# US 2019/0167552 A1 · Compositions and methods for improving the appearance of the hair

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2019/0167552 A1
- Document ID: US20190167552A1
- Status: Published application
- Kind: A1
- Application number: 16/313,702
- Filed: 2016-06-30
- Published: 2019-06-06
- Earliest claimed: 2016-06-30
- Assignees: L'oreal
- Applicants: L'oreal
- Inventors: Marina Tavares GREGOLIN; Ana Paula Leme DE MAGALHÃES; Manon CHAUMONTET; Sintia Aguiar MARTINS; Arthur Olimpio De Cunto CARVALHO
- Web page: https://patentgrep.com/patent/US20190167552A1

## CPC

- A61K 8/42: Amides
- A61K 8/34: Alcohols
- A61K 8/345: {containing more than one hydroxy group}
- A61K 8/898: containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
- A61Q 5/04: Preparations for permanent waving or straightening the hair
- A61K 2800/48: Thickener, Thickening system
- A61K 2800/882: Mixing prior to application
- 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

## Abstract

The disclosure relates to compositions and methods for treating keratin fibers. Compositions comprise part (A) comprising (a) at least one compound chosen from urea and urea derivatives; and part (B) comprising (b) at least one polyol compound. Methods comprise applying the composition to keratin fibers to provide long-lasting effects such as good curl definition and regularity, better movement and discipline, and/or good volume and frizz control. Kits comprising the composition are also disclosed.

## Claims

### Claim 1

A composition for treating keratin fibers, the composition comprising: (a) at least one compound chosen from urea and urea derivatives; and (b) at least one polyol compound, wherein the composition optionally further comprises at least one amino silicone.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the at least one compound chosen from urea and urea derivative is chosen from urea, methylurea, ethylurea, propylurea, n-butylurea, sec-butylurea, isobutylurea, tert-butylurea, cyclopentylurea, ethoxyurea, hydroxyethylurea, N-(2-hydroxypropyl)urea, N-(3-hydroxypropyl)urea, N-(2-dimethylaminopropyl)urea, N-(3-dimethylaminopropyl)urea, 1-(3-hydroxyphenyl)urea, benzylurea, N-carbamoylmaleamide, N-carbamoylmaleamic acid, piperidinecarboxamide, 1,2,4-triazol-4-ylurea, hydantoic acid, methyl allophanate, ethyl allophanate, acetylurea, hydroxyethyleneurea, 2-(hydroxyethyl)ethyleneurea, diallylurea, chloroethylurea, N,N-dimethylurea, N,N-diethylurea, N,N-dipropylurea, cyclopentyl-1-methylurea, 1,3-dimethylurea, 1,3-diethylurea, 1,3-bis(2-hydroxyethyl)urea, 1,3-bis(2-hydroxypropyl)urea, 1,3-bis(3-hydroxypropyl)urea, 1,3-dipropylurea, ethyl-3-propylurea, sec-butyl-3-methylurea, isobutyl-3-methylurea, cyclopentyl-3-methylurea, N-acetyl-N′-methylurea, trimethylurea, butyl-3,3-dimethylurea, tetramethylurea, parabanic acid, 1,2-dihydro-3H-1,2,4-triazol-2-one, barbituric acid, uracil, 1-methyluracil, 3-methyluracil, 5-methyluracil, 1,3-dimethyluracil, 5-azauracil, 6-azauracil, 5-fluorouracil, 6-fluorouracil, 1,3-dimethyl-5-fluorouracil, 5-aminouracil, 6-aminouracil, 6-amino-1-methyluracil, 6-amino-1,3-dimethyluracil, 4-chlorouracil, 5-chlorouracil, 5,6-dihydrouracil, 5,6-dihydro-5-methyluracil, 2-imidazolidone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 4,5-dihydroxyimidazolidin-2-one, 1-(2-hydroxyethyl)-2-imidazolidinone, 1-(2-hydroxypropyl)-2-imidazolidinone, 1-(3-hydroxypropyl)-2-imidazolidinone, 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one, 1,3-bis(2-hydroxyethyl)-2-imidazolidinone, 2-imidazolidone-4-carboxylic acid, 1-(2-aminoethyl)-2-imidazole, 4-methyl-1,2,4-triazoline-3,5-dione, 2,4-dihydroxy-6-methylpyrimidine, 1-amino-4,5-dihydro-1H-tetrazol-5-one, hydantoin, 1-methylhydantoin, 5-methylhydantoin, 5,5-dimethylhydantoin, 5-ethylhydantoin, 5-N-propylhydantoin, 5-ethyl-5-methylhydantoin, 5-hydroxy-5-methylhydantoin, 5-hydroxymethylhydantoin, 1-allylhydantoin, 1-aminohydantoin, hydantoin-5-acetic acid, 4-amino-1,2,4-triazolone-3,5-dione, hexahydro-1,2,4,5-tetrazine-3,6-dione, 5-methyl-1,3,5-triazinon-2-one, 1-methyltetrahydropyrimidin-2-one, 2,4-dioxohexahydro-1,3,5-triazine, urazole, 4-methylurazole, orotic acid, dihydroxyorotic acid, 2,4,5-trihydroxypyrimidine, 2-hydroxy-4-methylpyrimidine, 4,5-diamino-2,6-dihydroxypyrimidine, 1,3-dimethylbarbituric acid, cyanuric acid, 1-methylhexahydropyrimidine-2,4-dione, 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidinone, 5-(hydroxymethyl-2,4-(1H,3H)-pyrimidinedione, 2,4-dihydroxypyrimidine-5-carboxylic acid, 6-azathymine, 5-methyl-1,3,5-triazinan-2-one, N-carbamoylmaleamic acid, alloxan monohydrate, or a mixture thereof.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the total amount of compound chosen from urea and urea derivatives ranges from about 1% to about 15% by weight, relative to the total weight of the composition.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the at least one polyol compound is chosen from propylene glycol, butylene glycol, 1,3-propanediol, 1,3-butylene glycol, 1,2-pentanediol, dipropylene glycol, hexylene glycol, pentylene glycol, glycerol, ethylene glycol, or mixtures thereof.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the total amount of polyol ranges from about 1% to about 30% by weight, relative to the total weight of the composition.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the weight ratio of the total amount of compound chosen from urea and urea derivatives, to the total amount of polyol, is greater than or equal to about 0.1.

### Claim 7 (depends on 1)

The composition of claim 1, further comprising at least one amino silicone.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the at least one amino silicone is chosen from:
(a) the compounds corresponding to formula (III) below:
(R1)a(T)3-a-Si[OSi(T)2]n-[OSi(T)b(R1)2-b]m—OSi(T)3-a-(R1)a (III)
wherein in formula (III):
T is chosen from a hydrogen atom or a phenyl, hydroxyl (—OH), C1-C8 alkyl, methyl, C1-C8 alkoxy, or methoxy group,
a denotes the number 0 or an integer from 1 to about 3,
b denotes 0 or 1,
m and n are integers such that the sum (n+m) ranges from about 1 to about 2000, n denotes a number from 0 to about 1999, and m denotes a number from about 1 to about 2000,
R1 is a monovalent group of formula —CqH2qL in which q is an integer from about 2 to about 8 inclusive and L is an optionally quaternized amino group chosen from the following groups:
—N(R2)—CH2—CH2—N(R8)2,
—N(R2)2,
—N+(R2)3Q−,
—N+(R2)(H)2Q−,
—N+(R2)2HQ−,
—N(R2)—CH2—CH2—N+(R2)(H)2Q−,
in which R2 is chosen from a hydrogen atom, a phenyl group, a benzyl group, a saturated monovalent hydrocarbon-based group, or a C1-C20 alkyl group, and Q− represents an anionic counterion, a halide ion, fluoride, chloride, bromide, or iodide;
(b) the compounds corresponding to formula (VI) below:
wherein in formula (VI):
R3 is chosen from a monovalent C1-C18 hydrocarbon-based group, a C1-C18 alkyl group, a C2-C18 alkenyl group, or methyl;
R4 is chosen from a divalent hydrocarbon-based group, a C1-C18 alkylene group, a divalent C1-C18 group, or a C1-C8, alkyleneoxy group;
Q− represents an anionic counterion chosen from halide ions or chloride;
r represents a mean statistical value from about 2 to about 20;
s represents a mean statistical value from about 20 to about 200 inclusive;
(c) quaternary ammonium silicones or silicones of formula (VII):
wherein in formula (VII):
R6 is chosen from a divalent hydrocarbon-based group, a C1-C18 alkylene group, a divalent C1-C18 group, or a C1-C8 alkyleneoxy group linked to the Si atom via a SiC bond;
R7, which may be identical or different, is chosen from a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, a C1-C18 alkyl group, a C2-C18 alkenyl group, a ring comprising 5 or 6 carbon atoms, or methyl;
R8, which may be identical or different, are each chosen from a hydrogen atom, a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, a C1-C18 alkyl group, a C2-C18 alkenyl group, or a group —R6—N(H)—C(O)—R7 with R6 and R7 as defined previously;
X−, which may be identical or different, is chosen from an anionic counterion, a halide ion, chloride, an anionic counterion derived from an organic acid, or (C1-C6)alkylcarboxylate;
r represents a mean statistical value ranging from about 2 to about 200 inclusive;
(d) the amino silicones of formula (VIII):
wherein in formula (VIII):
R1, R2, R3 and R4, which may be identical or different, are each chosen from a C1-C4 alkyl group, an aryl group, or phenyl,
R5 is chosen from a C1-C4 alkyl group or a hydroxyl group,
n and m, which may be identical or different, represent an integer ranging from about 1 to about 5 inclusive, and
x is such that the amine number ranges from about 0.01 meq/g to about 1 meq/g;
(e) the amino silicones bearing polyalkoxylene groups of formula (IX):
wherein in formula (IX):
Ra, Rb, Rc and Rd, which may be identical or different, are each chosen from a hydroxyl group, a linear or branched (C1-C10)alkyl group, a (C1-C6)alkyl group, a linear (C1-C6)alkyl group, or methyl;
ALK and ALK′, which may be identical or different, represent a linear or branched (C1-C10)alkylene group, a linear (C1-C10)alkylene group, or propylene;
A and B, which may be identical or different, represent an aminopolyalkoxy group below:
ReRfN-[ALK″-O]z-[ALK′″-O]w-ALKa-N(Rg)-[ALKb-O]q—*
wherein:
* representing the point of attachment of the radical to the rest of the molecule via ALK or ALK′;
Re, Rf and Rg, which may be identical or different, are each chosen from a hydrogen atom or a linear or branched (C1-C10)alkyl group;
ALK″ and ALK′″, which may be identical or different, are chosen from a linear or branched (C1-C10)alkylene, a C2 or C3 alkylene group, a divalent group —CH2—CH(CH3)—, or an ethylene group;
ALKa and ALKb, which may be identical or different, are chosen from a linear or branched (C1-C10)alkylene, a C2 or C3 alkylene group, an ethylene group, a propylene group, a divalent group —CH2—CH(CH3)—, or a divalent group —CH2—CH(OH)—CH2—; any of the above which are optionally substituted, or which are optionally substituted with a hydroxyl group;
q, which may be identical or different, represent 0 or 1;
w, which may be identical or different, represent an integer, such that the sum of the w values (w of A+w of B) having a mean value ranging from about 10 to about 100 inclusive;
z, which may be identical or different, represent an integer, such that the sum of the z values (z of A+z of B) having a mean value ranging from about 1 to about 20 inclusive;
(f) amino silicones bearing polyalkoxylene groups constituted of polysiloxane blocks and of polyalkoxylene blocks comprising at least one amine group, and amino silicones chosen from:
those of formula (X):
wherein in formula (X):
Ra, Rb, Rc and Rd, which may be identical or different, are chosen from a hydroxyl group, a linear or branched (C1-C10) alkyl group, a (C1-C4)alkyl group, a linear (C1-C4)alkyl group, or methyl;
R, which may be identical or different, represent a linear or branched C2-C6 alkylene radical, which is optionally hydroxylated and/or optionally interrupted with an oxygen atom;
a and b, which may be identical or different, represent a number ranging from about 0 to about 100;
R′, which may be identical or different, is chosen from a hydrogen atom, a C1-C4 alkyl radical, or a methyl radical;
x denotes an integer ranging from about 1 to about 500 and y denotes an integer ranging from about 1 to about 10;
those containing units of formula (XI)
wherein in formula (XI):
R1 to R4, which may be identical or different, is chosen from a C1-C4 alkyl radical or methyl;
R and R″, which may be identical or different, represent a linear or branched C2-C6 alkylene radical, which is optionally hydroxylated and/or optionally interrupted with an oxygen atom;
a and b, which may be identical or different, represent an integer ranging from about 0 to about 100;
R′ and R′″, which may be identical or different, are chosen from a hydrogen atom, a C1-C4 alkyl radical, or a methyl radical; and
x denotes a number ranging from about 1 to about 500 and y denotes a number ranging from about 1 to about 10;
those containing units of formula (XII) or of formula (XIII)
wherein in formulae (XII) and (XIII):
R, which may be identical or different, is chosen from a linear or branched divalent C2-C12 alkyl radical, an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a radical —CH2CH2CH2OCH(OH)CH2—, any of the above optionally comprising at least one heteroatom or oxygen;
R′, which may be identical or different, is chosen from a linear or branched divalent C2-C12 alkyl radical, an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, a radical —CH2CH2CH2OCH(OH)CH2—, or a radical —CH(CH3)—CH2—, any of the above optionally comprising at least one heteroatom or oxygen;
R″ is chosen from a hydrogen atom or a methyl radical;
x denotes an integer ranging from about 1 to about 10,000;
a represents an integer greater than or equal to 1; and
b represents an integer ranging from about 0 to about 200; or
mixtures thereof.

### Claim 9 (depends on 7)

The composition of claim 7, wherein the at least one amino silicone is amodimethicone.

### Claim 10 (depends on 7)

The composition of claim 7, wherein the total amount of the amino silicone ranges from about 0.1% to about 4% by weight, relative to the total weight of the composition.

### Claim 11 (depends on 1)

The composition of claim 1, further comprising at least one thickener.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the at least one thickener is chosen from hydroxyethylcellulose, steareth-100/PEG-136/HDI copolymer, hydroxypropylcellulose, methylhydroxyethylcellulose, methylethylhydroxyethylcellulose, acrylates/C10-30 alkyl acrylate crosspolymer, hydroxypropylguar, xanthan gum, hydroxypropyl starch phosphate, sodium polyacrylate, polyacrylate crosspolymer-6, or mixtures thereof.

### Claim 13 (depends on 11)

The composition of claim 11, wherein the total amount of the thickener ranges from about 0.01% to about 10% by weight, relative to the total weight of the composition.

### Claim 14 (depends on 1)

The composition of claim 1, further comprising at least one solvent.

### Claim 15 (depends on 14)

The composition of claim 14, wherein the at least one solvent is chosen from a monoalcohol, preferably a monoalcohol comprising from 2 to 6 carbon atoms, and preferably chosen from ethanol, propanol, isopropanol, butanol, or mixtures thereof.

### Claim 16 (depends on 11)

The composition of claim 11, wherein the total amount of the solvent ranges from about 0.01% to about 50% by weight, relative to the total weight of the composition.

### Claim 17 (depends on 1)

The composition of claim 1, further comprising at least one additional components chosen from nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants; fixing polymers; conditioning agents, cationic polymers; silicones; silicones other than the at least one amino silicone; chitosans, and derivatives of chitosan; UV-screening agents; fillers, nacres, titanium dioxide, resins, clays; fragrances; peptizers; vitamins; preserving agents; acidic agents; alkaline agents; reducing agents; oxidizing agents; direct dyes, cationic direct dyes, natural direct dyes; oxidation dyes; or a mixture thereof.

### Claim 18 (depends on 1)

The composition of claim 1, wherein the composition comprises a first part (A) and a second part (B), wherein:
the first part (A) comprises the at least one compound chosen from urea and urea derivatives; and
the second part (B) comprises the at least one polyol compound.

### Claim 19

A method for improving curl definition of keratin fibers, said method comprising applying to the keratin fibers a composition comprising:
a first part (A) comprising:
(a) at least one compound chosen from urea and urea derivatives; and
a second part (B) comprising:
(b) at least one polyol compound; and
heating the keratin fibers.

### Claim 20 (depends on 19)

The method of claim 19, wherein the heating is performed using a heating tool chosen from a straightening iron, a flat iron, a curling iron, a crimping iron, a waving iron, a hood, a hairdryer, an infrared heating system, or a heating roller.

### Claim 21 (depends on 19)

The method of claim 19, wherein the heating tool is at a temperature of up to about 210° C., preferably up to about 190° C., more preferably equal to or lower than 150° C., such as at a temperature of about 149° C.

### Claim 22 (depends on 19)

The method of claim 19, wherein:
the heating is performed with a flat iron at a temperature of from about 100° C. to about 190° C., and from one pass up to five passes of the flat iron is used per lock of keratin fibers.

### Claim 23 (depends on 22)

The method of claim 22, wherein:
the heating is performed with a flat iron at a temperature of about 149° C., and one pass of the flat iron is used per lock of keratin fibers.

### Claim 24 (depends on 19)

The method of claim 19, further comprising combing the keratin fibers after applying the composition to the keratin fibers.

### Claim 25 (depends on 19)

The method of claim 19, wherein:
when the composition comprises urea, the first part (A) and the second part (B) are mixed prior to application to the keratin fibers.

### Claim 26

A kit comprising a composition comprising:
a first part (A) comprising:
(a) at least one compound chosen from urea and urea derivatives; and
a second part (B) comprising:
(b) at least one polyol compound.
wherein parts (A) and (B) are packaged in separate compartments.