Compositions comprising anionic functionalized polyorganosiloxanes for hydrophobically modifying surfaces and enhancing delivery of active agents to surfaces treated therewith

• US 20030211050A1
• Filed: 05/06/2003
• Published: 11/13/2003
• Est. Priority Date: 05/09/2002
• Status: Active Grant

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Majeti, Satyanarayana, Kovacs, Stephen Andras, Reno, Elizabeth Ann Brown
• Granted Patent: US 7,166,235 B2
• Time in Patent Office: Days
• US Class Current: 424/49
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61K 8/892 modified by a hydroxy group, e.g. dimethiconol
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: Y10T 428/31612 As silicone, silane or siloxane

Abstract

Disclosed are compositions and methods for treating and modifying surfaces and for enhancing delivery of active agents to surfaces treated therewith, wherein the compositions comprise siloxane polymers functionalized with pendant moieties comprising two or more anionic groups, at least one anionic group being a carboxy group. When applied to a suitable surface, the present composition forms a substantially hydrophobic coating of the anionic functionalized siloxane polymer on the treated surface. These polymers effectively deposit on surfaces that have cationic sites, which are capable of forming bonds or linkages with the anionic groups of the polymer. The treated surface becomes hydrophobic due to the deposition of the anionic functionalized siloxane polymer, which then imparts a variety of end use benefits to that surface such as ease of cleaning, soil release, stain removal and prevention, conditioning, etc. The anionic functionalized siloxane polymer further acts as a carrier to deposit active agents onto the surface and to improve retention and efficacy of the active agents on the treated surface. The present compositions are useful in a variety of applications including oral care, hair and skin care, personal care, cosmetics, and fabric and hard surface cleaning and conditioning.

Claims

1. A composition for treating and hydrophobically modifying surfaces containing cationic sites, comprising at least about 0.001% by weight of an anionic functionalized siloxane polymer of formula

R¹R²R³SiO(R⁴R⁵SiO)_p(R⁶ASiO)_qSiR³R²R¹

wherein

R¹ to R⁶, which may be identical or different, each represents a linear or branched C1-C8 alkyl or a phenyl radical;

A represents a carboxy group containing radical of formula

wherein B represents an alkylene residue having from 2 to 30 carbon atoms, optionally interrupted by up to 8 non-neighboring oxygen atoms or groups of the formula —

NR⁷—

, —

CO—

or —

C(O)—

O—

C(O)—

, (wherein R⁷ is hydrogen or C1-C4 alkyl,

L represents CR′

or phenyl, wherein R′

represents a hydrogen atom, an alkyl radical having from 1 to 30 carbon atoms or a carboxy group,

E is nil or is an alkylene residue having from 1 to 5 carbon atoms, optionally substituted by one or more alkyl radicals having from 1 to 8 carbon atoms,

Z represents an anionic functional group selected from hydroxy, amino, carboxy, or alkoxy, wherein when L is CR′

, Z is other than carboxy and when L is phenyl, the groups -E-C(O)OM and -E-Z are ortho to each other and E is nil, and

M is H, an alkyl group having from 1 to 4 carbon atoms optionally substituted with a hydroxy or alkoxy groups or a cation selected from the group consisting of alkali metal, alkaline earth metal, and substituted or non substituted ammonium, piperidinium or alkanolamine;

p is an average value ranging from 0 to 1000; and

q is an average value ranging from 1 to 100.

2. A composition according to claim 1, wherein the anionic functionalized siloxane polymer comprises pendant groups selected from one or a combination of:

—

(CH₂)_n—

C₆H₃(COOM)₂;

—

(CH₂)_n—

C₆H₃(OH)(COOM);

—

(CH₂)_n—

C₆H₃(OCOCH₃)(COOM);

—

(CH₂)_n—

C₆H₃(NHR)(COOM);

—

(CH₂)_n—

OC(O)—

CHOH—

CH₂COOM;

—

(CH₂)_n—

OC(O)—

CH₂—

C(OH)(COOM)—

CH₂COOM;

—

(CH₂)_n—

OC(O)—

CH(OH)—

COOM;

—

(CH₂)_n—

OC(O)—

(CHOH)_m—

CH(OH)COOM;

—

(CH₂)_n—

C(O)—

O—

C(O)—

CH2-CH(OH)—

COOM

wherein n is from 2 to 30, m is from 2 to 4 and R is H or C1-C8 alkyl.

3. A composition according to anyone of claim 1 for oral care use further comprising an oral care agent selected from the group consisting of a bleaching agent, whitening agent, enzyme, anti-tartar agent, anticaries agent, anti-microbial agent, anti-inflammatory agent, H2 antagonist, analgesic, anti-viral agent, denture adhesive, flavoring agent and mixtures thereof.

4. A composition for oral care use according to claim 3 wherein the oral care agent is a bleaching agent of from about 0.1% to about 20.0% by weight of the composition.

5. A composition for oral care use according to claim 4 wherein the bleaching agent is selected from the group consisting of peroxides, perborates, percarbonates, peroxyacids, persulfates, metal chlorites, and mixtures thereof.

6. A composition for oral care use according to claim 5 wherein the bleaching agent is selected from the group consisting of hydrogen peroxide, urea peroxide, calcium peroxide, sodium percarbonate, sodium chlorite, potassium chlorite and mixtures thereof.

7. A method of cleaning and whitening a subject'"'"'s teeth or dental prosthesis;

preventing or reducing plaque, caries, calculus and stains on teeth or dental prosthesis; and

providing shine, smoothness and positive feel benefits to teeth, comprising administering to the subject'"'"'s oral cavity a composition according to claim 1.

8. A method of cleaning and whitening a subject'"'"'s teeth or dental prosthesis;

preventing or reducing plaque, caries, calculus and stains on teeth or dental prosthesis; and

providing shine, smoothness and positive feel benefits to teeth, comprising administering to the subject'"'"'s oral cavity a composition according to claim 3.

9. A method of enhancing efficacy of compositions for treating surfaces containing cationic sites comprising adding to said compositions a carrier for active agents comprising an anionic functionalized siloxane polymer in an amount effective to hydrophobically modify said surfaces and to enhance deposition and retention of said active agents on said treated surfaces.

10. A method of whitening a subject'"'"'s teeth comprising treating the subject'"'"'s teeth with a composition comprising a bleaching agent and an anionic functionalized hydrophobic polymer, wherein said composition deposits and retains a hydrophobic coating and said bleaching agent on teeth for a sufficient period of time for effective bleaching and whitening.