Entrapment of vitamins with an elastomeric silicone polyether

• US 6,207,717 B1
• Filed: 01/12/1999
• Issued: 03/27/2001
• Est. Priority Date: 01/12/1999
• Status: Expired due to Term

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Lin, Zuchen, Schulz, William James Jr., Smith, Janet Mary
• Primary Examiner(s): Kulkosky, Peter F.
• Application Number:
  US09/228,301
• Time in Patent Office: 805 Days
• Field of Search: 424/78.17, 424/70.12, 514/772.1
• US Class Current: 514/772.1
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 8/671 Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
• CPC Class Codes: A61K 8/678 Tocopherol, i.e. vitamin E
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61K 9/107 Emulsions ; Emulsion preconcentrates; Micelles composition of emulsions A61K47/00
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 83/12 containing polyether sequences

Abstract

Oil-soluble vitamins such as vitamin A and vitamin E can be entrapped in the oil phase of an elastomeric silicone polyether. The vitamin entrapped oil phase can then be emulsified and stabilized without requiring the use of other surfactants. The vitamin entrapped oil phase and water-in-oil emulsions prepared from the vitamin entrapped oil phase are useful in water-based skin and cosmetic compositions.

Claims

1. A method of making a vitamin enhanced silicone elastomer comprising entrapping an effective amount of a vitamin in a silicone elastomer by mixing the vitamin with the silicone elastomer, the silicone elastomer being prepared by a method comprising reacting:

(A) an ═

Si—

H containing polysiloxane of the formula R₃SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₃ or the formula (R′

₂SiO)_a(R″

HSiO)_b, and optionally an ═

Si—

H containing polysiloxane of the formula HR₂SiO(R′

₂SiO)_cSiR₂H or an ═

Si—

H containing polysiloxane of 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, b is 1-250, and c is 0-250; and

(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 1-6, g is 4-30; and

h is zero or 1-100;

in the presence of a platinum catalyst, until an ═

Si—

H containing polysiloxane with polyether groups is formed; and

reacting;

(C) the ═

Si—

H containing polysiloxane with polyether groups; and

(D) an unsaturated hydrocarbon selected from the group consisting of alpha, omega-dienes of the formula CH₂═

CH(CH₂)_dCH═

CH₂, alpha, omega-diynes of the formula CH═

C(CH₂)_eC═

CH, and alpha, omega-ene-ynes of the formula CH₂═

CH(CH₂)_eC═

CH, where d and e are 1-20;

in the presence of

(E) 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

in the presence of a platinum catalyst, until a silicone elastomer is formed by crosslinking and addition of ═

SiH across double or triple bonds in the unsaturated hydrocarbon;

the equivalent ratio of the ═

SiH in the ═

SiH containing polysiloxane with polyether groups and the unsaturated hydrocarbon being 2;

1 to 1;

2.

2. A method according to claim 1 including the further steps of adding additional amounts of oil to the silicone elastomer, and shearing the oil and silicone elastomer until a silicone paste is formed.

3. A method according to claim 2 including the further steps of adding water to the silicone paste, and shearing the water and silicone paste until a silicone emulsion is formed.

4. A method according to claim 3 in which the silicone emulsion is formed free of the presence of a surfactant.

5. A method according to claim 1 in which the second step includes as an additional reactant (F) an ≡

Si—

H containing polysiloxane of the formula R₃SiO(R′

₂SiO)_a(R″

HSiO)_bSiR₃ or the formula (R′

₂SiO)_a(R″

HSiO)_b, and optionally an ≡

Si—

H containing polysiloxane of the formula HR₂SiO(R′

₂SiO)_cSiR₂H or an ≡

Si—

H containing polysiloxane of 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, b is 1-250, and c is 0-250.

6. A method 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.

7. A method according to claim 1 in which the molar ratio of the mono-alkenyl polyether to ≡

SiH in the ≡

SiH containing polysiloxane is between 0.9;

1 and 1;

12.

8. A method according to claim 1 in which the vitamin is present in combination with an oil-soluble drug.

9. A silicone elastomer composition prepared according to the method defined in claim 8.

10. A method of treating hair, skin, or the underarm comprising applying to the hair, skin, or the underarm, the silicone elastomer composition of claim 9.