IP Library Granted Patent US 8,975,357
Granted Patent B2
US 8,975,357 · App. 13/955,333 · Granted Mar 10, 2015

Silicone modified fatty acids, method of preparation and usage thereof

Inventors: Benjamin Falk (Yorktown Heights, NY); Jeferson A. Naue (Itatiba, BR)
Assignee: Natura Inovacao e Tecnologia de Produtos Ltda.
A61K8/585A61K47/24A61Q1/02A61Q19/00C08G77/38A61K8/361C08G77/045C08G77/12
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Quick Facts
Patent No.
US 8,975,357
App. No.
13/955,333
Granted
Mar 10, 2015
Kind
B2
Abstract

The present invention relates to silicone modified fatty carboxylic acid compounds. More specifically, the present invention is derived from low molecular weight, i.e., short chain, silicone modified fatty carboxylic acids, their use and method of making same. The present invention provides for a silicone compound partially derived from a natural product, sapucainha oil, for use in cosmetic formulations.

Claims (27)

1. A cosmetic product comprising a modified silicone compound comprising the reaction product of:

a) at least one cyclic ether silicone having the formula:

M a M A b D c D B d T e T C f Q g

wherein;

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

M A =R 4 R 5 R 6 SiO 1/2

D=R 7 R 8 SiO 2/2

D B 9 R 10 SiO 2/2

T=R 11 SiO 3/2

T C =R 12 SiO 3/2 ;

Q=SiO 4/2 ;

R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms;

R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group;

wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25,

with the proviso that at least one of subscripts b, d, and f is positive; and

b) a substantially pure fatty carboxylic acid said fatty carboxylic acid prepared from sapucainha oil.

2. The cosmetic product of claim 1 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 3 carbon atoms.

3. The cosmetic product of claim 1 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having 1 carbon atom.

4. The cosmetic product of claim 1 wherein the sum of subscripts a, b, c, d, e, f, and g is not greater than 20.

5. The cosmetic product of claim 4 wherein subscript b is zero, subscript a is 1 to 3, subscripts c, e, and g are zero or less than 3, and at least one of subscript d and f is positive.

6. The cosmetic product of claim 4 wherein subscript b is zero, subscript a is 2, subscripts c, e, f, and g are zero and d is 1.

7. The cosmetic product of claim 1 wherein the cyclic ether silicone is at least one selected from the group consisting of 3,4-epoxycyclohexyl-1-ethane heptamethyltrisiloxane; 1,1,1,3,5,5,5-heptamethyl-3[2-(7-oxa-bicyclo[4.1.0]hept-3-yl )-ethyl]-trisiloxane; 1,1,3,3,5,5,5-heptamethyl-1[2-(7-oxa-bicyclo[4.1.0]hept-3-yl)-ethyl]trisiloxane; bisethylcyclohexyloxidepolysiloxane; 1,1,1,3,5,5,5-heptamethyl-3-[2-(1-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-propyl]-trisiloxane; and 1,1,1,3,5,5,5-heptamethyl-3-oxiranylmethoxy-propyl-trisiloxane.

8. The cosmetic product of claim 1 wherein the amount of cyclic ether silicone compound used in the reaction is from about the stoichiometric equivalent, where there is not more than 1 epoxy or oxetane group per 1 carboxylic acid group said carboxylic acid group being the fatty carboxylic acid prepared from sapucainha oil.

9. The cosmetic product of claim 1 wherein the stoichiometric ratio of cyclic ether silicone to fatty acid used in the reaction is from about 1:1 to about 1:10.

10. The cosmetic product of claim 1 further comprising at least one personal care product ingredient.

11. The cosmetic product of claim 10 wherein the product ingredient is at least one selected from the group consisting of ester waxes, oils and fats of animal or vegetable origin, fatty alcohols, fatty acids, alkyl esters of fatty acids, hydrocarbon oils and waxes, water, organic solvents, perfumes, surfactants, oil-soluble vitamins and water-soluble vitamins.

12. A cosmetic composition comprising a modified silicone compound which is a reaction product of at least one cyclic ether silicone and a fatty carboxylic acid prepared from sapucainha oil, and at least one cosmetically acceptable carrier.

Assignments (13)
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054336/0279 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
BANKRUPTCY ORDER TO RELEASE SECURITY INTEREST AT REEL/FRAME NO. 032736/0457 Recorded Nov 21, 2017
From: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 044203/0513 →
BANKRUPTCY ORDER TO RELEASE SECURITY INTEREST AT REEL/FRAME NO. 032736/471 Recorded Aug 20, 2017
From: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 043608/0018 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
SECURITY INTEREST Recorded Jan 13, 2015
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 034759/0723 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 032736/0471 →
SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 032736/0457 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 2, 2013
From: MOMENTIVE PERFORMANCE MAERIALS INC.
To: NATURA INOVACAO E TECNOLOGIA DE PRODUTOS LTDA.
Reel/Frame 031328/0435 →
Continuity (3)
Continuation 12604684 · Oct 23, 2009
Provisional Application 61239215 · Sep 2, 2009
Related Publication 20130317105A1 · Nov 28, 2013