# US 9,433,571 B2 · Irritation mitigating polymers and uses therefor

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- Number: US 9,433,571 B2
- Document ID: US9433571B2
- Status: Granted
- Kind: B2
- Application number: 14/653,491
- Filed: 2013-12-12
- Published: 2015-12-03
- Granted: 2016-09-06
- Earliest claimed: 2012-12-20
- Assignees: Lubrizol Advanced Materials, Inc.
- Applicants: Lubrizol Advanced Materials, Inc.
- Inventors: Brian D. Figura; Krishnan Chari; Wei-Yeih Yang
- Web page: https://patentgrep.com/patent/US9433571B2

## CPC

- A61K 8/8176: {Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers}
- A61K 8/442: {substituted by amido group(s)}
- A61K 8/463: {containing sulfuric acid derivatives, e.g. sodium lauryl sulfate}
- A61K 8/8182: {Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers}
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 19/10: Washing or bathing preparations
- C11D 1/143: {Sulfonic acid esters}
- C11D 1/90: Betaines
- C11D 3/0005: {Other compounding ingredients characterised by their effect}
- C11D 3/3776: {Heterocyclic compounds, e.g. lactam}
- A61K 2800/5422: nonionic
- A61K 2800/75: Anti-irritant
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

The present invention provides mild cleansing and cleaning compositions and methods for mitigating irritation induced by harsh detersive surfactants. The invention relates to a method of reducing skin irritation associated with a cleansing composition comprising at least one surfactant, the method comprising combining an effective amount of at least one nonionic amphiphilic polymer with at least one detersive surfactant selected from anionic surfactants, amphoteric surfactants, nonionic surfactants and combinations of two or more thereof. The at least one nonionic amphiphilic irritation mitigating polymer is prepared from a free radically polymerizable monomer composition comprising at least one hydrophilic monomer and at least one hydrophobic monomer, wherein said N-vinyl lactam and wherein said hydrophobic monomer is selected from a vinyl ester of a C1-C22 carboxylic acid or at least one monomer selected from a C8-C22 alkyl (meth)acrylate an associative monomer, a semi-hydrophobic monomer, or mixtures thereof.

## Claims

### Claim 1

A method for mitigating ocular and/or skin irritation induced by detersive compositions containing at least one anionic surfactant said method comprising contacting the skin with a detersive composition comprising a crosslinked nonionic amphiphilic dispersion polymer prepared from a free radically polymerizable monomer mixture comprising:
i) 60 to 90 wt. % of N-vinyl pyrrolidone (based on the total monomer wt.);
ii) 10 to 35 wt. % of at least one vinyl ester selected from vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl valerate, vinyl hexanoate, vinyl 2-methylhexanate, vinyl 2-ethylhexanoate, vinyl iso-octanoate, vinyl nonanoate, vinyl neodecanoate, vinyl decanoate, vinyl versatate, vinyl laurate, vinyl palmitate, and vinyl stearate;
iii) 0 or 0.5 to 5 wt. % of an C8-C22 alkyl (meth)acrylate selected from octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tetradecyl (meth)acrylate, hexadecyl (meth)acrylate, stearyl (meth)acrylate, and behenyl (meth)acrylate; and
iv) 0 or 0.5 to 4.5 wt. % of at least one associative monomer and/or semi-hydrophobic monomer (said weight percent is based on the weight of the total monomers)
v) 0.01 to 1 wt. % in one aspect or from 0.1 to 0.3 wt. % of at least one crosslinker (based on the dry weight of the polymer), wherein said detersive composition comprises;
a) water;
b) 1 to 5 wt. % of said crosslinked nonionic amphiphilic dispersion polymer;
c) 6 to 20 wt. % of a surfactant mixture containing an anionic surfactant and an amphoteric surfactant; subject to the proviso that at least one of monomers iii) and iv) must be present and when both monomers iii) and iv) are present in said monomer mixture, the combined weight of said monomers iii) and iv) cannot exceed 5 wt. % of the weight of the total monomer mixture;
wherein said associative monomer is represented by formula VIIB:
R14 is hydrogen or methyl; R15 is a divalent alkylene moiety independently selected from C2H4, C3H6, and C4H8, and n represents an integer ranging from about 10 to about 60, (R15—O) can be arranged in a random or a block configuration; R16 is a substituted or unsubstituted alkyl selected from a C8-C30 linear alkyl, a C8-C30 branched alkyl, a C8-C30 carbocyclic alkyl, a C2-C30 alkyl-substituted phenyl, an araalkyl substituted phenyl, and an aryl-substituted C2-C30 alkyl, wherein the R16 alkyl group, aryl group, phenyl group optionally comprises one or more substituents selected from the group consisting of a hydroxyl group, an alkoxyl group, benzyl group styryl group, and a halogen group; and
wherein said semi-hydrophobic monomer is selected from at least one monomer represented by formulas VIIIA and VIIIB:
CH2═C(R14)C(O)O—(C2H4O)a(C3H6O)b—H VIIIA
CH2═C(R14)C(O)O—(C2H4O)a(C3H6O)b—CH3 VIIIB
R14 is hydrogen or methyl, and “a” is an integer ranging from 0 or 2 to about 120 in one aspect, from about 5 to about 45 in another aspect, and from about 10 to about 0.25 in a further aspect, and “b” is an integer ranging from about 0 or 2 to about 120 in one aspect, from about 5 to about 45 in another aspect, and from about 10 to about 0.25 in a further aspect, subject to the proviso that “a” and “b” cannot be 0 at the same time.

### Claim 2 (depends on 1)

The method of claim 1 wherein said at least one vinyl ester is selected from vinyl acetate, vinyl decanoate, or mixtures thereof.

### Claim 3 (depends on 1)

The method of claim 1 wherein said at least one associative monomer is behenyl polyethoxylated methacrylate, and said semi-hydrophobic monomer is methoxy polyethyleneglycol methacrylate.

### Claim 4 (depends on 1)

The method of claim 1 wherein said at least one C8-C22 alkyl (meth)acrylate monomer is selected from lauryl methacrylate, stearyl methacrylate, or mixtures thereof.

### Claim 5 (depends on 3)

The method of claim 3 wherein said associative and/or semi-hydrophobic monomer contains 2 to 30 moles of ethoxylation.

### Claim 6 (depends on 1)

The method of claim 1 wherein said anionic surfactant contains an average of 1 to 3 moles of ethoxylation.

### Claim 7 (depends on 1)

The method of claim 1 wherein the ratio of said anionic surfactant to said amphoteric surfactant ranges from about 10:1 to about 2:1 (wt./wt.).

### Claim 8 (depends on 7)

The method of claim 7 wherein said anionic surfactant is selected from the sodium or ammonium salts of dodecyl sulfate, lauryl sulfate, laureth sulfate, or mixtures thereof.

### Claim 9 (depends on 7)

The method of claim 7 wherein said amphoteric surfactant is cocamidopropyl betaine.

### Claim 10 (depends on 1)

The method of claim 1 wherein said associative monomer is selected from lauryl polyethoxylated (meth)acrylate, cetyl polyethoxylated (meth)acrylate, cetearyl polyethoxylated (meth)acrylate, stearyl polyethoxylated (meth)acrylate, arachidyl polyethoxylated (meth)acrylate, behenyl polyethoxylated (meth)acrylate, cerotyl polyethoxylated (meth)acrylate, montanyl polyethoxylated (meth)acrylate, melissyl polyethoxylated (meth)acrylate, where the polyethoxylated portion of the monomer contains about 2 to about 50 ethylene oxide units, and said semi-hydrophobic monomer is selected from methoxy polyethyleneglycol (meth)acrylate or polyethyleneglycol (meth)acrylate, where the polyethoxylated portion of the monomer contains about 2 to about 50 ethylene oxide units.

### Claim 11 (depends on 1)

The method of claim 1 wherein said crosslinker is selected from a monomer having an average of 3 crosslinkable unsaturated functional groups.

### Claim 12 (depends on 1)

The method of claim 1 wherein said crosslinker is pentaerythritol triallyl ether.

### Claim 13 (depends on 1)

The method of claim 1 wherein said dispersion polymer is prepared in the presence of a steric stabilizer polymer.

### Claim 14 (depends on 13)

The method of claim 13 wherein said steric stabilizer is selected from a copolymer of N-vinyl pyrrolidone/stearyl methacrylate/butyl acrylate, the ester of the reaction product of a C20 to C24 alkyl substituted succinic anhydride and a polyol selected from glycerin and/or a polyglycerol containing 2 to 6 glycerin units, and mixtures thereof.

### Claim 15 (depends on 1)

The method of claim 1 wherein said detersive composition is selected from shampoos, baby shampoos, body washes, shower gels, liquid hand soaps, liquid dishwashing detergents, pet cleansing product, moist cleansing wipes, or facial cleansers.