IP Library Granted Patent US 10,487,240
Granted Patent B2
US 10,487,240 · App. 15/204,379 · Granted Nov 26, 2019

Silicone based emulsion, method for making same, and waterborne co-binder resin compositions comprising such emulsions

Inventors: Ping Jiang (New York, NY); Louisa Maio (White Plains, NY); Vikram Kumar (Tarrytown, NY); Martin Wusik (Danbury, CT); Yogesh Tiwary (Bangalore, IN); Michael Seeber (New York, NY)
Assignee: MOMENTIVE PERFORMANCE MATERIALS INC.
C09D183/04C08K3/36C08L83/04C09D7/63C09D133/08C08G77/16C08K5/17
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Quick Facts
Patent No.
US 10,487,240
App. No.
15/204,379
Granted
Nov 26, 2019
Kind
B2
Abstract

A crosslinkable silicone based emulsion composition includes a hydroxylated polydiorganopolysiloxane grafted onto at least one colloidal silica dispersion, wherein the at least one hydroxylated polydiorganopolysiloxane grafted onto the least one colloidal silica dispersion contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane. Further, a waterborne co-binder silicone-organic resin composition includes (A) the crosslinkable silicone emulsion and (B) an organic resin emulsion which provides improved cured properties including, but not limited to, improved hydrophobicity (water resistance), scratch resistance and gloss retention as well as process for making the emulsions and the compositions.

Claims (77)

1. A crosslinkable silicone based emulsion composition comprising:

at least one hydroxylated polydiorganopolysiloxane grafted onto at least one colloidal silica dispersion having an average particle size of greater than 100 nanometers;

at least one catalyst;

at least one emulsion stabilizer;

at least one surfactant; and

water,

wherein the at least one hydroxylated polydiorganopolysiloxane grafted onto the at least one colloidal silica dispersion contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

2. The composition of claim 1 further comprising at least one organic resin.

3. The composition of claim 1 wherein the at least one surfactant is a non-ionic surfactant, an anionic surfactant or a combination thereof.

4. The composition according to claim 1 , wherein the hydroxylated polydiorganosiloxane has a weight average molecular weight of from about 5,000 to about 1,000,000.

5. The composition according to claim 1 , wherein the hydroxylated polydiorganosiloxane has a weight average molecular weight of from about 200,000 to about 1,000,000.

6. The composition of claim 1 , wherein the hydroxylated polydiorganosiloxane is a hydroxyl-terminated polydimethylsiloxane.

7. The silicone composition according to claim 1 , wherein the colloidal silica dispersion comprises silica particles having an average particle size of greater than 100 nanometers and less than or equal to about 125 nanometers.

8. The composition according to claim 1 , wherein the catalyst comprises a metal compound selected from the group consisting of tin, titanium, zirconium, lead, iron cobalt, antimony, manganese, bismuth, zinc compounds and combinations thereof.

9. A crosslinkable silicone based emulsion composition comprising:

at least one hydroxylated polydiorganopolysiloxane grafted onto at least one colloidal silica dispersion;

at least one catalyst;

at least one emulsion stabilizer which is one or more organic amine compounds selected from the group consisting of 2-amino-2-methyl-1-propanol (AMP), 2-amino-1-butanol, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol, 2-amino-2-hydroxymethyl-1,3-propanediol, N-methyl derivatives of 2-amino-2-hydroxymethyl-1,3-propanediol, N-ethyl derivatives of 2-amino-2-hydroxymethyl-1,3-propanediol, N,N-dimethyl derivatives of 2-amino-2-hydroxymethyl-1,3-propanediol, N,N-diethyl derivatives of 2-amino-2-hydroxymethyl-1,3-propanediol and combinations thereof;

at least one surfactant; and

water, wherein the at least one hydroxylated polydiorganopolysiloxane grafted onto the at least one colloidal silica dispersion contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

10. A water-borne co-binder silicone-organic resin composition comprising:

i) at least one hydroxylated polydiorganopolysiloxane;

ii) at least one colloidal silica dispersion having an average particle size of greater than 100 nanometers,

iii) at least one catalyst,

iv) at least one emulsion stabilizer,

v) at least one surfactant,

vi) at least one organic resin, and

vii) water,

wherein the at least one hydroxylated polydiorganopolysiloxane is grafted onto the at least one colloidal silica dispersion to form a reaction product which contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

11. The water-borne co-binder silicone-organic resin composition of claim 10 wherein the composition is a mixture comprising:

(A) a crosslinkable silicone based emulsion comprising the reaction product of (i) the at least one hydroxylated polydiorganopolysiloxane and (ii) the colloidal silica dispersion having an average particle size of greater than 100 nanometers, and

(i) the at least one catalyst,

(ii) the at least one emulsion stabilizer,

(iii) the at least one surfactant, and

(iv) water,

wherein the reaction product of the at least one hydroxylated polydiorganopolysiloxane grafted onto the at least one colloidal silica dispersion contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane; and

(B) an organic resin emulsion comprising water, the at least one surfactant and the at least one organic resin; and

optionally (C) an epoxy functional polysiloxane and/or an emulsion of an alkylpolysilsesquioxane.

12. The waterborne co-binder silicone-organic resin composition according to claim 11 , wherein the crosslinkable silicone based emulsion (A) is present in an amount of from about 5 to about 100 parts by weight per 100 parts of the organic resin emulsion (B).

13. The waterborne co-binder silicone-organic resin composition according to claim 11 , wherein the organic resin emulsion (B) is a latex polymer obtainable by emulsion polymerization of at least one ethylenically unsaturated monomer in water, a polyurethane emulsion or dispersion, a polyether emulsion, or an epoxy resin emulsion.

14. The waterborne co-binder silicone-organic resin composition according to claim 10 , wherein each of the at least one hydroxylated polydiorganosiloxane, the at least one catalyst and the at least one organic resin are emulsions.

15. A water-borne co-binder silicone-organic resin composition comprising:

(A) a crosslinkable silicone based emulsion comprising the reaction product of (i) at least one hydroxylated polydiorganopolysiloxane and (ii) colloidal silica having a particle size of greater than 100 nanometers, and

(iii) at least one catalyst,

(iv) at least one emulsion stabilizer,

(v) at least one surfactant, and

(vi) water,

wherein the reaction product of (i) and (ii) is formed by heating at a temperature of from about 40° C. to 100° C. for about 1 to about 72 hours the mixture of components (i) to (vi) and wherein the at least one hydroxylated polydiorganopolysiloxane (i) and the at least one catalyst (iii) are emulsified using the at least one surfactant (v); and

(B) an organic resin emulsion comprising water, at least one surfactant and the at least one organic resin,

wherein said water-borne co-binder silicone-organic resin composition is a coating, adhesive or sealant composition.

16. A waterborne co-binder silicone resin composition comprising an organic resin emulsion and a crosslinkable silicone based emulsion made by the process comprising:

(a) adding a colloidal silica dispersion having an average particle size greater than 100 nanometers, a catalyst, and an emulsion stabilizer to a first emulsion comprising a non-ionically or an anionically stabilized hydroxylated polydiorganosiloxane to form a second emulsion; and

(b) heating the second emulsion to a temperature of from about 40° C. to about 100° C. to form a reaction product of the at least one hydroxylated polydiorganopolysiloxane grafted onto the at least one colloidal silica dispersion which contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

17. A waterborne co-binder silicone resin composition comprising an organic resin emulsion, at least one epoxy functional polysiloxane and a crosslinkable silicone based emulsion made by a process comprising:

(a) adding a colloidal silica dispersion, a catalyst and an emulsion stabilizer to a first emulsion comprising a non-ionically or an anionically stabilized hydroxylated polydiorganosiloxane to form a second emulsion; and

(b) heating the second emulsion to a temperature of from about 40° C. to about 100° C. to form a reaction product of the at least one hydroxylated polydiorganopolysiloxane grafted onto the at least one colloidal silica dispersion which contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

18. A process for making a crosslinkable silicone based emulsion composition comprising:

(a) adding a colloidal silica having a particle size of greater than 100 nanometers, a catalyst and an emulsion stabilizer to a first emulsion comprising a non-ionically or an anionically stabilized hydroxylated polydiorganosiloxane to form a second emulsion; and

(b) heating the second emulsion to a temperature of from about 40° C. to about 100° C.,

to form a reaction product of the at least one hydroxylated polydiorganopolysiloxane grafted onto the at least one colloidal silica dispersion which contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

19. The process of claim 18 comprising heating the composition at a temperature of from about 70° C. to about 85° C.

20. The process of claim 18 , wherein the colloidal silica dispersion has an average particle size of greater than 100 nanometer to less than or equal to about 125 nanometers.

21. The process of claim 18 , wherein the colloidal silica is present in an amount of from about 1 to about 150 parts by weight of colloidal silica per 100 parts of the hydroxylated polydiorganosiloxane.

22. The process of claim 18 , wherein the hydroxylated polydiorganosiloxane comprises a hydroxylated polydimethylsiloxane.

23. The process of claim 22 , wherein the polydiorganosiloxane has a weight average molecular weight of about 5,000 to about 1,000,000.

24. A process for making the crosslinkable silicone based emulsion (A) according to claim 11 comprising heating at a temperature of from about 40° C. to 100° C. for about 1 to about 72 hours a silicone emulsion composition comprising:

(i) at least one hydroxylated polydiorganopolysiloxane,

(ii) colloidal silica having a particle size of greater than 100 nanometers,

(iii) at least one catalyst,

(iv) at least one emulsion stabilizer,

(v) at least one surfactant, and

(vi) water,

wherein the at least one hydroxylated polydiorganopolysiloxane and the at least one catalyst are emulsified using the at least one surfactant and wherein reaction products are formed from the grafting of the at least one hydroxylated polydiorganopolysiloxane onto the at least one colloidal silica dispersion and said reaction products contains residual silanol groups from the at least one hydroxylated polydiorganopolysiloxane.

25. A waterborne coating comprising the silicone composition according to claim 1 .

26. The waterborne coating of claim 25 , wherein the coating is a sealer.

27. An article comprising the waterborne coating of claim 25 disposed on at least a portion of a surface of the article.

28. A film formed from the composition of claim 16 .

Assignments (10)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2018
From: JIANG, PING; MAIO, LOUISA; KUMAR, VIKRAM; WUSIK, MARTIN; TIWARY, YOGESH; SEEBER, MICHAEL
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 044922/0187 →
Continuity (3)
Provisional Application 62190464 · Jul 9, 2015
Provisional Application 62275989 · Jan 7, 2016
Related Publication 20170009099A1 · Jan 12, 2017
Cited By (1)
US 12,410,321