IP Library Granted Patent US 10,131,794
Granted Patent B2
US 10,131,794 · App. 12/975,885 · Granted Nov 20, 2018

Network copolymer crosslinked compositions and products comprising the same

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Quick Facts
Patent No.
US 10,131,794
App. No.
12/975,885
Granted
Nov 20, 2018
Kind
B2
Abstract

The present invention provides for a household, agricultural, coating or personal care product composition containing the crosslinked reaction product of a network composition the reaction product of: (i) at least one anionic polymerizable ethylenically unsaturated monomer (I) selected from the group consisting of [CH 2 ═C(R 3 )C(O)OX a (C 2 H 4 O) b (C 3 H 6 O) c (C 4 H 8 O) d ] p P(O)(OY) q (OZ) r and CH 2 ═C(R 3 )C(O)OX a′ (C 2 H 4 O) b′ (C 3 H 6 O) c′ (C 4 H 8 O) d′ —SO 3 —Y) where R 3 =H or alkyl of 1 to about 6 carbon atoms; X=alkyl, aryl, or alkaryl diradical connecting group of 0 to about 9 carbon atoms; a, a′, b, b′, c, c′, d and d′ are 0 to about 100; q is 0 to about 2; r is 0 to about 2; p is 1 to about 3 subject to the limitation that p+q+r=3; and Y and Z is H, or metal ion; and (ii) one or more additional monomers (II) selected from the group consisting of acrylic acid/acrylate, methacrylic acid/methacrylate, acrylamides, vinyl acetate and styrene, which are copolymerizable with (I); and (iii) a cross-linking agent (III), capable of copolymerizing with (I) and (II).

Claims (59)

1. A personal care product composition comprising a crosslinked network polymer provided by the reaction of

(i) at least one anionic polymerizable ethylenically unsaturated monomer (I) selected from the group consisting of

[CH 2 ═C(R 3 )C(O)OX a (C 2 H 4 O) b (C 3 H 6 O) c (C 4 H 8 O) d ] p P(O)(OY) q (OZ) r

where

R 3 =H or alkyl of 1 to about 6 carbon atoms;

X=alkyl, aryl, or alkaryl diradical connecting group of 0 to about 9 carbon atoms; a is 0 to about 100;

b is 0 to about 100;

c is 0 to about 100;

d is 0 to about 100;

q is 0 to about 2;

r is 0 to about 2;

p is 1 to about 3 subject to the limitation that p+q+r=3; and

Y and Z is H, or metal ion;

wherein at least one of b, c, and d is from 8 to 50;

and

CH 2 ═C(R 3 )C(O)OX a′ (C 2 H 4 O) b′ (C 3 H 6 O) c′ (C 4 H 8 O) d′ —(SO 3 —Y)

where

R 3 =H or alkyl of from 1 to about 6 carbon atoms;

X=alkyl, aryl, or alkaryl diradical connecting group of 0 to about 9 carbon atoms;

a′ is 0 to about 100;

b′ is 0 to about 100;

c′ is 0 to about 100;

d′ is 0 to about 100;

Y is H, or metal ion;

wherein at least one of b′, c′, and d′ is from 8 to 50; and

(ii) one or more additional monomers (II) selected from the group consisting of acrylic acid/acrylate, methacrylic acid/methacrylate, acrylamides, vinyl acetate and styrene, which are copolymerizable with (I); and

(iii) a cross-linking agent (III), containing at least one ethylenically unsaturated group and capable of copolymerizing with (I) and (II), wherein the network polymer is simultaneously polymerized and cross-linked; and

wherein the personal care product composition has an oil and/or water swellability of 5 to 500 times its original volume,

the personal care product composition is swollen by water to form a solid or gel, and

the personal care product composition has improved sensory feeling through use of water.

2. The personal care product composition of claim 1 wherein said cross-linking agent is a polyfunctional vinylidene monomer containing at least two unsaturated groups.

3. The personal care product composition of claim 2 said polyfunctional vinylidene monomer is selected from the group consisting of butadiene, isoprene, divinyl benzene, allyl acrylates, polyalkylene glycol diacrylates and dimethacrylates, diallyl esters, and dimethallyl esters.

4. The personal care product composition of claim 1 wherein said composition comprises about 40 to about 99 weight percent based on the total weight of the monomers of said at least one anionic polymerizable ethylenically unsaturated monomer (I), about 0.5 to about 50 weight percent based on the total weight of the monomers of said additional monomers and about 0.1 to about 10 weight percent based on the total weight of the monomers of said cross-linking agent.

5. The personal care product composition of claim 1 wherein d, and d′ are from 1 to 50.

6. The personal care product composition of claim 1 wherein said cross-linking agent (III) is at least one anionic polymerizable ethylenically unsaturated monomer (I) selected from the group consisting of

[CH 2 ═C(R 3 )C(O)OX a (C 2 H 4 O) b (C 3 H 6 O) c (C 4 H 8 O) d ] p P(O)(OY) q (OZ) r

where

R 3 =H or alkyl of 1 to about 6 carbon atoms;

X=alkyl, aryl, or alkaryl diradical connecting group of 0 to about 9 carbon atoms;

a is 0 to about 100;

b is 0 to about 100;

c is 0 to about 100;

d is 0 to about 100;

q is 0 or 1;

r is 0 or 1; and

p is 2 to about 3 subject to the limitation that p+q+r=3;

Y and Z is H, or metal ion.

7. The personal care product composition of claim 1 wherein said at least one anionic polymerizable ethylenically unsaturated monomer (I) is selected from the group consisting of CH 2 ═C(CH 3 )C(O)O(C 3 H 6 O) 6 P(O)(OH)(ONa), CH 2 ═C(CH 3 )C(O)O(C 3 H 6 O) 6 P(O)(OH) 2 , CH 2 ═CHC(O)O(C 3 H 6 O) 6 P(O)(OH)(OH) 2 , and CH 2 ═C(CH 3 )C(O)O(C 2 H 4 O) n P(O)(OH) 2 ;

said one or more additional monomers (II) are selected from the group consisting of: CH 2 ═CHC(O)OH and CH 2 ═C(CH 3 )C(O)O(C 3 H 6 O) 6 H; and

said cross-linking agent (III) is selected from the group consisting of CH 2 ═CHC(O)O(C 2 H 4 O) n C(O)OCH═CH 2 , [CH 2 ═C(CH 3 )CO 2 CH 2 ] 3 CC 2 H 5 and [CH 2 ═C(CH 3 )C(O)O(C 3 H 6 O) 6 ] 2 P(O)(OH) and wherein said composition further comprises water.

8. A personal care product comprising the composition of claim 1 wherein the personal care formulation is selected from the group consisting of deodorants, antiperspirants, antiperspirant/deodorants, including 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, sunscreens, cosmetics, hair care products, skin care products, toothpastes, drug delivery systems for topical application of medicinal compositions that are to be applied to the skin and combinations comprising at least one of the foregoing applications.

9. The personal care product composition of claim 8 further comprising personal care ingredient selected from the group consisting of emollient, moisturizer, humectant, pigment, coated mica, colorant, fragrance, biocide, preservative, antioxidant, anti-microbial agent, anti-fungal agent, antiperspirant agent, exfoliant, hormone, enzyme, medicinal compound, vitamin, salt, electrolyte, alcohol, polyol, absorbing agent for ultraviolet radiation, botanical extract, surfactant, silicone oil, organic oil, wax, film former, thickening agent, particulate filler, clay, and combinations thereof.

10. The personal care product composition of claim 9 further comprising at least one additive selected from the group consisting of surfactants, emulsifiers, solvents, emollients, moisturizers, humectants, pigments, colorants, fragrances, biocides, preservatives, chelating agents, antioxidants, anti-microbial agents, anti-fungal agents, antiperspirant agents, exfoliants, hormones, enzymes, medicinal compounds, vitamins, alpha-hydroxy acids, beta-hydroxy acids, retinols, niacinamide, skin lightening agents, salts, electrolytes, alcohols, polyols, absorbing agents for ultraviolet radiation, botanical extracts, organic oils, waxes, film formers, thickening agents, particulate fillers, silicones, clays, plasticizers, humectants, occlusives, sensory enhancers, esters, resins, film formers, film forming emulsifiers and high refractive index materials.

11. The product composition of claim 1 wherein at least one of b, c, and d is from 1 to about 50.

12. The product composition of claim 11 wherein d is at least 1.

13. The product composition of claim 1 wherein at least one of Y and Z is a metal ion.

14. The product composition of claim 11 wherein at least one of Y and Z is a metal ion.

15. The personal care product composition of claim 1 , when applied to skin, provides significantly low tack of the skin.

16. The personal care product composition of claim 1 , when applied to hair, improves sleekness of the hair.

Assignments (18)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded May 4, 2023
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063548/0281 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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 →
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 →
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 →
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
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 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 AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →