US 6,616,709 B2Granted

Hair dye composition

AssigneeKao Corporation

InventorsYukihiro Ohashi, Hajime Miyabe, Kenichi Matsunaga, Shintaro Totoki, Yoshinori Saito

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Abstract

Provided is a hair dye composition containing a direct dye (1). This hair dye composition has markedly high hair dyeing power, has less color fade over time and undergoes a small change in the color tone of the dye after storage. wherein, ring A may represents a benzene ring which may have a substituent or the like, B represents an aryl or heterocyclic group, D represents N or CR4 (wherein R4 represents H or alkyl), E represents NR5, CR6R7 or CR6═CR7 (wherein R5 represents alkyl or the like, and R6 and R7 each represents H or alkyl) or, O or S, R1 represents alkyl or the like, and n stands for 0 or 1, with the proviso that at n=0, R2 and R5 form, when taken together with N—C—C, a heterocycle, or R2 is bonded to B, thereby forming a heterocycle and at n=1, R2 and R3 form, when taken together with C═D—N, a heterocycle, and X− represents an anion.

Claims17

Dependent claims

A hair dye composition, comprising:

a one-part aqueous formulation containing a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent;
and
X− represents an anion, the composition having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent and containing at least one cosmetic ingredient selected from the group consisting of hydrocarbons, animal or vegetable fats and oils, fatty acids, organic solvents, hair penetration promoters, cationic surfactants, natural or synthetic polymers, alcohols, ethers, amphoteric surfactants, nonionic surfactants, protein derivatives, amino acids, antiseptics, chelating agents, stabilizing agents, antioxidants, plant extracts, crude drug extracts, vitamins, colorants, perfumes, aerosolizing agents and UV absorbers.

8 more elements

A hair dye composition, comprising:

a two-part aqueous formulation comprising, in a first part, a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent;
and
X− represents an anion;
the first part having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent;
and
a second part, comprising an aqueous solution of an oxidizing agent.

11 more elements

A hair dye composition, comprising:

a three-part aqueous formulation comprising, in a first part, a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent;
and
X− represents an anion;
the first part having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent;
a second part, comprising an aqueous solution of an oxidizing agent;
and
a third part, comprising a powdered oxidizing agent.

12 more elements

A method of dyeing hair, comprising:

treating the hair with a one-part aqueous formulation containing a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent;
and
X− represents an anion;
the composition having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent and containing at least one cosmetic ingredient selected from the group consisting of hydrocarbons, animal or vegetable fats and oils, fatty acids, organic solvents, hair penetration promoters, cationic surfactants, natural or synthetic polymers, alcohols, ethers, amphoteric surfactants, nonionic surfactants, protein derivatives, amino acids, antiseptics, chelating agents, stabilizing agents, antioxidants, plant extracts, crude drug extracts, vitamins, colorants, perfumes, aerosolizing agents and UV absorbers.

9 more elements

A method of dyeing hair, comprising:

treating the hair with a two-part aqueous formulation comprising, in a first part, a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent;
and
X− represents an anion;
the first part having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent;
and
a second part, comprising an aqueous solution of an oxidizing agent.

11 more elements

A method of dyeing hair, comprising:

treating the hair with a three-part aqueous formulation comprising, in a first part, a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent;
and
X− represents an anion;
the first part having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent;
a second part, comprising an aqueous solution of an oxidizing agent;
and
a third part, comprising a powdered oxidizing agent.

12 more elements

A hair dye composition, comprising:

a one-part aqueous formulation containing a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent and with the proviso that the group in formula (1) of —CR2═D—(NR3)n—B can not be an amino substituted quinoline group;
and
X− represents an anion, the composition having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent and containing at least one cosmetic ingredient selected from the group consisting of hydrocarbons, animal or vegetable fats and oils, fatty acids, organic solvents, hair penetration promoters, cationic surfactants, natural or synthetic polymers, alcohols, ethers, amphoteric surfactants, nonionic surfactants, protein derivatives, amino acids, antiseptics, chelating agents, stabilizing agents, antioxidants, plant extracts, crude drug extracts, vitamins, colorants, perfumes, aerosolizing agents and UV absorbers.

8 more elements

A hair dye composition, comprising:

a two-part aqueous formulation comprising, in a first part, a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent and with the proviso that the group in formula (1) of —CR2═D—(NR3)n—B can not be an amino substituted quinoline group;
and
X− represents an anion;
the first part having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent;
and
a second part, comprising an aqueous solution of an oxidizing agent.

11 more elements

A hair dye composition, comprising:

a three-part aqueous formulation comprising, in a first part, a direct dye compound represented by formula (1):
wherein, ring A represents a benzene ring which may have a substituent and may be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R2 to form a heterocyclic structure, or a heterocyclic group which may have a substituent or may be coupled with R2 to form a heterocyclic structure,
D represents a nitrogen atom or a group CR4, wherein R4 represents a hydrogen atom or a C1-6 alkyl group;
E represents a group NR5, CR6R7 or CR6═CR7, wherein R5 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R2, a ring, and R6 and R7 each independently represents a hydrogen atom or a C1-6 alkyl group, an oxygen atom or a sulfur atom;
R1 represents a C1-6 alkyl group which may have a substituent, a C2-6 alkenyl group which may have a substituent or an aryl group which may have a substituent;
R2 represents a divalent group bonded to B or forms a ring, when taken together with R3 or R5,
R3 forms a ring when taken together with R2;
n is 0 or 1, with the proviso that when n=0, R2 and R5, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R2 is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R2 and R3, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent and with the proviso that the group in formula (1) of —CR2═D—(NR3)n—B can not be an amino substituted quinoline group;
and
X− represents an anion;
the first part having a pH ranging from 6-11 that is adjusted to within said range by an alkali agent;
a second part, comprising an aqueous solution of an oxidizing agent;
and
a third part, comprising a powdered oxidizing agent.

12 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/887,473Filed 25 Jun 2001
Priority: JP 2000-19317527 Jun 2000
Published: US 2002/0088063 A111 Jul 2002
Granted: 9 Sep 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61K 8/492
Having five membered rings, e.g. pyrrolidone carboxylic acid: having condensed rings, e.g. indol
A61K 8/4926
With one nitrogen as the only hetero atom: having six membered rings
A61K 8/4946
With more than one nitrogen as the only hetero atom: imidazoles or their condensed derivatives, e.g. benzimidazoles
A61K 8/498
With oxygen as the only hetero atom: having 6-membered rings or their condensed derivatives, e.g. coumarin