloxane polymer has a weight-average molecular weight ranging from 1 kDa to 50 kDa.
11 . The siloxane polymer of claim 1 , wherein the segments of formula (1) make up at least 50% by weight of the siloxane polymer.
12 . The siloxane polymer of claim 1 , wherein the segments of formula (1) make up no more than 70% by weight of the siloxane polymer.
13 . The siloxane polymer of claim 1 , wherein the segments of formula (II) make up at least 10% by weight of the siloxane polymer.
14 . The siloxane polymer of claim 1 , wherein the segments of formula (II) make up no more than 10% by weight of the siloxane polymer.
15 . The siloxane polymer of claim 1 , having two or more endcap groups, wherein the endcap groups are moieties of formula (III):
—(O) m —Si(R 21 )(R 22 )(R 23 ) (III)
wherein:
R 21 , R 22 , and R 23 are independently a hydrogen atom, —OH, C 1-14 hydrocarbyl, or C 1-14 hydrocarbyloxy; and
m is 0 or 1.
16 . The siloxane polymer of claim 15 , wherein at least two of R 21 , R 22 , and R 23 is a hydrogen atom or C 1-14 hydrocarbyl.
17 . The siloxane polymer of claim 15 , wherein one of R 21 , R 22 , and R 23 is a —OH or C 1-14 hydrocarbyloxy.