SWOLLEN SILICONE COMPOSITION, PROCESS OF PRODUCING SAME AND PRODUCTS THEREOF

• US 20110085988A1
• Filed: 12/17/2010
• Published: 04/14/2011
• Est. Priority Date: 11/15/2005
• Status: Abandoned Application

• Current Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Original Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Nicholson, John, Falk, Benjamin, Kerschner, Judith, Murphy, Gerald J.
• Application Number:
  US12/971,857
• Publication Number:
  US 20110085988A1
• Time in Patent Office: Days
• US Class Current: 424/43
• 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

1-46. -46. (canceled)

47. A first silicone composition comprising:

a) a reaction product which is formed by at least one of the self-reaction of a silicone containing at least one silyl hydride moiety and at least one monovalent unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms;

the reaction of an organohydrogenpolysiloxane and an olefinically unsaturated polysiloxane and/or an alkenyl resin;

addition product of silane functional silicones;

a silicone condensation product of at least one silicone and one of the following;

amino resin formed from urea monomer or melamine monomer and formaldehyde monomer, furan polymer produced by polymerizing furfuryl alcohol monomer, polyacetal polymer formed from diaklehyde monomer and dialcohol monomer, poly(alkylene sulfide) polymers formed from alkyl bromide monomer and potassium sulfide monomer, polyimide 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 (brined 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;

where the reaction product (a) does not result in a polymer containing a polyether crosslink; and

,

b) a swelling amount of an ethyltrisiloxane wherein said reaction product (a) is swollen by said ethyltrisiloxane 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 (a) and a linear silicone fluid other than said ethyltrisiloxane, whereby second silicone composition and first silicone composition have equivalent viscosities.

48. The first silicone composition of claim 47, 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.

49. The first silicone composition of claim 47, 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.

50. The first silicone composition of claim 47, 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.

51. The first silicone composition of claim 47 where reaction product (a) comprises the self-reaction of a silicone where such self-reaction comprises the reaction product of silicone (X)

M_aM^H_bM″

_cM″

_dM*_cD_fD^H_gD^vi_iD*_jT_kT^H_LT^vi_mT″

_nT*_oQ_p 

 

X

where

M=R¹R²R³SiO_1/2;

M^H=R⁴R⁵HSiO_1/2;

M=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, h, 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+≧

1 and where reaction product (a) formed by the self reaction of the silicone also optionally further comprises reaction with an alkenyl resin containing of from about 2 to about 2000 carbon atoms.

54. The first silicone composition of claim 47 where reaction product-(a) comprises the reaction product of (I) a compound comprising the formula:

M^H_bD_fD*_jD^H_gM_2-b

where

M^H=R⁴R⁵HSiO_1/2;

D=R¹³R¹⁴SiO_2/2;

D*=R¹⁹R*SiO_2/2;

D^H=R¹⁵HSiO_2/2;

M=R¹R²R³SiO_1/2;

where R¹, R², R³, R¹³ and R¹⁴ 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;

R¹⁹ is a monovalent hydrocarbon radical 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; and

the stoichiometric subscripts b, f, j and g are zero or positive subject to the limitations;

f is 0 or a number from 1 to 500, j is a number from 0.1 to 10, g is a number from zero to 50, b is a number from zero to two, subject to the limitation that b+g is from 1 to 100; and

(II) M^vi_cD_fD^vi_hM_2-c and/or an alkenyl resin of from 2 to about 2000 carbon atoms, where D and M are as defined; and

M^vi=R⁶R⁷R⁸SiO_1/2;

D^vi=R¹⁶R¹⁷SiO_2/2;

where 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; and

the stoichiometric subscripts c, f, and h are zero or positive subject to the limitations that f is a number from 1 to 300, h is a number of from zero to 20, and c is a number of from zero to 2, provided that c+h is a number of from 1 to 22.

64. A silicone gel substantially comprising first silicone composition of claim 47.

65. A silicone gel substantially comprising first silicone composition of claim 48.

66. A silicone gel substantially comprising first silicone composition of claim 49.

67. A silicone gel substantially comprising first silicone composition of claim 50.

68. A personal care formulation comprising the silicone gel of claim 64 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.

69. The personal care formulation of claim 68 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, cyclic silicone and combinations thereof.

90. The personal care formulation of claim 68 where the personal care formulation is a sunscreen and/or a cosmetic composition.

52-53. -53. (canceled)

55-62. -62. (canceled)

63. A first silicone composition comprising:

a) a reaction product which is formed by at least one of the self-reaction of a silicone containing at least one silyl hydride moiety and at least one monovalent unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms;

the reaction of an organohydrogenpolysiloxane and an olefinically unsaturated polysiloxane and/or an alkenyl resin;

addition product of silane functional silicones;

a silicone condensation product of at least one silicone and one of the following;

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 (nester 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;

where the reaction product (a) does not result in a polymer containing a polyether crosslink; and

,

b) a swelling amount of an ethyltrisiloxane wherein said reaction product (a) is swollen by said ethyltrisiloxane 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 (a) and a linear silicone fluid other than said ethyltrisiloxane, whereby second silicone composition and first silicone composition have equivalent viscosities,

wherein the ethyltrisiloxane is selected from the group consisting of 1,1,1,3,5,5,5-heptamethyl-3-ethyltrisiloxane;

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

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

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

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

combinations thereof.

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

combining

(a) a reaction product which is formed by at least one of the self-reaction of a silicone containing at least one silyl hydride moiety and at least one monovalent unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms;

the reaction of an organohydrogenpolysiloxane and an olefinically unsaturated polysiloxane and/or an alkenyl resin;

addition product of silane functional silicones;

a silicone condensation product of at least one silicone and one of the following;

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;

where the reaction product (a) does not result in a polymer containing a polyether crosslink; and

,

b) a swelling amount of an ethyl trisiloxane;

wherein said reaction product (a) is swollen by said ethyltrisiloxane 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 (a) and a linear silicone fluid other than said ethyltrisiloxane, whereby second silicone composition and first silicone composition have equivalent viscosities.

71. The process of claim 70 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.

72. The process of claim 70 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.

73. The process of claim 70 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.

74. The process of claim 70 where reaction product (a) comprises the self-reaction of a silicone where such self-reaction comprises the reaction product of silicone (X)

M_aM^H_bM^vi_cM″

_dM*_eD_fD^H_gD^vi_hD″

_iD*^jT^H_lT^vi_mT″

_nT*_oQ_p 

 

X

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 a+b+c+d+e>

1;

b+g+L≧

1; and

c+h+m≧

1 and where reaction product (a) formed by the self reaction of the silicone also optionally further comprises reaction with an alkenyl resin containing of from about to about 2000 carbon atoms.

77. The process of claim 70 where reaction product (a) comprises the reaction product of (I) a compound comprising the formula:

M^H_bD_fD*_jD^D_gM_2-b

where

M^H=R⁴R⁵HSiO_1/2;

D=R¹³R¹⁴SiO_2/2;

D*=R¹⁹R*SiO_2/2;

D^H=R¹⁵HSiO_2/2;

M=R¹R²R³SiO_1/2;

where R¹, R², R³, R¹³ and R¹⁴ 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;

R¹⁹ is a monovalent hydrocarbon radical 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; and

the stoichiometric subscripts b, f, j and g are zero or positive subject to the limitations;

f is 0 or a number from 1-500, j is a number from 0.1 to 10, g is a number from zero to 50, b is a number from zero to two, subject to the limitation that b+g is from 1 to 100;

(II);

M^vi_cD_fD^vi_hM_2-c and/or an alkenyl resin of from 2 to about 2000 carbon atoms, where D and M are as defined; and

M^vi=R⁶R⁷R⁸SiO_1/2;

D^vi=R¹⁶R¹⁷SiO_2/2;

where 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; and

the stoichiometric subscripts c, f, and h are zero or positive subject to the limitations that f is a number from 1 to 300, h is a number of from zero to 20, and c is a number of from zero to 2, provided that c-h is a number of from 1 to 22.

86. The process of claim 70 wherein the ethyltrisiloxane is selected is selected from the group consisting of 1,1,1,3,5,5,5-heptamethyl-3-ethyltrisiloxane;

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

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

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

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

combinations thereof.

87. The process of claim 70 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 ethyltrisiloxane (b).

88. A personal care formulation compromising the first silicone composition produced by the process of claim 70 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.

89. The personal care formulation of claim 88 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, cyclic silicone, and combinations thereof.

75-76. -76. (canceled)

78-85. -85. (canceled)