# US 2021/0290518 A1 · Multicomponent composition

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- Number: US 2021/0290518 A1
- Document ID: US20210290518A1
- Status: Published application
- Kind: A1
- Application number: 17/052,431
- Filed: 2019-03-27
- Published: 2021-09-23
- Earliest claimed: 2018-05-03
- Assignees: HFC Prestige International Holding Switzerland S.a.r.l
- Applicants: HFC Prestige International Holding Switzerland S.a.r.l.
- Inventors: Mathias Kurt Herrlein; Graham Neil McKelvey; Matija Crne; Corinne Mohr; Simon Paul Godfrey; Galina Gross; Tatjana Schaefer; Axel Meyer
- Web page: https://patentgrep.com/patent/US20210290518A1

## CPC

- A61K 8/8147: {Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers}
- A61K 8/84: obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes}
- A61Q 5/10: Preparations for permanently dyeing the hair
- D06P 3/145: {using polymeric dyes}
- D06P 3/146: {preparing non-azo dyes on the material}
- A61K 2800/43: Pigments; Dyes
- A61K 2800/4322: in preparations for temporarily coloring the hair further containing an oxidizing agent
- A61K 2800/624: by macromolecular compounds
- A61K 2800/88: Two- or multipart kits
- A61K 2800/884: Sequential application
- A61K 2800/95: Involves in-situ formation or cross-linking of polymers
- 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
- D06P: DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM

## Abstract

The instant disclosure generally relates to a multicomponent composition for coloring mammalian or synthetic keratin fibers, the multicomponent composition comprising first, second, third and fourth components. The first component includes an organic polymer, the second component includes an in situ linking material, the third component includes a base compound and the fourth component includes a catalyst or other substance. One or more of the components includes pigment microparticles. The multicomponent composition in situ links upon application, forms a solid coating on treated material such as hair and has a substantially long color remanence following development. Methods of using such compositions are also described herein.

## Claims

### Claim 1

A multicomponent in situ linkable composition for coloring treated material, comprising:
a first component comprising a linear or branched organic polymer having pendant or terminal or pendant and terminal first functional groups;
a second component comprising an in situ linking material having second functional groups;
a third component comprising a base compound having third functional groups;
pigment microparticles and medium in one or more of the first, second and third components, wherein
the first, second and third functional groups are complementary reactive pairs and are capable of forming covalent, coordinate, entanglement or electrostatic linkages in situ or any combination thereof among themselves.

### Claim 2 (depends on 1)

A multicomponent composition of any of claim 1 further comprising
a fourth component comprising a catalyst agent, an accelerator agent or an inorganic complexation agent, the agent being capable of promoting the covalent, ionic, entanglement, electrostatic or coordination in situ linkage or combination thereof among the first, second and third functional groups or any combination thereof, or the inorganic complexation agent capable of forming coordination linkages for the first component.

### Claim 3 (depends on 1)

A multicomponent composition according to claim 1 wherein
the first component comprises the linear or branched organic polymer comprising repeating units of a hydrophobic monomer or a hydrophilic monomer or a combination thereof;
the hydrophobic monomer is selected from one or more of an olefinic carboxylate ester monomer or one or more of a non-polar olefinic monomer or any combination thereof;
the olefinic carboxylate ester comprises an ester of an olefinic carboxylic acid and at least one saturated linear or branched C1 to C24 primary or secondary alcohol or a C4 to C24 cyclic alcohol;
the non-polar olefin monomer has the formula
H2C═CHR
wherein R is selected from hydrogen, linear or branched alkyl of one to twenty four carbons, unsubstituted phenyl or phenyl substituted by one or more linear or branched alkyl of 1 to twenty four carbons, a vinyl group or a polyester polyol group having terminal and/or pendant hydroxyl groups, or R is selected from —CR2═CHR1 wherein R1 is hydrogen, methyl, ethyl or phenyl and R2 is hydrogen or methyl;
the hydrophilic olefinic monomer is selected from a hydroxyl ester of an olefinic carboxylic acid and a linear or branched alkyl diol of 2 to 24 carbons or a cyclic alkyl diol of 5 to 24 carbons; or an aminoalkyl ester of an olefinic carboxylic acid and a linear or branched aminoalkyl alcohol of 2 to 24 carbon or a cyclic aminoalkyl alcohol of 5 to 24 carbons; or a thioalkyl ester of an olefinic carboxylic acid, and a linear or branched thioalkyl alcohol of 2 to 24 carbons or a cyclic thioalkyl alcohol of 5 to 24 carbons, an olefinic acid, vinyl alcohol, or a polar styrene compound selected from hydroxy styrene, carboxy styrene, carboxamido styrene or styrene sulfonate; or is any combination of two or more of the hydroxyl ester, the aminoalkyl ester, the thioalkylester, the olefinic acid or the polar styrene compound;
the olefinic carboxylic acid is an alkenoic acid of 3 to 24 carbons or alkendioic acid of 4 to 24 carbons or partially hydrolyzed polyacrylonitile or any combination thereof;
the organic polymer comprises at least two pendant or terminal or pendant and terminal first functional groups which are selected from a hydroxyl group, a carboxylic acid group, an amine group, a mercapto group, a sulfonic acid group, a sulfinic acid group, a vinyl group, an olefinoyloxy group, alkynyl group or a combination thereof;
or the first functional group is the residue of a polymerized alkenylalkylalkoxysilane monomer of the formula
H2C═CH—(CH2)n—Oj—Si(R1)a(R2)3-a
wherein n is an integer of 0 to 6, j is zero of 1, R1 is alkoxy of 1 to 3 carbons or OH, an —OAc group, a —O—N═CHR1 group or a —CH═CH2 group, R2 is alkyl of 1 to 3 carbons and a is an integer 1, 2 or 3;
the in situ linking material comprises an organic core comprising a saturated aliphatic compound, aromatic compound, polymeric compound designated as Cpd or a silicone core comprising a siloxane, a polysiloxane, a polyorganosiloxane or a polysilicone designated as Sicpd,
wherein the organic core or the silicone core has at least two pendant or terminal or pendant and terminal second functional groups, and
wherein the saturated aliphatic compound comprises a linear or branched alkyl group of 2 to 24 carbons or is a cyclic alkyl group of 5 to 24 carbons; the aromatic compound comprises a phenyl, naphthyl, diphenylmethyl, pyridyl, quinolinyl, quinazolinyl or anthracenyl group;
the polymeric compound Cpd comprises a poly(meth)acrylate with methyl or ethyl ester groups except for the second functional groups, polycrotonate with methyl or ethyl ester groups except for the second functional groups, a polyether, a polyol, a polyurethane, a polyurea, a polyester of a diacid and a diol or of a hydroxy acid, a polymer of one or more monomers of C1-C6 alkyl (meth)acrylate, styrene and a C6-C12 olefin; the polymeric compound Cpd has a weight average molecular weight of from about 0.2 kDa to about 10 kDa;
the silicone core, Sicpd comprises a silane, a di, tri or tetrasilane, an oligosilane, a siloxane, a di, tri or tetrasiloxane, a polysiloxane, a poly organosiloxane, a polyorganosilicone wherein organo groups, if any, are C1-C3 alkyl groups, the Sicpd compound having a weight average molecular weight of from about 0.2 kDa to about 10 kDa; and
wherein each second functional group independently has the structure of Formula I
—R—Oq-R′—X Formula I
wherein (i) the designator q is zero or one;
(ii) R is a C6-C10 aromatic group, a C1-C24 alkyl or a C1-C24 oxyalkyl residue or a dimethylsiloxanyl chain of 3 to 9 —O—Si(Me)2- units and the valence bond of R is attached to directly to the organic core or attached through an ether oxygen to the organic core, or
(iii) R is a C1-C24 alkylenyl residue, a C1-C24 oxyalkylenyl residue or a C1-C24 carbonylalkenyl residue and the valence bond of R is attached directly or through an ether oxygen —O— to the silicone core, Sicpd;
and,
(iv) R′ is a linear or branched alkyl or alkanoxyalkyl or alkanaminoalkyl group of the Formula III or is a bond when all designators m, n, p, r, z and s are zero;
[—(C1-C6)m-] or [—(C1-C6)n—(CHOH)p(C1-C6)r-Yz—(C1-C6)s-] Formula III
wherein the C1-C6 group is a linear or branched alkyl group of 1 to 6 carbons and the designators m, n, r and s associated with each C1-C6 indicates the total number of carbons possible for the group, the maximum being 24; m is zero or an integer of 1 to 4, n is zero or an integer of 1 to 4, p is zero or one, r is zero or an integer of 1 to 4, z is zero or 1, s is zero or an integer of 1 to 4, Y is O or N;
X is isocyanato, thioisocyanato, linear, branched or cyclic epoxy, olefinoyloxy, malonic anhydrido, formyl, amino, hydroxyl, mercapto, furanyl, cyclopentadienyl or azido;
or
X of Formula I is a mono, di, tri or tetra dimethyl siloxane group to which is terminally bonded —Si(R1)a(R2)3-a wherein leis alkoxy of 1 to 6 carbons or OH, an —OAc group, a —O—N═CHR1 group, or hydrogen, R2 is alkyl of 1 to 3 carbons and a is an integer 1, 2 or 3.

### Claim 4 (depends on 3)

A multicomponent composition of claim 3 wherein the first and second functional groups are reactive pairs and the reactive pairs are isocyanate/thioisocyanato and hydroxyl, amine or mercapto or any combination of hydroxyl, amine and mercapto; carboxyl and hydroxyl, amine or mercapto or any combination of hydroxyl, amine and mercapto; epoxy and hydroxyl, amine or mercapto or any combination of hydroxyl, amine and mercapto; cyclohexylepoxy and hydroxyl, amine or mercapto or any combination of hydroxyl, amine and mercapto; (meth)acryloxy and hydroxyl, amine or mercapto or any combination of hydroxyl, amine and mercapto; melonic anhydride and hydroxyl, amine or mercapto or any combination of hydroxyl, amine and mercapto; formyl and amine or mercapto or any combination of amine and mercapto; azido and alkynyl; vinyl and mercapto; mercapto and mercapto; and Si—OH and Si—OR or Si—OH and Si—OH or Si—OR and Si—OR.

### Claim 5 (depends on 3)

A composition according to claim 3 wherein the olefinic carboxylic acid is selected from one or more of (meth)acrylic acid, crotonic acid, pentenoic acid, hexenoic acid, maleic acid, fumaric acid, glutaconic acid, itaconic acid, citraconic acid, mesaconic acid or any combination thereof.

### Claim 6 (depends on 3)

A composition according to claim 3 wherein the ester alcohol is a C1-C6 linear, branched or cyclic primary or secondary alcohol, an ester amino alcohol is amino ethanol, amino propanol or aminobutanol, the ester diol is ethylene diol, propylene diol, butylene diol, pentylene diol or cyclohexane diol; and the ester mercapto alcohol is mercaptoethanol, mercaptopropanol or mercapto butanol.

### Claim 7 (depends on 3)

A composition according to claim 3 wherein the organic polymer is essentially free to completely free of the non-polar olefinic monomer.

### Claim 8 (depends on 3)

A composition according to claim 3 wherein the non-polar olefinic monomer is present.

### Claim 9 (depends on 3)

A composition of claim 3 wherein the third component comprises the base compound having a weight average molecular weight of about 150 Da to about 1 MDa and the base compound is selected from aminosilane, aminosiloxane, aminosilicone or a linear or branched polymer comprising linear polyethyleneimine, branched polyethylene imine, a copolymer of aminoethyl (meth)acrylate and ethyl (meth)acrylate, polyallylamine hydrochloride, polydiallyldimethyl ammonium chloride, polyvinylamine, (vinylamine-styrene) copolymer, poly(omega-aminoalkyl(meth)acrylate), polyvinylpyrrolidone poly (2-oxazoline) and random or block copolymers thereof and mixtures thereof.

### Claim 10 (depends on 9)

A composition according to claim 9 wherein the in situ linking material contains amine groups as the second functional group, the organic polymer is a copolymer of alkyl (meth)acrylate, hydroxyalkyl (meth)acrylate, optional styrene, from 2 to 10 mole percent (meth)acrylic acid, the base compound is polyethyleneimine and the fourth component is an aliphatic carbodiimide.

### Claim 11 (depends on 10)

A multicomponent composition of claim 10 wherein:
the organic polymer is a copolymer of ethyl (meth)acrylate, C2-C6 hydroxyalkyl (meth)acrylate and about 0.1 to about 5 wt % of (meth)acrylic acid relative to the weight of the organic polymer;
the in situ material comprises unimolecular and/or oligomeric and/or polymeric versions of one or more of toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, bis isocyanatocyclohexyl methane, isophorone diisocyanate, trimethylolpropane tri-hexamethylene diisocyanate adduct, biuret triisocyanate, isocyanurate triisocyanate, uretdione hexamethylene diisocyanate, trimers of hexamethylene diisocyanate, or a blocked polyisocyanate of hexamethylene diisocyanate and a phenol, E-caprolactom, butanone oxime or dimethyl pyrazole blocker;
the base compound comprises polyethyleneimine;
the agent is a catalyst for the conversion of isocyanate to urethane and/or urea groups.

### Claim 12 (depends on 3)

A composition according to claim 3 wherein the olefinic monomer comprises styrene, butadiene, phenyl butadiene, isoprene, 4-vinylbenzenecarboxamide, 4-vinyl benzoic acid, ethyl 4-vinyl benzoate, vinyl phenol, 4-vinyl-1-hydroxymethyl benzene, butene, pentene, hexene, divinyl benzene or any combination thereof.

### Claim 13 (depends on 3)

A multicomponent composition of claim 3 wherein the base compound is polyethyleneimine.

### Claim 14

(canceled)

### Claim 15 (depends on 1)

A multicomponent composition of claim 1 wherein a dispersion of pigment microparticles and dispersant is incorporated in any one of the first, second and third components, in any two of the components or in all three of the components.

### Claim 16

A multicomponent composition comprising:
a first component comprising an organic polymer;
a second component comprising an in situ linking material;
a third component comprising a base compound;
pigment particles in one or more of the first, second and third components; wherein,
the organic polymer comprises a copolymer of a hydrophobic monomer and hydrophilic monomer, the hydrophobic monomer comprising a C1-C24 alkyl linear or branched (meth)acrylate monomer or a C1-C24 alkyl linear or branched crotonate monomer and styrene or a combination thereof wherein the styrene is present at a weight percentage amount of from none up to about 50 wt % relative to the total weight of the organic copolymer; and the hydrophilic monomer comprising an olefinic acid selected from (meth)acrylic acid or crotonic acid or a combination thereof, and a hydroxyalkyl olefinic ester selected from hydroxymethyl or hydroxyethyl (meth)acrylate or crotonate or any combination thereof;
the in situ linking material comprises toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, bis isocyanatocyclohexyl methane, isophorone diisocyanate, trimethylolpropane tri-hexamethylene diisocyanate adduct, biuret triisocyanate, isocyanurate triisocyanate, uretdione hexamethylene diisocyanate, trimers of hexamethylene diisocyanate, or a blocked polyisocyanate of hexamethylene diisocyanate and a phenol, E-caprolactom, butanone oxime or dimethyl pyrazole blocker;
the base compound comprises an aminosilane, aminosiloxane, aminosilicone or a linear or branched polymer comprising linear polyethyleneimine, branched polyethylene imine, a copolymer of aminoethyl (meth)acrylate and ethyl (meth)acrylate, polyallylamine hydrochloride, polydiallyldimethyl ammonium chloride, polyvinylamine, (vinylamine-styrene) copolymer, poly(omega-aminoalkyl(meth)acrylate), polyvinylpyrrolidone poly (2-oxazoline) and random or block copolymers thereof and mixtures thereof wherein the base compound has a weight average molecular weight of about 150 Da to about 1 MDa;
the acid number of the organic copolymer is in a range of about 7 to about 90;
the hydroxyalkyl olefinic ester portion of the organic copolymer is in a range of about 1-5 wt % relative to the total weight of the organic copolymer;
the molar ratio of free isocyanate groups to hydroxyl groups is in a range of about 0.5:2 to 25:1, preferably about 1:1 to about 15:1.

### Claim 17 (depends on 16)

A multicomponent composition of claim 16 wherein the base compound is polyethyleneimine at a concentration of 0.1-5% in medium relative to the total weight of the combination of the base compound and the medium.

### Claim 18 (depends on 16)

A multicomponent composition of claim 16 wherein the weight percentage of the organic polymer and the in situ linking material is between 1-20 wt. %, preferably about 1-10 wt %, more preferably 2-8 wt % of the combined first and second components.

### Claim 19 (depends on 16)

A multicomponent composition of claim 16, wherein the organic copolymer comprises ethyl (meth)acrylate, hydroxyethyl (meth)acrylate and (meth)acrylic acid and styrene at a weight percentage relative to the total weight of the organic copolymer of from none up to about 30 wt %.

### Claim 20

(canceled)

### Claim 21

A multicomponent composition comprising:
a first component comprising an organic polymer;
a third component comprising a base compound;
a fourth component;
the organic polymer comprising repeating units of a first hydrophobic monomer and a first hydrophilic monomer; wherein
the first hydrophobic monomer is selected from a non-polar olefinic monomer having the formula
H2C═CHR
wherein R is selected from hydrogen, ethyl, propyl, isopropyl, butyl, phenyl, hydroxyphenyl, nitrile or —CR2═CHR1 wherein R1 is hydrogen, methyl, ethyl or phenyl; wherein R2 is H or methyl; or any combination thereof;
the first hydrophilic olefinic monomer comprises an olefinic carboxylic acid wherein the the olefinic carboxylic acid comprises alkendioic acid of 3 to 12 carbons or alkenoic acid of 3 to 12 carbons;
the base compound comprising the base compound comprises an aminosilane, aminosiloxane, aminosilicone or a linear or branched polymer comprising linear polyethyleneimine, branched polyethylene imine, a copolymer of aminoethyl (meth)acrylate and ethyl (meth)acrylate, polyallylamine hydrochloride, polydiallyldimethyl ammonium chloride, polyvinylamine, (vinylamine-styrene) copolymer, poly(omega-aminoalkyl(meth)acrylate), polyvinylpyrrolidone poly (2-oxazoline) and random or block copolymers thereof and mixtures thereof;
the fourth component comprising a catalyst, coordination agent or free radical initiator for producing covalent, ionic, electrostatic or coordination among the copolymer molecules of the first component;
pigment particles in the first or third component or in both of the first and third components;
the first, third and fourth components being separate.

### Claim 22 (depends on 21)

A multicomponent composition of claim 21 wherein the polymer component of the first component has a weight percentage of about 1 wt % to about 40 wt % relative to the total weight of the first component and the base compound has a weight average molecular weight of about 150 Da to about 1 MDa.

### Claim 23 (depends on 21)

A multicomponent composition of claim 21 wherein the organic copolymer comprises a polymer of styrene, butadiene and itaconic or (meth)acrylic acid wherein the weight percentages respectively are between about 5-50 wt. % of styrene, about 50-95 wt. % butadiene, and about 0-5 wt. % itaconic or (meth) acrylic acid.

### Claim 24 (depends on 21)

A multicomponent composition of claim 21 wherein the fourth component is a carbonate salt of a cation selected from an alkali or alkali earth metal or transition metal.

### Claim 25

(canceled)

### Claim 26 (depends on 21)

A multicomponent composition of claim 21 further comprising a second component comprising a tri or tetra mercaptan or a combination of the tri or tetramercapton and a free radical initiator.

### Claim 27

(canceled)

### Claim 28 (depends on 3)

The composition of claim 3, wherein at least one portion of the pigment microparticles is an organic pigment.

### Claim 29 (depends on 3)

A composition of claim 3 further comprising one or more of a medium, plasticizer, a dispersant, wetting agent, anti-agglomeration agent, preservative, fragrance, an organic dye compound, a feel modification agent or a thickening agent; the dispersant, anti-agglomeration agent capable of providing dispersion of the pigment particles, the plasticizer and thickener capable of providing viscosity parameters to enable flow and hold of the composition on the keratin fibers.

### Claim 30 (depends on 3)

A kit comprising a multicompartment container, each container comprising one of the first, second and third components of the multicomponent composition of claim 3.

### Claim 31 (depends on 30)

A method for coloring treated material comprising applying first to the treated material the third component of claim 30 to form pretreated treated material and optionally at least partially drying the third component on the treated material.

### Claim 32 (depends on 30, 31)

A method of claim 31 further comprising combining the first and second components of claim 30 to form to form an in situ coloring mixture, applying the in situ coloring mixture to the pretreated treated material and causing the in situ coloring mixture to form a colored coating on the treated material.

### Claim 33 (depends on 32)

A colored coating for hair strands produced according to the method of claim 32.

### Claim 34

(canceled)

### Claim 35 (depends on 33)

A color removal composition for applying to color coated hair strands comprising applying one or more of surfactant, solvent, acid, base, polymer, polyelectrolyte, source of fluorine, salt source of fluorine, and/or ionic liquid whereby the composition is capable of removing the color coating of claim 33.

### Claim 36

(canceled)