Method for producing post-treatment agents for textile fibers and their use

Abstract

The present invention relates to a method for producing a post-treatment agent for textile fibers using an extract of polyphenols from at least one plant component, to the compounds obtained by this method and their uses.

Description

[Technical Field]

[0001] The present invention relates to a method for producing a post-treatment agent for textile fibers using an extract of polyphenols from at least one plant component, to the compounds obtained by said method and to their uses.

[0002] Polyamide is a synthetic fiber mainly used in the clothing field, especially in underwear, sports equipment or swimwear, and technical fields. Its fiberized form is, for example, flock, yarn and textile sheet material. In the case of textile sheet material, besides pure polyamide, blends of elastic materials, such as polyamide 6.6 and elastane, are increasingly used.

[0003] Depending on the material composition, the finishing process and the choice of dyes, it is important to achieve the required wear fastness. The fastness of textiles and their colours is understood to mean their durability, in particular their light fastness. The required wear fastnesses are wash fastness (e.g. to 50°C), contact fastness (water fastness and / or sweat fastness) and / or chlorine bath water fastness.

[0004] Fastness to use is achieved by post-treatments or dye fixation for the fibers. Polyamide microfibers, especially in blends with elastane, require the correct selection of post-treatments with anionic and / or cationic spinning auxiliaries.

[0005] DE 25 07 108 A1 describes fixing agents for improving the fastness properties of dyeings on polyamide fibers, in particular condensation products of 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfonic acid with lower aliphatic aldehydes, such as formaldehyde or acetaldehyde, or their metal salts, which condensation products have an average molecular weight of about 5000 to about 30,000 and a ratio of carbon atom content to sulfur atom content of 3.0:1 to 4.8:1.

[0006] Traditionally, post-treatment is carried out with syntans, i.e. synthetic tannins. Syntans are produced by condensation of phenol or bisphenols with formaldehyde. In recent decades, the synthesis of commercially available products has generally been carried out via acidic (novolak) or basic (resol) catalysis.

[0007] DE 699 33 752 T2 discloses phenol-novolaks, in particular phenol-glyoxal condensates, glycidylated derivatives thereof, compositions containing them, and a process for their preparation, which is carried out by synthesizing glyoxal and phenol at temperatures of 80 to 100°C in the presence of 1 to 6% of an acid catalyst.

[0008] A drawback of both novolac and resole products is their general lack of water solubility. A fundamental requirement for textile applications is a product that is either emulsified or completely soluble in water. Therefore, additional functionalization is required to enhance solubility through sulfonation reactions.

[0009] As the use of phenol, bisphenol, or formaldehyde in textiles is also increasingly restricted, there is a demand for phenol-, bisphenol-, and formaldehyde-free products that cannot be met by syntan.

[0010] Alternatively, natural substances such as tannins are also used. Natural substances, especially tannins, meet the demand for products that are free of phenols, bisphenols, and formaldehyde, and are therefore preferably used to improve fastness to chlorinated tank water, but have weaknesses in terms of contact fastness and long-term effectiveness (reduced effectiveness).

[0011] Korean Patent Publication No. 1020030010802 discloses the use of about 0.1 to 5.0% by weight of an inorganic acidic iron salt, particularly iron(II) sulfate or iron(II) chloride, followed by 0.5 to 5.0% by weight of tannic acid or synthetic tannic acid as a fastness improver for dyed polyamide fibers.

[0012] DE 3621410 A1 describes the aftertreatment of dyed textile materials from synthetic polyamides with (A) 2 to 6% by weight of a polyhydroxyphenol or its derivatives, followed by (B) 0.5 to 3% by weight of a cationic condensation product to improve the waterfastness of the dyeing, (B) being obtained by reacting (a) piperazine and derivatives of piperazine with (b) a bifunctional crosslinker such as ethyl halohydrin in a molar ratio of 1:0.5 to 1.1, and quaternizing the condensation product with benzyl chloride, using 0.15 to 1.5 mol of benzyl chloride per nitrogen equivalent of component (a) during quaternization.

[0013] Arbenz and Averous described the extraction and purification of tannins and their chemical modification (Arbenz and Averous 2015). Chemical modifications include the reaction of heterocycles, nucleophilic reactive sites, and hydroxyl groups. Arbenz and Averous also disclosed the reaction of nucleophilic reactive sites of tannins with formaldehyde using an OH catalyst for the production of adhesives or foams.

[0014] WO 2011 / 001105 describes composite materials based on fibers and natural resins, a manufacturing method and their uses, in particular a natural composite material comprising a reinforcement based on a nonwoven fabric made from natural fibers or fibers obtained from biomass, the natural matrix being selected from the group consisting of plant fibers or cellulose fibers derived from biomass, such as viscose fibers; and a mixture containing low molecular weight tannin and lignin pre-reacted with aldehydes in a ratio of 100 / 0 to 30 / 70% by weight of the total weight of the solids, the resin making up 20 to 50% by weight of the total weight, and 30% sodium hydroxide is used for the pre-reaction to maintain a pH value of 12 to 12.5.

[0015] The problem is therefore to provide a post-treatment agent for polyamide fibers that is free of phenols, bisphenols and formaldehyde and that preferably improves the fastness level of polyamide fibers after treatment.

[0016] According to the invention, this problem is solved by the methods and compounds set forth in the independent claims. Advantageous embodiments of the invention are set forth in the dependent claims.

[0017] According to a first aspect of the present invention, the object is to provide a method for producing an after-treatment agent for textile fibers, the method comprising the steps of: a) providing an extract of polyphenols from at least one plant component; b) dissolving the polyphenol extract in water; c) condensing the polyphenol with at least one C2-C10 aldehyde using an acid catalyst Including, As an acid catalyst, pK <5 a using an organic or inorganic acid having a value, The acid catalyst is used in an amount ranging from 0.01% by weight to 2% by weight. It is solved by the method.

[0018] Advantageously, the process according to the invention makes it possible to provide a post-treatment agent for textile fibres which is obtained from plant components and is free of bisphenols, phenols and formaldehyde.

[0019] A further advantage is that the acid-catalyzed condensation in step c) is an endothermic reaction, which makes the reaction easy to control on an industrial scale, compared to the acid-catalyzed condensation of phenol with formaldehyde (novolak), which is exothermic.

[0020] Extract is understood to mean a substance or mixture of substances which is separated from plant constituents by means of an extractant (solid, liquid or gaseous), preferably by means of a solvent, in particular water and / or an organic solvent.

[0021] In embodiments, the extract contains plant components dissolved from the plant components by extraction with aqueous and / or organic solvents. Various extraction methods are known to those skilled in the art. For example, Arbenz and Averous describe the extraction and purification of tannins (Arbenz and Averous 2015).

[0022] In an embodiment, the extract is a fluid extract, a concentrated extract and / or a dry extract.

[0023] "Dry extract" (also total extract) is understood to mean an extract comprising the substances of at least one plant component remaining after distillation of the extract.

[0024] In a preferred embodiment, the extract of polyphenols is a dry extract.

[0025] In an embodiment, the extract of polyphenols has a solids content in the range of 85% to 100% by weight.

[0026] In an embodiment, the polyphenol is selected from tannin, lignin, a lignin derivative and / or cardanol.

[0027] In an embodiment, the lignin derivative is a salt of lignin, preferably sodium lignosulfonate or ammonium lignosulfonate.

[0028] In a preferred embodiment, the polyphenol is selected from hydrolyzable tannins, especially tannic acid.

[0029] "Tannic acid" is understood to mean polyphenolic tannins with weakly acidic properties, in particular esters or mixtures of esters of glucose with gallic acid and / or 3-galloylgallic acid (polygalloyl-glucose).

[0030] In an embodiment, the tannic acid has a number average molecular weight ranging from 1,350 g / mol to 1,450 g / mol. "Number average molecular weight" is understood to mean the molecular weight of a polymer weighted according to the relative number fraction that this polymer possesses.

[0031] In an embodiment, the tannic acid has a weight-average molecular weight ranging from 1,400 g / mol to 1,500 g / mol. "Weight-average molecular weight" is understood to mean the molecular weight of a polymer weighted according to the relative mass fraction that this polymer possesses.

[0032] In an embodiment, the extract of polyphenols has a water content ranging from 0% to 15% by weight, preferably from 5% to 10% by weight.

[0033] In embodiments, the plant ingredients are fresh, composted, frozen, and / or dried plant material, with or without residual moisture.

[0034] In embodiments, the extract is obtained from above ground parts of the plant, such as fruit, leaves, wood and / or bark.

[0035] In an embodiment, the extract is obtained from residues of plant processing.

[0036] In an embodiment, the tannins are extracted from bloodroot, hops, black tea, green tea, grapes, preferably their fruits; dividivi tree, persimmon tree, myrobalan, sumac plant, trillo, valonia, pine, mimosa, oak, chestnut or acacia, preferably oak, chestnut or acacia bark, wood and / or plant galls.

[0037] In an embodiment, the extract comprises a polyphenol content in the range of 10% to 45% by weight, preferably 10% to 40% by weight, particularly preferably 10% to 35% by weight.

[0038] The determination of the polyphenol content can be carried out using Fourier transform infrared spectroscopy (FTIR) or redox titration, in particular using colorimetric determination of dry matter, for example using the Folin-Ciocalteu reagent or the Phenolfix test.

[0039] In an embodiment, the extract is an aqueous and / or organic extract of at least one plant component.

[0040] In an embodiment, the extraction of polyphenols comprises grinding and / or homogenizing at least one plant component.

[0041] In an embodiment, the extraction of polyphenols comprises: i. extracting at least one plant component with water; and / or ii. Extracting the aqueous extract with a solvent mixture comprising diethyl ether and ethanol, preferably in a ratio of 1:4. Includes.

[0042] In an embodiment, the extraction of polyphenols further comprises separation of the organic phase and evaporation of the solvent.

[0043] In an embodiment, the extraction of polyphenols comprises at least one filtration and / or distillation.

[0044] In an embodiment, step b) is carried out at a temperature in the range of 20°C to 100°C, preferably in the range of 30°C to 90°C, particularly preferably in the range of 40°C to 80°C.

[0045] According to the invention, in step c) a pK of less than 5 a Any organic or inorganic acid having a desired acidity can be used as the acid catalyst.

[0046] In an embodiment, in step c) oxalic acid, monochloroacetic acid or sulfuric acid, preferably oxalic acid, is used as the acid catalyst.

[0047] According to the invention, in step c) the acid catalyst is used in a proportion ranging from 0.01% to 2% by weight, preferably in the range from 0.1% to 0.5% by weight.

[0048] In an embodiment, step c) is carried out at a pH value in the range of 0.5 to 3, preferably in the range of 1 to 2.5.

[0049] According to the invention, in step c) condensation is carried out with at least one C2-C10 aldehyde. C2-C10 aldehyde is understood to mean an aldehyde having 2 to 10 C atoms in its molecular formula and having at least one aldehyde group, preferably one or two aldehyde groups. Preferably, the aldehyde is a C2-C6 aldehyde.

[0050] In an embodiment, the aldehyde in step c) is glyoxal, 5-hydroxymethylfurfural, or glutaraldehyde.

[0051] In a preferred embodiment, the aldehyde in step c) is glyoxal.

[0052] In an embodiment, in step c), the stoichiometric ratios of polyphenol to C2-C10 aldehyde and OH group to aldehyde group are each in the range of 1:0.4 to 1:2, i.e., 0.4 to 2 aldehyde groups per OH group. Preferably, the stoichiometric ratio of polyphenol to C2-C10 aldehyde is in the range of 1:0.4 to 1:0.8, particularly preferably in the range of 1:0.5 to 1:0.7.

[0053] In an embodiment, step c) is carried out at a temperature in the range of 90°C to 120°C, preferably in the range of 95°C to 105°C.

[0054] In an embodiment, step c) is carried out under an inert gas atmosphere, preferably under a nitrogen atmosphere.

[0055] In an embodiment, step c) is carried out over a period ranging from 2.5 hours to 5 hours, preferably about 4 hours.

[0056] In an embodiment, the process according to the invention further comprises preparation of the compound obtained according to step c), "preparation" being understood to mean the adjustment of its properties for use as a post-treatment agent for textile fibers.

[0057] In an embodiment, the method according to the present invention includes adjusting the viscosity after step c). In an embodiment, the viscosity is adjusted by adding glycerol, propylene glycol, 2,3-O-isopropylideneglycerol, butyl glycol, and / or butyl diglycol. In an embodiment, the viscosity is adjusted by adding glycerol, propylene glycol, 2,3-O-isopropylideneglycerol, butyl glycol, and / or butyl diglycol in the range of 4% to 12% by weight, preferably 8% to 10% by weight.

[0058] In a further embodiment, the method according to the invention comprises adjusting the pH value after step c).

[0059] In an embodiment, the method according to the present invention further comprises adding an extract of polyphenols from at least one plant component after step c), in an embodiment, the amount of the extract of polyphenols from at least one plant component added after step c) is in the range of 10% to 15% by weight.

[0060] Advantageously, the extract of polyphenols from at least one plant component in the post-treatment agent can reduce and / or prevent yellowing and / or darkening of polyamide, wool and / or silk fibers.

[0061] A further aspect of the present invention is a compound obtainable by the process according to the present invention.

[0062] In an embodiment, the compound obtainable by the process according to the invention has a viscosity in the range of up to 200 mPa·s, preferably in the range of 100 mPa·s to 200 mPa·s, at a temperature of 20° C. The viscosity can be measured by a rheometer or viscometer, in particular a rotational viscometer, for example from Brookfield®.

[0063] In an embodiment, the compound obtained by the method according to the invention has a solids content ranging from 26% to 40% by weight, preferably from 37% to 39% by weight.

[0064] According to the invention, the compound obtained by the method according to the invention has a pH value in the range of 2-5, preferably 3-4.

[0065] A similar embodiment of the present invention is the use of the compounds according to the invention as aftertreatment and / or dye resist agents for textile fibers, preferably polyamide fibers, wool fibers, silk fibers and / or blends thereof, in particular as a treatment to increase wash fastness, chlorine bath water fastness and / or contact fastness.

[0066] Advantageously, the available after-treatment agents allow for improved wash fastness, chlorine bath water fastness and / or contact fastness to polyamide fibers and their blends, in particular polyamide-polyurethane blends, such as polyamide-elastane blends, as well as improved fastness to wool and silk fibers. Furthermore, the available after-treatment agents are acid stable and / or have no "aging" effect.

[0067] The fastness of textiles and their colors is understood to mean the resistance of textiles to various factors such as light, skin contact or chlorinated bath water, especially fastness to light, fastness to contact or fastness to chlorinated bath water.

[0068] In an embodiment, the polyamide fibers are pure fibers or blended fibers.

[0069] In an embodiment, the polyamide blend or polyamide blend fiber is a polyamide-wool blend fiber, a polyamide-cellulose blend fiber, or a polyamide-polyurethane blend fiber, especially a polyamide-elastane blend fiber.

[0070] In an embodiment, the polyamide fibers are selected from polyamide 6.6 or polyamide 6.6-elastane blend fibers, especially 90% polyamide 6.6 microfiber / 10% elastane or 86% polyamide 6.6 / 14% elastane.

[0071] In an embodiment, the compounds according to the invention are used as post-treatment agents for wool and / or silk fibers dyed with acid dyes or metal complex dyes, and advantageously, the compounds according to the invention improve the fastness of wool and / or silk fibers dyed with acid dyes or metal complex dyes.

[0072] In an embodiment, the compounds according to the invention are used as after-treatment agents for polyamide / wool and / or polyamide / silk blends dyed with acid dyes or metal complex dyes.

[0073] In an embodiment, the compounds according to the invention are used as resist agents for polyamide / wool blends which are subsequently dyed with acid dyes or metal complex dyes.

[0074] In an embodiment, the compounds according to the invention are used as resists for polyamide / cellulose blends which are subsequently dyed with direct or reactive dyes. Depending on the application concentration of the compounds according to the invention, the fiber components are resisted, i.e., blocked, from dye uptake.

[0075] The present invention is not limited to the embodiments shown and described, but also includes all embodiments that have the same effect within the meaning of the present invention. Furthermore, the present invention is also not limited to the specifically described combinations of features, but can also be defined by other combinations of specific features of all individual features disclosed as a whole, unless the individual features are mutually exclusive or specific combinations of individual features are explicitly excluded.

[0076] In the following, the invention is intended to be explained in more detail by means of examples, which are intended to illustrate the invention without limiting it.

[0077] Extraction of polyphenols from at least one plant component Plant components, such as plant galls, are first crushed and extracted with water. The aqueous extract is then extracted with a solvent mixture of diethyl ether / ethanol in a ratio of 1:4, the organic phase is separated, and the aqueous solution is evaporated to dryness. The polyphenol extract thus obtained is a yellow-brown solid.

[0078] The process according to the invention for producing a post-treatment agent for polyamides comprises: Example 1: A polyphenol extract with a tannic acid content ranging from 22 to 35% by weight is reacted with 1) glyoxal, 2) glutaraldehyde, or 3) 5-hydroxymethylfurfural (5-HMF) in a stoichiometric ratio of 1:1, 1:0.8, 1:0.6, or 1:0.4. The polyphenol extract is first dissolved in water at 60°C. The reaction is carried out using an acid catalyst. To this end, 0.25% by weight of oxalic acid is added to the reaction mixture. This is followed by the addition of an aldehyde to induce condensation. The condensation is carried out at a temperature of approximately 100°C for 4 hours. The reaction mixture is then cooled to room temperature, and approximately 4 to 6% by weight of glycerol and 1,2-propylene glycol are added to adjust the viscosity.

[0079] Example 2: A polyphenol extract with a tannic acid content ranging from 10 to 15% by weight is reacted with 1) glyoxal, 2) glutaraldehyde, or 3) 5-HMF in a stoichiometric ratio of 1:1, 1:0.8, 1:0.6, or 1:0.4. The polyphenol extract is first dissolved in water at 60°C. The reaction is carried out using an acid catalyst. For this, 0.25% by weight of oxalic acid is added to the reaction mixture. An aldehyde is then added and the condensation takes place. The condensation is carried out at a temperature of approximately 100°C for 4 hours. After cooling to 60°C, a further amount of polyphenol extract (10 to 15% by weight) is added to the product in a second partial step. The reaction mixture is then cooled to room temperature. Approximately 4 to 6% by weight of glycerol and 1,2-propylene glycol, respectively, are added to the reaction mixture to adjust the viscosity.

[0080] Example 3 A polyphenol extract with a tannic acid content ranging from 10 to 15% by weight is mixed with sodium lignosulfonate, or alternatively, ammonium lignosulfonate, in a 1:1 stoichiometric ratio and reacted with 1) glyoxal, 2) glutaraldehyde, or 3) 5-HMF in a 1:1, 1:0.8, 1:0.6, or 1:0.4 ratio. The reaction is acid-catalyzed. To this end, 0.25% by weight of oxalic acid is added to the reaction mixture. This is followed by the addition of an aldehyde to induce condensation. The condensation is carried out at a temperature of approximately 120°C for 4 hours. The reaction mixture is then cooled to room temperature, and approximately 4 to 6% by weight of glycerol and 1,2-propylene glycol, respectively, are added to the reaction mixture to adjust the viscosity.

[0081] Example 4: Sodium lignosulfonate, or alternatively ammonium lignosulfonate, having a polyphenol content ranging from 22 to 35% by weight is reacted with 1) glyoxal, 2) glutaraldehyde, or 3) 5-HMF in a stoichiometric ratio of 1:1, 1:0.8, 1:0.6, or 1:0.4. The lignin derivative is first dissolved in water at 60°C. The reaction is carried out using an acid catalyst. To this end, 0.25% by weight of oxalic acid is added to the reaction mixture. This is followed by the addition of an aldehyde, which then induces condensation. The condensation is carried out at a temperature of approximately 120°C for 4 hours. The reaction mixture is then cooled to room temperature, and approximately 4 to 6% by weight of glycerol and 1,2-propylene glycol, respectively, are added to the reaction mixture to adjust the viscosity.

[0082] Example 5: A cardanol extract from cashew nut shells, having a polyphenol content ranging from 22 to 35% by weight, is reacted with 1) glyoxal, 2) glutaraldehyde, or 3) 5-HMF in a ratio of 1:1, 1:0.8, 1:0.6, or 1:0.4. The cardanol extract is dissolved in water at 60°C. The reaction is carried out using an acid catalyst. For this, 0.25% by weight of oxalic acid is added to the reaction mixture. An aldehyde is then added to cause condensation. The condensation is carried out at a temperature of approximately 120°C for 4 hours. The reaction mixture is then cooled to room temperature, and approximately 4 to 6% by weight of glycerol and 1,2-propylene glycol are added to the reaction mixture to adjust the viscosity.

[0083] Characterization of the resulting post-treatment agent for polyamides Post-treatment for polyamide: Dye aftertreatment leads to an improvement in the level of wet fastness of dyeings carried out with acid dyes or metal complex dyes, especially in the case of medium and dark shades and / or in cases where special requirements such as fastness to chlorine bath water are required.

[0084] Anionic dyeing aftertreatment is typically carried out on polyamide 6.6 (nylon) at 75°C for an average treatment time of 20 minutes at an acidic pH range, especially between 4 and 4.5. The amount of aftertreatment agent varies depending on the required level of fastness, the strength of the aftertreatment agent and the dye or dyes used, and is calculated in % (x% of aftertreatment agent based on the weight of the dyed textile) in the exhaust method.

[0085] For other polyamides (e.g. polyamide 6) or special colors such as rhodamine (bright pink) and flavin (bright yellow), there are temperature-related deviations, where the temperature and / or pH value ranges are varied.

[0086] After post-treatment, the textile material is rinsed thoroughly and subjected to further treatment depending on the requirements profile (e.g. lustre, treatment of synthetic threads and yarns with fat-containing substances to improve handle, softness and suppleness).

[0087] Example 1: Improvement of washing fastness at 60°C of "navy" dyed (acid dye 3.6% Sellanyl Navy Blue N-5R 180%) on 100% PA6.6 knitwear 100% polyamide 6.6 (knitwear) was dyed with dye under standard conditions, rinsed, and then post-treated in a fresh treatment bath as follows: pH adjustment to pH 4 (using 60% acetic acid), addition of different amounts of post-treatment agent, treatment at 75°C for 20 minutes, rinse at 40°C for 10 minutes, rinse at 20°C for 10 minutes, dry. The wash fastness was tested at 60°C according to ISO 105-C03, and bleeding of the polyamide on the multi-fiber associated fabric section was assessed using a grey scale (1 - very bad, heavy bleeding; ~5 - very good, no bleeding) and the mean value calculated from the ratings by three subjects. The change in shade due to each post-treatment agent or process was also assessed.

[0088] [Table 1]

[0089] [Table 2]

[0090] Example 2: Improvement of wet fastness at 40°C of "Blue Mallow" dyeing (1.5% acid dye 1% Erionyl Red A3B + 0.5% Erionyl Bordeaux A5B) on 90% polyamide 6.6 / 10% elastane, especially wash fastness according to ISO 105-C06 A2S, water fastness (heavy water) according to ISO 105-E01 and sweat fastness (alkaline) according to ISO 105-E04 90% polyamide 6.6 microfiber / 10% elastane (pre-fixed knitwear) was dyed under standard conditions with 1% Erionyl Red A3B + 0.5% Erionyl Bordeaux A5B dyestuff, rinsed, and then post-treated in a fresh treatment bath as follows: pH adjustment to pH 4 (using 60% acetic acid), addition of 3% of each post-treatment agent, treatment at 75°C for 20 minutes, rinse at 40°C for 10 minutes, rinse at 20°C for 10 minutes, dry, wash fastness test at 40°C according to ISO 105-C06 A2S, water fastness test (heavy water) according to ISO 105-E01, ISO Sweat fastness (alkaline) test according to 105-E04, evaluation of bleeding of polyamide on multi-fiber fabric parts using a gray scale (1 - very bad, bleeding a lot, ~5 - very good, no bleeding) and calculation of the average value from the evaluations by three subjects. Additionally, the change in color tone due to each post-treatment or process was also evaluated.

[0091] [Table 3]

[0092] [Table 4]

[0093] Example 3: Improvement of "Blue" dyeing (1% acid dye Telon Blue M-GLW) on 86% Polyamide 6.6 / 14% Elastane in chlorinated tank water according to ISO 105-E03 86% polyamide 6.6 / 14% elastane (pre-fixed knitwear) was dyed under standard conditions with 1% Telon Blue M-GLW (a chlorine-sensitive dye), rinsed, and then post-treated in a fresh treatment bath as follows: pH adjustment to pH 4 (using 60% acetic acid), addition of different amounts of post-treatment agent, treatment at 75°C for 20 minutes, rinse at 40°C for 10 minutes, rinse at 20°C for 10 minutes, dried, tested for fastness to chlorine bath water (active chlorine concentrations of 20, 50, and 100 ppm), rated for color change using a gray scale (1 - very poor, complete dye destruction by chlorine, ~5 - very good, no dye destruction or color change), and averaged from the ratings by three subjects.

[0094] [Table 5]

[0095] [Table 6]

[0096] Example 4: "Aging" study, i.e., study of the effect of artificial aging of post-treatment agents on the wash fastness at 60°C of "navy" dyeing (acid dye 3.6% Sellanyl Navy Blue N-5R 180%) on 100% PA6.6 knitwear 100% polyamide 6.6 (knitwear) was dyed under standard conditions with 3.6% Sellanyl Navy Blue N-5R 180% acid dye, rinsed, and post-treated in a fresh treatment bath as follows: pH adjustment to pH 4 (using 60% acetic acid), addition of 2% of each post-treatment agent in different artificial aging stages, i.e., "fresh" post-treated samples versus post-treated samples artificially "aged" in a drying cabinet depending on time (10 and 20 days) and temperature (50°C); treatment at 75°C for 20 minutes, rinsing at 40°C for 10 minutes, rinsing at 20°C for 10 minutes, drying. Washing fastness test at 60°C according to ISO 105-C03. Evaluation of the bleeding of the polyamide on the multi-fiber fabric section using a gray scale (1 - very bad, heavy bleeding; ~5 - very good, no bleeding) and calculation of the average value from the evaluations by three subjects.

[0097] [Table 7]

[0098] Example 5: Resist dyeing of a 50 / 50 (equal weight ratio) polyamide / wool blend fabric with a "navy" metal complex dye (1% Lanacron Navy SG 150% metal complex dye). Depending on the fiber affinity, the purpose of the treatment is to partially block the fiber components to achieve various fashion effects (tone-in-tone dyeing or two-tone effects). For dyeing PA / WO blends, chemical auxiliaries are added, followed by a 10-minute lead time for the post-treatment before the addition of the dye used and acidic pH adjustment (1% Lanacron Navy SG 150% - metal complex dye). Dyeing is carried out at 98°C for a 30-minute process, followed by rinsing with water at 40°C and 20°C. The dye resistance of the PA parts is assessed using the following scale (5 = no resistance, 1 = complete resistance).

[0099] Result: No post-treatment agent: 5 points 2% of the compound according to the invention: score 3.

[0100] Non-patent literature citations: Arbenz A, Averous L, Chemical modification of tannins to elaborate aromatic biobased macromolecular architectures. Green Chemistry, 2015, 17, 2626-2646.

Claims

1. 1. A method for producing a post-treatment for textile fibers, comprising: a) providing an extract of polyphenols from at least one plant component; b) dissolving the polyphenol extract in water; c) condensing said polyphenol with at least one C2-C10 aldehyde using an acid catalyst; Including, As an acid catalyst, a pK of less than 5 ａ using an organic or inorganic acid having a value, The acid catalyst is used in an amount ranging from 0.01% by weight to 2% by weight. method.

2. 2. The method according to claim 1, characterized in that the polyphenol is selected from tannin, lignin, lignin derivatives and / or cardanol.

3. 3. The method of claim 2, wherein the tannins are extracted from bloodroot, hops, black tea, green tea, grapes, dividivi trees, persimmon trees, myrobalan, sumac plants, trillo, valonia fruit, oak, chestnut or acacia bark and / or wood, or plant galls.

4. 4. The process according to claim 1, wherein step b) is carried out at a temperature in the range of from 20°C to 100°C.

5. 5. The process according to claim 1, wherein the C2-C10 aldehyde in step c) is glyoxal, 5-hydroxymethylfurfural or glutaraldehyde.

6. 6. The method according to claim 1, wherein in step c) the ratio of polyphenols to C2-C10 aldehydes is in the range of 1:0.4 to 1:

2.

7. 7. The process according to claim 1, wherein step c) is carried out at a temperature in the range of from 90°C to 120°C.

8. 8. The process according to claim 1, wherein step c) is carried out under an inert gas atmosphere.

9. 9. The process according to any one of claims 1 to 8, characterized in that step c) is carried out for a period ranging from 2.5 hours to 5 hours.

10. 10. The method of claim 1, further comprising adjusting the viscosity after step c).

11. A compound obtainable by the process of any one of claims 1 to 10, having a pH value in the range of 2 to 5.

12. 12. The compound of claim 11, having a pH value in the range of 3 to 4.

13. 13. Use of the compounds according to claim 11 or 12 as after-treatment and / or dye-resist agents for textile fibres.

14. 14. Use according to claim 13, characterized in that the textile fibres are polyamide fibres, wool fibres, silk fibres and / or blends thereof.

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