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Polymeric hair dyes

IP.com Disclosure Number: IPCOM000167068D
Publication Date: 2008-Jan-30

Publishing Venue

The IP.com Prior Art Database

Abstract

Disclosed are polymeric dyes represented by formulas (1a), (1b) and (1c) comprising a polymer backbone and a residue of an organic dye. The dyes are distinguished by their depth of shade and their good fastness properties to washing, such as, for example, fastness to light, shampooing and rubbing.

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Polymeric hair dyes

The present invention relates to novel polymeric dyes and compositions comprising these compounds, to a process for their preparation and to their use for dyeing of organic materials, such as keratin-containing fibers, wool, leather, silk, cellulose or polyamides.
5

It is well known that cationic compounds have a good affinity to negative charged hair. These characteristics have been used to contact the hair with small molecules, but also with polymers.

    Numerous cationic polymeric dyes have been disclosed for use as a colorant for human hair, 10
for example in US 4,228,259, US 4,182,612 or FR 2 456 764. These references teach that the polymer moiety has the cationic charge.

Surprisingly it was found that very good dyeing results are obtainend with polymeric hair dyes wherein the cationic charge is located in dye moiety.
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Therefore the present invention relates to polymeric dyes of formula (1a)

(1a)

(Y2b+)

b An2-

X2

*

A B

a An1-

m *

;

    X1 (Y1a+)

n

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(Y2b+)

X2

b An2-

(1b)

*

A B

m A

* ; or

a An1-

X1

n

   a An1- X1

(Y1a+)

(Y1a+)

p

; wherein

A and B, independently from each other represent a polymer backbone;

X1 and X2 independently from each other are a linkage group selected from -C1-C30alkylene- or -C2-C12alkenylene-, which is interrupted and/or terminated at one or both ends by one 5
or more than one -S-, -N-, -N=-, -N(R1)-, -S(O)-, -SO2-, -(CH2CH2-O)1-5-,

-(CH2CH2CH2-O)1-5-, -C(O)-, -C(O)O-, -OCO-, N+

R1

R2

(1c)

a An1-

    A B
X1 (Y1a+) m n A p X2 (Y2b+) b An2-

, -CON(R1)-, -C(NR1R2)2-,

-(R1)NC(O)- , -C(S)R1-; or an optionally substituted, saturated or unsaturated, fused or non-fused aromatic or nonaromatic (heterocyclic) bivalent radical optionally comprising at least one heteroatom; a saturated or unsaturated, fused or non-fused aromatic or
10
nonaromatic bivalent radical comprising at least one heteroatom, which is optionally substituted by C1-C30alkyl, C1-C30alkoxy, C2-C12alkenyl, C5-C10aryl, C5-C10cycloalkyl, C1- C10alkyl(C5-C10arylene), hydroxy or halogen;

R1 and R2 independently from each other are hydrogen; unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C1-
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   C14alkyl; C2-C14alkenyl; C6-C10aryl; C6-C10aryl-C1-C10alkyl; or C5-C10alkyl(C5-C10aryl); Y1 and Y2 independently from each other are a residue of an organic dye; or hydrogen; wherein at least one of Y1 and Y2 is a residue of an organic dye;

An1, An2 and An3, independently from each other are an anion;
a and b independently from each other are a number from 1 to 3;
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m is a number from 0 to 5000;
n is a number from 0 to 5000; and
p is a number from 1 to 5000;
wherein the sum of m + n + p ≥ 3.

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   C1-C14alkyl is for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2'-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl, n-octyl, 1,1',3,3'-tetramethylbutyl or 2-ethyl...