# US 11,298,305 B2 · Compositions and methods for improving the appearance of the hair

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- Number: US 11,298,305 B2
- Document ID: US11298305B2
- Status: Granted
- Kind: B2
- Application number: 16/313,702
- Filed: 2016-06-30
- Published: 2019-06-06
- Granted: 2022-04-12
- 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/US11298305B2

## 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 method for improving curl definition of keratin fibers curly hair, 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 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; at least one aminosilicone; and at least one solvent chosen from a monoalcohol; wherein the weight ratio of the total amount of compound chosen from urea and urea derivatives, to the total amount of polyol, ranges from about 0.1 to about 1.5;
and
heating the keratin fibers to a temperature of at least 100° C.;
wherein the method does not include a fixing step.

### Claim 2 (depends on 1)

The method of claim 1, 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, wherein the heating tool is heated at a temperature of up to about 210° C.

### Claim 3 (depends on 1)

The method of claim 1, wherein: the keratin fibers are heated-with a flat iron at a temperature of from about 100° C. to about 190° C., and wherein the flat iron is passed over the keratin fibers for one to five passes per lock of keratin fibers.

### Claim 4 (depends on 3)

The method of claim 3, wherein: the keratin fibers are heated with a flat iron at a temperature of about 149° C., and wherein the flat iron is passed over the keratin fibers once per lock of keratin fibers.

### Claim 5 (depends on 1)

The method of claim 1, wherein: the composition comprises urea, and wherein the first part (a) and the second part (b) are mixed prior to application to the keratin fibers.

### Claim 6 (depends on 1)

The method 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 7 (depends on 1)

The method of claim 1, wherein the total amount of the at least one 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 8 (depends on 1)

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

### Claim 9 (depends on 1)

The method of claim 1, wherein the at least one amino silicone is chosen from:
(a) 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, phenyl, hydroxyl (—OH), C1-C8 alkyl, methyl, C1-C8 alkoxy, or methoxy group,
a is the number 0 or an integer from 1 to about 3,
b is 0 or 1,
m and n are integers such that the sum (n+m) ranges from about 1 to about 2000, n is a number from 0 to about 1999, and m is a number from about 1 to about 2000,
R1 is a monovalent group of formula —CqH2qL wherein 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−,
wherein 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) 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, is 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;
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) 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 a phenyl group,
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) 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:
* represents the point of attachment of the aminopolyalkoxy group 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—;
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 of A and the w of B have a 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 of A and the z of B have a 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:
(1) amino silicones 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;
(2) amino silicones containing units of formula (XI)
wherein in formula (XI):
R1, R2, R3, and R4, which may be identical or different, are 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 is a number ranging from about 1 to about 500 and y is a number ranging from about 1 to about 10;
(3) amino silicones 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—;
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;
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 10 (depends on 1)

The method of claim 1, wherein the at least one amino silicone is amodimethicone.

### Claim 11 (depends on 1)

The method of claim 1, 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 12 (depends on 1)

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

### Claim 13 (depends on 12)

The method of claim 12, 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 14 (depends on 12)

The method of claim 12, 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 15 (depends on 1)

The method of claim 1, 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.