Swollen silicone composition, process of producing same and products thereof

• US 20070112146A1
• Filed: 06/26/2006
• Published: 05/17/2007
• Est. Priority Date: 11/15/2005
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated
• Original Assignee: Momentive Performance Materials Incorporated
• Inventors: Falk, Benjamin, Nicholson, John, Murphy, Gerald, Kerschner, Judith
• Granted Patent: US 7,863,361 B2
• Time in Patent Office: Days
• US Class Current: 525/477
• CPC Class Codes: A61K 8/585 Organosilicon compounds
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• 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: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 3/075 Macromolecular gels
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/12 containing polyether sequences

Abstract

There is provided herein, in one specific embodiment, silicone composition(s) comprising unique combination(s) of silicone polymer and alkyltrisiloxane(s) which can produce silicone composition(s) with lower solids content than silicone compositions that use other than alkyltrisiloxane(s); while still maintaining a desirable viscosity.

Claims

1. A first silicone composition comprising:

a) the reaction product of

M_aM^H_bM^vi_cM″

_dM*_eD_fD^H_gD^vi_hD″

_iD*_jT_kT^H_LT^vi_mT″

_nT*_oQ_p

where

M=R¹R²R³SiO_1/2;


M^H=R⁴R⁵HSiO_1/2;


M^vi=R⁶R⁷R⁸SiO_1/2;


M″

=R⁹R¹⁰R″

SiO_1/2;


M*=R¹¹R¹²R*SiO_1/2;


D=R¹³R¹⁴SiO_2/2;


D^H=R¹⁵HSiO_2/2;


D^vi=R¹⁶R¹⁷SiO_2/2;


D″

=R¹⁸R″

SiO_2/2;


D*=R¹⁹R*SiO_2/2;


T=R²⁰SiO_3/2;


T^H=HSio_3/2;


T^vi=R²¹SiO_3/2;


T″

=R″

SiO_3/2;


T*=R*SiO_3/2; and

,
Q=SiO_4/2

where R¹, R², R³, R¹³, R¹⁴ and R²⁰ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

R⁴, R⁵ and R¹⁵ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms or hydrogen;

R⁶ is a monovalent unsaturated hydrocarbon radical having from two to about ten carbon atoms, and R⁷ and R⁸ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

R¹⁶ is a monovalent unsaturated hydrocarbon radical having from two to about ten carbon atoms; and

R¹⁷ is a monovalent hydrocarbon radical having from one to about sixty carbon atoms;

R²¹ is a monovalent unsaturated hydrocarbon radical having from two to about ten carbon atoms;

R⁹, R¹⁰, and R¹⁸ are independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms or R″

;

each R″

is independently a monovalent alkoxy radical having from one to about sixty carbon atoms;

R¹¹, R¹², and R¹⁹ are independently monovalent hydrocarbon radicals having from one to about 200 carbon atoms or R*;

each R* is independently a monovalent ether radical having from one to about two hundred carbon atoms and containing one or more ether moieties;

the stoichiometric subscripts a, b, c, d, e, f, g, h, i, j, k, L, m, n, o and p are either zero or positive subject to the following limitations;

a+b+c+d+e>

1;

b+g+L≧

1; and

c+h+m≧

1 and/or where reaction product also optionally comprises reaction with an alkenyl resin containing of from about 1 to about 2000 carbon atoms; and

reaction product does not result in a polymer containing a polyether crosslink; and

,

b) a swelling amount of an alkyltrisiloxane wherein said reaction product is swollen by said alkyltrisiloxane to form a first silicone composition and wherein said first silicone composition possesses a lower solids content than a solids content present in a second silicone composition comprising said reaction product and a linear silicone fluid other than an alkyltrisiloxane, whereby second silicone composition and first silicone composition have equivalent viscosities.

2. The first silicone composition of claim 1, where first silicone composition has a given cross-linked structure and a given cross-link density and said lower solids content of first silicone composition is at least about 10 percent lower than the solids content for second silicone composition which has an equivalent cross-linked structure and an equivalent cross-link density to first silicone composition;

and where first silicone composition has a viscosity of greater than about 10,000 centistokes.

3. The first silicone composition of claim 1, where first silicone composition has a given cross-linked structure and a given cross-link density and said lower solids content of first silicone composition is at least about 25 percent lower than the solids content for second silicone composition which has an equivalent cross-linked structure and an equivalent cross-link density to first silicone composition;

and where first silicone composition has a viscosity of greater than about 100,000 centistokes.

4. The first silicone composition of claim 1, where first silicone composition has a given cross-linked structure and a given cross-link density and said lower solids content of first silicone composition is at least about 40 percent lower than the solids content for second silicone composition which has an equivalent cross-linked structure and an equivalent cross-link density to first silicone composition;

and where first silicone composition has a viscosity of greater than about 200,000 centistokes.

5. The first silicone composition of claim 1 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

6. The first silicone composition of claim 5 wherein compound of formula (I) comprises MD₂₀D^H₃M and (II) comprises 1,5-hexadiene.

7. The first silicone composition of claim 1 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

8. The first silicone composition of claim 7 wherein compound of formula (I) comprises MD₂₄D*_0.3D^H_3.7M and (II) comprises M^viD₂₀M^vi.

9. The first silicone composition of claim 7 wherein compound of formula (I) comprises MD₁₀₀D*_1.25D^H_5.4M and (II) comprises 1,5-hexadiene.

10. The first silicone composition of claim 1 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

11. The first silicone composition of claim 10 wherein compound of formula (I) comprises M^H₂Q and (II) comprises M^viD₈₉₇M^vi.

12. The first silicone composition of claim 1 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

13. The first silicone composition of claim 12 wherein compound of formula (I) comprises MD_24.5D^H_3.5M and (II) comprises M^viD₂₀M^vi.

14. The first silicone composition of claim 12 wherein compound of formula (I) comprises MD₃₂D″

₃D^H₆M and (II) comprises M^viD₂₀M^vi.

15. The first silicone composition of claim 1 where reaction product (a) can comprise polymerization product selected from the group consisting of addition product;

condensation product of amino resin formed from urea monomer or melamine monomer and formaldehyde monomer, furan polymer produced by polymerizing furfuryl alcohol monomer, polyacetal polymer formed from dialdehyde monomer and dialcohol monomer, poly(alkylene sulfide) polymers formed from alkyl bromide monomer and potassium sulfide monomer, polyamide polymer formed from diacid monomer and diamine monomer, polyamine formed from diamine monomer and dihalide monomer, polyaminotriazole polymer formed from dihydride monomer and hydrazine monomer, polyanhydride formed from polymerization of diacid monomer, polycarbonate formed from diol monomer and phosgene monomer, polyhydrazide polymer formed from phenyl diester monomer and dihydrazine monomer, polyimide formed from tetraacid monomer and diamine monomer, polyquinoxaline polymer formed from tetracarbonyl monomer and diamine monomer, polysaccharide formed from polymerization of monosaccharide monomer, polysulfide polymer formed from dihalide monomer and polysulfide monomer, polyurea formed from diamine monomer and phosgene monomer, protein polymer formed from polymerization of amino acid monomer, silicone formed from dihaloalkylsilane monomer and water, polyester formed from difunctional acid monomer and difunctional alcohol monomer;

step reaction polymerization of diisocyanato monomers and polyol monomers, as well as step reaction polymerization of the condensation polymerizations; and

combinations thereof.

16. The first silicone composition of claim 1 where at least one alkyltrisiloxane (b) material results from the alkylation of a polyorganosiloxane having the formula (A):

MD^HM 

 

(A)

where

M=R^AR^BR^CSiO_1/2; and


D^H=R^DHSiO_2/2;

where R^A, R^B, and R^C are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms; and

RD is a monovalent hydrocarbon radical having from one to sixty carbon atoms or hydrogen.

17. The first silicone composition of claim 1 where at least one alkyltrisiloxane (b) has the formula:

18. The first silicone composition of claim 1 where at least one alkyltrisiloxane is a linear alkyltrisiloxane selected from the group consisting of ethyltrisiloxane, octyltrisiloxane, hexyltrisiloxane, and combinations thereof.

19. The first silicone composition of claim 1 where at least one alkyltrisiloxane is a linear alkyltrisiloxane selected from the group consisting of 1,1,1,3,5,5,5-heptamethyl-3-ethyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-octyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-hexyltrisiloxane, octamethyltrisiloxane;

3-pentyl-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1-hexyl-1,1,3,3,5,5,5-heptamethyltrisiloxane;

1,1,1,3,3,5,5-heptamethyl-5-octyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-octyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-hexyltrisiloxane;

1,1,3,3,5,5-hexamethyl-1,5-dipropyltrisiloxane;

3-(1-ethylbutyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-(1-methylpentyl)trisiloxane;

1,5-diethyl-1,1,3,3,5,5-hexamethyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-(1-methylpropyl)trisiloxane;

3-(1,1-dimethylethyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1,1,1,5,5,5-hexamethyl-3,3-bis(1-methylethyl)trisiloxane;

1,1,1,3,3,5,5-hexamethyl-1,5-bis(1-methylpropyl)trisiloxane;

1,5-bis(1,1-dimethylethyl)-1,1,3,3,5,5-hexamethyltrisiloxane;

3-(3,3-dimethylbutyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-(3-methylbutyl)trisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-(3-methylpentyl)trisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-(2-methylpropyl)trisiloxane;

1-butyl-1,1,3,3,5,5,5-heptamethyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-propyltrisiloxane;

3-isohexyl-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1,3,5-triethyl-1,1,3,5,5-pentamethyltrisiloxane;

3-butyl-1,1,1,3,5,5,5-heptamethyltrisiloxane;

3-tert-pentyl-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1,1,1,5,5,5-hexamethyl-3,3-dipropyltrisiloxane;

3,3-diethyl-1,1,1,5,5,5-hexamethyltrisiloxane;

1,5-dibutyl-1,1,3,3,5,5-hexamethyltrisiloxane;

1,1,1,5,5,5-hexaethyl-3,3-dimethyltrisiloxane;

3,3-dibutyl-1,1,1,5,5,5-hexamethyltrisiloxane;

3-ethyl-1,1,1,3,5,5,5-heptamethyltrisiloxane;

3-heptyl-1,1,1,3,5,5,5-heptamethyltrisiloxane;

1-ethyl-1,1,3,3,5,5,5-heptamethyltrisiloxane;

1,1,1,5,5,5-hexamethyl-3,3-diethyltrisiloxane;

1,1,3,3,5,5-hexamethyl-1,5-diethyltrisiloxane;

1,1,1,3,5,5,5-heptamethyl-3-butyltrisiloxane and combinations thereof.

20. A silicone gel substantially comprising first silicone composition of claim 1.

21. A silicone gel substantially comprising first silicone composition of claim 2.

22. A silicone gel substantially comprising first silicone composition of claim 3.

23. A silicone gel substantially comprising first silicone composition of claim 4.

24. A silicone gel substantially comprising first silicone composition of claim 17.

25. A personal care formulation comprising the silicone gel of claim 20 where the personal care formulation is selected from the group consisting of deodorant, antiperspirant, antiperspirant/deodorant, shaving product, skin lotion, moisturizer, toner, bath product, cleansing product, hair care product manicure product, protective cream, color cosmetic, a vehicle for fragrance delivery benefits, drug delivery system for topical application of medicinal composition that is to be applied to the skin, and combinations thereof.

26. The personal care formulation of claim 25 further comprising personal care ingredient selected from the group consisting of emollient, moisturizer, humectant, pigment, coated mica, colorant, fragrance, biocide, preservative, antioxidant, anti-microbial agent, anti-fungal agent, antiperspirant agent, exfoliant, hormone, enzyme, medicinal compound, vitamin, salt, electrolyte, alcohol, polyol, absorbing agent for ultraviolet radiation, botanical extract, surfactant, silicone oil, organic oil, wax, film former, thickening agent, particulate filler, clay, and combinations thereof.

27. A process for producing a first silicone composition comprising:

combining;

a) the reaction product of

M_aM^H_bM^vi_cM″

_dM*_eD_fD^H_gD^vi_hD″

_iD*_jT_kT^H_LT^vi_mT″

_nT*_oQ_p

where

M=R¹R²R³SiO_1/2;


M^H=R⁴R⁵HSiO_1/2;


M^vi=R⁶R⁷R⁸SiO_1/2;


M″

=R⁹R¹⁰R″

SiO_1/2;


M*=R¹¹R¹²R*SiO_1/2;


D=R¹³R¹⁴SiO_2/2;


D^H=R¹⁵HSiO_2/2;


D^vi=R¹⁶R¹⁷SiO_2/2;


D″

=R¹⁸R″

SiO_2/2;


D*=R¹⁹R*SiO_2/2;


T=R²⁰SiO_3/2;


T^H=HSiO_3/2;


T^vi=R²¹SiO_3/2;


T″

=R″

SiO_3/2;


T*=R*SiO_3/2; and

,
Q=SiO_4/2

where R¹, R², R³, R¹³, R¹⁴ and R²⁰ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

R⁴, R⁵ and R¹⁵ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms or hydrogen;

R⁶ is a monovalent unsaturated hydrocarbon radical having from two to about ten carbon atoms, and R⁷ and R⁸ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

R¹⁶ is a monovalent unsaturated hydrocarbon radical having from two to about ten carbon atoms; and

R¹⁷ is a monovalent hydrocarbon radical having from one to about sixty carbon atoms;

R²¹ is a monovalent unsaturated hydrocarbon radical having from two to about ten carbon atoms;

R⁹, R¹⁰, and R¹⁸ are independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms or R″

;

each R″

is independently a monovalent alkoxy radical having from one to about sixty carbon atoms;

R¹¹, R¹², and R¹⁹ are independently monovalent hydrocarbon radicals having from one to about 200 carbon atoms or R*;

each R* is independently a monovalent ether radical having from one to about two hundred carbon atoms and containing one or more ether moieties;

the stoichiometric subscripts a, b, c, d, e, f, g, h, i, j, k, L, m, n, o and p are either zero or positive subject to the following limitations;

a+b+c+d+e>

1;

b+g+L≧

1; and

c+h+m≧

1 and/or where reaction product also optionally comprises reaction with a alkenyl resin containing of from about 1 to about 2000 carbon atoms; and

reaction product does not result in a polymer containing a polyether crosslink; and

,

b) a swelling amount of an alkyltrisiloxane wherein said reaction product is swollen by said alkyltrisiloxane to form a first silicone composition and wherein said first silicone composition possesses a lower solids content than a solids content present in a second silicone composition comprising said reaction product and a linear silicone fluid other than an alkyltrisiloxane, whereby second silicone composition and first silicone composition have equivalent viscosities.

28. The process of claim 27 where first silicone composition has a given cross-linked structure and a given cross-link density and said lower solids content of first silicone composition is at least about 10 percent lower than the solids content for second silicone composition which has an equivalent cross-linked structure and an equivalent cross-link density to first silicone composition;

and where first silicone composition has a viscosity of greater than about 10,000 centistokes.

29. The process of claim 27 where first silicone composition has a given cross-linked structure and a given cross-link density and said lower solids content of first silicone composition is at least about 25 percent lower than the solids content for second silicone composition which has an equivalent cross-linked structure and an equivalent cross-link density to first silicone composition;

and where first silicone composition has a viscosity of greater than about 100,000 centistokes.

30. The process of claim 27 where first silicone composition has a given cross-linked structure and a given cross-link density and said lower solids content of first silicone composition is at least about 40 percent lower than the solids content for second silicone composition which has an equivalent cross-linked structure and an equivalent cross-link density to first silicone composition;

and where first silicone composition has a viscosity of greater than about 200,000 centistokes.

31. The process of claim 27 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

32. The process of claim 31 wherein compound of formula (I) comprises MD₂₀D^H₃M and (II) comprises 1,5-hexadiene.

33. The process of claim 27 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

34. The process of claim 33 wherein compound of formula (I) comprises MD₂₄D*_0.3D^H_3.7M and (II) comprises M^viD₂₀M^vi.

35. The process of claim 33 wherein compound of formula (I) comprises MD₁₀₀D*_1.25D^H_5.4M and (II) comprises 1,5-hexadiene.

36. The process of claim 27 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

37. The process of claim 36 wherein compound of formula (I) comprises M^H₂Q and (II) comprises M^viD₈₉₇M^vi.

38. The process of claim 27 where reaction product (a) can comprise the reaction product of (I) a compound comprising the formula:

39. The process of claim 38 wherein compound of formula (I) comprises MD_24.5D^H_3.5M and (II) comprises M^viD₂₀M^vi.

40. The process of claim 38 wherein compound of formula (I) comprises MD₃₂D″

₃D^H₆M and (II) comprises M^viD₂₀M^vi.

41. The process of claim 27 where reaction product (a) can comprise polymerization product selected from the group consisting of addition product;

condensation product of amino resin formed from urea monomer or melamine monomer and formaldehyde monomer, furan polymer produced by polymerizing furfuryl alcohol monomer, polyacetal polymer formed from dialdehyde monomer and dialcohol monomer, poly(alkylene sulfide) polymers formed from alkyl bromide monomer and potassium sulfide monomer, polyamide polymer formed from diacid monomer and diamine monomer, polyamine formed from diamine monomer and dihalide monomer, polyaminotriazole polymer formed from dihydride monomer and hydrazine monomer, polyanhydride formed from polymerization of diacid monomer, polycarbonate formed from diol monomer and phosgene monomer, polyhydrazide polymer formed from phenyl diester monomer and dihydrazine monomer, polyimide formed from tetraacid monomer and diamine monomer, polyquinoxaline polymer formed from tetracarbonyl monomer and diamine monomer, polysaccharide formed from polymerization of monosaccharide monomer, polysulfide polymer formed from dihalide monomer and polysulfide monomer, polyurea formed from diamine monomer and phosgene monomer, protein polymer formed from polymerization of amino acid monomer, silicone formed from dihaloalkylsilane monomer and water, polyester formed from difunctional acid monomer and difunctional alcohol monomer;

step reaction polymerization of diisocyanato monomers and polyol monomers, as well as step reaction polymerization of the condensation polymerizations; and

combinations thereof.

42. The process of claim 27 where at least one alkyltrisiloxane (b) has the formula

43. The process of claim 27 further comprising where reaction product (a) is produced in the presence of at least one first fluid component and is subsequently swollen, where swelling said reaction product (a) comprises diluting the reaction product (a), that has been produced in the presence of at least one first fluid component, with at least one second fluid component with the proviso that at least one first fluid component and/or at least one second fluid component is alkyltrisiloxane (b).

44. A personal care formulation comprising the first silicone composition produced by the process of claim 43 where the personal care formulation is selected from the group consisting of deodorants, antiperspirants, antiperspirant/deodorants, shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, hair care products, manicure products, protective creams, color cosmetics, a vehicle for fragrance delivery benefits, drug delivery systems for topical application of medical compositions that are to be applied to the skin, and combinations thereof.

45. The personal care formulation of claim 44 further comprising personal care ingredient selected from the group consisting of emollient, moisturizer, humectant, pigment, coated mica, colorant, fragrance, biocide, preservative, antioxidant, anti-microbial agent, anti-flugal agent, antiperspirant agent, exfoliant, hormone, enzyme, medicinal compound, vitamin, salt, electrolyte, alcohol, polyol, absorbing agent for ultraviolet radiation, botanical extract, surfactant, silicone oil, organic oil, wax, film former, thickening agent, particulate filler, clay, and combinations thereof.