IP Library Granted Patent US 10,633,539
Granted Patent B2
US 10,633,539 · App. 15/066,395 · Granted Apr 28, 2020

Composition comprising organosiloxane nano latex and preparation of organosiloxane nano latex

Inventors: Monjit Phukan (Bangalore, IN); Anubhav Saxena (Bangalore, IN); Shrutisagar D. Haveli (Maharashtra, IN); Sandeep Naik (Maharashtra, IN); Amar Pawar (Elmsford, NY); Dian Liu (Shanghai, CN); Yun Huang (Shanghai, CN)
Assignee: Momentive Performance Materials Inc.
C08L83/06A61K8/89A61K8/895A61Q1/02A61Q1/10A61Q17/04C08F290/062C08F290/142C08F290/148C08G77/442C08L83/10A61K2800/413A61K2800/54
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Quick Facts
Patent No.
US 10,633,539
App. No.
15/066,395
Granted
Apr 28, 2020
Kind
B2
Abstract

A hydrophobic hybrid organosiloxane nano latex is provided as the copolymerizate of: (a) organosiloxane monomer of the general formula M a M v b D c D v d T e T v f Q g wherein: M=R 1 R 2 R 3 SiO 1/2 , M v =R 4 R 5 R u SiO 1/2 , D=R 6 R 7 SiO 2/2 , D v =R 8 R u SiO 2/2 , T=R 9 SiO 3/2 , T v =R u SiO 3/2 , and Q=SiO 4/2 in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently is hydrogen, a hydroxyl group, a hydrocarbyl group having up to 100 carbon atoms and optionally containing at least one hetroatom; R u is a free-radical polymerizable group; subscripts a, b, c, d, e, f and g each independently range from 0 to 10,000 subject to the limitation that b+d+f is at least 1, p, q and r are integers independently selected from 0 to 100 and subscript h is 0 or 1; and, (b) monomer possessing a group which is free-radical copolymerizable with group R u of organosiloxane monomer (a).

Claims (57)

1. A hydrophobic hybrid organosiloxane nano latex comprising the copolymerizate of:

(a) organosiloxane monomer consisting of the general formula M a M v b D c D v d

wherein:

M=R 1 R 2 R 3 SiO 1/2 ,

M v =R 4 R 5 R u SiO 1/2 ,

D=R 6 R 7 SiO 2/2 , and

D v =R 8 R u SiO 2/2 ,

in which each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from hydrogen, a hydroxyl group, or a hydrocarbyl group having up to 100 carbon atoms, but containing no heteroatoms; R u is a; free-radical polymerizable group; subscripts a, b, c, and d, each independently range from 0 to 10,000 subject to the limitation that b+d is at least 1; and,

(b) monomer possessing a group which is free-radical copolymerizable with group R u of organosiloxane monomer (a) and, wherein the copolymerizate has a particle size ranging from 10 to 990 nm.

2. The hydrophobic hybrid organosiloxane nano latex of claim 1 in the form of a film having a contact angle of at least 50°.

3. The hydrophobic hybrid organosiloxane nano latex of claim 1 in the form of a film having a contact angle of at least 60°.

4. The hydrophobic hybrid organosiloxane nano latex of claim 1 in the form of a film having a contact angle of at least 70°.

5. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein in organosiloxane monomer (a), each R u is independently an ethylenically unsaturated group selected from Formulas I, II(a), II(b) and II(c):

wherein:

each R 10 is independently selected from linear or branched alkyl groups of up to 10 carbon atoms; A 1 and A 2 each independently is a group capable of undergoing free radical addition reaction; and, subscripts p, q and r each independently range from 0 to 100.

6. The hydrophobic hybrid organosiloxane nano latex of claim 5 wherein A 1 and A 2 each independently is a group of formula III:

wherein R 11 , R 12 and R 13 each independently is hydrogen or hydrocarbyl group of up to 5 carbon atoms, Y is absent or is a linking group selected from the group consisting of divalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 2 to 16 carbons.

7. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein monomer (a) is selected from the group consisting of vinyl functional silicone, hydroxy functional silicone acrylates, organo modified silicone (meth)acrylates, organo modified silicone acrylamides, organo modified silicone (meth)acrylamides, their derivatives and mixtures thereof.

8. The hydrophobic hybrid organosiloxane nano latex of claim 7 which is the copolymerizate of monomer (a) and at least two monomers (b).

9. The hydrophobic hybrid organosiloxane nano latex of claim 1 , wherein monomer (b) is selected from the group consisting of acrylic acid, methacrylic acid, their esters, their amide derivatives and mixtures thereof.

10. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein monomer (b) is selected from the group consisting of methyl methacrylate, butyl acrylate, propyl acrylate, tert-butyl methacrylate, N,N-dimethylacrylamide, N-isopropyl acrylamide, 2-ethylhexyl acrylate, cyclohexyl acrylate, vinlyl acrylate, allyl acrylate, hydroxyethyl acrylate, perfluoroethyl acrylate, isobornyl acrylate, lauryl methacrylate, lauryl arylate, cetyl methacrylate, behenyl acrylate, phenoxyethyl acrylate, tetraethylene glycol diacrylate, tripropylene glycol diacrylate, acrylamide, methacrylamide, acrylated silane, methacrylated silane, methacryloxyl silane, 2-hydroxyethyl methacrylate, 3-[tris(trimethylsiloxy)silyl]propyl methacrylate, acrylate and methacrylate functional carbosilanes, hexafunctional urethane acrylates, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol tetraacrylate, di-trimethylolpropane tetraacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, butanediol diacrylate, tripropylene glycol diacrylate, trimethylolpropane trimethacrylate, oligofunctional urethane acrylates, tetraacrylate monomer, polyester acrylate oligomers, and combinations thereof.

11. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the particle size of the copolymerizate is from 30 to 750 nm.

12. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the particle size of the copolymerizate is from 50 to 500 nm.

13. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the content of copolymerizate is from 0.1 to 40 weight percent of the latex.

14. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the content of copolymerizate is from 0.1 to 35 weight percent of the latex.

15. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the viscosity is from 0.1 to about 250 cps.

16. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the viscosity is from 0.5 to about 230 cps.

17. The hydrophobic hybrid organosiloxane nano latex of claim 1 wherein the viscosity is from 1 to about 200 cps.

18. A personal care composition comprising a film-forming amount of hydrophobic hybrid organosiloxane nano latex of claim 1 .

19. The personal care composition of claim 18 wherein the film obtained from the hydrophobic hybrid organosiloxane nano latex has a contact angle of at least 50°.

20. The personal care composition of claim 18 wherein the film obtained from the hydrophobic hybrid organosiloxane nano latex has a contact angle of at least 60°.

21. The personal care composition of claim 18 wherein the film obtained from the hydrophobic hybrid organosiloxane nano latex has a contact angle of at least 70°.

22. The personal care composition of claim 18 which is selected from the group consisting of deodorants, antiperspirants, antiperspirant/deodorants, stick and roll-on products, skin lotions, moisturizers, toners, cleansing products, styling gels, hair dyes, hair color products, hair straighteners, nail polish, nail polish remover, sunscreens, anti-aging products, lipsticks, lip balms, lip glosses, foundations, face powders, eye liners, eye shadows, blushes, makeup, beauty balms, mascaras, moisturizing preparations, foundations, concealers, body and hand preparations, skin care preparations, face and neck preparations, fragrance preparations, soft focus applications, night and day skin care preparations, tanning preparations, hand liquids, non-woven applications for personal care, baby lotions, facial cleansing products, hair cuticle coats, gels, foam baths, body washes, scrubbing cleansers, controlled-release personal care products, hair shampoos, hair conditioners, hair sprays, skin care moisturizing mists, skin wipes, pore skin wipes, pore cleaners, blemish reducers, skin exfoliators, skin desquamation enhancers, skin towelettes and cloths, depilatory preparations, personal care lubricants, nail coloring preparations and drug delivery systems for topical application of medicinal compositions that are to be applied to the skin.

23. The personal care composition of claim 22 wherein the film obtained from the hydrophobic hybrid organosiloxane nano latex has a contact angle of at least 50°.

24. The personal care composition of claim 22 wherein the film obtained from the hydrophobic hybrid organosiloxane nano latex has a contact angle of at least 60°.

25. The personal care composition of claim 22 wherein the film obtained from the hydrophobic hybrid organosiloxane nano latex has a contact angle of at least 70°.

26. A hydrophobic hybrid organosiloxane nano latex consisting essentially of the copolymerizate of:

(a) organosiloxane monomer consisting of the general formula M a M v b D c D v d

wherein:

M=R 1 R 2 R 3 SiO 1/2 ,

M v =R 4 R 5 R u SiO 1/2 ,

D=R 6 R 7 SiO 2/2 , and

D v =R 8 R u SiO 2/2 ,

in which each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from hydrogen, a hydroxyl group, or a hydrocarbyl group having up to 100 carbon atoms, but containing no heteroatoms; R u is a; free-radical polymerizable group; subscripts a, b, c, and d, each independently range from 0 to 10,000 subject to the limitation that b+d is at least 1; and,

(b) monomer possessing a group which is free-radical copolymerizable with group R u of organosiloxane monomer (a).

27. A hydrophobic hybrid organosiloxane nano latex comprising the copolymerizate of:

(a) organosiloxane monomer consisting of the general formula M a M v b D c D v d

wherein:

M=R 1 R 2 R 3 SiO 1/2 ,

M v =R 4 R 5 R u SiO 1/2 ,

D=R 6 R 7 SiO 2/2 , and

D v =R 8 R u SiO 2/2 ,

in which each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from hydrogen, a hydroxyl group, or a hydrocarbyl group having up to 100 carbon atoms, but containing no heteroatoms; R u is independently an ethylenically unsaturated group selected from Formulas I, II(a), II(b) and II(c):

wherein:

each R 10 is independently selected from linear or branched alkyl groups of up to 10 carbon atoms; A 1 and A 2 each independently is a group capable of undergoing free radical addition reaction; and, subscripts p, q and r each independently range from 0 to 100;

subscripts a, b, c, d, each independently range from 0 to 10,000 subject to the limitation that b+d is at least 1; and,

(b) monomer possessing a group which is free-radical copolymerizable with group R u of organosiloxane monomer (a) and, wherein the copolymerizate has a particle size ranging from 10 to 990 nm.

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 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 11, 2016
From: PHUKAN, MONJIT; SAXENA, ANUBHAV; HAVELI, SHRUTISAGAR D; NAIK, SANDEEP; PAWAR, AMAR; LIU, DIAN; HUANG, YUN
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 037952/0597 →
Cited By (2)
US 12,370,134 US 12,577,338