Cosmetic skin covering sheets and their method of preparation

• US 9,498,409 B2
• Filed: 12/16/2014
• Issued: 11/22/2016
• 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, Dubey, Mayank Kumar, Navale, Tushar, Presti, Richard A.
• Primary Examiner(s): Sasan, Aradhana
• Application Number:
  US14/572,118
• Publication Number:
  US 20160166476A1
• Time in Patent Office: 707 Days
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/56 Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
• CPC Class Codes: A61K 2800/87 Application Devices; Containers; Packaging
• CPC Class Codes: A61K 2800/95 Involves in-situ formation or cross-linking of polymers
• CPC Class Codes: A61K 8/0208 Tissues; Wipes; Patches
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• CPC Class Codes: A61K 8/899 containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
• 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
• CPC Class Codes: C08G 77/44 containing only polysiloxane sequences

Abstract

The invention is directed to a cosmetic skin covering sheet which comprises a patch containing a cosmetic material for application to the skin or a cosmetic formulation which forms the cosmetic skin covering sheet in-situ upon topical application of the cosmetic formulation onto the skin, wherein each of said patch or cosmetic formulation comprises an ionic silicone as described herein.

Claims

1. A cosmetic skin covering sheet which comprises a patch containing a cosmetic material for application to the skin or a cosmetic formulation which forms the cosmetic skin covering sheet in-situ upon topical application of the cosmetic formulation onto the skin, and the said cosmetic skin covering sheet is produced by a reaction selected from a condensation reaction, a hydrosilylation reaction, a free-radical polymerization reaction, a ring-opening polymerization reaction and combinations thereof,

wherein the reaction is conducted in the presence of

(i) at least one ionic silicone having the general formula:

M¹_aM²_bM³_cD¹_dD²_eD³_fT^t_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 independently an aliphatic, an aromatic or fluoro containing monovalent hydrocarbon radicals containing from 1 to about 60 carbon atoms;

where R⁴, R¹², R¹⁷ are monovalent or multi-valent radical bearing ion-pairs,

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

OR²⁰ and an unsaturated monovalent radical, wherein each R²⁰ is independently selected from hydrogen, and a monovalent hydrocarbon radical of from 1 to about 60 carbon atoms,

where the subscripts 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, and b+e+h is greater than 0; and

(ii) at least one compound selected from a hydrosilylation effective component, a condensation effective component, free radical polymerization effective component and a ring-opening polymerization component;

with the proviso that when R⁷, R¹⁴ and R¹⁸ are hydrogen then the hydrosilylation effective component is selected from a vinyl silicone and hydrosilylation effective catalyst, and when R⁷, R¹⁴ and R¹⁸ are unsaturated monovalent radicals the hydrosilylation effective component is selected from a hydride silicone and hydrosilylation effective catalyst.

2. The cosmetic skin covering sheet of claim 1 further comprising a solvent, a cosmetically acceptable additive, an excipient and combinations thereof.

3. The cosmetic skin covering sheet of claim 1, wherein the patch containing a cosmetic material for application to the skin comprises greater than one layer and wherein at least one such layer comprises the ionic silicone.

4. The cosmetic skin covering sheet of claim 1, wherein the cosmetic formulation which forms the cosmetic skin covering sheet in-situ upon topical application of the cosmetic formulation onto the skin takes the contour of the skin substrate upon application to the skin.

5. The cosmetic skin covering sheet of claim 1, wherein the sheet further comprises from 0.01% to 25% by weight of an active ingredient, based on a total weight of the sheet.

6. The cosmetic skin covering sheet of claim 1 where in the ionically modified silicone the monovalent radicals R⁴, R¹², R¹⁷ are independently 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 each containing from 1 to about 60 carbon atoms, wherein the hydrocarbonoxy group contains at least one oxygen heteroatom,

where superscripts x and y are positive integers, subject to the proviso that x is a product of n and y, and each subscript n independently has a value of from 1 to 6,

where I is an ionic group, and

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.

7. The cosmetic skin covering sheet of claim 1 where in the ionically modified silicone 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 optionally, one or more of a sulfur atom, a nitrogen atom, oxygen atom,

where R′

″

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

, I is an ionic group.

8. The cosmetic skin covering sheet of claim 1 wherein the reaction(s) is conducted as a neat reaction or in presence of at least one of a cosmetic ingredient and an excipient.

9. The cosmetic skin covering sheet of claim 1, wherein the ionic silicone composite network further comprises a physical blend of the silicone ionomer of formula (I) and an organic structuring polymer and/or another network.

10. The cosmetic skin covering sheet of claim 9, wherein the physical blend further comprises at least one of a cosmetic ingredient, an active ingredient and an excipient.

11. The cosmetic skin covering sheet of claim 10, wherein the active ingredient 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.

12. A method for providing the skin cosmetic covering sheet of claim 1 which comprises physically blending (1) the ionic silicone and (ii) at least one compound selected from a hydrosilylation effective component, a condensation effective component, free radical polymerization effective component and a ring-opening polymerization component.

13. The method of claim 12 wherein the skin cosmetic covering sheet is a patch containing a cosmetic material for application to the skin.

14. The method of claim 12, wherein the skin cosmetic covering sheet is a cosmetic formulation which forms the cosmetic skin covering sheet in-situ upon topical application of the cosmetic formulation onto the skin.

15. The method of claim 12 where in the ionically modified silicone the monovalent radicals R⁴, R¹², R¹⁷ are independently 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 each containing from 1 to about 60 carbon atoms, wherein the hydrocarbonoxy group contains at least one oxygen heteroatom,

where superscripts x and y are positive integers, subject to the proviso that x is a product of n and y, and each subscript n independently has a value of from 1 to 6,

where I is an ionic group, and

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 12 where in the ionically modified silicone 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 optionally, one or more of a sulfur atom, a nitrogen atom, oxygen atom,

where R′

″

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

, I is an ionic group.

17. The method of claim 12, wherein the ionic silicone is produced by a reaction selected from a condensation reaction, a hydrosilylation reaction, a free-radical polymerization reaction, a ring-opening polymerization reaction and combinations thereof.

18. The cosmetic skin covering sheet of claim 1 wherein the component (ii) is selected from silicone hydride, silicone vinyl, silanol, alkoxy silicone, alkoxy silane or silicone resins.

19. The cosmetic skin covering sheet of claim 1 wherein the hydrosilylation effective component is selected from organic molecules bearing two or more hydrosilylation effective unsaturations.