Elastomeric silicone containing an active ingredient

• US 6,168,782 B1
• Filed: 05/24/1999
• Issued: 01/02/2001
• Est. Priority Date: 05/24/1999
• Status: Expired due to Term

• Current Assignee: Dow Corning Corporation (Dow, Inc.)
• Original Assignee: Dow Corning Corporation (Dow, Inc.)
• Inventors: Lin, Zuchen, Schulz, William James Jr., Smith, Janet Mary
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US09/317,459
• Time in Patent Office: 589 Days
• Field of Search: 424/78.03, 424/65, 424/70.1, 424/76.1, 424/401, 524/709, 524/714, 524/722, 524/725, 524/726, 524/751, 524/754, 524/755, 524/759, 524/762, 524/765, 524/770, 524/773, 524/774, 524/792, 524/231, 524/837, 524/861, 524/862, 528/15, 528/25, 523/102, 523/103, 523/105, 523/122
• US Class Current: 424/78.03
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence

Abstract

Elastomeric silicones, especially elastomeric silicone polyethers, are prepared by combining and reacting (A) an ≡Si—H containing polysiloxane, (B) a mono-alkenyl polyether, (C) an active ingredient such as a vitamin, antimicrobial agent, sunburn prevention agent, astringent, or sex hormone, (D) an α,ω-unsaturated hydrocarbon, (E) a platinum catalyst, and (F) an oil. The reaction of components (A)-(F) is allowed to continue, forming a crosslinked three-dimensional gelled network of the elastomeric silicone polyether containing the active ingredient and the oil. The compositions are useful in personal and health care applications, personal hygiene, and household cleaning applications.

Claims

1. A composition comprising an elastomeric silicone polyether prepared by a method comprising combining and reacting:

(A) an ≡

Si—

H containing polysiloxane of the formula R₃SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₃, the formula (R′

₂SiO)_a′

(R″

HSiO)_b′

, the formula HR₂SiO(R′

₂SiO)_cSiR₂H, or the formula HR₂SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₂H, where R, R′

, and R″

are alkyl groups with 1-6 carbon atoms, a is 0-250, a′

is 0-7, b is 1-250, b′

is 3-10, and c is 0-250;

(B) a mono-alkenyl polyether of the formula CH₂═

CH(CH₂)_fO(CH₂CH₂O)_g(CH₂CH₃CHO)_hT, or the formula CH₂═

CH—

Q—

O(CH₂CH₂O)_g(CH₂CH₃CHO)_hT, where T is hydrogen, a C₁-C₁₀ alkyl group, an aryl group, or a C₁-C₂₀ acyl group;

Q is a divalent linking group containing unsaturation;

f is 0-6, g is 4-100; and

h is zero or 1-100;

(C) an active ingredient capable of furnishing pharmacological activity or other direct effect in diagnosis, cure, mitigation, treatment, or prevention of disease, or which affects structures or functions of the body of man or other animal, including components that undergo chemical change in the manufacture of drug products or are present in drug products in a modified form intended to furnish specified activities or effects;

(D) an α

,ω

-unsaturated hydrocarbon selected from the group consisting of α

,ω

-dienes of the formula CH₂═

CH(CH₂)_dCH═

CH₂, α

,ω

-diynes of the formula CH≡

C(CH₂)_eC≡

CH, and α

,ω

-ene-ynes of the formula CH₂═

CH(CH₂)_eC≡

CH, where d is 0-20 and e is 0-20; and

(E) a platinum catalyst;

in the presence of

(F) an oil selected from the group consisting of (i) organic compounds, (ii) compounds containing a silicon atom, (iii) mixtures of organic compounds, (iv) mixtures of compounds containing a silicon atom, and (v) mixtures of organic compounds and compounds containing a silicon atom;

and allowing the reaction to continue until there is formed a crosslinked three-dimensional gelled network of an elastomeric silicone polyether containing the active ingredient and the oil.

2. A composition according to claim 1 in which the oil is a linear volatile methyl siloxane of the formula (CH₃)₃SiO{(CH₃)₂SiO}_kSi(CH₃)₃ where k is 0-5, or a cyclic volatile methyl siloxane of the formula {(CH₃)₂SiO}_m where m is 3-8, the volatile methyl siloxane have a boiling point less than about 250°

C. and a viscosity of 0.65-5.0 mm²/s.

3. A composition according to claim 1 in which the active ingredient is an oil-soluble active ingredient.

4. A composition according to claim 1 in which the active ingredient is a water-soluble active ingredient.

5. An emulsion containing the composition according to claim 4.

6. An emulsion containing the composition according to claim 4.

7. A multiple emulsion containing the composition according to claim 3.

8. A multiple emulsion containing the composition according to claim 4.

9. A method of treating hair, skin, or underarm comprising applying to the hair, skin, or underarm, the composition according to claim 1.

10. A composition comprising an elastomeric silicone polyether prepared by a method comprising combining and reacting:

(A) an ≡

Si—

H containing polysiloxane of the formula R₃SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₃, the formula (R′

₂SiO)_a′

(R″

HSiO)_b′

, the formula HR₂SiO(R′

₂SiO)_cSiR₂H, or the formula HR₂SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₂H, where R, R′

, and R″

are alkyl groups with 1-6 carbon atoms, a is 0-250, a′

is 0-7, b is 1-250, b′

is 3-10, and c is 0-250;

(B) a mono-alkenyl polyether of the formula CH₂═

CH(CH₂)_fO(CH₂CH₂O)_g(CH₂CH₃CHO)_hT, or the formula CH₂═

CH—

Q—

O(CH₂CH₂O)_g(CH₂CH₃CHO)_hT, where T is hydrogen, a C₁-C₁₀ alkyl group, an aryl group, or a C₁-C₂₀ acyl group;

Q is a divalent linking group containing unsaturation;

f is 0-6, g is 4-100; and

h is zero or 1-100;

(C) an active ingredient selected from the group consisting of vitamins, antimicrobial agents, sunburn prevention agents, astringents, and hormones;

(D) an α

,ω

-unsaturated hydrocarbon selected from the group consisting of α

,ω

-dienes of the formula CH₂═

CH(CH₂)_dCH═

CH₂, α

,ω

-diynes of the formula CH≡

C(CH₂)_eC≡

CH, and α

,ω

-ene-ynes of the formula CH₂═

CH(CH₂)_eC≡

, where d is 0-20 and e is 0-20; and

(E) a platinum catalyst;

in the presence of

(F) an oil selected from the group consisting of (i) organic compounds, (ii) compounds containing a silicon atom, (iii) mixtures of compounds, (iv) mixtures of compounds containing a silicon atom, and (v) mixtures of organic compounds and atom;

compounds containing a silicon atom;

and allowing the reaction to continue until there is formed a crosslinked three-dimensional gelled network of an elastomeric silicone polyether containing the active ingredient and the oil.

11. A composition comprising an elastomeric silicone prepared by a method comprising combining and reacting:

(A) an ≡

Si—

H containing polysiloxane of the formula R₃SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₃, the formula (R′

₂SiO)_a′

(R″

HSiO)_b′

, the formula HR₂SiO(R′

₂SiO)_cSiR₂H, or the formula HR₂SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₂H, where R, R′

, and R″

are alkyl groups with 1-6 carbon atoms, a is 0-250, a′

is 0-7, b is 1-250, b′

is 3-10, and c is 0-250;

(B) optionally, a mono-alkenyl polyether, an α

-olefin, or a mono-alkenyl polyether and an α

-olefin;

(C) an active ingredient selected from the group consisting of vitamins, antimicrobial agents, sunburn prevention agents, astringents, and hormones;

(D) an α

,ω

-unsaturated hydrocarbon selected from the group consisting of α

,ω

-dienes of the formula CH₂═

CH(CH₂)_dCH═

CH₂, α

,ω

-diynes of the formula CH≡

C(CH₂)_eC≡

CH, and α

,ω

-ene-ynes of the formula CH₂═

CD(CH₂)_eC≡

CH, where d is 0-20 and e is 0-20; and

(E) a platinum catalyst;

in the presence of (F) an oil selected from the group consisting of (i) organic compounds, (ii) compounds containing a silicon atom, (iii) mixtures of organic compounds, (iv) mixtures of compounds containing a silicon atom, and (v) mixtures of organic compounds and compounds containing a silicon atom;

and allowing the reaction to continue until there is formed a crosslinked three-dimensional gelled network of an elastomeric silicone containing the active ingredient and the oil.