Dye fixing agents for improving fastness and methods for their preparation

Abstract

The presently claimed invention relates to a dye fixing agent and a method for its preparation. The dye fixing agent is obtainable by polymerizing at least one aromatic sulfonic acid or sulfonate, at least one substituted phenol or salt thereof, and at least one aldehyde; with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

Description

[0001] Meissner Bolte M / ARCH-023-PC

[0002] Dye fixing agents for improving fastness and methods for their preparation

[0003] Field of the invention

[0004] The presently claimed invention relates to dye fixing agents for improving fastness and methods for their preparation. Particularly, the presently claimed invention relates to improving wet fastness of fabric materials.

[0005] Background of the invention

[0006] Polyamides, such as nylon, are widely used in textiles for the preparation of apparels and footwear such as workwear, yoga wear, swimwear, shoes and socks. Polyamides are characterized by an excellent wear resistance, high strength, elasticity and other advantages. In order to improve the comfort and breathability, polyamides are often blended with spandex. Acid dyes are commonly used for dyeing polyamides and its blends. Acid dyes bear groups such as amino, hydroxyl, and sulfonic acid, which imparts water-solubility and interacts with nylon through ionic bonds, hydrogen bonds, and Van der Waal’s forces. However, the good water solubility of acid dyes and their weak interaction with polyamide fibres through weak hydrogen bond and Van der Waal’s forces is also responsible for easy removal of the acid dyes from polyamide fibres and its blends during wearing and due to the action of detergents, sweat, and friction, resulting in a poor wet fastness, alkali sweat fastness, and friction fastness of the dyed polyamide fabrics and its blends.

[0007] Therefore, after dyeing with acid dyes, polyamide fabrics and its blends are usually subjected to treatment with a dye fixing agent to improve their fastness properties.

[0008] Commonly used dye fixing agents for polyamide fabrics and its blends are based on the synthetic tannin route, among which sulfonated phenolic resins and bisphenol S formaldehyde resins are most widely used.

[0009] However, these types of resins contain residues such as phenol, bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S, which are hazardous. Accordingly, these resins do not meet the increasingly stringent textile regulations and the requirements of major brands.

[0010] Accordingly, it is an object of the presently claimed invention to provide dye fixing agents for polyamides and its blends that do not contain hazardous residues such as phenol, bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S. It is desired that dye fixing agents have a good wet fastness and alkali sweat fastness. Further, it is desired that the dye fixing agents have improved properties such as dye blocking effect, chlorine fastness, and dye levelness, i.e. uniformity of color shade along the substrate to be dyed, especially in case of blends. It is also an object of the present invention to provide a method for the preparation dye fixing agents.

[0011] Summary of the invention

[0012] It was surprisingly found that the dye fixing agents of the presently claimed invention provide a good dye fixing effect for polyamide fabrics and its blends. Further, the dye fixing agents provide an improved wet fastness and alkali sweat fastness to the polyamide fabrics and its blends. Furthermore, the dye fixing agents provide improved dyeing properties such as dyeMeissner Bolte M / ARCH-023-PC

[0013] blocking effect, chlorine fastness, and anti-staining effect. The dye fixing agents of the presently claimed invention are environmentally friendly as they do not contain hazardous residues such as phenol, bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S. Accordingly, an aspect of the presently claimed invention is directed to a dye fixing agent obtainable by polymerizing

[0014] a. at least one aromatic sulfonic acid or sulfonate;

[0015] b. at least one substituted phenol or salt thereof; and

[0016] c. at least one aldehyde;

[0017] with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

[0018] Another aspect of the presently claimed invention is directed to a method for preparing the dye fixing agents.

[0019] Another aspect of the presently claimed invention is directed to an aqueous composition comprising the dye fixing agent.

[0020] Another aspect of the presently claimed invention is directed to use of the dye fixing agent for improving wet fastness of a textile material.

[0021] Another aspect of the presently claimed invention is directed to a method for improving wet fastness of a textile material comprising treating the textile material with the dye fixing agent. Yet another aspect of the presently claimed invention is directed to a treated textile material obtainable by treatment of a textile material with the dye fixing agent or with an aqueous composition comprising with the dye fixing agent or by the method of the presently claimed invention or by use of the dye fixing agent according to the presently claimed invention.

[0022] Detailed description of the invention

[0023] Before the present compositions and formulations of the presently claimed invention are described, it is to be understood that this invention is not limited to particular compositions and formulations described, since such compositions and formulation may, of course, vary. It is also to be understood that the terminology used herein is not intended to be limiting, since the scope of the presently claimed invention will be limited only by the appended claims.

[0024] If hereinafter a group is defined to comprise at least a certain number of embodiments, this is meant to also encompass a group which preferably consists of these embodiments only. Furthermore, the terms 'first', 'second', 'third' or 'a', 'b', 'c', etc. and the like in the description and in the claims, are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the presently claimed invention described herein are capable of operation in other sequences than described or illustrated herein. In case the terms 'first', 'second', 'third' or '(A)', '(B)' and '(C)' or '(a)', '(b)', '(c)', '(d)', 'i', 'ii' etc. relate to steps of a method or use or assay there is no time or time interval coherence between the steps, that is, the steps may be carried out simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks,Meissner Bolte M / ARCH-023-PC

[0025] months or even years between such steps, unless otherwise indicated in the application as set forth herein above or below.

[0026] Furthermore, the ranges defined throughout the specification include the end values as well i.e. a range of 1 to 10 implies that both 1 and 10 are included in the range. For the avoidance of doubt, applicant shall be entitled to any equivalents according to applicable law.

[0027] In the following passages, different aspects of the presently claimed invention are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.

[0028] Reference throughout this specification to 'one embodiment' or 'an embodiment' means that a particular feature, structure or characteristic described in connection with the embodiment is included in at least one embodiment of the presently claimed invention. Thus, appearances of the phrases 'in one embodiment' or 'in an embodiment' in various places throughout this specification are not necessarily all referring to the same embodiment but may refer to so. Furthermore, the particular features, structures or characteristics may be combined in any suitable manner, as would be apparent to a person skilled in the art from this disclosure, in one or more embodiments. Furthermore, while some embodiments described herein include some, but not other features included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the presently claimed invention, and form different embodiments, as would be understood by those in the art. For example, in the appended claims, any of the claimed embodiments can be used in any combination.

[0029] Accordingly, an aspect of the presently claimed invention is directed to a dye fixing agent obtainable by polymerizing

[0030] a. at least one aromatic sulfonic acid or sulfonate;

[0031] b. at least one substituted phenol or salt thereof; and

[0032] c. at least one aldehyde;

[0033] with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

[0034] In a preferred embodiment, the at least one substituted phenol salt is selected from sodium salt, potassium salt and ammonium salt.

[0035] In a preferred embodiment, the at least one aromatic sulfonic acid or sulfonate is selected from sodium 4-hydroxybenzenesulfonate, sodium 6-hydroxynaphthalene-2-sulfonate, sodium 2,3-dihydroxy-6-naphthalenesulfonate, 4-hydroxybenzenesulfonic acid, sodium naphthalene-2-sulfonate, 2,4-dihydroxybenzenesulfonic acid, and 3,5-dihydroxybenzenesulfonic acid. In a preferred embodiment, the at least one substituted phenol or salt thereof, wherein the at least one substituted phenol is selected from formula E, F, G, H, I, and J.

[0036] The substituted phenols of formula E, F, G, H, I, and J are as follows:Meissner Bolte M / ARCH-023-PC

[0037] OH

[0038]

[0039] formula E

[0040] wherein R1, R2, R3are independently selected from -H, -COOH, -NO2, -SO3H, -CH2OH, -OCH3, -COOCH3, -COOC2H5, -CN, -CHO, and -F,

[0041] wherein all R1, R2and R3are not H at the same time;

[0042] OH

[0043]

[0044] formula F;

[0045] wherein R4and R5are independently selected from -H

[0046]

[0047] , -COOH, -C1-C4, , and -

[0048] OH

[0049]

[0050] OH formula G;

[0051] wherein R6is selected from -SO3H, and C-i-Ce alkyl;

[0052]

[0053] formula H;Meissner Bolte M / ARCH-023-PC

[0054] wherein linker L is selected from a direct bond, w

[0055]

[0056] herein R7and R8together form a cyclohexyl ring or R7is CH3, and R8is -CH2CH2COOH;

[0057]

[0058] formula I;

[0059] wherein R9, R10, R11, R12, R13and R14are independently selected from H and OH, wherein at least one of R9, R10, R11, R12, R13and R14is -OH;

[0060]

[0061] formula J;

[0062] wherein R15is selected from -H or -CH3.

[0063] In a preferred embodiment, at least one aldehyde is selected from formaldehyde (01), acetaldehyde (02) and glyoxal (03).

[0064] An aspect of the presently claimed invention is directed to, a dye fixing agent is obtainable by polymerizing

[0065] a. at least one aromatic sulfonic acid or sulfonate selected from sodium 4- hydroxybenzenesulfonate, sodium 6-hydroxynaphthalene-2-sulfonate, sodium 2,3-dihydroxy-6-naphthalenesulfonate, 4-hydroxybenzenesulfonic acid, sodium naphthalene-2-sulfonate, 2,4-dihydroxybenzenesulfonic acid, and 3,5- dihydroxybenzenesulfonic acid;

[0066] b. at least one substituted phenol or salt thereof, wherein the at least one substituted phenol is selected from compounds of formula E, F, G, H, I, and J;Meissner Bolte M / ARCH-023-PC

[0067]

[0068] formula E

[0069] wherein R1, R2, R3are independently selected from -H, -COOH, -NO2, -SO3H, -CH2OH, -OCH3, -COOCH3, -COOC2H5, -CN, -CHO, and -F,

[0070] wherein all R1, R2and R3are not H at the same time;

[0071] 5

[0072]

[0073] Rformula F;

[0074] wherein R4and R5are independently selected from -H, -COOH, and -C1-C4 alkyl,

[0075] O O OH

[0076]

[0077] OH formula G;

[0078] wherein R6is selected from -SO3H, and C-i-Ce alkyl;

[0079] formula H;

[0080] 8 wherein linker L is selected from a direct bond, , -O-, -S-, and w

[0081]

[0082] herein R7and R8together form a cyclohexyl ring or R7is CH3 and R8is -CH2CH2COOH;Meissner Bolte M / ARCH-023-PC

[0083]

[0084] formula I;

[0085] wherein R9, R10, R11, R12, R13and R14are independently selected from H and OH, wherein at least one of R9, R10, R11, R12, R13and R14is -OH;

[0086]

[0087] formula J;

[0088] wherein R15is selected from -H or -CH3; and

[0089] c. at least one aldehyde selected from formaldehyde, acetaldehyde and glyoxal.

[0090] with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

[0091] Within the context of the presently claimed invention, the term ‘alkyl’ refers to saturated or unsaturated, linear or branched hydrocarbons. The examples of alkyl include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and tert-butyl.

[0092] Within the context of the presently claimed invention, if not stated otherwise, all given molecular weights are those determined by gel permeation chromatography (GPC) according to DIN 55672-3-2016 with water as the eluent.

[0093] In an embodiment of the presently claimed invention, the dye fixing agent is obtainable by reacting at least one aromatic sulfonic acid or sulfonate, at least one substituted phenol or salt thereof, at least one aldehyde and urea.

[0094] In a preferred embodiment, the at least one substituted phenol salt is selected from sodium salt, potassium salt and ammonium salt.

[0095] In a preferred embodiment, the at least one aromatic sulfonic acid or sulfonate is selected from sodium 4-hydroxybenzenesulfonate, sodium 6-hydroxynaphthalene-2-sulfonate, sodium 2,3-dihydroxy-6-naphthalenesulfonate, 4-hydroxybenzenesulfonic acid, and sodium naphthalene-2-sulfonate.Meissner Bolte M / ARCH-023-PC

[0096] OH

[0097] SO3Na

[0098] (A1)

[0099] OH

[0100] SO3H

[0101] (A4)

[0102]

[0103] In a preferred embodiment, the molar ratio of the at least one aromatic sulfonic acid or sulfonate to the at least one aldehyde is in the range of 0.1 to 4.0, more preferably 0.5 to 2.0, and most preferably 0.7 to 1.0.

[0104] In a preferred embodiment, the molar ratio of the at least one substituted phenol or salt thereof to the at least one aldehyde is in the range of 0.1 to 2.0, preferably 0.5 to 1.5, and most preferably 0.7 to 1.0.

[0105] In a preferred embodiment, the molar ratio of the at least one substituted phenol or salt thereof to urea is in the range of 2.0 to 40.0, preferably 10.0 to 30.0, and most preferably 15.0 to 20.0. In a preferred embodiment, the dye fixing agent has a weight average molecular weight in the range of 500 to 100000 g / mol according to DIN 55672-3-2016.

[0106] In a preferred embodiment, the at least one substituted phenol of formula E is selected from

[0107] OH

[0108] COOH

[0109]

[0110] (B2) (B13)Meissner Bolte M / ARCH-023-PC

[0111] OH

[0112] COOMe F

[0113] (

[0114]

[0115] B18) and (B22)

[0116] In a preferred embodiment, the at least one substituted phenol of formula E is selected from B7 and B8.

[0117] In a preferred embodiment, R4is -CH3.

[0118] In a preferred embodiment, the at least one substituted phenol of formula F is selected from

[0119] (B16), and

[0120]

[0121] In a preferred embodiment, R6is -C(CH3)3.

[0122] In a preferred embodiment, the at least one substituted phenol of formula G is selected from

[0123]

[0124] In a preferred embodiment, the at least one substituted phenol of formula H is selected from

[0125] (B4)

[0126]

[0127] Meissner Bolte M / ARCH-023-PC

[0128] (B6)

[0129]

[0130] (B17), and

[0131] In a preferred embodiment, the at least one substituted phenol of formula I is selected from

[0132]

[0133] Meissner Bolte M / ARCH-023-PC In a preferred embodiment, the at least one substituted phenol of formula J is

[0134]

[0135] (B11)

[0136] In a preferred embodiment, the at least one substituted phenol is selected from

[0137]

[0138] Meissner Bolte M / ARCH-023-PC

[0139] (B10) (B11) (B12)

[0140] (B17)

[0141] (B21)

[0142]

[0143] Another aspect of the presently claimed invention is directed to a method for preparing the dye fixing agents, the method comprising at least the steps ofMeissner Bolte M / ARCH-023-PC

[0144] a. mixing the at least one aromatic sulfonic acid or sulfonate, the at least one substituted phenol or salt thereof, at least one alkali or at least one acid, and at least one solvent to obtain a mixture;

[0145] b. heating the mixture to a temperature in the range of 80 to 100 °C; and

[0146] c. adding at least one aldehyde to the mixture at a temperature in the range of 60 to 85°C over 0.5 to 1 hours; followed by heating the resultant mixture at a temperature in the range of 85 to 100 °C for 2 to 6 hours.

[0147] In a preferred embodiment, step (a) further comprises mixing urea.

[0148] In a preferred embodiment, the method for preparing the dye fixing agents comprising at least the steps of

[0149] a. mixing the at least one aromatic sulfonic acid or sulfonate, the at least one substituted phenol or salt thereof, at least one alkali, and at least one solvent to obtain a mixture; b. heating the mixture to a temperature in the range of 80 to 100 °C; and

[0150] c. adding at least one aldehyde to the mixture at a temperature in the range of 60 to 85°C over 0.5 to 1 hours; followed by heating the resultant mixture at a temperature in the range of 85 to 100 °C for 2 to 6 hours; and

[0151] d. cooling the mixture obtained in step (c).

[0152] In a preferred embodiment, the method for preparing the dye fixing agent comprising at least the steps of

[0153] a. mixing the at least one aromatic sulfonic acid or sulfonate, the at least one substituted phenol or salt thereof, at least one acid and at least one solvent to obtain a mixture; wherein the pH of the mixture is in the range of 1 to 4;

[0154] b. heating the mixture to a temperature in the range of 80 to 100 °C;

[0155] c. adding at least one aldehyde to the acidic mixture at a temperature in the range of 60 to 85 °C over 0.5 to 1 hours; followed by heating the resultant mixture at a temperature in the range of 85 to 100 °C for 2 to 6 hours; and

[0156] d. cooling the mixture obtained in step (c) and adding alkali to the cooled mixture till pH of the mixture is in the range of 9 to 12.

[0157] In a preferred embodiment, the at least one alkali is selected from potassium hydroxide, sodium hydroxide, ethanolamine, and triethanolamine.

[0158] In a preferred embodiment, the at least one solvent is a mixture of water, and at least one solvent other than water.

[0159] In a preferred embodiment, the at least one solvent other than water is selected from ether, ester, alcohol, and glycol.

[0160] In a preferred embodiment, the at least one solvent other than water is selected from ethylene glycol, diethylene glycol, propylene glycol, glycerol, diethylene glycol butyl ether, triethylene glycol butyl ether, and ethylene glycol butyl ether acetate.

[0161] In a preferred embodiment, the at least one solvent other than water is diethylene glycol.Meissner Bolte M / ARCH-023-PC

[0162] In a preferred embodiment, the at least one aldehyde is formaldehyde. In a preferred embodiment, the formaldehyde is in the form selected from an aqueous solution and paraformaldehyde.

[0163] Another aspect of the presently claimed invention is directed to an aqueous composition comprising the dye fixing agent or according to the method of the presently claimed invention. In a preferred embodiment, the aqueous composition comprises the dye fixing agent, water, and at least one solvent other than water.

[0164] In a preferred embodiment, the at least one solvent other than water is selected from ether, ester, alcohol, and glycol.

[0165] In a more preferred embodiment, the at least one solvent other than water is selected from ethylene glycol, diethylene glycol, propylene glycol, glycerol, diethylene glycol butyl ether, triethylene glycol butyl ether, and ethylene glycol butyl ether acetate.

[0166] In a preferred embodiment, the at least one solvent other than water is diethylene glycol. In a preferred embodiment, the weight ratio of the dye fixing agent to the total amount of water and the at least one solvent other than water is in the range of 1 :1 to 1:10.

[0167] Another aspect of the presently claimed invention is directed to use of the dye fixing agent for improving wet fastness of a textile material.

[0168] Another aspect of the presently claimed invention is directed to use of the dye fixing agent for improving dye blocking effect of a textile material.

[0169] Another aspect of the presently claimed invention is directed to use of the dye fixing agent for improving anti-staining effect of a textile material.

[0170] Another aspect of the presently claimed invention is directed to use of the dye fixing agent for improving chlorine resistance fastness of a textile material.

[0171] In a preferred embodiment, the textile material is selected from polyamide and blends of polyamide with cellulose, wool, or elastane.

[0172] Another aspect of the presently claimed invention is directed to a method for improving wet fastness of a textile material comprising the following steps:

[0173] a. dyeing a textile material with at least one dye to obtain a dyed textile material; b. treating the dyed textile material with the dye fixing agent according to the presently claimed invention or the dye fixing agent prepared according to the method of the presently claimed invention or the aqueous composition comprising the dye fixing agent of the presently claimed invention of the presently claimed invention to obtain a fixed dyed textile material; and

[0174] c. drying the fixed dyed textile material.

[0175] In a preferred embodiment, the textile material is a blend of nylon and elastane.Meissner Bolte M / ARCH-023-PC

[0176] In a preferred embodiment, the textile material is a blend of nylon and cellulose.

[0177] In a preferred embodiment, the step of treating the dyed textile material with the aqueous composition comprising the dye fixing agent is carried out by padding process or exhaustion process.

[0178] In a preferred embodiment, the step of treating the dyed textile material with the aqueous composition comprising the dye fixing agent is carried out by padding process.

[0179] In a preferred embodiment, the dosage of the dye fixing agent for application by padding process is in the range of 1.0 to 15.0 g / l, and more preferably 2.0 to 10.0 g / l.

[0180] In a preferred embodiment, the step of treating the dyed textile material with the aqueous composition comprising the dye fixing agent is carried out by exhaustion process.

[0181] In a preferred embodiment, the dosage of the dye fixing agent for application by exhaustion process is in the range of 1.0 to 15.0 % o.w.f, and more preferably 2.0 to 10.0 % o.w.f.

[0182] In a preferred embodiment, the textile material is selected from polyamide and blends of polyamide with cellulose, wool, or elastane.

[0183] In a preferred embodiment, the at least one dye is an acid dye.

[0184] In a preferred embodiment, the concentration of the dye fixing agent in the aqueous dyeing composition is in the range of 1.0 to 15.0 g / L.

[0185] In a preferred embodiment, the step of drying is carried out using dry heat or steam.

[0186] Yet another aspect of the presently claimed invention is directed to a treated textile material obtainable by treatment of a textile material with the dye fixing agent or the aqueous composition comprising the dye fixing agent or by the method of the presently claimed invention or by using the dye fixing agent according to the presently claimed invention.

[0187] In a preferred embodiment, the textile material is selected from polyamide and blends of polyamide with cellulose, wool, or elastane.

[0188] The presently claimed invention offers one or more of the following advantages:

[0189] - the dye fixing agents of the presently claimed invention do not contain hazardous residues such as phenol, bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S;

[0190] - the dye fixing agents show comparable or better wet fastness on various fabric materials;

[0191] and

[0192] - the dye fixing agents improve properties of polyamide fabrics such as dye blocking effect, anti-staining effect and chlorine resistance fastness.

[0193] In the following, there are provided a list of embodiments to further illustrate the present disclosure without intending to limit the disclosure to specific embodiments listed below.Meissner Bolte M / ARCH-023-PC

[0194] 1. A dye fixing agent obtainable by polymerizing

[0195] a. at least one aromatic sulfonic acid or sulfonate;

[0196] b. at least one substituted phenol or salt thereof; and

[0197] c. at least one aldehyde;

[0198] with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

[0199] 2. The dye fixing agent obtainable by polymerizing

[0200] a. at least one aromatic sulfonic acid or sulfonate selected from sodium 4- hydroxybenzenesulfonate, sodium 6-hydroxynaphthalene-2-sulfonate, sodium 2,3-dihydroxy-6-naphthalenesulfonate, 4-hydroxybenzenesulfonic acid, sodium naphthalene-2-sulfonate, 2,4-dihydroxybenzenesulfonic acid, and 3,5- dihydroxybenzenesulfonic acid;

[0201] b. at least one substituted phenol or salt thereof, wherein the at least one substituted phenol is selected from formula E, F, G, H, I, and J;

[0202] OH

[0203]

[0204] Rformula E

[0205] wherein R1, R2, R3are independently selected from -H, -COOH, -NO2, -SO3H, -CH2OH, -OCH3, -COOCH3, -COOC2H5, -CN, -CHO, and -F,

[0206] wherein all R1, R2and R3are not H at the same time;

[0207] OH

[0208]

[0209] R formula F;

[0210] wherein R4and R5are independently selected from -H, -COOH, -C1-C4 alkyl,

[0211]

[0212] Meissner Bolte M / ARCH-023-PC

[0213] OH

[0214] °H formula G;

[0215] wherein R6is selected from -SO3H, and C-i-Ce alkyl;

[0216]

[0217] formula H;

[0218] wherein linker L is selected from a direct bond,

[0219]

[0220] wherein R7and R8together form a cyclohexyl ring or R7is CH3 and R8is - CH2CH2COOH;

[0221]

[0222] formula I;

[0223] wherein R9, R10, R11, R12, R13and R14are independently selected from H and OH,

[0224] wherein at least one of R9, R10, R11, R12, R13and R14is -OH;Meissner Bolte M / ARCH-023-PC

[0225]

[0226] wherein R15is selected from -H or -CH3;

[0227] c. at least one aldehyde selected from formaldehyde, acetaldehyde and glyoxal; with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

[0228] 3. The dye fixing agent according to embodiment 1 or embodiment 2, wherein the at least one substituted phenol salt is selected from sodium salt, potassium salt and ammonium salt.

[0229] 4. The dye fixing agent according to any of embodiments 1 to 3, wherein the dye fixing agent is obtainable by reacting at least one aromatic sulfonic acid or sulfonate, at least one substituted phenol or salt thereof, at least one aldehyde and urea.

[0230] 5. The dye fixing agent according to any of embodiments 1 to 4, wherein the molar ratio of the at least one aromatic sulfonic acid or sulfonate to the at least one aldehyde is in the range of 0.1 to 4.0, preferably 0.5 to 2.0, and most preferably 0.7 to 1.0.

[0231] 6. The dye fixing agent according to any of embodiments 1 to 5, wherein the molar ratio of the at least one substituted phenol or salt thereof to the at least one aldehyde is in the range of 0.1 to 2.0, preferably 0.5 to 1.5, and most preferably 0.7 to 1.0.

[0232] 7. The dye fixing agent according to any of embodiments 4 to 6, wherein the molar ratio of the at least one substituted phenol or salt thereof to urea is 2.0 to 40.0, preferably 10.0 to 30.0, and most preferably 15.0 to 20.0.

[0233] 8. The dye fixing agent according to any of embodiments 1 to 7 having a weight average molecular weight in the range of 500 to 100000 g / mol according to DIN 55672-3-2016.

[0234] 9. The dye fixing agent according to any of embodiments 1 to 8, wherein the at least one substituted phenol of formula E is selected fromMeissner Bolte M / ARCH-023-PC

[0235] OH OH OH

[0236] COOH CN CH2OH (B2) (B8) ’ (B13)

[0237] OH

[0238] COOMe (

[0239]

[0240] B18) and

[0241] 10. The dye fixing agent according to any of embodiments 1 to 9, wherein the at least one substituted phenol of formula F is selected from

[0242] (B16), and

[0243]

[0244] 11. The dye fixing agent according to any of embodiments 1 to 10, wherein the at least one substituted phenol of formula G is selected from

[0245]

[0246] (B21) and

[0247] 12. The dye fixing agent according to any of embodiments 1 to 11, wherein the at least one substituted phenol of formula H is selected fromMeissner Bolte M / ARCH-023-PC

[0248]

[0249] 13. The dye fixing agent according to any of embodiments 1 to 12, wherein the at least one substituted phenol of formula I is selected from

[0250]

[0251] Meissner Bolte M / ARCH-023-PC

[0252] (

[0253]

[0254] B19) and (B25)

[0255] 14. The dye fixing agent according to any of embodiments 1 to 13, wherein the at least one substituted phenol of formula J is

[0256] OH

[0257]

[0258] (B11)

[0259] 15. A method for preparing the dye fixing agent according to any of embodiments 1 to 14 comprising at least the steps of

[0260] a. mixing the at least one aromatic sulfonic acid or sulfonate, the at least one substituted phenol or salt thereof, at least one alkali or at least one acid, and at least one solvent to obtain a mixture;

[0261] b. heating the mixture to a temperature in the range of 80 to 100 °C; and

[0262] c. adding at least one aldehyde to the mixture at a temperature in the range of 60 to 85°C over 0.5 to 1 hours; followed by heating the resultant mixture at a temperature in the range of 85 to 100 °C for 2 to 6 hours.

[0263] 16. The method according to embodiment 15, wherein step (a) further comprises mixing urea.

[0264] 17. The method according to embodiment 15 or embodiment 16, wherein the aldehyde is formaldehyde; wherein the formaldehyde is in the form selected from an aqueous solution and paraformaldehyde.

[0265] 18. An aqueous composition comprising the dye fixing agent according to any of embodiments 1 to 14 or obtainable according to the method of any of the embodiments 15 to 17.

[0266] 19. The composition according to embodiment 18 comprising the dye fixing agent, water, and at least one solvent other than water, wherein the weight ratio of the dye fixingMeissner Bolte M / ARCH-023-PC

[0267] agent to the total amount of water and at least one solvent other than water is in the range of 1 :1 to 1:10.

[0268] 20. The composition according to embodiment 19, wherein the at least one solvent other than water is selected from ether, ester, alcohol, and glycol.

[0269] 21. Use of the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agent obtainable according to any of the embodiments 15 to 17 or the aqueous composition comprising the dye fixing agent according to any of embodiments 18 to 20 for improving color fastness of a textile material.

[0270] 22. Use of the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agent obtainable according to any of the embodiments 15 to 17 or the aqueous composition comprising the dye fixing agent according to any of embodiments 18 to 20 for improving wet fastness of a textile material.

[0271] 23. Use of the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agent obtainable according to any of the embodiments 15 to 17 or the aqueous composition comprising the dye fixing agent according to any of embodiments 18 to 20 for improving dye blocking effect of a textile material.

[0272] 24. Use of the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agent obtainable according to any of the embodiments 15 to 17 or the aqueous composition comprising the dye fixing agent according to any of embodiments 18 to 20 for improving anti-staining effect of a textile material.

[0273] 25. Use of the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agent obtainable according to any of the embodiments 15 to 17 or the aqueous composition comprising the dye fixing agent according to any of embodiments 18 to 20 for improving chlorine resistance fastness of a textile material.

[0274] 26. The use according to any of embodiments 21 to 25, wherein the textile material is selected from polyamide and blends of polyamide with cellulose, wool, orelastane.

[0275] 27. A method for improving wet fastness of a textile material comprising the following steps:

[0276] a. dyeing the textile material with at least one dye to obtain dyed textile material; b. treating the dyed textile material with the composition comprising the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agent obtainable according to any of the embodiments 15 to 17 or the aqueous composition comprising the dye fixing agent according to any of the embodiments 18 to 20 to obtain a fixed dyed textile material; and

[0277] c. drying the dyed fixed textile material.

[0278] 28. The method according to embodiment 27, wherein the textile material is selected from polyamide and blends of polyamide with cellulose, wool, or elastane.

[0279] 29. A treated textile material obtainable by treatment of a textile material with the dye fixing agent according to any of the embodiments 1 to 14 or the dye fixing agentMeissner Bolte M / ARCH-023-PC

[0280] obtainable according to any of the embodiments 15 to 17 or the composition according to any of the embodiments 18 to 20 or by treating a textile material by the method according to embodiment 27 or embodiment 28 or by use of the dye fixing agent according to any of the embodiments 21 to 26.

[0281] 30. The treated textile material according to embodiment 29, wherein the textile material is selected from polyamide and blends of polyamide with cellulose, wool, or elastane.

[0282] While the presently claimed invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the presently claimed invention.Meissner Bolte M / ARCH-023-PC

[0283] Examples

[0284] The presently claimed invention is illustrated in detail by non-restrictive working examples which follow. More particularly, the test methods specified hereinafter are part of the general disclosure of the application and are not restricted to the specific working examples.

[0285] Preparation examples: Preparation of fixing agents and compositions

[0286] Examples 1-90

[0287] The dye fixing agents of examples 1-90 were prepared by a similar procedure.

[0288] A representative example of the procedure involving polymerization of components a, b, and c is provided below as Example 70. Another representative example of the procedure involving polymerization of A, B, C and urea is provided below as Example 87.

[0289] The components a, b, and c, and their weight ratios used for the preparation of the dye fixing agents are provided in Tables 2-5.

[0290] Example 70

[0291] In a 250 ml four-necked flask maintained under nitrogen atmosphere, and equipped with a condenser, and a dropping funnel, were added 8.56 g sodium 4-hydroxybenzenesulfonate, 15.72 g Sodium 6,7-dihydroxy 2-naphthalenesulfonate, and 2.14 g 4,4'-Dihydroxybenzophenone, 15 g diethylene glycol in sequence. The flask was charged with 45.0 g deionized water and 6.0 g 50% aqueous sodium hydroxide solution.

[0292] The reaction mixture was gradually heated to 80 °C while stirring at 200 rpm.

[0293] When the temperature of the reaction mixture reaches 80 °C, dropwise addition of 6.25 g of 37% aqueous formaldehyde to the reaction mixture was started. The dropwise addition was completed in 45 minutes.

[0294] The temperature of the reaction mixture was raised to 95°C and maintained at that temperature for 2.5 hours.

[0295] The reaction mixture was cooled to room temperature. The resultant mixture was filtered to obtain a clear red liquid as product.

[0296] Example 87:

[0297] In a 250 ml four-necked flask maintained under nitrogen atmosphere, and equipped with a condenser, and a dropping funnel, were added 23.6 g Sodium 6,7-dihydroxy 2-naphthalenesulfonate, 13.5 g Bisphenol Z, 4.8 g urea, 20 g diethylene glycol in sequence. The flask was charged with 30.0 g deionized water and 8.0 g 50% aqueous sodium hydroxide solution.

[0298] The reaction mixture was gradually heated to 80 °C while stirring at 200 rpm.

[0299] When the temperature of the reaction mixture reaches 80 °C, dropwise addition of 19.5 g of 37% aqueous formaldehyde to the reaction mixture was started. The dropwise addition was completed in 45 minutes.

[0300] The temperature of the reaction mixture was raised to 95°C and maintained at that temperature for 2.5 hours.

[0301] The reaction mixture was cooled to room temperature. The resultant mixture was filtered to obtain a clear red liquid as product.Meissner Bolte M / ARCH-023-PC

[0302] Example 91-100

[0303] The dye fixing agents of examples 91-100 were prepared by a similar procedure. A representative example of the procedure is provided as example 100. The components a, b, and c used, and their weight ratios use are provided in Table 6.

[0304] In a 250 ml four-necked flask maintained under nitrogen atmosphere, and equipped with a condenser and a dropping funnel, were added 9.2 g sodium naphthalenesulfonate, 10.8 g Bisphenol Z, 6.0 g diethylene glycol and 26.0 g deionized water in sequence. The pH of the reaction mixture was adjusted to 3.0 with acetic acid.

[0305] The reaction mixture was gradually heated to 80 °C while stirring at 200 rpm.

[0306] When temperature of the reaction mixture reached 80 °C, dropwise addition of 5.28 g acetaldehyde was started. The dropwise addition was completed in 45 minutes.

[0307] The temperature of the reaction mixture was raised to 95°C and maintained at that temperature for 2.5 hours.

[0308] The reaction mixture was cooled to room temperature, followed by adjusting the pH of the reaction mixture to 11 with 50% aqueous sodium hydroxide solution. The resultant mixture was filtered to obtain a clear brown liquid as product.

[0309] Application Examples

[0310] Example 101: Fixing effect

[0311] To study the fixing effect nylon / spandex 80 / 20 substrate was dyed with an acid dye Erionyl® Red A-2BF. The dyeing was carried out with the aqueous dyeing composition provided in Table 1.

[0312] Table 1: Dyeing aqueous composition

[0313] Sr. Component Compound Amount

[0314] 1 Dye Erionyl® Red A-2BF (red) 2.25 % (wt.%)

[0315] 2 Leveling agent Univadine® PA 2 % (wt.%)

[0316] 3 Penetration enhancer Albaflow® UNI-01 0.5 g / l

[0317] 4 Buffer Ammonium acetate 1 g / 1

[0318] 5 Buffer Acetic acid Adjust pH to 4.5

[0319] 6 Liquor ratio - 1:20

[0320]

[0321] Procedure for dyeing

[0322] The above components 1 to 5 were added to a dye bath in sequence, and dyeing was carried out according to the following dyeing process. The dye bath was heated to 40 °C and the temperature was maintained for 10 min. The temperature of the dye vat was gradually raised at 1.2 °C / min over next 50 min to reach at 98°C. The temperature was maintained for 60 min. After this step, the temperature of the dye vat was gradually reduced at 5.0 °C / min to reachMeissner Bolte M / ARCH-023-PC

[0323] room temperature. The dyeing was removed from the bath, rinsed with hot water and then with cold water and dried.

[0324] Analysis of fastness of the dyed fabric

[0325] After dyeing, the dyed fabric samples were tested for fastness by the following methods: 1. Washing fastness was measured in accordance with ISO105 C06 / B1 M method.

[0326] 2. The alkali perspiration fastness was carried out according to the IS0105-E04 method. 3. Chlorine fastness test IS0105-E03.

[0327] Results

[0328] 1) Washing fastness and alkali perspiration fastness

[0329] The results of washing fastness according to ISO105 C06 / B1M method and alkali perspiration fastness according to IS0105-E04 method of the dye fabric samples are shown in Tables 2 -6.

[0330] The dye fixing agent used in an experiment is defined as a polymeric material in the form of monomers (components a, b, c, and optionally urea) used for its preparation and their molar ratio. The fastness values were determined for various fabric samples. In the tables, CA is Cellulose acetate, CO is Cotton, PA is Polyamide, PES is Polyester, PAN is Acrylic and WO is Wool.

[0331] The results are shown in Tables 2-6.Meissner Bolte M / ARCH-023-PC

[0332] Table 2: Color Fastness values for example 1-32

[0333] Inhouse Color fastness to washing 50°C Color fastness to perspiration mole fraction

[0334] Sr. No. ISO105 C06 B1M IS0105-E04 Alkaline A B

[0335] C1 CA CO PA PES PAN WO CA CO PA PES PAN WO A1 B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12

[0336] blank sample 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4-5 3-4 1-2 4-5 4-5 2 3 3 1-2 3 3 2-3 Example 1 1 2 3 4-5 3-4 2-3 4 4-5 2-3 3 3 2 3 3 2-3 Example 2 2 1 3 4-5 3-4 2-3 4 4-5 2-3 3 3 2 3 3 2-3 Example 3 1 1 2 4-5 3-4 2-3 4 4-5 2-3 3 3 2 3 3 3 Example 4 2 2 4 4-5 3-4 2-3 4 4-5 2-3 3 2 2 3 3 2-3 Example 5 1 3 4 4 3-4 2-3 4 4-5 2-3 3 3 2 3 3 2-3 Example 6 3 4 8 4-5 3-4 2-3 4 4-5 2-3 3 3 2-3 3 3 3 Example 7 1 1 2 4-5 3-4 2-3 4 4-5 2 3 3 2-3 3 3 3 Example 8 1 6 8 3-4 3-4 2-3 4 4 2 3 3 2-3 3 3 3 Example 9 1 1 2 4-5 3-4 2-3 4-5 4-5 2-3 3 3 2 3 3 3 Example 10 10 17 20 4-5 3-4 3 4-5 4-5 2-3 3 3 3 3 3 3 Example 11 10 6 1 18 4-5 3-4 3 4 4-5 3 3 3 2 3 3 3 Example 12 10 8 1 20 4-5 3-4 3 4-5 4-5 3 3 3 3 3 3 3 Example 13 10 1 8 20 4-5 3-4 3 4-5 4-5 3 3 3 3 3 3 3 Example 14 10 1 8 20 4-5 3-4 2-3 4 4-5 3 3 3 2-3 3 3 3 Example 15 10 9 20 4-5 3-4 3-4 4 4-5 2-3 3 3 3 3 3 3 Example 16 10 4 5 23 4 3-4 4 4 4-5 2-3 3 3 3 3 3 2-3 Example 17 10 5 6 26 4 3-4 4 4 4-5 2-3 3 3 3 3 3 3 Example 18 10 5 6 22 4 3-4 4 4 4-5 2-3 3 3 3 3 3 2-3 Example 19 8 6 20 1 3 40 4-5 4 3-4 4-5 4-5 3 3 3 3 3 3 2-3 Example 20 8 1 20 1 3 40 4-5 4 3-4 4-5 4-5 3 3 3 3 3 3 2-3 Example 21 8 4 1 1 12 12 40 4-5 4 3-4 4-5 4-5 3 3 3 2-3 3 3 2-3 Example 22 17 7 1 1 5 30 4-5 4 3 4-5 4-5 3 3 3 2-3 3 3 2-3

[0337]

[0338] Example 23 10 7 1 30 2 6 56 4-5 4 3 4-5 4-5 3 3 3 2-3 3 3 3Meissner Bolte M / ARCH-023-PC

[0339] Example 24 20 14 4 40 1 80 4-5 4 3 4-5 4-5 3 3 3 2-3 3 3 2-3 Example 25 10 4 6 1 24 4-5 3-4 3 4-5 4-5 3 3-4 3-4 2-3 3 3 3 Example 26 20 8 12 1 44 4-5 3-4 4 4-5 4-5 2-3 3-4 3-4 2-3 3 3 3 Example 27 10 4 6 1 20 4-5 3-4 3-4 4-5 4-5 2-3 3 3 2-3 3 3 2-3 Example 28 5 9 3 1 18 4-5 3-4 2-3 4-5 4-5 2-3 3 3 2-3 3 3 2-3 Example 29 20 8 2 12 5 2 50 4-5 3-4 2-3 4-5 4-5 2-3 3 3 2-3 3 3 2-3 Example 30 4 4 1 2 1 13 4-5 3-4 3-4 4-5 4-5 2-3 3 3 2-3 3 3 2-3 Example 31 10 8 1 3 1 24 4-5 3-4 3-4 4-5 4-5 3- 3 3 2-3 3 3 2-3

[0340]

[0341] Example 32 10 8 1 3 23 4-5 4 3-4 4-5 4-5 3 3-4 3 2-3 3 3-4 3Meissner Bolte M / ARCH-023-PC

[0342] Table 3: Color Fastness values for example 33-62

[0343] Inhouse Color fastness to

[0344] mole fraction Color fastness to perspiration washing 50°C

[0345] IS0105-E04 Alkaline Sr. No. ISO105 C06 B1M

[0346] A B

[0347] C1 CA CO PA PES PAN WO CA CO PA PES PAN WO A1 B5 B6 B8 B9 B11 B12 B13 B14 B15 B16 B17 B18

[0348] blank sample 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4-5 3-4 1-2 4-5 4-5 2 3 3 1-2 3 3 2-3 Example 33 2 3 5 4-5 3-4 2-3 4 4-5 2 3 3 2-3 3 3 3-4 Example 34 2 6 1 9 4-5 4 3 4-5 4-5 3-4 3 3 2-3 3 3-4 3-4 Example 35 1 2 3 4-5 3-4 2-3 4-5 4-5 3-4 3-4 3 2-3 3 3-4 3-4 Example 36 1 2 3 4-5 3-4 3 4-5 4-5 2-3 2-3 2-3 2-3 2-3 3 3-4 Example 37 4 1 2 7 4-5 4 3-4 4-5 4-5 3 3 3 2-3 3 3-4 3-4 Example 38 10 8 1 2 20 4-5 4 3 4-5 4-5 3-4 3 3 2-3 3 3-4 3-4 Example 39 10 4 1 1 15 1 25 4-5 3-4 4 4-5 4-5 3 4 3 3 3-4 3-4 3-4 Example 40 10 6 1 1 18 4-5 4 2 4-5 4-5 3- 4 2-3 2-3 3 3 3-4 Example 41 5 1 3 1 3 13 4-5 4 3 4-5 4-5 3-4 4 3 2-3 3-4 3-4 3-4 Example 42 5 3 1 1 20 1 31 4-5 4 3-4 4-5 4-5 3 3-4 4 2-3 3-4 3-4 3-4 Example 43 10 6 4 1 21 4-5 4 2-3 4-5 4-5 3 3 3 2-3 3-4 3-4 3-4 Example 44 4 2 2 1 2 11 4 4 2-3 4-5 4-5 2-3 3 3 2-3 3 3-4 3-4 Example 45 4 2 1 1 8 4 4 3-4 4-5 4-5 2-3 3 3 2-3 3 3 3-4 Example 46 4 1 1 1 2 9 4-5 3-4 2-3 4-5 4-5 2-3 3-4 3 2-3 3-4 3-4 3-4 Example 47 10 2 1 5 2 6 26 4-5 3-4 3-4 4-5 4-5 2-3 3 3 2-3 3 3 3-4 Example 48 5 2 2 1 3 13 4-5 3-4 2-3 4-5 4-5 3 3-4 3 2-3 3-4 3-4 3-4 Example 49 10 1 6 2 17 4-5 3 2-3 4 4-5 2 3 3 2-3 3 3-4 3-4 Example 50 1 1 3 3-4 3-4 2-3 4 4-5 2 3 3 2-3 3 3 3-4 Example 51 10 1 12 30 4 3-4 2-3 4-5 4-5 2 3 3 2-3 3 3 3-4 Example 52 1 2 3 4 3-4 2-3 4 4-5 2-3 3 3 2-3 3 3 3-4 Example 53 10 8 6 3 2 29 4 3-4 2-3 4 4-5 2-3 3 3 2-3 3-4 3 3-4

[0349]

[0350] Example 54 5 3 3 1 12 4-5 3-4 2-3 4 4-5 2-3 3-4 3 2-3 4 3-4 3-4Meissner Bolte M / ARCH-023-PC

[0351] Example 55 5 1 1 3 1 1 12 4-5 3-4 2-3 4 4-5 3 3 3 2-3 3-4 3 3-4 Example 56 5 2 3 1 1 12 4-5 3-4 2-3 4 4-5 3 3 3 2-3 3 3 3-4 Example 57 5 3 4 12 4-5 3-4 2-3 4-5 4-5 3 4 3 2-3 3-4 3-4 3-4 Example 58 5 2 3 2 12 4-5 3-4 2-3 4 4-5 3 3 3 2-3 3-4 3-4 3-4 Example 59 5 3 2 10 4-5 3 2-3 4 4-5 2 3-4 3 2-3 3-4 3-4 3-4 Example 60 5 1 3 3 12 4-5 3 2-3 4 4-5 2 3 3 2-3 3 3 3-4 Example 61 5 1 1 3 1 11 4-5 4-5 2-3 4-5 4-5 3-4 4 3 2-3 4-5 4 3-4

[0352]

[0353] Example 62 10 5 8 5 5 33 4-5 4 2-3 4-5 4-5 2-3 4 3 2-3 3-4 3-4 3-4Meissner Bolte M / ARCH-023-PC

[0354] Table 4: Color Fastness values for example 63-75

[0355] Inhouse color fastness to

[0356] Color fastness to perspiration mole fraction washing 50° C IS0105 C06

[0357] IS0105-E04 Alkaline Sr. No. B1M

[0358] A B

[0359] C1 CA CO PA PES PAN WO CA CO PA PES PAN WO A1 A2 A3 B11 B12 B13 B14 B15 B17 B21 B22 B23 B24

[0360] blank sample 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4-5 3-4 1-2 4-5 4-5 2 3 3 1-2 3 3 2-3 Example 63 10 6 1 18 4-5 3-4 3-4 4 4-5 3 3-4 3 2-3 3 3-4 3 Example 64 20 14 3 55 4-5 4 4 4-5 4-5 3 3-4 3 3 3 3-4 3 Example 65 1 2 3 3-4 3-4 4 4 4-5 3 3-4 3 3 3 3-4 3 Example 66 1 1 2 4-5 3-4 3-4 4-5 4-5 2-3 3-4 3 2-3 3 3-4 3 Example 67 1 1 2 4-5 3-4 4 4-5 4-5 3 3-4 3 2-3 3 3-4 3 Example 68 10 1 10 30 4-5 3-4 2-3 4-5 4-5 2-3 3-4 3-4 2-3 3-4 3-4 3 Example 69 5 2 2 3 1 13 4-5 4 4 4 4-5 3 3-4 3 3 3 3-4 3 Example 70 4 6 1 11 4-5 3-4 2-3 4 4-5 2-3 3 3 3 3 3-4 3 Example 71 4 6 1 2 13 4-5 4 2-3 4-5 4-5 2-3 2-3 2-3 2-3 2-3 3-4 3 Example 72 10 20 6 3 40 4-5 4 2-3 4-5 4-5 2-3 3 3 2-3 3 3-4 3 Example 73 10 15 2 2 29 4-5 3-4 3 4-5 4-5 2-3 3-4 3 2-3 3 3-4 3 Example 74 20 30 4 4 1 60 4-5 3-4 3-4 4-5 4-5 3 4 2-3 2-3 3 3-4 3

[0361]

[0362] Example 75 20 30 5 4 4 63 4 3-4 4 4 4 3 3 2-3 3 2-3 3-4 3Meissner Bolte M / ARCH-023-PC

[0363] Table 5: Color Fastness values for example 76-90

[0364] Inhouse Color fastness to

[0365] mole fraction Color fastness to perspiration washing 50°C

[0366] IS0105-E04 Alkaline Sr. No. ISO105 C06 B1M

[0367] A B

[0368] C1 CA CO PA PES PAN WO CA CO PA PES PAN WO A1 A3 B6 B8 B10 B11 B12 B15 B17 B19 B22 B23 B25 B26

[0369] blank sample 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4-5 3-4 1-2 4-5 4-5 2 3 3 1-2 3 3 2-3 Example 76 20 30 3 4 2 59 4-5 4 3-4 4-5 4-5 3 3 3 2-3 3 3 3 Example 77 20 30 5 4 2 61 4-5 3-4 3 4-5 4-5 3 3 3 2-3 3 3 2-3 Example 78 20 30 5 4 4 63 4-5 3-4 4 4 4-5 3 3 3 2-3 3 3 3 Example 79 20 30 3 4 2 59 4-5 3-4 4 4 4-5 3 2-3 3 2-3 2-3 2-3 2-3 Example 80 7 34 13 3 56 4-5 4 3-4 4-5 4-5 3-4 4 3 2-3 3-4 3-4 3 Example 81 13 5 40 3 60 4-5 3-4 4 4-5 4-5 3-4 3 3 2-3 3-4 3-4 3 Example 82 13 5 40 3 3 60 4-5 4 3 4-5 4-5 3 4 3 2-3 3-4 3-4 3 Example 83 5 1 15 5 1 30 4-5 4 3-4 4-5 4-5 3-4 3-4 3-4 2-3 3-4 3-4 3 Example 84 9 3 9 26 9 3 50 4-5 4 3-4 4-5 4-5 3 3 3-4 2-3 3-4 3-4 3 Example 85 13 3 26 13 60 4-5 3-4 4 4-5 4-5 3-4 3-4 3-4 2-3 3-4 3-4 3 Example 86 19 10 9 42 4-5 4 2-3 4-5 4-5 3 3 3 2-3 3 3 3 Example 87 9 5 8 24 4-5 3-4 3 4 4-5 3 3 3 2-3 3 3 3 Example 88 9 5 5 26 4-5 3-4 3 4 4-5 3 3 3 2-3 3 3 3 Example 89 8 6 4 3 50 4-5 3-4 3 4 4-5 3 3 3-4 2-3 3-4 3-4 3

[0370]

[0371] Example 90 8 3 8 3 30 4-5 3-4 3-4 4-5 4-5 3 4 3 2-3 3 3 2-3Meissner Bolte M / ARCH-023-PC

[0372] Table 6: Color Fastness values for example 91-100

[0373] Inhouse Color fastness to

[0374] mole fraction Color fastness to perspiration washing 50°C

[0375] IS0105-E04 Alkaline Sr. No. ISO105 C06 B1M

[0376] A B

[0377] C2 CA CO PA PES PAN WO CA CO PA PES PAN WO A4 A5 B11 B15 B19 B22 B23

[0378] blank sample

[0379] 0 0 0 0 0 0 0 4-5 3-4 1-2 4-5 4-5 2 3 3 1-2 3 3 2-3 Example 91 4 2 2 1 4-5 4 3-4 4-5 4-5 3-4 4 3-4 2-3 3-4 3-4 3 Example 92 4 4 4 1 4-5 3-4 3 4-5 4-5 3-4 3-4 3-4 2-3 3-4 3-4 3 Example 93 2 2 2 4 1 4-5 3-4 3 4 4-5 3 3 3-4 2-3 3-4 3-4 3 Example 94 4 10 14 12 5 4-5 4 3-4 4-5 4-5 3 3 3-4 2-3 3 3-4 3 Example 95 4 10 14 12 5 4-5 3 3-4 4 4-5 3 3-4 3-4 2-3 3 3-4 3 Example 96 4 10 13 13 5 4-5 3-4 4 4-5 4-5 3-4 3-4 3-4 3 3-4 3-4 3 Example 97 2 2 4 1 4-5 3-4 3 4-5 4-5 3 3-4 3-4 2-3 3 3-4 3 Example 98 2 4 4 4 4-5 3-4 4 3-4 2 4 4-5 3-4 3 3 3-4 3 Example 99 2 4 5 5 4-5 3-4 3-4 3-4 2-3 3-4 4-5 3-4 2-3 3-4 3-4 3

[0380]

[0381] Example 100 4 4 12 4-5 3-4 3 4 2-3 3 4-5 3-4 2-3 3 3-4 3Meissner Bolte M / ARCH-023-PC

[0382] It is clear from the Table 2 that the washing fastness or alkali perspiration fastness or both of the polyamide fabric samples are improved by the use of the polymeric material of the presently claimed invention as a fixing agent. The blank example showed that the polyamide fabric sample have a poor washing fastness and alkali perspiration fastness.

[0383] In Table 3, the blank example showed that the polyamide fabric sample have a poor washing fastness and alkali perspiration fastness. It is clear from the Table 3 that the washing fastness or alkali perspiration fastness or both of the polyamide fabric samples are improved by the use of the polymeric material of the presently claimed invention as a fixing agent.

[0384] In Table 4, the blank example showed that the polyamide fabric sample have a poor washing fastness and alkali perspiration fastness. It is clear from the Table 4 that the washing fastness or alkali perspiration fastness or both of the polyamide fabric samples are improved by the use of the polymeric material of the presently claimed invention as a fixing agent.

[0385] In Table 5, the blank example showed that the polyamide fabric sample have a poor washing fastness and alkali perspiration fastness. It is clear from the Table 5 that the washing fastness or alkali perspiration fastness or both of the polyamide fabric samples are improved by the use of the polymeric material of the presently claimed invention as a fixing agent.

[0386] It is clear from the Table 6 that the washing fastness or alkali perspiration fastness or both of the polyamide fabric samples are improved by the use of the polymeric material of the presently claimed invention as a fixing agent.

[0387] 2) Chlorine fastness test

[0388] Chlorine fastness according to IS0105-E03was evaluated for polyamide blends using the following three dyes:

[0389] Erionyl RED A-2BF

[0390] 6% Tectilon® Yellow 4R 200% and 1 ,2% Tectilon® Blue 6G 200%

[0391] 7% Lanaset® Black B

[0392] The results are shown in Table 7.

[0393] Table 7: Chlorine fastness

[0394] Sr. No. Chlorine resistance fastness test ISO105 E03 (50ppm)

[0395] 0,6% Tectilon® Yellow

[0396] 2,25% Erionyl® Red 4R 200%

[0397] 7% Lanaset® Black B A-2BF 1,2% Tectilon® Blue 6G

[0398] 200%

[0399] Blank 2.5 2 3

[0400] Example

[0401] 3.5 3 4.5

[0402] 10

[0403] Example

[0404] 4 3.5 4

[0405]

[0406] Meissner Bolte M / ARCH-023-PC

[0407] Example

[0408] 3.5 3 4.5

[0409] 45

[0410] Example

[0411] 3.5 3.5 4.5

[0412] 80

[0413] Example

[0414] 4 3 4.5

[0415] 92

[0416]

[0417] Table 7 showed excellent chlorine fastness results of the agents of the presently claimed invention.

[0418] 3) Dye blocking effect

[0419] Dye blocking effect was evaluated for polyamide blends containing 25% polyamide and 75% blend material. Dyeing was carried out using the following three 1 :2 metal-complex dyes: 0.64 % Lanaset® Yellow (4GN),

[0420] 0.28% Lanaset® Blue (2R), and

[0421] 0.03% Lanaset® Grey (G).

[0422] A dyeing composition was prepared using the following: 0.5 g / l Albaflow® CIR, 1.0 g / l Sodium acetate, 1.25 g / l acetic acid 80%, 1.5 % Albegal® Set, 5.0 % Glauber’s salt calc. The pH of the dyeing composition was 4.5.

[0423] Dyeing was carried out by exhaustion method. The liquor ratio was 1 :20.

[0424] The results are shown in Table 8.

[0425] Table 8: Blocking effect

[0426] 2% sample Blocking effect on

[0427] Sr. No. PA / WO

[0428] PA WO

[0429] Blank 100% 0%

[0430] Example 22 85% 84%

[0431] Example 30 78% 79%

[0432] Example 51 78% 74%

[0433] Example 83 77% 79%

[0434] Example 100 85% 82%

[0435]

[0436] Table 8 clearly showed excellent blocking effect of the dye fixing agents of the presently claimed invention.

[0437] 4) Reserving effect

[0438] Reserving effect test was carried out on 50 parts PA 66 textured tricot (stock No. 5-4112) and 50 parts cotton, bleached (stock No. 1-4002) as substrates.Meissner Bolte M / ARCH-023-PC

[0439] The dye was 1% Solophenyl® Blue GL 250% solution. The dyeing solution comprises 0 -0.25 - 0.5 - 1 - X %

[0440] Erional® PA, Erional® RN or Erional® RF or test sample

[0441] Dyeing was carried out by exhaustion method. The liquor ratio was 1 :40.

[0442] The strength parity which ensures the best reservation of PA (optimum whiteness) with the minimum amount of reserving agent is determined.

[0443] The test report must further indicate whether a white resist can be achieved on the PA component with the reserving agent or whether residual staining occurs. Attention must also be paid to yellowing (PA component) and to possible modification of handle or light fastness by the reserving agent.

[0444] The results are shown in Table 9.

[0445] Table 9: Reserving effect

[0446] 2% sample Reserving effect on PA

[0447] Sr. No. (PA / CO blends)

[0448] Blank 100%

[0449] Example 22 87%

[0450] Example 30 82%

[0451] Example 50 78%

[0452] Example 78 72%

[0453] Example 98 80%

[0454]

[0455] Table 9 clearly showed excellent reserving effect of the dye fixing agents of the presently claimed invention.

Claims

Meissner Bolte M / ARCH-023-PCClaims1. A dye fixing agent obtainable by polymerizinga. at least one aromatic sulfonic acid or sulfonate;b. at least one substituted phenol or salt thereof; andc. at least one aldehyde;with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

2. The dye fixing agent according to claim 1 obtainable by polymerizinga. at least one aromatic sulfonic acid or sulfonate selected from sodium 4- hydroxybenzenesulfonate, sodium 6-hydroxynaphthalene-2-sulfonate, sodium 2,3-dihydroxy-6-naphthalenesulfonate, 4-hydroxybenzenesulfonic acid, sodium naphthalene-2-sulfonate, 2,4-dihydroxybenzenesulfonic acid, and 3,5- dihydroxybenzenesulfonic acid;b. at least one substituted phenol or salt thereof, wherein the at least one substituted phenol is selected from formula E, F, G, H, I, and J,;OHR formula Ewherein R1, R2, R3are independently selected from -H, -COOH, -NO2, -SO3H, -CH2OH, -OCH3, -COOCH3, -COOC2H5, -ON, -OHO, and -F,wherein all R1, R2and R3are not H at the same time;OHformula F;wherein R4and R5are independently selected from -H, -COOH, -C1-C4 alkyl, O OHMeissner Bolte M / ARCH-023-PCOH0Hformula G;wherein R6is selected from -SO3H, and C-i-Ce alkyl;formula H;wherein linker L is selected from a direct bond,wherein R7and R8together form a cyclohexyl ring or R7is CH3, and R8is - CH2CH2COOH;formula I;wherein R9, R10, R11, R12, R13and R14are independently selected from H and OH,wherein at least one of R9, R10, R11, R12, R13and R14is -OH;Meissner Bolte M / ARCH-023-PCformula J;wherein R15is selected from -H or -CH3;c. at least one aldehyde selected from formaldehyde, acetaldehyde and glyoxal. with the proviso that the at least one substituted phenol is not bisphenol A, bisphenol B, bisphenol F, bisphenol AF or bisphenol S.

3. The dye fixing agent according to claim 1 or claim 2, wherein the dye fixing agent is obtainable by reacting at least one aromatic sulfonic acid or sulfonate, at least one substituted phenol or salt thereof, at least one aldehyde and urea.

4. The dye fixing agent according to any of claims 1 to 3, wherein the molar ratio of the at least one aromatic sulfonic acid or sulfonate to the at least one aldehyde is in the range of 0.1 to 4.0.

5. The dye fixing agent according to any of claims 1 to 4, wherein the molar ratio of the at least one substituted phenol or salt thereof to the at least one aldehyde is in the range of 0.1 to 2.0.

6. The dye fixing agent according to any of claims 3 to 5, wherein the molar ratio of the at least one substituted phenol or salt thereof to urea is 2.0 to 40.0.

7. The dye fixing agent according to any of claims 1 to 6 having a weight average molecular weight in the range of 500 to 100000 g / mol according to DIN 55672-3-2016.

8. A method for preparing the dye fixing agent according to any of claims 1 to 7 comprising at least the steps ofa. mixing the at least one aromatic sulfonic acid or sulfonate, the at least one substituted phenol or salt thereof, at least one alkali or at least one acid, and at least one solvent to obtain a mixture;b. heating the mixture to a temperature in the range of 80 to 100 °C; andc. adding at least one aldehyde to the mixture at a temperature in the range of 60 to 85°C over 0.5 to 1 hours; followed by heating the resultant mixture at a temperature in the range of 85 to 100 °C for 2 to 6 hours.

9. The method according to claim 8, wherein step (a) further comprising mixing urea.Meissner Bolte M / ARCH-023-PC10. An aqueous composition comprising the dye fixing agent according to any of claims 1 to 7 or obtainable according to the method according to claim 8 or 9.

11. The aqueous composition according to claim 10 comprising the dye fixing agent water, and at least one solvent other than water, wherein the weight ratio of the dye fixing agent to the total amount of water and the at least one solvent other than water is in the range of 1:1 to 1:10.

12. Use of the dye fixing agent according to any of the claims 1 to 7 or the dye fixing agent obtainable according to claim 8 or 9 or the aqueous composition comprising the dye fixing agent according to claim 10 or claim 11 for improving wet fastness of a textile material.

13. A method for improving wet fastness of a textile material comprising the following steps:a. dyeing the textile material with at least one dye to obtain dyed textile material; b. treating the dyed textile material with the aqueous composition comprising the dye fixing agent according to any of the claims 1 to 7 or the dye fixing agent obtainable according to claim 8 or 9 or the aqueous composition comprising the dye fixing agent according to claim 10 or claim 11 to obtain a fixed dyed textile material; andc. drying the dyed fixed textile material.

14. A treated textile material obtainable by treatment of a textile material with the dye fixing agent according to any of the claims 1 to 7 or the dye fixing agent obtainable according to claim 8 or 9 or the aqueous composition according to claim 10 or claim 11 or by use of the dye fixing agent according to claim 12 or by treating a textile material by the method according to claim 13.

15. The treated textile material according to claim 14, wherein the textile material is selected from polyamide and blends of polyamide with cellulose, wool, orelastane.

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