IP Library Granted Patent US 10,358,389
Granted Patent B2
US 10,358,389 · App. 15/513,680 · Granted Jul 23, 2019

Silicone composition, substrate coated with the silicone composition and a process therefor

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Quick Facts
Patent No.
US 10,358,389
App. No.
15/513,680
Granted
Jul 23, 2019
Kind
B2
Abstract

The present invention relates to a silicone composition, a substrate, such as cement, coated with the silicone composition, together with a process for providing a cross-linked silicone coated substrate, the silicone composition comprising at least: (A) an organopolysiloxane comprising an organocyclosiloxane; (B) an organosilane comprising at least two cross-blinking groups, X; and (C) an organosilicone resin comprising at least two cross-linking groups, X; wherein at least one of the organosilane (B) and the organosilicone resin (C) comprises at least three cross-linking groups.

Claims (46)

1. A silicone composition comprising:

(A) an organopolysiloxane comprising;

an organocyclosiloxane, and

a linear organopolysiloxane comprising at least two cross-linking groups (X);

(B) an organosilane comprising at least two cross-linking groups (X), the organosilane (B) having at least one group independently selected from ketoxime groups and a group of general formula —R 16 —NH—R 15 —NH 2 in which R 15 and R 16 are independently alkylene groups having from one to ten carbon atoms; and

(C) an organosilicone resin comprising at least two cross-linking groups (X);

wherein at least one of the organosilane (B) and the organosilicone resin (C) comprises at least three of the cross-linking groups (X); and

wherein the organosilicone resin (C) is a silsesquioxane resin comprising at least one structural unit of general formula (2):

(R 3 SiO (3-b)/2 (R 2 X) b )  (2)

and at least 80 mol. % of a structural unit of general formula (8):

R 19 SiO 3/2   (8)

wherein each of R 3 and R 19 is independently selected from the group consisting of an alky group having one to ten carbon atoms and an alkenyl group having from two to ten carbon atoms, R 2 is a covalent bond or a divalent organic linking group which does not contain an aryl group, and subscript b is 0, 1 or 2, with the proviso that the silsesquioxane resin (C) comprises at least two of the cross-linking groups (X).

2. The silicone composition of claim 1 , wherein the cross-linking groups (X) are independently selected from one or more of the group consisting of hydrogen directly bonded to silicon, hydroxyl, acrylate, acyl, acyloxy, ketoxime, alkenyl, alkoxy, epoxy, amine, mercapto, and methacrylate.

3. The silicone composition of claim 2 , wherein the organosilane (B) comprises at least one compound of general formula (1):

R (4-a) Si(R 1 X) a   (1)

wherein X is the cross-linking group (X), R 1 is a covalent bond or a divalent organic linking group, R is a substituted or unsubstituted organic radical, and subscript a is 2, 3 or 4, optionally wherein subscript a is 3 or 4, provided at least one X is a ketoxime and/or at least one R is of general formula —R 16 —NH—R 15 —NH 2 in which R 15 and R 16 are independently alkylene groups having from one to ten carbon atoms.

4. The silicone composition of claim 3 , wherein R is an alkyl group having from one to ten carbon atoms, R 1 is a covalent bond, and at least one X is a ketoxime of general formula (11):

—P—N═CR 11 R 12   (11)

in which R 11 and R 12 are independently an alkyl group having from one to ten carbon atoms.

5. The silicone composition of claim 2 , wherein the silsesquioxane resin (C) comprises at least three of the cross-linking groups (X).

6. The silicone composition of claim 2 , wherein the linear organopolysiloxane of the organopolysiloxane (A) is of general formula (5):

wherein X is the cross-linking group (X), R 4 is a covalent bond or a divalent organic linking group, each of R 5 to R 10 is independently a substituted or unsubstituted organic radical or the group R 4 X, and subscript e is an integer in the range of from 1 to 70.

7. The silicone composition of claim 1 , wherein the organocyclosiloxane of the organopolysiloxane (A) comprises an organocyclosiloxane having from three to ten silicon atoms in the organocyclosiloxane ring.

8. The silicone composition of claim 1 , wherein the organocyclosiloxane of the organopolysiloxane (A) is of general formula (6):

wherein each of R 13 and R 14 is independently a substituted or unsubstituted organic radical and subscript f is an integer in the range of from 3 to 10, optionally subscript f is an integer in the range of from 4 to 6.

9. A cross-linked silicone obtained by cross-linking the silicone composition according to claim 1 .

10. A substrate coated with the silicone composition of claim 1 , optionally wherein the silicone composition has been cross-linked on the substrate to provide a cross-linked silicone and/or optionally wherein the substrate is cement.

11. A construction material comprising the substrate of claim 10 .

12. A process for providing a cross-linked silicone coated substrate comprising the steps of:

providing a substrate;

applying the silicone composition of claim 1 to the substrate to provide a substrate coated with the silicone composition; and

cross-linking the silicone composition on the substrate to provide the cross-linked silicone coated substrate;

optionally wherein the substrate is cement.

13. The process of claim 12 , wherein the cross-linking step comprises:

contacting the silicone composition on the substrate with water, optionally in the presence of acid or alkali.

14. A process for providing a cross-linked silicone coated substrate comprising the steps of:

providing a substrate; and

mixing the substrate with the cross-linked silicone of claim 9 to provide the cross-linked silicone coated substrate;

optionally wherein the cross-linked silicone is a silicone powder; and/or

optionally wherein the mixing step comprises grinding the substrate with the cross-linked silicone.

15. A hydrophobizing additive, a bulk density improver, or a flow improver comprising the silicone composition of claim 1 , optionally wherein the silicone composition is cross-linked such that it is a cross-linked silicone composition.

16. The silicone composition of claim 4 , wherein the organosilane (B) comprises methyltri(ethylmethylketoxime) silane.

17. The silicone composition of claim 3 , wherein at least one R is of general formula —R 16 —NH—R 15 —NH 2 in which R 15 and R 16 are independently alkylene groups having from one to ten carbon atoms, R 1 is a covalent bond, and X is one or both of an alkoxy group having from one to ten carbon atoms and a ketoxime of general formula:

—O—N═CR 11 R 12

in which R 11 and R 12 are independently an alkyl group having from one to ten carbon atoms.

18. The silicone composition of claim 17 , wherein the organosilane (B) comprises (ethylenediaminepropyl) trimethoxysilane.

Assignments (3)
CHANGE OF NAME Recorded Feb 28, 2018
From: DOW CORNING CORPORATION
To: DOW SILICONES CORPORATION
Reel/Frame 045470/0188 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2017
From: DANDEKAR, DEEPAK VIJAY; DAUND, GANESH; RAJE, VIVEK PRABHAKAR; VAIDYA, MILIND
To: DOW CORNING INDIA PVT. LTD.
Reel/Frame 041773/0396 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2017
From: DOW CORNING INDIA PVT. LTD.
To: DOW CORNING CORPORATION
Reel/Frame 041773/0457 →