IP Library Granted Patent US 9,895,306
Granted Patent B2
US 9,895,306 · App. 13/733,482 · Granted Feb 20, 2018

Personal care compositions containing end-functionalized ionic silicone

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Quick Facts
Patent No.
US 9,895,306
App. No.
13/733,482
Filed
Jan 3, 2013
Granted
Feb 20, 2018
Kind
B2
Art Unit
1612
USPC
424/59
Abstract

A personal care composition contains at least one personal care component and at least one end-functionalized ionic silicone.

Claims (36)

1. A personal care composition comprising at least one personal care component and at least one end-functionalized ionic silicone wherein the silicone comprises at least two terminal ionic groups that form ionic aggregates, and where the ionic interactions have a reversible nature,

wherein the end-functionalized ionic silicone has the formula:

M 1 a M 2 b M 3 c D 1 d D 2 e D 3 f T 1 g T 2 h T 3 i Q j   (I)

wherein:

M 1 =R 1 R 2 R 3 SiO 1/2

M 2 =R 4 R 5 R 6 SiO 1/2

M 3 =R 7 R 8 R 9 SiO 1/2

D 1 =R 10 R 11 SiO 2/2

D 2 =R 12 R 13 SiO 2/2

D 3 =R 14 R 15 SiO 2/2

T 1 =R 16 SiO 3/2

T 2 =R 17 SiO 3/2

T 3 =R 18 SiO 3/2

Q=SiO 4/2

in which:

R 1 , R 2 , R 3 , R 5 , R 6 , R 8 , R 9 , R 10 , R 11 , R 13 , R 15 and R 16 each independently is an aliphatic, aromatic or fluoro monovalent hydrocarbon group having from 1 to 60 carbon atoms;

R 4 , R 12 and R 17 each independently is a monovalent group bearing ion-pairs and having the formula -A-I x− M n y+ , or zwitterion having the formula —R′—N + (R″) 2 —R′″—I − , in which A is a spacing moiety having at least one spacing atom, the spacing moiety being selected from the group consisting of divalent hydrocarbon group and hydrocarbonoxy group, I is an ionic group, R′ is a divalent hydrocarbon group having from 1 to 20 carbon atoms, R″ is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, R′″ is a divalent hydrocarbon group having from 2 to 20 carbon atoms, and each M independently is hydrogen or a cation independently selected from alkali metals, alkali earth metals, transition metals, quaternary ammonium groups and phosphonium groups;

R 7 , R 14 and R 18 each independently is —CH 2 CH(R 19 )(C n H 2n )—O—(C 2 H 4 O) o —(C 3 H 6 O) p —(C 4 H 8 O) q —R 19 in which R 19 is hydrogen or an R 1 group as defined above;

superscripts x and y are positive integers subject to the limitation that x=ny;

each subscript n independently has a value of from 0 to 6 and subscripts o, p and q each independently has a value of from 0 to 1000, subject to the limitation that o+p+q≧1; and,

subscripts a, c, d, e, f, g, h, i and j each independently is zero or a positive integer subject to the limitations that 2≦a+b+c+d+e+f+g+h+i+j≦4500 and b≧2.

2. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), each R 1 , R 2 , R 3 , R 5 , R 6 , R 8 , R 9 , R 10 , R 11 , R 13 , R 15 and R 16 group is independently selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclohexyl, naphthyl; tolyl, xylyl, ethylphenyl and benzyl.

3. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), divalent spacing group A is an alkylene group CHR 20 m wherein R 20 is hydrogen or an R 1 group and subscript m is a positive integer ranging from 1 to 100.

4. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), divalent spacing group A is an arylene group selected from —(CHR 21 ) k C 6 H 4 (CH 2 ) r — —CH 2 CH(R′)(CH 2 ) k C 6 H 4 — or —CH 2 CH(R 22 )(CH 2 ) r C 6 H 3 R 23 wherein R′ is hydrogen or an R 1 group, R 21 is hydrogen or an R 1 group, R 22 is hydrogen or an R 1 group, R 23 is a monovalent radical of from 1 to 20 carbon atoms and subscripts k and r are zero or positive integers subject to the limitation 0≦k+r≦100.

5. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), divalent spacing group A is a hydrocarbonoxy group selected from CHR 24 ) s —(O—CHR 24 CH 2 ) s′ and —O—(CH 2 t wherein R 24 is hydrogen or an R 1 group, s has a value of from 0 to 50, s′ has a value of from 1 to 50 and t has a value of from 0 to 50 subject to the limitation 1≦s+s′+t≦100.

6. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), I − in the ion-pair-bearing group and in the zwitterion is selected from sulfonate —SO 3 − and sulfate —OSO 3 .

7. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), M + is selected from Li, Na, K, Cs, Mg, Ca, Ba, Zn, Cu, Fe, Ni, Ga, Al, Mn, Cr, Ag, Au, Pt, Pd, Ru and Rh.

8. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), in the zwitterion, R′ is a divalent hydrocarbon radical having from 1 to 20 carbon atoms, R″ is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and R′″ is a divalent hydrocarbon radical having from 2 to 20 carbon atoms.

9. The personal care composition of claim 1 wherein in end-functionalized ionic silicone (I), subscripts a, c, d, e, f, g, h, i and j each independently is zero or a positive number subject to the limitations that 2≧a+b+c+d+e+f+g+h+i+j≧4500, b>2.

10. The personal care composition of claim 9 wherein in end-functionalized ionic silicone (I), subscript b is 2; subscripts a, c, e, f, g, h, i, j, k, l and m are 0; subscript d is from 5 to 1000, R 5 , R 6 , R 10 and R 11 are methyl or ethyl; R 10 is —CH 2 CH(H or CH 3 )-A-SO 3 M; A is a divalent benzyl radical; and, M + is Li, Na, K, Ag, a quaternary ammonium group, ammonium salt or phosphonium group.

11. The personal care composition of claim 1 wherein end-functionalized ionic silicone (I) is at least one of sodium sulfonate-capped polydimethylsiloxane, silver sulfonate-capped polydimethylsiloxane, magnesium sulfonate-capped polydimethylsiloxane, calcium sulfonate-capped polydimethylsiloxane, zinc sulfonate-capped polydimethylsiloxane and triethanolammonium sulfonate-capped polydimethylsilane.

12. The personal care composition of claim 1 further comprising at least one non-functionalized silicone.

13. The personal care composition of claim 1 further comprising at least one organic solvent.

14. The personal care composition of claim 1 formulated as an oil-in-water or water-in-oil emulsion.

15. The personal care composition of claim 1 wherein said personal care composition is selected from the group consisting of deodorants, antiperspirants, sprays, sticks and roll-on products, shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, shampoos, conditioners, combined shampoo/conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair bleaches, waving products, hair straighteners, nail polish, nail polish remover, nail creams and lotions, cuticle softeners, sunscreen, insect repellent, anti-aging products, lipsticks, foundations, face powders, eye liners, eye shadows, blushes, makeup, mascaras, moisturizing preparations, foundations, body and hand preparations, skin care preparations, face and neck preparations, tonics, dressings, hair grooming aids, aerosol fixatives, fragrance preparations, aftershaves, make-up preparations, soft focus applications, night and day skin care preparations, non-coloring hair preparations, tanning preparations, synthetic and non-synthetic soap bars, hand liquids, nose strips, non-woven applications for personal care, baby lotions, baby baths and shampoos, baby conditioners, shaving preparations, cucumber slices, skin pads, make-up removers, facial cleansing products, cold creams, sunscreen products, mousses, spritzes, paste masks and muds, face masks, colognes and toilet waters, hair cuticle coats, shower gels, face and body washes, personal care rinse-off products, gels, foam baths, scrubbing cleansers, astringents, nail conditioners, eye shadow sticks, powders for face or eye, lip balms, lip glosses, hair care pump sprays and other non-aerosol sprays, hair-frizz-control gels, hair leave-in conditioners, hair pomades, hair de-tangling products, hair fixatives, hair bleach products, skin lotions, pre-shaves and pre-electric shaves, anhydrous creams and lotions, oil/water, water/oil, multiple and macro and micro emulsions, water-resistant creams and lotions, anti-acne preparations, mouth-washes, massage oils, toothpastes, clear gels and sticks, ointment bases, topical wound-healing products, aerosol talcs, barrier sprays, vitamin and anti-aging preparations, herbal-extract preparations, bath salts, bath and body milks, hair styling aids, hair-, eye-, nail- and skin-soft solid applications, controlled-release personal care products, hair conditioning mists, skin care moisturizing mists, skin wipes, pore skin wipes, pore cleaners, blemish reducers, skin exfoliators, skin desquamation enhancers, skin towelettes and cloths, depilatory preparations, personal care lubricants, nail coloring preparations, drug delivery systems for topical application of medicinal compositions that are to be applied to the skin and combinations thereof.

16. The personal care composition of claim 1 wherein said personal care composition is selected from the group consisting of deodorants, antiperspirants, sprays, sticks and roll-on products, shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, shampoos, conditioners, combined shampoo/conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair bleaches, waving products, hair straighteners, nail polish, nail polish remover, nail creams and lotions, cuticle softeners, sunscreen, insect repellent, anti-aging products, lipsticks, foundations, face powders, eye liners, eye shadows, blushes, makeup, mascaras, moisturizing preparations, foundations, body and hand preparations, skin care preparations, face and neck preparations, tonics, dressings, hair grooming aids, aerosol fixatives, fragrance preparations, aftershaves, make-up preparations, soft focus applications, night and day skin care preparations, non-coloring hair preparations, tanning preparations, synthetic and non-synthetic soap bars, hand liquids, nose strips, non-woven applications for personal care, baby lotions, baby baths and shampoos, baby conditioners, shaving preparations, cucumber slices, skin pads, make-up removers, facial cleansing products, cold creams, sunscreen products, mousses, spritzes, paste masks and muds, face masks, colognes and toilet waters, hair cuticle coats, shower gels, face and body washes, personal care rinse-off products, gels, foam baths, scrubbing cleansers, astringents, nail conditioners, eye shadow sticks, powders for face or eye, lip balms, lip glosses, hair care pump sprays and other non-aerosol sprays, hair-frizz-control gels, hair leave-in conditioners, hair pomades, hair de-tangling products, hair fixatives, hair bleach products, skin lotions, pre-shaves and pre-electric shaves, anhydrous creams and lotions, oil/water, water/oil, multiple and macro and micro emulsions, water-resistant creams and lotions, anti-acne preparations, mouth-washes, massage oils, toothpastes, clear gels and sticks, ointment bases, topical wound-healing products, aerosol talcs, barrier sprays, vitamin and anti-aging preparations, herbal-extract preparations, bath salts, bath and body milks, hair styling aids, hair-, eye-, nail- and skin-soft solid applications, controlled-release personal care products, hair conditioning mists, skin care moisturizing mists, skin wipes, pore skin wipes, pore cleaners, blemish reducers, skin exfoliators, skin desquamation enhancers, skin towelettes and cloths, depilatory preparations, personal care lubricants, nail coloring preparations, drug delivery systems for topical application of medicinal compositions that are to be applied to the skin and combinations thereof.

Assignments (21)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
BANKRUPTCY ORDER TO RELEASE SECURITY INTEREST AT REEL/FRAME NO. 032736/0457 Recorded Nov 21, 2017
From: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 044203/0513 →
BANKRUPTCY ORDER TO RELEASE SECURITY INTEREST AT REEL/FRAME NO. 032736/471 Recorded Aug 20, 2017
From: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 043608/0018 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 032736/0457 →
SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 032736/0471 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →