Branched organosilicon compound, method of preparing same, and copolymer formed therewith

Patent metadata

Field	Value
Publication number	US-12338259-B2
Application number	US-201917419003-A
Country	US
Kind code	B2
Filing date	Dec 27, 2019
Priority date	Dec 31, 2018
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

A branched organosilicon compound (“compound”) having the general formula (R1) 3 Si—X—Y is provided. In the formula: each R 1 is selected from R and —OSi(R 4 )3, with the proviso that at least one R 1 is —OSi(R 4 )3; each R is independently a substituted or unsubstituted hydrocarbyl group; each R 4 is selected from R, —OSi(R 5 )3, and —[OSiR 2 ]mOSiR 3 ; each R 5 is selected from R, —OSi(R 6 )3, and —[OSiR 2 ]mOSiR 3 ; each R 6 is selected from R and —[OSiR 2 ]mOSiR 3 ; with the proviso that at least one of R 4 , R 5 and R 6 is —[OSiR 2 ]mOSiR 3 ; 0<m≤100; X is a divalent linking group; and Y is selected from one of formulas (1)-(111) described herein. Also provided is a method of preparing the compound via hydrosilylation reaction, a copolymer comprising the reaction product of the compound and a second compound reactive with the compound, a method of forming the copolymer, and a composition including at least one of the compound and the copolymer.

First claim

What is claimed is:

1. A branched organosilicon compound having the following general formula:

where each R 1 is selected from R and —OSi(R 4 ) 3 , where each R 4 is selected from R, —OSi(R 5 ) 3 , and —[OSiR 2 ] m OSiR 3 , where 0≤m≤100; where each R 5 is selected from R, —OSi(R 6 ) 3 , and —[OSiR 2 ] m OSiR 3 , where m is defined above; where each R 6 is selected from R and —[OSiR 2 ] m OSiR 3 , where m is defined above; with the proviso that at least one of R 4 , R 5 and R 6 is —[OSiR 2 ] m OSiR 3 , where m is defined above;
X is a divalent linking group; and
Y is selected from one of formulas (I)-(III):

where each R is an independently selected substituted or unsubstituted hydrocarbyl group; each D 1 is an independently selected divalent hydrocarbon group; each subscript a is independently 0 or 1; each subscript b is independently 0 or 1; each subscript e is independently 1 or 2; each subscript f is independently 0 or 1, with the proviso that when f is 1, b is 1; subscript t is ≥0; subscript u is >0; 0≤n≤10; and R 3 comprises a halogen atom, an acryloxy functional moiety, an alkoxysilyl functional moiety, or an epoxy functional moiety; and
wherein at least one of the following provisos is true:
a) two R 1 are OSi(R 4 ) 3 ; or
b) at least two R 4 are —OSi(R 5 ) 3 or —[OSiR 2 ] m OSiR 3 ; or
c) at least two R 5 are —OSi(R 6 ) 3 or —[OSiR 2 ] m OSiR 3 ; or
d) at least two R 6 are —[OSiR 2 ] m OSiR 3 .

2. The branched organosilicon compound of claim 1 , wherein each R 1 is —OSi(R 4 ) 3 , and wherein at least one of R 4 is —[OSiR 2 ] m OSiR 3 , where R and m are defined above.

3. The branched organosilicon compound of claim 1 , having the following general formula:

where R is independently selected and defined above, and each R 5 is independently selected and defined above, and X and Y are defined above.

4. The branched organosilicon compound of claim 1 , having the following general formula:

where R is independently selected and defined above, each R 5 is independently selected and defined above, and X and Y are defined above.

5. The branched organosilicon compound of claim 1 , having the following general formula:

where R is independently selected and defined above, each R 5 is independently selected and defined above, and X and Y are defined above.

6. The branched organosilicon compound of claim 1 , wherein: (i) X is a divalent hydrocarbon group; (ii) m is 0 or 1; (iii) each R is methyl; or (iv) any combination of (i)-(iii).

7. A method of preparing a branched organosilicon compound, said method comprising:
reacting an organosilicon compound and a functional compound in the presence of a hydrosilylation catalyst to give the branched organosilicon compound;
wherein the organosilicon compound includes one of a silicon-bonded hydrogen atom and a silicon-bonded ethylenically unsaturated group, with the proviso that when the organosilicon compound includes a silicon-bonded hydrogen atom, the functional compound includes an ethylenically unsaturated group, and when the organosilicon compound includes a silicon-bonded ethylenically unsaturated group, the functional compound includes a silicon-bonded hydrogen atom; and
wherein the branched organosilicon compound is the branched organosilicon compound of claim 1 .

8. The method of claim 7 , wherein the organosilicon compound has the following general formula:

where X is a divalent linking group;
each R is independently a substituted or unsubstituted hydrocarbyl group;
0 ≤n ≤10;

each R 1 is selected from R and —OSi(R 4 ) 3 , with the proviso that at least one R 1 is —OSi(R 4 ) 3 ;
where each R 4 is selected from R, —OSi(R 5 ) 3 , and —[OSiR 2 ] m OSiR 3 , where 0≤m≤100;
where each R 5 is selected from R, —OSi(R 6 ) 3 , and —[OSiR 2 ] m OSiR 3 , where m is defined above;
where each R 6 is selected from R and —[OSiR 2 ] m OSiR 3 , where m is defined above; with the proviso that at least one of R 4 , R 5 and R 6 is —[OSiR 2 ] m OSiR 3 , where m is defined above; and
where R 7 is H or comprises a silicon-bonded hydrogen atom or an ethylenically unsaturated group.

9. The method of claim 7 , wherein the functional compound includes a halogen atom, an acryloxy functional moiety, an alkoxysilyl functional moiety, or an epoxy functional moiety.

10. The method of claim 8 , wherein R 7 comprises an ethylenically unsaturated group, and wherein the functional compound has one of the following general formulas (VI) and (VII):

where each R is an independently selected substituted or unsubstituted hydrocarbyl group; each D 1 is an independently selected divalent hydrocarbon group; each subscript a is independently 0 or 1; each subscript b is independently 0 or 1; each subscript e is independently 1 or 2; each subscript f is independently 0 or 1, with the proviso that when f is 1, b is 1; subscript t is ≥0; and subscript u is >0.

11. A copolymer comprising the reaction product of a branched organosilicon compound and a second compound reactive with the branched organosilicon compound;
wherein the branched organosilicon compound is the branched organosilicon compound of claim 1 .

12. A method of preparing a copolymer, said method comprising reacting a branched organosilicon compound and a second compound reactive with the branched organosilicon compound to give the copolymer;
wherein the copolymer is the copolymer of claim 11 .

13. A composition comprising the branched organosilicon compound of claim 1 .

14. The composition of claim 13 , further defined as at least one of: (i) an emulsion; (ii) an aqueous composition; (iii) a surfactant composition; (iv) a wetting composition; (v) an aqueous film-forming foam; (vi) a surface tension modifier; (vii) an antiblocking additive; (viii) an agricultural composition; (ix) a coating composition; (x) a paint composition; (xi) a surface treating composition; (xii) a film-forming composition; and (xiii) a cosmetic composition.

15. A composition comprising the copolymer of claim 11 .

Assignees

• Dow Silicones Corp

Inventors

• Jeletic Matthew
• Liu Nanguo

Classifications

• C08G77/50

  by carbon linkages · CPC title

• C08G77/44 Primary

  containing only polysiloxane sequences · CPC title

• C08G77/385

  containing halogens · CPC title

• C08G77/24

  halogen-containing groups · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title