IP Library Granted Patent US 12,371,535
Granted Patent B2
US 12,371,535 · App. 17/418,950 · Granted Jul 29, 2025

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

Inventors: Nanguo Liu (Midland, MI); Tatsuo Souda (Tokyo, JP); Tsunehito Sugiura (Tokyo, JP); Michael Telgenhoff (Midland, MI)
Assignees: Dow Silicones Corporation; Dow Toray Co., Ltd.
C08G77/26C07F7/10
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Quick Facts
Patent No.
US 12,371,535
App. No.
17/418,950
Granted
Jul 29, 2025
Kind
B2
Abstract

A branched organosilicon compound (“compound”) is provided having the general formula: (R 1 ) 3 Si—X—NR 2 R 3 , where X is a divalent linking group; R 2 is H or R; R 3 comprises an acryloxy moiety; 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 ]mOSiR 3 ; where each R 5 is selected from R, —OSi(R 6 ) 3 , and —[OSiR 2 ] m OSiR 3 ; and where each R 6 is selected from R and —[OSiR 2 ] m OSiR 3 , with the proviso that at least one of R 4 , R 5 and R 6 is —[OSiR 2 ] m OSiR 3 ; 0≤m≤100; and each R is a substituted or unsubstituted hydrocarbyl group. Also provided is a method of preparing the compound, 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.

Claims (30)

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

wherein X is a divalent linking group; R 2 is H or R, where R is a substituted or unsubstituted hydrocarbyl group; R 3 comprises an acryloxy moiety; and 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 each R 5 is selected from R, —OSi(R 6 ) 3 , and —[OSiR 2 ] m OSiR 3 ; where each R 6 is selected from R and —[OSiR 2 ] m OSiR 3 ; and where 0≤m≤100; with the proviso that at least one of R 4 , R 5 and R 6 is —[OSiR 2 ] m OSiR 3 ; and

having one of the following provisos or ii):

i) the branched organosilicon compound has the following general formula:

where each R, R 2 , R 3 , R 5 , and X are independently selected and defined above; or

ii) the branched organosilicon compound has the following general formula:

where each R, R 2 , R 3 , R 5 , and X are independently selected and defined above.

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

where each R, R 2 , R 3 , R 5 , and X are independently selected and defined above.

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

where each R, R 2 , R 3 , R 5 , and X are independently selected and defined above.

4. The branched organosilicon compound of claim 1 , wherein R 3 has the following formula: -D-O—C(O)C(R 7 )CH 2 , where D is a divalent linking group, and R 7 is H or R, where R is defined above.

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

where each R, R 2 , R 5 , X, D, and R 7 are independently selected and defined above.

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

where each R, R 2 , R 5 , X, D, and R 7 are independently selected and defined above.

7. A method of preparing a branched organosilicon compound, said method comprising:

reacting (A) an organosilicon compound and (B) a functional compound, optionally in the presence of (C) a catalyst, to give the branched organosilicon compound;

wherein the branched organosilicon compound is the branched organosilicon compound of claim 1 .

8. The method of claim 7 , wherein the organosilicon compound (A) has one of the following general formulas:

where X is a divalent linking group; D is a divalent linking group; each R is an independently selected substituted or unsubstituted hydrocarbyl group; R 2 is H or R; and each R 5 is selected from R, —OSi(R 6 ) 3 , and —[OSiR 2 ] m OSiR 3 ; where each R 6 is selected from R and —[OSiR 2 ] m OSiR 3 ; and 0≤m≤100.

9. The method of claim 7 , wherein the functional compound (B) has the formula:

where R 7 is H or R, where R is a substituted or unsubstituted hydrocarbyl group; and Y is a substituted or unsubstituted hydrocarbyl group.

10. 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 .

11. 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 10 .

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

13. The composition of claim 12 , 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.

14. A composition comprising the copolymer of claim 10 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2021
From: TELGENHOFF, MICHAEL; LIU, NANGUO
To: DOW SILICONES CORPORATION
Reel/Frame 056696/0827 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2021
From: SOUDA, TATSUO; SUGIURA, TSUNEHITO
To: DOW TORAY CO., LTD.
Reel/Frame 056697/0165 →
Continuity (2)
Provisional Application 62786843 · Dec 31, 2018
Related Publication 20220119597A1 · Apr 21, 2022
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