Swollen silicone composition, process of producing same and products thereof

• US 7,863,361 B2
• Filed: 06/26/2006
• Issued: 01/04/2011
• Est. Priority Date: 11/15/2005
• 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: Falk, Benjamin, Nicholson, John, Kerschner, Judith, Murphy, Gerald J.
• Primary Examiner(s): Moore; Margaret G
• Application Number:
  US11/474,571
• Publication Number:
  US 20070112146A1
• Time in Patent Office: 1,653 Days
• Field of Search: 524/268, 524/731, 528/15, 528/31, 424/401
• US Class Current: 524/268
• 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) a reaction product of (I) a compound comprising the formula;

M^H_bD_fD^H_gM_2-b

where

M=R¹R²R³SiO_1/2;

M^H=R⁴R⁵HSiO_1/2;

D=R¹³R¹⁴SiO_2/2;

D^H=R¹⁵HSiO_2/2;

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

f is a number from about 10 to about 50, g is a number from zero to about 50, b is a number of from zero to two, provided that b+g is from 1 to about 100; and

(II) alkenyl resin;

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.

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

3. A first silicone composition comprising:

a) a reaction product of (I) a compound comprising the formula;

MD₂₄D*_0.3D^H_3.7M

where

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;

R¹⁵ is a monovalent hydrocarbon radical 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

M^viD₂₀M^vi, 

 

(II)

where D is as defined; and

M^vi=R⁶R⁷R⁸SiO_1/2;

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, 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.

4. A first silicone composition comprising:

a) a reaction product of (I) a compound comprising the formula;

MD₁₀₀D*_1.25D^H_5.4M

where

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;

R¹⁵ is a 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;

an

(II) 1,5-hexadiene, 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.

5. A first silicone composition comprising:

a) a reaction product of (I) a compound comprising the formula;

M^H_bQ_pM_2-b

where

M^H=R⁴R⁵HSiO_1/2;

Q=SiO_4/2

M=R¹R²R³SiO_1/2;

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

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

the stoichiometric subscripts b and p are zero or positive subject to the limitations;

p is a number ≧

1, b is a number of from one to two, subject to the limitation that b+p is a number of from 2 to about 20; and

M^vi_cD_fD^vi_hM_2-c 

 

(II)

where M is as defined and

M^vi=R⁶R⁷R⁸SiO_1/2;

D^vi=R¹⁶R¹⁷SiO_2/2;

D=R¹³R¹⁴SiO_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, R¹³ and R¹⁴ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

the stoichiometric subscripts c, f and h, are zero or positive subject to the limitations that f is 0 or a number of from about 1 to about 1200, h is a number of from zero to about 20, and c is a number of from zero to 2, provided that c+h is a number of from 1 to about 22;

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.

6. The first silicone composition of claim 5 wherein compound of formula (I) comprises M^H₂Q and (II) comprises M^viD₈₉₇M^vi.

7. A first silicone composition comprising:

a) a reaction product of (I) a compound comprising the formula;

M^H_bD_fD″

_iD^H_gM_2-b

where

M=R¹R²R³SiO_1/2;

M^H=R⁴R⁵HSiO_1/2;

D=R¹³R¹⁴SiO_2/2;

D″

=R¹⁸R″

SiO_2/2;

D^H=R¹⁵HSiO_2/2;

where R¹, R² and R³ 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;

R¹³ and R¹⁴ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

R¹⁸ is a monovalent hydrocarbon radical 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; and

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

f is a number of from 0 to 500, i is zero or a number of from 1 to 20, g is a number of from zero to 20, and b is a number of from zero to 2, provided that b+g is a number of from 1 to 100; and

M^vi_cD_fD^vi_hM_2-c 

 

(II)

where M and D are as defined and where

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;

the stoichiometric subscripts c, f and h, are zero or positive subject to the limitations that f is a number of from 0 to 500, h is a number of from zero to 20, c is a number of from zero to 2 and c+h is a number of from 1 to 22;

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.

8. The first silicone composition of claim 7 wherein compound of formula (I) comprises MD_24.5D^H_3.5M and (II) comprises M^viD₂₀M^vi.

9. The first silicone composition of claim 7 wherein compound of formula (I) comprises MD₃₂D″

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

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

combining

(a) a reaction product of (I) a compound comprising the formula;

M^H_bD_fD^H_gM_2-b

where

M=R¹R²R³SiO_1/2;

M^H=R⁴R⁵HSiO_1/2;

D=R¹³R¹⁴SiO_2/2;

D^H=R¹⁵HSiO_2/2;

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

f is a number from about 10 to about 50, g is a number from zero to about 50, b is a number of from zero to two, provided that b+g is from 1 to about 100; and

(II) alkenyl resin;

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.

11. The process of claim 10 wherein compound of formula (I) comprises MD₂₀D^H₃M and (II) comprises 1,5-hexadiene.

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

combining

(a) a reaction product of (I) a compound comprising the formula;

MD₂₄D*_0.3D^H_3.7M

where

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;

R¹⁵ is a monovalent hydrocarbon radical 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

M^viD₂₀M^vi, 

 

(II)

where D is as defined; and

M^vi=R⁶R⁷R⁸SiO_1/2;

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 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.

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

combining

(a) a reaction product of (I) a compound comprising the formula;

MD₁₀₀D*_1.25D^H_5.4M

where

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;

R¹⁵ is a monovalent hydrocarbon radical 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

(II) 1,5-hexadiene;

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.

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

combining

(a) a reaction product of (I) a compound comprising the formula;

M^H_bQ_pM_2-b

where

M^H=R⁴R⁵HSiO_1/2;

Q=SiO_4/2

M=R¹R²R³SiO_1/2;

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

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

the stoichiometric subscripts b and p are zero or positive subject to the limitations;

p is a number ≧

1, b is a number of from one to two, subject to the limitation that b+p is a number of from 2 to about 20; and

M^viD₂₀M^vi, 

 

(II)

where M is as defined and

M^vi=R⁶R⁷R⁸SiO_1/2;

D^vi=R¹⁶R¹⁷SiO_2/2;

D=R¹³R¹⁴SiO_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, R¹³ and R¹⁴ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

the stoichiometric subscripts c, f and h, are zero or positive subject to the limitations that f is 0 or a number of from about 1 to about 1200, h is a number of from zero to about 20, and c is a number of from zero to 2, provided that c+h is a number of from 1 to about 22;

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.

15. The process of claim 14 wherein compound of formula (I) comprises M^H₂Q and (II) comprises M^viD₈₉₇M^vi.

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

combining (a) a reaction product 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, and where said reaction product (a) comprises the reaction product of (I) a compound comprising the formula;

M^H_bD_fD″

_iD^H_gM_2-b

where

M=R¹R²R³SiO_1/2;

M^H=R⁴R⁵HSiO_1/2;

D=R¹³R¹⁴SiO_2/2;

D″

=R¹⁸R″

SiO_2/2;

D^H=R¹⁵HSiO_2/2;

where R¹, R² and R³ 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;

R¹³ and R¹⁴ are each independently monovalent hydrocarbon radicals having from one to about sixty carbon atoms;

R¹⁸ is a monovalent hydrocarbon radical 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; and

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

f is a number of from 10 to 50, i is zero or a number of from 1 to 20, g is a number of from zero to 20, and b is a number of from zero to 2, provided that b+g is a number of from 1 to 100; and

M^viD₂₀M^vi, 

 

(II)

where M and D are as defined and where

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;

the stoichiometric subscripts c, f and h, are zero or positive subject to the limitations that f is a number of from 10 to 50, h is a number of from zero to 20, c is a number of from zero to 2 and c+h is a number of from 1 to 22.

17. The process of claim 16 wherein compound of formula (I) comprises MD_24.5D^H_3.5M and (II) comprises M^viD₂₀M^vi.

18. The process of claim 16 wherein compound of formula (I) comprises MD₃₂D″

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