Multifunctional organosilicon compound and related methods, compounds, and compositions

Patent metadata

Field	Value
Publication number	US-12378264-B2
Application number	US-201917418998-A
Country	US
Kind code	B2
Filing date	Dec 30, 2019
Priority date	Dec 31, 2018
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

A multifunctional organosilicon compound is provided which has the general formula XSi([OSiR 2 ]p-0-SiR 2 Y)a(R 1 ) 3-a — ln the formula, X is selected from H and ethylenically un saturated moieties; each Y independently comprises a functional moiety selected from alkoxysilyl moieties, acryloxy moieties, and epoxide moieties; each R is an independently selected hydrocarbyl group; each R1 is an independently selected hydrocarbyl group; subscript a is 1, 2, or 3; and each subscript b is independently 0, 1, or 2. A method of preparing the multifunctional organosilicon compound is also provided. The method comprises reacting (A) an organosilanol compound and (B) a silane compound having at least two hydrolysable groups. A functionalized siloxane compound prepared from the multifunctional organosilicon compound, a method of preparing the functionalized siloxane compound, and an adhesive comprising the functionalized siloxane compound are also provided.

First claim

The invention claimed is:

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

where X is selected from H, alkenyl groups, and alkynyl groups; each Y independently comprises a functional moiety selected from alkoxysilyl moieties, acryloxy moieties, and epoxide moieties, wherein at least one Y is selected from alkoxysilyl and acryloxy moieties; each R is an independently selected hydrocarbyl group; each R 1 is an independently selected hydrocarbyl group; subscript a is 2 or 3; and each subscript b is independently 0, 1, or 2.

2. The multifunctional organosilicon compound of claim 1 , wherein X is selected from H and alkenyl moieties having the formula —(CH 2 ) n CHCH 2 , where subscript n is from 0 to 4.

3. The multifunctional organosilicon compound of claim 1 , wherein at least one Y is of formula -D-R 2 , where each D is an independently selected divalent linking group and each R 2 independently comprises an alkoxysilyl group or an acryloxy group.

4. The multifunctional organosilicon compound of claim 3 , wherein in at least one moiety Y: (i) divalent linking group D comprises a hydrocarbon group of formula —(CH 2 ) m —, where subscript m is from 1 to 6; (ii) divalent linking group D comprises an ether moiety; or (iii) both (i) and (ii).

5. The multifunctional organosilicon compound of claim 3 , wherein:
(i) R 2 of at least one moiety Y is an alkoxysilyl group having the formula:

where each R 3 is an independently selected hydrocarbyl group, subscript c is 0, 1, or 2, and each R is as defined above;
(ii) R 2 of at least one moiety Y is an acryloxy group having the formula:

where R 4 is an independently selected hydrocarbyl group or H;
(iii) R 2 of at least one moiety Y is an epoxide group having one of formulas (I) and (II):

 or
(iv) any combination of (i) to (iii).

6. The multifunctional organosilicon compound of claim 1 , wherein: (i) each R is methyl; (ii) subscript a is 2 and R 1 is methyl; (iii) subscript b is independently 0 or 1 in each moiety designated by subscript a; or (iv) any combination of (i) to (iii).

7. A method of preparing a multifunctional organosilicon compound, said method comprising:
reacting (A) an organosilanol compound and (B) a silane compound having at least two hydrolysable groups, thereby preparing the multifunctional organosilicon compound;
wherein the multifunctional organosilicon compound is the multifunctional organosilicon compound of claim 1 .

8. The method of claim 7 , wherein the organosilanol compound (A) has the following formula:

where Y comprises a functional moiety selected from alkoxysilyl moieties, acryloxy moieties, and epoxide moieties, with the proviso that Y is an alkoxysilyl moiety or an acrloxy moiety in at least one molecule of the organosilanol compound (A); each R is an independently selected hydrocarbyl group; and subscript b is 0, 1, or 2.

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

where each Z is an independently selected hydrolysable group; X is selected from H and ethylenically unsaturated moieties; each R 1 is an independently selected hydrocarbyl group; and subscript a is 2 or 3.

10. The method of claim 9 , wherein: (i) each hydrolysable group Z is independently selected from halogens, acetoxy groups, alkoxy groups, oxime groups, and aminoxy groups; (ii) X is selected from H and alkenyl moieties having the formula —(CH 2 ) n CHCH 2 , where subscript n is from 0 to 4; (iii) subscript a is 2 and R 1 is methyl; or (iv) any combination of (i) to (iii).

11. The method of claim 7 , further comprising reacting the organosilanol compound (A) and the silane compound (B): (i) in the presence of (C) a reaction catalyst; (ii) at a temperature of less than 25° C.; or (iii) both (i) and (ii).

12. The method of claim 11 , wherein the organosilanol compound (A) and the silane compound (B) are reacted in the presence of the reaction catalyst (C), and wherein the reaction catalyst (C) comprises: (i) a base catalyst; (ii) an acid catalyst; (iii) a transition metal catalyst; or (iv) any combination of (i) to (iii).

13. A multifunctional organosilicon compound prepared according to the method of claim 7 .

14. A functionalized siloxane compound having the following general formula:
[R 5 3 SiO 1/2 ] e [R 5 2 SiO 2/2 ] f [R 5 SiO 3/2 ] g [SiO 4/2 ] h ,
where subscripts e, f, g, and h are each mole fractions such that e+f+g+h=1, with the proviso that e+f+g>0; each R 5 is independently selected from substituted and unsubstituted hydrocarbyl groups and A, with the proviso that at least one R 5 is A; wherein each A is independently of the following formula:

where each Y is independently selected from alkoxysilane moieties, acryloxy moieties, and epoxide moieties, wherein at least one Y is selected from alkoxysilyl and acryloxy moieties; each R is an independently selected hydrocarbyl group; each R 1 is an independently selected hydrocarbyl group; D 1 is a divalent hydrocarbon group; subscript a is 2 or 3; and each subscript b is independently 0, 1, or 2.

15. The functionalized siloxane compound of claim 14 , wherein in at least one moiety A: (i) each R is methyl; (ii) each R 1 is methyl; (iii) subscript b is independently 0 or 1 in each moiety designated by subscript a; (iv) D 1 comprises an ethylene group; or (v) any combination of (i) to (iv).

16. A method of preparing a functionalized siloxane compound, said method comprising:
reacting a multifunctional organosilicon compound and a polysiloxane in the presence of a hydrosilylation catalyst, thereby preparing the preparing the functionalized siloxane compound;
wherein the multifunctional organosilicon compound is the multifunctional organosilicon compound of claim 1 ;
with the proviso that when X of the multifunctional organosilicon compound is H, the polysiloxane includes at least one silicon-bonded ethylenically unsaturated group, and when X of the multifunctional organosilicon compound is an ethylenically unsaturated moiety, the polysiloxane includes at least one silicon-bonded hydrogen atom.

17. An adhesive comprising the functionalized siloxane compound of claim 14 .

18. The multifunctional organosilicon compound of claim 1 , wherein subscript a is 3.

19. The multifunctional organosilicon compound of claim 1 , wherein each Y is an alkoxysilyl moiety or an acrloxy moiety.

20. The functionalized siloxane compound of claim 14 , wherein each Y is an alkoxysilyl moiety or an acrloxy moiety.

Assignees

• Dow Silicones Corp

Inventors

• Eldred Donald
• Jeletic Matthew
• Joffre Eric
• Liu Nanguo
• Kadleck Cameron
• Olsen Matthew
• Roberts John
• Shephard Nick E
• Thomas Ryan
• Wenzlick Zachary

Classifications

• C09J133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08G77/18

  to alkoxy or aryloxy groups · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title