Cosmetic composition and method of preparation

• US 9,744,119 B2
• Filed: 10/27/2016
• Issued: 08/29/2017
• Est. Priority Date: 12/16/2014
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Original Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Phukan, Monjit, Saxena, Anubhav, Navale, Tushar
• Primary Examiner(s): DICKINSON, PAUL W
• Application Number:
  US15/335,917
• Publication Number:
  US 20170042787A1
• Time in Patent Office: 306 Days
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 2800/95 Involves in-situ formation or cross-linking of polymers
• CPC Class Codes: A61K 31/455 Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 8/042 Gels
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/368 with carboxyl groups directly bound to carbon atoms of aromatic rings
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61K 8/4926 having six membered rings
• CPC Class Codes: A61K 8/602 Glycosides, e.g. rutin
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61K 8/899 containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
• CPC Class Codes: A61K 9/06 Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels composition of ointments, creams or gels A61K47/00
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/02 for chemically bleaching or whitening the skin
• CPC Class Codes: A61Q 19/04 for chemically tanning the skin topical sun or radiation screening or tanning preparations A61Q17/04
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations

Abstract

The invention is directed to a cosmetic which comprises an ionic silicone as described herein.

Claims

1. A method of preparing a cosmetic composition comprising an oil phase and optionally an aqueous phase wherein the method comprising

(a) reacting

i) at least one silicone hydride bearing at least two Si—

H residues,

ii) at least one cross-linker silicone with two or more Si-unsaturated radicals,

wherein at least one of (i) or (ii) silicone is an ionic silicone having the general formula (I);

M¹_aM²_bM³_cD¹_dD²_eD³_fT¹_gT²_hT³_iQ_j 

 

(I)

wherein;

M¹=R¹R²R³SiO_1/2

M²=R⁴R⁵R⁶SiO_1/2

M³=R⁷R⁸R⁹SiO_1/2

D¹=R¹⁰R¹¹SiO_2/2

D²=R¹²R¹³SiO_2/2

D³=R¹⁴R¹⁵SiO_2/2

T¹=R¹⁶SiO_3/2

T²=R¹⁷SiO_3/2

T³=R¹⁸SiO_3/2

Q=SiO_4/2

where R¹, R², R³, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹³, R¹⁵, R¹⁶ are each independently aliphatic, aromatic or fluoro containing monovalent hydrocarbon radicals containing from 1 to about 60 carbon atoms;

where R⁴, R¹², R¹⁷ are each monovalent radical bearing ion-pairs,

where R⁷, R¹⁴ and R¹⁸ are each independently selected from hydrogen, —

OR²⁰, unsaturated monovalent radicals or monovalent epoxy group-containing radicals, monovalent sulfur atom-containing radicals and monovalent organosilane groups, wherein R²⁰ is independently selected from hydrogen, monovalent hydrocarbon radical of from 1 to about 60 carbon atoms,

where the subscript a, b, c, d, e, f, g, h, i, j are zero or positive subject to the following limitations;

the sum a+b+c+d+e+f+g+h+i+j is greater than or equal to 2 and less than or equal to 6000, b+e+h is greater than 0; and

iii) an effective amount of precious metal catalyst suitable for facilitating addition cure reaction between i) and ii) to obtain a crosslinked ionic silicone network,

(b) combining the crosslinked ionic silicone network of step (a), at least one cosmeceutical active, and optionally one or more cosmetically acceptable additives;

(c) shearing the combined components of step (b) during and/or after the combining step (b) with a solvent to form a crosslinked ionic silicone network gel, and

(d) adding the crosslinked ionic silicone network gel to an oil phase to obtain the cosmetic composition.

2. The method of claim 1, wherein the crosslinked ionic silicone network gel comprises 0.1 to 99% of the crosslinked ionic silicone network obtain in step (a) and 0.01% to 25% of the cosmeceutical active.

3. The method of claim 1, wherein the monovalent radicals R⁴, R¹², R¹⁷ are each selected from the formula (II):

-A-I^x−

M_n^y+;

 

 

(II)

where A is a spacing group having selected from a divalent hydrocarbon and hydrocarbonoxy group,

where superscripts n and y are independently from 1 to 6 and x is a product of n and y,

where I is an ionic group independently selected from sulfonate —

SO₃⁻

, sulfate —

OSO₃⁻

, carboxylate —

COO⁻

, phosphonate —

PO₃²⁻

and phosphate —

OPO₃²⁻

group, where M is hydrogen or a cation independently selected from alkali metals, alkaline earth metals, rare earth metals, transition metals, metals, metal complexes, quaternary ammonium, polymeric cations and phosphonium groups.

4. The method of claim 1 wherein the monovalent radicals R⁴, R¹², R¹⁷ are each independently selected from zwitterions having the formula (III):

—

R′

—

NR″

₂⁺—

R′

″

—

I 

 

(III)

where R′

is a divalent hydrocarbon radical containing from 1 to about 60 carbon atoms, where R″

is monovalent hydrocarbon radical containing from 1 to about 60 carbon atoms, and

where R′

″

is divalent hydrocarbon radical containing from 2 to about 20 carbon atoms; and

, I is an ionic group independently selected from sulfonate —

SO₃⁻

, sulfate —

OSO₃⁻

, carboxylate —

COO⁻

, phosphonate —

PO₃²⁻

group and phosphate —

OPO₃²⁻

group.

5. The method of claim 1, wherein the crosslinking reaction mixture is reacted by condensation, hydrosilylation, free-radical polymerization, ring opening polymerization and combinations thereof.

6. The method of claim 5, wherein the reaction is carried out neat or in presence of the cosmetically acceptable additive.

7. The method of claim 1, wherein said crosslinked ionic silicone network comprises a physical blend of the ionic silicone of the formula (I) with structuring polymer and/or networks other than the said ionic silicone (I).

8. The method of claim 1 wherein the combined components of step (b) further comprises film-forming additives selected from the group comprising of polysilicone dimethicone, polysilicone acrylate copolymer, dimethylsiloxane/3-thiopropyl methyl siloxane copolymer, vinylpyyrolidone/vinylacetate copolymer, polyvinylacetate, starch, polyquaternium-4, polyquaternium-11, acrylates/steareth-2 methacrylate crosspolymer, vinylacetate/vinyl neodecanoate copolymer, polyester-5, cetyl ethylhexanoate, vinyl acetate, crotonate/vinyl neodecanoate copolymer, 2-acryamido-2-methyl propane sulfonic acid/acrylic acid copolymer, acryamido-2-methyl propane sulfonic acid/acrylic acid/acryl methacrylate copolymer, polyacrylamide, C13-C14 isoparaffin, laureth-7, octylacrylamide, acrylate/butylaminoethylmethacrylate copolymer, and combinations thereof.

9. The method of claim 1 wherein the combined components of step (b) further comprises cross-linked matrixes selected from the group comprising of non-ionic silicone cross-polymers, urethane cross-polymer, acrylated cross-polymers, cross-linked polysaccharides and combinations thereof.

10. The method of claim 1, wherein the cosmeceutical active is selected from the group consisting of photoprotective agents, self-tanning agents, desquamating agents, depigmenting agents, moisturizing agents, skin lightening agents, anti-aging ingredients, anti-wrinkle agents and combinations thereof.

11. The method of claim 1, wherein the crosslinked ionic silicone network obtain in step (a) is combined with the cosmetically acceptable additive prior to forming the combination with the cosmeceutical active.

12. The method of claim 1, wherein the cosmeceutical active is present in the crosslinking reaction mixture with the ionic silicone of formula (I).

13. The method of claim 1, wherein the cosmeceutical active is kept separate from the crosslinking reaction mixture with the ionic silicone of formula (I), and then both are combined following the formation of the ionic silicone network to form the crosslinked ionic silicone network gel in-situ during a topical application of the cosmetic composition.

14. A method of preparing a cosmetic composition comprising an oil phase and optionally an aqueous phase, wherein the method comprisingreacting a silicone hydride with an oxirane-functionalized ionic silicone, an oxirane ring-opening polymerization catalyst, a carrier solvent;

and optionally, one or more silicon hydride activators to obtain a crosslinked ionic silicone network by the ring-opening polymerization of oxirane moiety with hydride;

2) shearing the crosslinked ionic silicone network of step

     1) in the presence of at least one cosmeceutical active and optionally one or more cosmetically acceptable additives during and/or after polymerization of step

     1) with at least a carrier solvent to form a crosslinked ionic silicone network gel; and

3) adding the crosslinked ionic silicone network gel of step

     2) to an oil phase of the cosmetic composition;

wherein the oxirane-functionalized ionic silicone has the general formula (I);

M¹_aM²_bM³_cD¹_dD²_eD³_fT¹_gT²_hT³_iQ_j 

 

(I)

wherein;

M¹=R¹R²R³SiO_1/2

M²=R⁴R⁵R⁶SiO_1/2

M³=R⁷R⁸R⁹SiO_1/2

D¹=R¹⁰R¹¹SiO_2/2

D²=R¹²R¹³SiO_2/2

D³=R¹⁴R¹⁵SiO_2/2

T¹=R¹⁶SiO_3/2

T²=R¹⁷SiO_3/2

T³=R¹⁸SiO_3/2

Q=SiO_4/2

where R¹, R², R³, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹³, R¹⁵, R¹⁶ are each independently aliphatic, aromatic or fluoro containing monovalent hydrocarbon radicals containing from 1 to about 60 carbon atoms;

where R⁴, R¹², R¹⁷ are each monovalent radical bearing ion-pairs,

where R⁷, R¹⁴ and R¹⁸ are each independently selected from hydrogen, —

OR²⁰, unsaturated monovalent radicals or monovalent epoxy group-containing radicals, monovalent sulfur atom-containing radicals and monovalent organosilane groups, wherein R²⁰ is independently selected from hydrogen, monovalent hydrocarbon radical of from 1 to about 60 carbon atoms,

where the subscript a, b, c, d, e, f, g, h, i, j are zero or positive subject to the following limitations;

the sum a+b+c+d+e+f+g+h+i+j is greater than or equal to 2 and less than or equal to 6000, b+e+h is greater than 0.

15. The method of claim 14 wherein the monovalent radicals R⁴, R¹², R¹⁷ are selected from the formula (II):

-A-I^x−

M_n^y+;

 

 

(II)

where A is a spacing group having selected from a divalent hydrocarbon and hydrocarbonoxy group,

where superscripts n and y are independently from 1 to 6 and x is a product of n and y,

where I is an ionic group independently selected from sulfonate —

SO₃⁻

, sulfate —

OSO₃⁻

, carboxylate —

COO⁻

, phosphonate —

PO₃²⁻

and phosphate —

OPO₃²⁻

group, more specifically sulfonate —

SO₃⁻

, where M is hydrogen or a cation independently selected from alkali metals, alkaline earth metals, rare earth metals, transition metals, metals, metal complexes, quaternary ammonium, polymeric cations and phosphonium groups.

16. The method of claim 14 wherein the monovalent radicals R⁴, R¹², R¹⁷ are independently selected from zwitterions having the formula (III):

—

R′

—

NR″

₂⁺—

R′

″

—

I 

 

(III)

where R′

is a divalent hydrocarbon radical containing from 1 to about 60 carbon atoms, where R″

is monovalent hydrocarbon radical containing from 1 to about 60 carbon atoms, and

where R′

″

is divalent hydrocarbon radical containing from 2 to about 20 carbon atoms; and

, I is an ionic group independently selected from sulfonate —

SO₃⁻

, sulfate —

OSO₃⁻

, carboxylate —

COO⁻

, phosphonate —

PO₃²⁻

group and phosphate —

OPO₃²⁻

group.

17. The method claim 14 wherein the crosslinking reaction mixture is reacted by condensation, hydrosilylation, free-radical polymerization, ring opening polymerization and combinations thereof.

18. The method of claim 14 wherein the cosmeceutical active is selected from the group consisting of photoprotective agents, self-tanning agents, desquamating agents, depigmenting agents, moisturizing agents, skin lightening agents, anti-aging ingredients, anti-wrinkle agents and combinations thereof.