Delivery of hydrophobic benefit agents from bodywashes and the like onto a keratinous substrate

• US 20100135936A1
• Filed: 04/22/2009
• Published: 06/03/2010
• Est. Priority Date: 04/23/2008
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Koroskenyi, Balint, Dueva-Koganov, Olga V., Zhou, Xian-Zhi
• Granted Patent: US 9,669,243 B2
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 8/899 containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations

Abstract

This invention relates to a delivery system for hydrophobic benefit agents to keratinous substrates. The delivery system comprises amphiphilic block copolymers, and a hydrophobic benefit agent, which amphiphilic block copolymers comprise a siloxane segment and a cationic segment. The invention also relates to methods of delivering the hydrophobic benefit agents to the keratinous substrate. Furthermore, the delivery systems and methods of delivery are effective in retaining an hydrophobic benefit agents on the keratinous substrate after rinsing.

More particularly, the delivery systems are especially suitable in personal cleansing, body wash or rinse off lotion compositions and comprise certain amphiphilic polymers which effectively deposit the hydrophobic benefit agents onto a keratinous substrate, such as skin or hair.

Claims

1. A cosmetically acceptable delivery system for hydrophobic benefit agents to a keratinous substrate wherein the delivery system comprises

i.) an amphiphilic block copolymer,

which amphiphilic block copolymer comprises a hydrophilic (A) block and a hydrophobic (B) block,

wherein the hydrophilic block (A) comprises at least a cationic monomer unit or a potentially cationic monomer unit in the conditions of use and the unit is represented by formulae (I) or (II)

wherein R₁ is hydrogen or methyl,

R₂ is hydrogen, a branched or unbranched C_1-4 alkyl,

R₃ and/or R₄ are independently branched or unbranched C_1-22 alkyl, C₁-C₄ alkylhydroxy, benzyl

or

R₃ and R₄ can be combined to form a five or six membered ring with the nitrogen,

said ring containing one or more hetero atoms,

Z⁻

is the conjugate base of an acid,

X is oxygen or —

NR₅,

wherein R₅ is as defined in R₁ above,

A is an alkylene group of 1 to 4 carbons,

R₆ and R₇ are hydrogen, branched or unbranched C_1-22 alkyl, benzyl or C₁-C₄ alkylhydroxy,

n and m are 2, 3, 4 or greater;

and

the hydrophobic polymeric block (B) comprises siloxane monomer units,

and

ii.) a hydrophobic benefit agent.

2. The delivery system according to claim 1, wherein hydrophobic block (B) comprises siloxane monomer units of formula (III)

R₈ and R₉ are independently C_1-4alkyl, phenylalkyl, alkoxy, aryl, aryloxy, alkylaryl, alkylamine, alkylhydroxy, polyoxyalkylene, polyalkylene polyamine or

—

R-L—

Polycationic Block,

wherein the Polycationic block is defined as block A in claim 1,

R is C₁ to C₁₀ alkylene, arylene, alkarylene or alkoxyalkylene,

L is a linking group,

y is an integer from 1 to 10,000,

a is an integer from 1 to 12,

and

x is and integer from 2 to 10,000.

3. The delivery system according to claim 1, wherein block A comprises at least a cationic monomer unit or a potentially cationic monomer unit in the conditions of use and the unit is represented by formula (I).

4. The delivery system according to claim 1, wherein block A comprises at least a cationic monomer unit or a potentially cationic monomer unit in the conditions of use and the unit is represented by formula (II).

5. The delivery system according to claim 2, wherein either or both

R₈ or R₉ is

6. The delivery system according to claim 1, wherein the hydrophobic benefit agent is

organic sunscreen agents or UV absorbers;

petrolatum;

ester oils;

ester oils that are predominantly comprised of triglycerides and modified triglycerides;

plant and seed extracts;

hydrophobic modified pigment particles;

vitamins or any mixture of the above.

7. The delivery system according to claim 6, wherein the hydrophobic benefit agent is an organic sunscreen agent and the organic sunscreen agent is micronized.

8. The delivery system according to claim 1, wherein the delivery system further contains an anionic surfactant.

9. The delivery system according to claim 1, wherein the average molecular weight of the amphiphilic block copolymer ranges from about 500 g/mole to about 1,000,000 g/mole.

10. The delivery system according to claim 1 wherein the keratinous substrate is hair, skin, finger nails or toe nails.

11. A body rinsable composition comprising:

i.) an amphiphilic block copolymer,

which amphiphilic block copolymer comprises a hydrophilic (A) block and a hydrophobic (B) block,

wherein the hydrophilic block (A) comprises at least a cationic monomer unit or a potentially cationic monomer unit in the conditions of use and the unit is represented by formulae (I) or (II)

wherein R₁ is hydrogen or methyl,

R₂ is hydrogen, a branched or unbranched C_1-4 alkyl,

R₃ and/or R₄ are independently branched or unbranched C_1-22 alkyl, C₁-C₄ alkylhydroxy, benzyl

or

R₃ and R₄ can be combined to form a five or six membered ring with the nitrogen, said ring containing one or more hetero atoms,

Z⁻

is the conjugate base of an acid,

X is oxygen or —

NR₅,

wherein R₅ is as defined in R₁ above,

A is an alkylene group of 1 to 4 carbons,

R₆ and R₇ are hydrogen, branched or unbranched C_1-22 alkyl, benzyl or C₁-C₄ alkylhydroxy,

n and m are 2, 3, 4 or greater;

and

the hydrophobic polymeric block (B) comprises siloxane monomer units,

siloxane monomer units of formula (III)

R₈ and R₉ are independently C_1-4alkyl, phenylalkyl, alkoxy, aryl, aryloxy, alkylaryl, alkylamine, alkylhydroxy, polyoxyalkylene, polyalkylene polyamine or

wherein the Polycationic block is defined as block A in claim 1,

L is a linking group,

y is an integer from 1 to 10,000,

a is an integer from 1 to 12,

and

x is and integer from 2 to 10,000.

and

ii.) a hydrophobic benefit agent.

12. The body rinsable composition according to claim 11 wherein the hydrophobic benefit agent is

organic sunscreen agents or UV absorbers;

petrolatum;

ester oils;

ester oils that are predominantly comprised of triglycerides and modified triglycerides;

plant and seed extracts;

hydrophobic modified pigment particles;

vitamins or any mixture of the above.

13. The body rinsable composition according to claim 11 wherein the body rinsable composition is a body wash, shower cream, shower gel, liquid soap or a bar soap.

14. A method of delivering a hydrophobic benefit agent to a keratinous substrate which method comprises the steps of

forming a mixture comprising said hydrophobic benefit agent with an amphiphilic block copolymer comprising,

i.) an amphiphilic block copolymer,

which amphiphilic block copolymer comprises a hydrophilic (A) block and a hydrophobic (B) block,

wherein the hydrophilic block (A) comprises at least a cationic monomer unit or a potentially cationic monomer unit in the conditions of use and the unit is represented by formulae (I) or (II)

wherein R₁ is hydrogen or methyl,

R₂ is hydrogen, a branched or unbranched C_1-4 alkyl,

R₃ and/or R₄ are independently branched or unbranched C_1-22 alkyl, C₁-C₄ alkylhydroxy, benzyl

or

R₃ and R₄ can be combined to form a five or six membered ring with the nitrogen,

said ring containing one or more hetero atoms,

Z⁻

is the conjugate base of an acid,

X is oxygen or —

NR₅,

wherein R₅ is as defined in R₁ above,

A is an alkylene group of 1 to 4 carbons,

R₆ and R₇ are hydrogen, branched or unbranched C_1-22 alkyl, benzyl or C₁-C₄ alkylhydroxy,

n and m are 2, 3, 4 or greater;

and

the hydrophobic polymeric block (B) comprises siloxane monomer units,

of formula (III)

wherein R₈ and R₉ are independently C_1-4alkyl, phenylalkyl, alkoxy, aryl, aryloxy, alkylaryl, alkylamine, alkylhydroxy, polyoxyalkylene, polyalkylene polyamine or

wherein the Polycationic block is defined as block A in claim 1,

L is a linking group,

y is an integer from 1 to 10,000,

a is an integer from 1 to 12,

and

x is and integer from 2 to 10,000,

applying the mixture to the keratinous substrate

and

rinsing said mixture from the keratinous substrate, wherein an effective amount of the hydrophobic benefit agent is retained on the keratinous substrate.

15. A method according to claim 14, wherein the hydrophobic benefit agents is

organic sunscreen agents or UV absorbers;

petrolatum;

ester oils;

ester oils that are predominantly comprised of triglycerides and modified triglycerides;

plant and seed extracts;

hydrophobic modified pigment particle;

and

vitamins.

16. A method according to claim 14, wherein the keratinous substrate is skin.

17. A method according to claims 14, wherein the mixture further comprises a nonionic or ionic surfactant.

18. A method according to claim 14, wherein

if the hydrophobic benefit agent is

an organic sunscreen agent, the sunscreen agent is present in about 0.1 to about 30 wt. %;

if the hydrophobic benefit agent is petrolatum, the petrolatum is present in about 1 to about 50 wt. %;

if the hydrophobic benefit agent is an ester oil or ester oils that are predominantly comprised of triglycerides and modified triglycerides, the ester oil or ester oils are present in about 1 to about 20 wt. %;

if the hydrophobic benefit agent is a plant of seed extract, the extract is present in about 0.01 to about 10 wt. %;

if the hydrophobic benefit agent is a hydrophobic modified pigment particle, the particle is present in about 0.01 to about 20 wt. %;

and

if the hydrophobic benefit agent is a vitamin, the vitamin is present in about 0.001 to about 5 wt. %,

wherein the wt. % is based on the total weight of the mixture applied to said substrate.