Personal care composition comprising silicone network

• US 9,801,805 B2
• Filed: 12/16/2014
• Issued: 10/31/2017
• 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: Sarkar, Alok, Saxena, Anubhav, Samantara, Laxmi, Lu, Ning
• Primary Examiner(s): Loewe, Robert S
• Application Number:
  US14/572,139
• Publication Number:
  US 20160166495A1
• Time in Patent Office: 1,050 Days
• Field of Search: None
• 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 8/042 Gels
• 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: A61Q 19/00 Preparations for care of the skin

Abstract

The invention is directed to a personal care composition which contains a crosslinked ionic silicone network wherein the crosslinked ionic silicone network is formed by the ring-opening polymerization of oxirane moiety.

Claims

1. A process of preparing a personal care composition comprising at least an oil phase, wherein the process comprising

a) reacting a silicone hydride with a sulfonic acid functionalized siloxane;

b) neutralizing the acid;

c) adding an oxirane compound to react with the in intermediate product of step b) to obtain an oxirane-functionalized ionic silicone compound;

d) reacting the oxirane-functionalized ionic silicone compound of step c), oxirane ring-opening polymerization catalyst, a carrier solvent; and

optionally, one or more silicon hydride activators to obtain an ionically-modified cross-linked silicone network by the ring-opening polymerization of oxirane moiety with hydride;

e) shearing the ionically-modified cross-linked silicone network of step d) during and/or after polymerization of step d) with at least an carrier solvent to form an ionically-modified cross-linked silicone network gel; and

f) adding the ionically-modified cross-linked silicone network gel of step d) to an oil phase of a personal care composition;

wherein the oxirane-functionalized ionic silicone compound obtained in step c) 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 aliphatic, aromatic or fluoro containing monovalent hydrocarbon radicals containing from 1 to 60 carbon atoms;

where R⁴, R¹², R¹⁷ are monovalent or multivalent radical bearing ionic group(s),

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

OR²⁰ or hydrosilylation effective unsaturated monovalent radicals, wherein R²⁰ is selected from hydrogen, monovalent hydrocarbon radicals of from 1 to 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.

2. The process of claim 1 wherein 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 each containing from 1 to 60 carbon atoms, wherein the hydrocarbonoxy group contains at least one oxygen heteroatom,

where superscripts x and y are positive integers such to the proviso that and 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,

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 or phosphonium groups;

or,

zwitterions having the formula (III);

—

R′

—

NR″

₂⁺—

R′

″

—

I 

 

(III)

where R′

is a divalent hydrocarbon radical containing from 1 to 60 carbon atoms,

where R″

is monovalent hydrocarbon radical containing from 1 to 60 carbon atoms, and optionally, one or more of a sulfur atom, a nitrogen atom, oxygen atom, and

where R′

″

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

, I is an ionic group.

3. The process of claim 1 wherein the subscripts in general formula (I) are such that 2≦

a+b+c+d+e+f+g+h+i+j≦

4000.

4. The process of claim 1 wherein the subscripts in general formula (I) are such that b+f+j>

1.

5. The process of claim 1 wherein the oxirane-functionalized compound is of the general formula (IV):

M²_a′

M^H_b′

M^E_c′

M^I_d′

D²_e′

D^H_f′

D^E_g′

D^I_h′

T²_i′

T^H_j′

T^E_k′

T^I_l′

Q_m′

 

 

(IV)

wherein;

M²=R¹⁹R²⁰R²¹SiO_1/2

M^H=R²³R²⁴HSiO_1/2

M^E=R²⁵R²⁶R^ESiO_1/2

M^I=R²⁷R²⁸R^ISiO_1/2

D²=R²⁹R³⁰SiO_2/2

D^H=R³¹HSiO_2/2

D^E=R³²R^ESiO_2/2

D^I=R³³R^ISiO_2/2

T²=R³⁴SiO_3/2

T^H=HSiO_3/2

T^E=R^ESiO_3/2

T^I=R^ISiO_3/2

Q=SiO_4/2;

where R^I is an ionic group, and R^E is independently a monovalent hydrocarbon radical containing at least one oxirane moiety, which contains from 2 to 60 carbon atoms;

R¹⁹, R²⁰, R²¹, R²⁹, R³⁰ and R³⁴ are independently monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

R²³, R²⁴, are R³¹ independently hydrogen, or monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

R²⁵, R²⁶ and R³² are independently R^E or monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

R²⁷, R²⁸, and R³³ are independently R^I or nmonovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

and where the stoichiometric subscripts a′

, b′

, c′

, d′

, e′

, f′

, g′

, h′

, i′

, j′

, k′

, l′ and

m′

are either zero or positive subject to the following limitations;

c′

+g′

+k′

>

1;

d′

+h′

+l′

>

1; and

b′

+f′

+j′

, if present, is greater than c′

+g′

+k′

; and

3≧

a′

+b′

+c′

+d′

+e′

+f′

+g′

+h′

+i′

+j′

+k′

+l′

+m′

≦

6000; and

, with the proviso that b′

+f′

+j′

>

1 when silicone hydride activator is absent and wherein the crosslinked ionic silicone network is formed by the ring-opening polymerization of oxirane moiety.

6. The process of claim 1 wherein at least one of R⁷, R¹⁴ and R¹⁸ is selected from hydrogen.

7. The process of claim 1 wherein the carrier solvent comprises an ionically-modified silicone polymer having the general structure (V):

M³<sub>α

′</sub>

M⁴<sub>β

′</sub>

D³<sub>χ

′</sub>

D⁴<sub>δ

′</sub>

T³<sub>ε

′</sub>

T⁴<sub>φ

′</sub>

Q<sub>γ

′</sub>

 

 

(V)

wherein;

M³=R¹R²R³SiO_1/2

M⁴=R⁴R⁵R^ISiO_1/2

D³=R⁶R⁷SiO_2/2

D⁴=R⁸R^ISiO_2/2

T³=R⁹SiO_3/2

T⁴=R¹⁰SiO_3/2

Q=SiO_4/2,

and wherein, the radicals R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ are independently selected from aliphatic or aromatic monovalent hydrocarbon radicals having from 1 to 60 carbon atoms, and optionally each Containing at least one hetero atom, wherein at least one R^I is an ionic group, and the subscripts α

′

, β

′

, χ

′

, δ

′

, ε

′

, φ

′

, and γ

′

are zero or positive subject to the following limitations;

2≦

α

′

+β

′

+χ

′

+δ

′

+ε

′

+φ

′

+γ

′

≦

6000; and

, β

′

+δ

′

+φ

′

>

0.

8. The process of claim 1 wherein the silicon hydride activator is of the general formula (VI):

M³_α

M^H_β

M^I_χ

D³_δ

D^H_ε

D^I_φ

T³_γ

T^H_η

T^I_ι

Q_φ

 

 

(VI)

wherein;

M³=R³⁵R³⁶R³⁷SiO_1/2

M^H=R³⁸R³⁹HSiO_1/2

M^I=R⁴⁰R⁴¹R^ISiO_1/2

D³=R⁴²R⁴³SiO_2/2

D^H=R⁴⁴HSiO_2/2

D^I=R⁴⁵R^ISiO_2/2

T³=R⁴⁶SiO_3/2

T^H=HSiO_3/2

T^I=R^ISiO_3/2

Q=SiO_4/2; and

where

R³⁵, R³⁶, R³⁷, R⁴², R⁴³ and R⁴⁶ are independently monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

R³⁸, R³⁹ and R⁴⁴ are independently hydrogen or monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

R⁴⁰, R⁴¹ and R⁴⁵ are independently R^I or monovalent hydrocarbon radicals having from 1 to 60 carbon atoms,

and where the stoichiometric subscripts α

, β

, χ

, δ

, ε

, φ

, γ

, η

, ι and

φ

to are either zero or positive subject to the following limitations;

2≧

α

+β

+χ

+δ

+ε

+φ

+γ

+η

+ι

+φ

≦

6000;

β

+ε

+η

>

1; and

χ

+φ

+ι

≧

0;

and wherein the crosslinked ionic silicone network is formed by the ring-opening polymerization of oxirane moiety.

9. The process of claim 1 wherein the oxirane ring-opening polymerization-effective catalyst is selected from the group consisting of platinum compounds, metal salts and acid catalysts and its derivatives that are capable of polymerizing an epoxy group.

10. The process of claim 9 wherein the acid catalyst capable of polymerizing an epoxy group is selected from onium salt generated acids;

metal salts selected from the group consisting of aluminum trichloride and ferric chloride;

lanthium triflates; and

platinum compounds.

11. The process of claim 1 wherein the carrier solvent is at least one selected from silicone fluids, hydrocarbon fluids, esters, alcohols, fatty alcohols, glycols, organic waxes and organic oils.

12. The process of claim 1 wherein the crosslinked ionic silicone network is swelled by the carrier solvent.

13. The process of claim 12 wherein the carrier solvent is a hydrophilic emollient selected from the group consisting of glycerine, sorbitol, aqueous solution of moisturizing additives and combinations thereof.

14. The process of claim 1 where the silicon hydride activator is, a Si—

H functional linear polysiloxane polymer represented by the formula;

15. The process of claim 1 wherein the crosslinked ionic silicone network is compatible with a particulate additive.

16. The process of claim 15 wherein the particulate additive is selected from inorganic particulates, polymeric latexes, and pigments.

17. A process of claim 1 wherein the carrier solvent is water.

18. The process of claim 1 wherein the composition is a homogenous system selected from aqueous or non-aqueous formulations.

19. The process of claim 1 wherein the composition comprises two or more non-miscible phases.

20. The process of claim 19 wherein the non-miscible phases are selected from the group consisting of aqueous, non-aqueous, solid particulates and combinations thereof.

21. The process of claim 1 wherein the crosslinked ionic silicone network gel can bind and release cosmetic actives.

22. A personal care application comprising the personal care composition prepared by the process of claim 1 wherein the personal care application is selected from the group consisting of deodorants, antiperspirants, antiperspirant/deodorants, shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, hair care products such as shampoos, conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair bleaches, waving products, hair straighteners, manicure products, protective creams, color cosmetics and other personal care formulations where silicone components have been conventionally added, as well as drug delivery systems for topical application of medicinal compositions that are to be applied to the skin.

23. A process of preparing a personal care composition wherein the personal care composition comprises at least an oil phase, and is made by the process comprising adding an ionically-modified cross-linked silicone network gel to the oil phase of the personal care composition wherein the ionically-moditied cross-linked silicone network gel is made by:

(a) reacting a molecule having the general formula (Ia);

M_aM^H_b′

M^I_dD_eD^H_f′

D^I_hT_iT^H_j′

T^I_lQ_m 

 

(Ia)

wherein;

M³=R³⁵R³⁶R³⁷SiO_1/2

M^H=R³⁸R³⁹HSiO_1/2

M^I=R⁴⁰R⁴¹R^ISiO_1/2

D³=R⁴²R⁴³SiO_2/2

D^H=R⁴⁴HSiO_2/2

D^I=R⁴⁵R^ISiO_2/2

T³=R⁴⁶SiO_3/2

T^H=HSiO_3/2

T^I=R^ISiO_3/2

Q=SiO_4/2; and

where

R³⁵, R³⁶, R³⁷, R⁴², R⁴³ and R⁴⁶ are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms;

R³⁸, R³⁹ and R⁴⁴ are independently hydrogen or monovalent hydrocarbon radicals having from one to sixty carbon atoms;

R⁴⁰, R⁴¹ and R⁴⁵ are independently R^I or monovalent hydrocarbon radicals having from one to sixty carbon atoms,

where R^I is a monovalent or multivalent radical bearing ionic group(s),

and where the stoichiometric subscripts a, b′

, d, e, f′

, h, i, j′

, l and m are either zero or positive subject to the following limitations;

2≧

a+b′

+d+e+f′

+h,+i+j′

+l+m≦

6000;

b+f+j>

1; and

d+h+l≧

0;

with an olefinically unsaturated molecule containing one or more oxirane moieties,

and polymerizing the reaction product of step (a) by epoxy ring-opening polymerization with the hydride moiety in the presence of an (ii) oxirane ring-opening polymerization catalyst, (iii) a carrier solvent, and, (iv) optionally a silyl-hydridc molecule to produce the crosslinked ionic silicone network,

provided, wherein the silyl-hydride molecule (iv) is absent, the molar amount of olefinic unsaturated moiety in the olefinically unsaturated molecule containing one or more oxirane moieties of step (a) is less than the molar amount of silyl hydride moiety in general formula (Ia); and

,

(b) shearing the reaction product of step (a) in the presence of at least one carrier solvent (iii) to provide the crosslinked ionic silicone network gel.