TW202402861A - Non-reactive extender compounds for durable water repellence in textile fabrics - Google Patents

Abstract

The present invention relates to the use of a compound, which is the reaction product of: (i) at least one di- or poly-isocyanate; (ii) at least one aromatic compound selected from the group consisting of: , wherein R ¹, R ², R ³, R ⁴and R ⁵are independently selected from the group consisting of H and C _1-4alkyl; Y is OH, NH ₂or SH; X is O, N or S; and (iii) optionally one or more further reactants; as a non-reactive extender for durable water-repellence in textile fabrics. The present invention further relates to a durable water-repellence (DWR) system comprising at least one non-fluorinated water-repellent compound and at least one non-reactive extender compound as above, their use in water-repellent finishing of fibre materials, as well as a process for treating a textile fabric composed on fibre materials.

Description

Non-reactive synergist compounds for durable water repellency of textiles

The present invention relates to the use of compounds that are the reaction products of diisocyanates or polyisocyanates and aromatic compounds as non-reactive synergists for durable water repellency in textiles, and to products containing such non-reactive synergists and water-repellent compounds. Durable water-repellence (DWR) systems, their use in water-repellent processing of fiber materials and methods of treating textiles using the non-reactive synergist or DWR system. Non-reactive synergists and DWR systems according to the present invention are fluorochemical-free and impart water-repellent properties to natural and synthetic textiles.

Over the past few years, many countries have committed to improving environmental quality by conserving natural resources and reducing emissions of climate-damaging substances. The government provides financial support to industry to achieve these goals. Consumers demand environmentally friendly textiles manufactured to the highest ecological standards. Brands and retailers are translating these requirements into actual demand, and textile manufacturers continue to improve their manufacturing superiority by investing in modern equipment and choosing environmentally friendly chemicals.

It is known to provide certain properties, such as water repellency, to textiles such as woven, knitted or non-woven fabrics by treating the fabrics with aqueous dispersions containing specific chemical components. The water-repellent properties of textiles are often achieved by using fluorine-containing products as such chemical components. However, fluorinated products are expensive and their use is limited due to the development of chemical regulatory frameworks.

Fluorochemical treatments are relatively expensive and are often combined with less expensive non-fluorinated "boosters". Among known synergists, blocked isocyanates are a desirable class because they are cheap, easy to prepare and very effective. Blocked isocyanate builders are usually supplied as emulsions in water. An example of such a synergist for use in oil- and water-repellent products is PHOBOL® C curing temperature.

The term "blocked isocyanate" includes monoisocyanates, diisocyanates and polyisocyanates in which the isocyanate groups have reacted with a blocking agent which releases the isocyanate and blocking agent upon heating. End-capping agents are, for example, amines, amides, compounds with active hydrogen atoms or alcohols. Improved adhesion can result if the heating is carried out in the presence of a compound having a functional group that can react with the isocyanate group, for example the hydroxyl or amine groups of a suitable substrate such as a fiber. Therefore, these blocked isocyanates are called reactive synergists, which have the disadvantages of requiring curing temperatures above 150°C and the release of blocking agents that are often environmentally harmful.

Alternatively, aqueous systems containing paraffin and/or acrylic polymers have been proposed for obtaining water-repellent properties on textiles. The ultimate goal is to reduce the amount of chemicals used and energy consumption during the method. Such substances and methods are described, for example, in WO2010115496 A1, WO2018054712 A1 and WO2011035906 A2.

It is an object of the present invention to provide non-reactive synergists and systems that help provide excellent water repellency properties to all textiles, including polyester-containing fabrics, and reduce the energy consumption and chemical usage of the process. The present invention also provides a method of obtaining excellent water repellency properties on such fabrics.

According to the above, the present invention relates to the use of a compound as a non-reactive synergist for durable water repellency in textiles, which compound is the reaction product of: (i) at least one diisocyanate or polyisocyanate; (ii) ) at least one aromatic compound selected from the group consisting of: and , (I) (II) wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are independently selected from the group consisting of: H and C _1-4 alkyl; Y is OH, NH ₂ or SH; X is O, N or S; and (iii) one or more other reactants are selected as necessary.

Throughout this disclosure, the term "non-reactive synergist" means that the respective compound does not react with the functional groups of textile fibers.

The non-reactive synergist and durable water repellent (DWR) system according to the present invention contains neither any fluorochemicals nor styrene. In addition, since it does not react with the functional groups of textile fibers, the non-reactive synergist and DWR system of the present invention will not release any potentially toxic compounds when the textile is cured. In light of the above, the present invention further limits the number of ingredients used in the preparation of synergists and DWR systems for textile applications that are potentially hazardous to health and the environment.

At least one diisocyanate or polyisocyanate (i) is preferably at least one, such as one, two or three aromatic isocyanates, aliphatic isocyanates, precondensates or condensates thereof.

In a preferred embodiment, the aromatic isocyanate is methylene diphenyl isocyanate (MDI) or toluene diisocyanate (TDI ) , and the precondensate or condensate is a precondensate based on methylene diphenyl isocyanate (MDI) or condensates based on hexamethylene diisocyanate (HDI).

In this article, the terms "precondensate" and "prepolymer" are used interchangeably and refer to stable, usually partially polymerized chemical intermediates that are still reactive, i.e. can be fully polymerized at a later time (e.g. from Hangsmann's MDI precondensate Suprasec® 2021 or 2010).

The at least one aromatic compound (ii) is preferably benzyl alcohol or furfuryl alcohol.

In a specific example of the present invention, 50 mol% of at least one aromatic compound (ii) is replaced by an aliphatic compound of formula (III) (III), wherein Y is OH, _NH2 or SH.

In a preferred embodiment, the aliphatic compound of formula (III) is stearyl alcohol.

In one aspect, about 40% or more, preferably about 60% or more of the −N=C=O groups of at least one diisocyanate or polyisocyanate (i) are reacted with the aromatic compound (ii).

Other reactants (iii) are selected from the group consisting of one or more diols or polyols, N-methyldiethanolamine (NMDEA), 2,2,6,6-tetramethylpiperidine (TMP) and mixtures thereof group.

Suitable glycols according to the invention include ethylene glycol, diethylene glycol, triethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,5-heptanediol Diols or combinations thereof.

Suitable polyols according to the present invention contain three or more hydroxyl groups and include glycerol, trimethylolethane, trimethylolpropane, 1,2,6-hexanetriol, pentaerythritol, tripentaerythritol, dipentaerythritol, trimethylolpropane Methoxymethylpropane, propoxylated pentaerythritol, ethoxylated pentaerythritol, ethoxylated trimethylolpropane, xylitol, sorbitol, glucose, fructose and sucrose.

In one aspect, the other reactant (iii) reacts with about 60% or less, or preferably about 40% or less, of the −N=C=O groups of at least one diisocyanate or polyisocyanate (i). In another aspect, the other reactant (iii) is reacted with about 10% to about 30% of the −N=C=O groups of at least one diisocyanate or polyisocyanate (i).

In a preferred aspect, the compound according to the present invention is the reaction product of: (i) a precondensate based on methylene diphenyl isocyanate (MDI), which has a functionality equal to or greater than 2, (ii) furfuryl alcohol or benzyl alcohol, which reacts with about 60% or more of the −N=C=O groups of at least one diisocyanate or polyisocyanate (i); and N-methyldiethanolamine (NMDEA) (iii), which reacts with About 10% of the −N=C=O groups of at least one diisocyanate or polyisocyanate (i), or 2,2,6,6-tetramethylpiperidine (TMP) (iii), which reacts with about 30 % of the −N=C=O groups of at least one diisocyanate or polyisocyanate (i) react.

Compounds according to the invention may be formulated as aqueous dispersions, preferably containing from about 20% to about 35% by weight of dry ingredients (including surfactants).

Suitable surfactants according to the invention are dispersants, including known commercially available surfactants, such as non-ionic ethoxylated compounds, for example ethoxylated alcohols or ethoxylated carboxylic acids, cationic surfactants, Such as quaternary ammonium salts, or fatty amines. Suitably, the fatty amine is used in combination with a suitable acid, for example an organic acid such as acetic acid.

If desired, other ingredients known to be useful as components of compositions for treating textiles may be added to the aqueous dispersions obtained according to the present invention.

The invention also relates to a durable water repellency (DWR) system comprising (a) at least one non-fluorinated water repellent compound; and (b) at least one non-reactive builder compound according to the invention.

The at least one non-fluorinated water repellent compound (a) is preferably selected from the group consisting of: polyurethanes, acrylic copolymers, waxes, melamine condensates, silicone water repellents, hyperbranched/dendritic water repellents and its mixture.

In one aspect, the ratio of at least one non-fluorinated water-repellent compound (a) to compound (b) is about 90:10 to about 10:90, preferably about 80:20 to about 20:80, more preferably about 70 :30 to about 30:70, best about 60:40 to about 40:60.

In a preferred embodiment, compound (a) is polyurethane, acrylic copolymer or a mixture thereof, and the ratio of (a) to (b) is about 5:1 to about 1:2, preferably about 3:1 to about 1 :1.

The DWR system according to the present invention may further comprise one or more substances selected from the group consisting of additives, solvents and surfactants.

Suitable additives are wetting agents (e.g. INVADINE ^® PBN from Hangsmann), pH control agents (e.g. acetic acid, citric acid, hydrochloric acid, propionic acid, benzoic acid and their sodium salts), resins, catalysts (e.g. from Hangsmann) ^Knittex® type from SMAN) and co-solvents for stabilization (e.g. ethylene glycol).

Suitable solvents are any type of substance that can dissolve the compounds of the DWR system of the invention to form a solution, such as alkyl acetates (e.g., ethyl acetate, n-propyl acetate, butyl acetate), methyl ethyl ketone (MEK) , methyl isobutyl ketone (MiBK) and dimethyl formamide (DMF).

The non-reactive synergist and DWR system according to the present invention can be used for water-repellent processing of fiber materials.

The invention further relates to a method of treating textile fabrics consisting of fibrous materials, comprising the steps of padding the fabric with a non-reactive synergist or DWR system of the invention and then drying.

The method according to the invention may further comprise a curing step. The maximum curing temperature is equal to or lower than 180°C, preferably equal to or lower than 150°C, more preferably equal to or lower than 110°C, more preferably equal to or lower than 100°C, and most preferably equal to or lower than 80° C.

Textiles to be treated with the compounds or DWR systems according to the invention are, for example, polyester, polyamide, cotton, blends or variants thereof. Preferably, the fabric is polyester or polyamide, or blends or variations thereof. Typically, such textiles are woven, knitted or non-woven.

In the method according to the present invention, the concentration of the compound according to the present invention in the pad bath is about 2 to about 20 g/L, preferably about 5 to about 15 g/L, most preferably about 10 g /L to about 200 g/L.

The compounds and DWR systems according to the invention are particularly suitable for imparting water-repellent properties to natural and synthetic textiles. Surprisingly, the required level of water-repellent effect is achieved on synthetic textiles such as polyester fabrics or blends of cotton and polyester, but the effect is also seen on cotton fabrics. Textiles treated with compounds according to the invention and DWR systems are particularly suitable for outerwear.

The following examples illustrate the invention. Unless otherwise stated, temperatures are in degrees Celsius and concentrations in g/L. Chemicals Suprasec ^® 2021: Prepolymerized diphenylmethane diisocyanate (MDI) - functionality with 2.5 NCO groups per unit (Hangsmann AG) MiBK: Methyl isobutyl ketone BuAc: Butyl acetate tris Methylmethylpropane NMDEA: N -Methyldiethanolamine TMP: 2,2,6,6-Tetramethylpiperidine Furfuryl alcohol Benzyl alcohol Stearyl alcohol 2-HEA: 2-Hydroxyethylacrylate Marlipal O13/100: Ethyl alcohol Oxylated isotridecyl alcohol 10EO Ethoquad HT/25: Ethoxylated tallow Methyl ammonium chloride Propylene glycol HAc: Acetic acid IVADINE ^® PBN: Wetting agent (Hangsmann Company) Neoseed ^® NR-7080: Based on polyacrylic acid Ester-based water repellent (Nicca Textile Chemicals) Zelan ^® R3: Polyurethane-based water repellent (Chemours/Hangsmann) UXN: Phobol Extender® UXN reaction synergist (Hangsmann) Examples Example 1 - Synthesis of the non-reactive synergist compound (NonREx 1) of the present invention

In a 500 mL three-neck round bottom flask equipped with a mechanical stirrer, internal thermometer and reflux condenser, add 90.5 g Suprasec® 2021 (0.500 eq NCO, assuming a molar weight of 362 g/mol ) and 96 g MiBK. After stirring at room temperature for several minutes, a clear, low-viscosity solution was obtained. Then, 6.70 g (50 mmol; 0.150 eq) trimethylolpropane was added and the temperature was raised to 50°C while continuously stirring the solution. Use infrared spectroscopy to track the reaction progress and monitor the peak area at 2260 cm ^-1 (NCO valence vibration). After 90 min at 50°C, 2.98 g (25 mmol; 0.050 eq) NMDEA in 5.75 g MiBK was added; a temperature rise of 7°C showed a strong exothermic reaction. After stirring for 1 hour at 50°C, the reaction mass was diluted with 50.0 g MiBK. Prepare and add 29.40 g (300 mmol; 0.3 eq) of furfuryl alcohol dropwise. During the addition, an exothermic reaction increased the internal temperature by 9°C. After stirring at 50°C for a further 90 minutes, the reaction mass was allowed to cool to room temperature overnight. During this period as the viscosity increased, an additional 46 gMiBK was added. 370 g of reactant with a mass of 35% dry content were obtained.

Further non-reactive synergist compounds were prepared using benzyl alcohol alone (NonREx 2) and a mixture of furfuryl alcohol and stearyl alcohol (NonREx 3), which were synthesized from polyvalent isocyanate prepolymers according to the same reaction scheme.

Table 1 shows non-reactive synergist compounds obtained according to the present invention (NonREx 1-3), as well as comparative synergist compositions using 2-HEA in place of one or more aromatic/aliphatic alcohols (Comp. 1). These compositions have been used to prepare the aqueous dispersion in Example 2. Table 1 : Non-reactive synergist compounds according to the invention (NonREx 1-3) and comparative synergists (Comp.1) Components unit NonREx 1 NonREx 2 NonREx 3 Comp. 1 Isocyanate S. 2021 (2.5 NCO) g 90.5 90.5 60.7 90.5 alcohol FFA g 29.4 16.37 BZA g 32.4 SA g 8.91 compare 2-HEA g 34.8 other TMP g 6.7 6.7 4.47 6.7 NMDEA g 2.98 2.98 1.96 2.98 Solvent ikB g 240.35 246.22 134.98 AHr g 214.62 organic phase quantity g 369.93 378.8 306.6 269.96 Dry content % 35.0 35.0 30.0 50 * S. 2021 = Suprasec® 2021 FFA = Furfuryl alcohol BZA = Benzyl alcohol SA = Stearyl alcohol 2-HEA = 2 -Hydroxyethylacrylate TMP = 2,2,6,6-TetramethylpiperidineNMDEA = N - Methyldiethanolamine MiBK = Methyl-Isobutyl Ketone BuAc = Butyl Acetate Example 2 - General Procedure for Preparation of Aqueous Dispersions

150 g of the organic solution obtained in Example 1 (organic solution ex. 1, 35.0% dry content) was maintained at 60°C for 45 minutes. Prepare a solution of 2.1 g Marlipal O13/100, 1.05 g Ethoquad HT/25, 7.87 g propylene glycol and 243.75 g water at 55-60°C, then add 6.3 g 60% HAc to achieve a pH of approximately 3. Add the organic solution to the surfactant mixture while using a high-speed shear mixer. The resulting material is passed through a high-pressure homogenizer four times at 200 bar (2x10 ⁷ Pa) and 54-62°C. The organic solvent was removed from the resulting emulsion under reduced pressure. Add water to obtain a white emulsion with a dry content of 25% (infrared drying conditions and 1 hour at 120°C).

Table 2 below illustrates the different aqueous dispersions obtained with the non-reactive builder compounds according to the invention (Non-REx 1-3) and the comparative builder (Comp. 1). Table 2 : Aqueous dispersions according to the invention and comparative aqueous dispersions Components unit NonREx 1 NonREx 2 NonREx 3 Comp. 1 Organic solution ex. 1 g 150 150 145 150 surfactant Marlipal O13/100 g 2.1 2.1 1.74 2.1 Ethoquad HT/25 g 1.05 1.05 0.87 1.05 diol propylene glycol g 7.87 7.87 6.52 7.87 HAc 60% g 6.3 6.3 0.44 5.2 water g 243.75 243.75 253.75 243.75 Aqueous dispersion Yield g 194.6 266 168 185.3 Dry content % 25 17.3 21.9 25 pH 3.2 3.2 4.2

The following example (as a representative example) describes the treatment of a PES textile (blue polyester, ID004) with a DWR system using an aqueous dispersion prepared according to the general procedure of Example 2. Example 3 - Application Example (Processing) General Conditions - Application

All loadings in g/L refer to a standard solids content of 25% and are corrected in the report to match this level. The standard formulation of synthetic materials contains 1 g/L HAc 60% and 5 mL/L IVADINE ^® PBN as wetting agents. Based on product safety reasons for blocked isocyanates, typical cure conditions for synergist-containing formulations are drying at 110°C for 10 minutes and curing at 150°C for a minimum of 5 minutes in a drying cabinet, or drying at Mathis Laboratories Performed under conditions equivalent to those of a dry machine. Application is accomplished by packing in a manual lab foulard. -Laundry _

Samples were tested before and after the last wash/last tumble dryer cycle (LTD, Laundry Tumble Dry). A 4N laundry type at 40°C is used here to simulate typical household laundry. The fabric is washed with an amount of additional load to match a certain stress level on the sample.

The finished fabric obtained according to the application examples was subjected to the following tests:

(I) Spray testing in accordance with AATCC Results: droplets falling of the fabric, spray rating 100 (best), 50 (worst); 0 (completely wet)

(II) According to AATCC’s Bundesmann test (BM) - Results: Bondesmann rating after 1, 5 and 10 minutes, just like the spray rating, 5 (no water residue on the surface, i.e. best effect) to 1 (complete surface wetting) - Water absorption: relative weight gain percentage of fabric sample after test - Leakage: Amount of water penetrating the sample (mL)

Different DWR systems according to the invention have been prepared and compared with different concentrations of water repellent agent alone (standard) as well as comparative DWR systems. The results are summarized in Table 3 below. Table 3 : Performance comparison of water repellent alone (standard) and different DWR systems subjected to Bondsmann test Standard 1 DWR system 1 Standard 2 DWR system 2 DWR system 3 Comp. DWR System 1 Standard 3 DWR system 4 Comp. DWR System 2 g/L g/L g/L g/L g/L g/L g/L g/L g/L water repellent NR-7080 80 50 30 20 10 5 30 20 10 5 2 20 10 30 30 30 30 10 30 10 10 10 Zelan R3 80 60 20 20 NonREx 1 FFA 10 5 5 5 5 10 10 3 FFA/SA 5 2 BZA 10 5 15 5 compare Comp 1 2-HEA 10 5 UXN 8.3 solidify (°C) 150 150 150 150 150 150 150 150 150 150 150 150 150 150 150 150 150 150 150 150 80 80 80 80 80 80 BM Abs% 21.9 29.9 22.2 21.1 24.9 40.9 12.2 16.4 16.4 21.3 32.6 4.7 9 6.8 2.2 5,5,5 13.1 20.3 15.7 23.6 19.6 30.3 31.5 21.7 20.4 20.7 26.8 0 HL Rating 2,2,2 2,2,2 2,2,2 2,2,2 2,2,2 1,1,1 4,3,3 2,2,2 2,2,2 2,2,1 2,2,1 3,3,3 4,4,4 4,3,3 3,3,2 2,2,2 4,3,3 2,2,2 2,2,2 2,2,2 2,2,2 3,2,2 3,2,2 3,3,3 2,2,2 BM Abs% 2.7 1.8 11.2 0.9 9.4 9.4 7.6 7.6 1.8 1.8 0.9 4.9 1.3 1.5 1.5 13.4 5 HL Rating 3,4,4 4,4,4 2,2,2 4,4,4 3,3,2 3,3,2 3,3,3 3,3,3 4,4,4 4,4,4 4,4,4 3,3,3 4,4,4 3,3,3 3,3,3 2,2,2 BM Abs% 4.5 9.4 16.6 3.1 16.4 16.4 0.9 15.7 13.8 15.2 15.6 0.9 7.6 13.4 3.6 14.9 6.2 16.7 15.7 16.6 20 HL Rating 4,3,3 3,3,2 2,2,2 4,3,3 2,2,2 2,2,2 4,4,4 2,1,1 1,1,1 2,2,2 2,2,2 4,4,4 4,3,3 3,2,2 3,3,3 2,2,2 3,3,3 2,2,2 2,2,2 2,2,2 *NR-7080: ^Neoseed® NR-7080 FFA = Furfuryl Alcohol SA = Stearyl Alcohol BZA = Benzyl Alcohol 2-HEA = 2 -Hydroxyethylacrylate UXN: Phobo® Booster UXN HL: Home Laundry Cycle

As can be seen from Table 3 above, the DWR system according to the present invention (ie, the combination of NonREx 1-3 and water repellent acrylates -Neoseed® NR7080 and Zelan R3) significantly reduces the water absorption of PES fabrics under different circumstances. Spray ratings are not affected and all samples are rated at 100 unless otherwise stated.

Importantly, the formulation cures at 80°C (DWR System 4) rather than 150°C, maintaining or improving performance levels, saving energy and eliminating the need for high cure temperatures compared to standard synergist types. Residual blocking agent for fabrics and exhaust.

Additionally, 30 g/L NR7080 (Standard 3) achieved approximately 30% water absorption at all cure times at 80°C, while the combination of 30 g/L NR7080 with 10 g/L NonREx 1 (DWR System 4) absorbed approximately Water absorption of 21%, meeting or exceeding the level of NR7080 alone (Standard 1) at 150°C.

Reducing the amount of water repellent agent NR-7080 to 10 g/L (Standard 3) and comparing it to the formulation adding 5 g/L Non-REx 2 or 3 (DWR System 4), again at 80°C About 21% water absorbency. Leakage and Bondesmann ratings return to the level of 30 g/L water repellent alone, i.e. the combination of 10 g/L NR-7080 and 5g/L NonREx 2 or 3 at 80°C reaches the same level as 30g/L NR- Similar results for 7080 at 150°C. Changing the functional groups in the polyurethane from furan (Non-REx 1 type) to phenyl (Non-REx 2 type) affects the properties in a similar way, i.e. they are exchangeable (DWR system 4) and therefore Non-REx 1 can be replaced with Non-REx 2 at 150°C or 80°C at Non-REx dosages of 5 and 10 g/L with comparable results.

When the amount of water-repellent agent is further reduced to 5 g/L, which is lower than the effective level of NR7080 type (spray: 80/75/70; 41% Abs.), add at least 5 g/L Non-REx 1 to restore the effect (Spray 100/100/90; 21% Abs.) - See Standard 1 with DWR System 1. For comparison, a fabric water absorption of approximately 21% (Bondesmann test) and a spray rating of 100/100/100 (spray test) are the baseline effects of water repellent agent NR7080 alone at higher loads.

Mixing a furfur-based type builder (Non-REx 1) with a polyurethane wax (a low-functional isocyanate reacted with stearyl alcohol) as a builder system is also effective and shows similar performance compared to Non-REx 1. Stearyl-based ingredients are added directly to the formula to increase the effectiveness.

The DWR system according to the present invention provides significant improvements with respect to the pre-laundering Bondesmann rain test, even with the application of lower levels of water repellent, thus reducing the cost of the formulation and reducing the chemicals used on the textiles total amount. After 5 wash cycles (HL), the effect will be reduced but still visible. After 20 laundry cycles, no differences were observed, i.e. the product did not affect performance. The main effect measurement index is the mass percentage of water absorbed by the fabric during the test. The lower the better. NonREx compounds according to the invention alone may contribute to water repellency, although not shown in the above results.

DWR systems according to the invention already provide effect levels at 80°C that would otherwise only be seen above 120°C (e.g. Phobol® ExtenderXAN or UXN requiring a curing temperature of at least 150°C), again reducing costs and environmental impact, making it also suitable for fabrics requiring special processing conditions. Abbreviation: PUR = polyurethane PES = polyester TDI = toluene diisocyanate MDI = methylene diphenyl diisocyanate HDI = hexamethylene diisocyanate DWR = Durable Water Repellent System BM = Bondsman rain test AATCC = American Association of Textile Chemists and Colorists

without

without

Claims (20)

The use of a compound as a non-reactive synergist for durable water repellency in textiles, which compound is the reaction product of: (i) at least one diisocyanate or polyisocyanate; (ii) at least one aromatic compound, which Selected from the group consisting of: and , (I) (II) wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are independently selected from the group consisting of: H and C _1-4 alkyl; Y is OH, NH ₂ or SH; X is O, N or S; and (iii) one or more other reactants are selected as necessary. The use of claim 1, wherein the at least one diisocyanate or polyisocyanate (i) is aromatic isocyanate, aliphatic isocyanate, precondensate or condensate thereof. The use of claim 2, wherein the aromatic isocyanate is selected from methylene diphenyl isocyanate (MDI) or toluene diisocyanate (TDI), and the precondensate or condensate is based on methylene diphenyl isocyanate ( MDI) or a condensate based on hexamethylene diisocyanate (HDI). The use of any one of claims 1 to 3, wherein the at least one aromatic compound (ii) is benzyl alcohol or furfuryl alcohol. Use as claimed in any one of claims 1 to 4, wherein up to about 50 mol % of the at least one aromatic compound (ii) is substituted by an aliphatic compound of formula (III) (III), wherein Y is OH, _NH2 or SH. The use of claim 5, wherein the aliphatic compound of formula (III) is stearyl alcohol. The use of any one of claims 1 to 6, wherein about 40% or more; preferably about 60% or more of the −N=C=O groups of the at least one diisocyanate or polyisocyanate (i) React with the aromatic compound (ii). The use of any one of claims 1 to 7, wherein the at least one other reactant (iii) is selected from the group consisting of one or more diols or polyols, N-methyldiethanolamine (NMDEA), 2,2,6 , a group composed of 6-tetramethylpiperidine (TMP) and its mixtures. The use of any one of claims 1 to 8, wherein the at least one other reactant (iii) is combined with about 60% or less, preferably about 40% or less of the at least one diisocyanate or polyisocyanate (i ), or react with about 10% to about 30% of the −N=C=O groups of the at least one diisocyanate or polyisocyanate (i). Such as the use of any one of the requirements 1 to 9, where The at least one diisocyanate or polyisocyanate (i) is a precondensate based on methylene diphenyl isocyanate (MDI), which has a functionality equal to or greater than 2; The at least one aromatic compound (ii) is furfuryl alcohol or benzyl alcohol, which reacts with about 60% or more of the −N=C=O groups of the at least one diisocyanate or polyisocyanate (i); and The other reactant (iii) is N-methyldiethanolamine (NMDEA) reacted with about 10% of the −N=C=O groups of the at least one diisocyanate or polyisocyanate (i), or 2, 2,6,6-tetramethylpiperidine (TMP) reacted with approximately 30% of the −N=C=O groups of the at least one diisocyanate or polyisocyanate (i). A durable water-repellence (DWR) system containing: (a) at least one non-fluorinated water-repellent compound; and (b) At least one compound according to any one of claims 1 to 10. The DWR system of claim 11, wherein the at least one water-repellent compound (a) is selected from the group consisting of: polyurethane, acrylic copolymer, wax, melamine condensate, polysiloxy water-repellent agent, hyperbranched/dendritic Water repellent agents and mixtures thereof. The DWR system of claims 11 and 12, wherein the ratio of the at least one non-fluorinated water-repellent compound (a) to compound (b) is about 90:10 to about 10:90, preferably about 80:20 to about 20 :80, preferably about 70:30 to about 30:70, optimally about 60:40 to about 40:60. The DWR system of any one of claims 11 to 13, wherein (a) is polyurethane, acrylic copolymer or a mixture thereof, and the ratio of (a) to (b) is from about 5:1 to about 1:2, which is greater than Good about 3:1 to about 1:1. The DWR system of any one of claims 11 to 14, further comprising one or more substances selected from the group consisting of additives, solvents and surfactants. Use of a compound as claimed in any one of claims 1 to 10 or a DWR system as claimed in any one of claims 11 to 15 in water repellent processing of fiber materials. A method of treating textile fabrics composed of fibrous materials, comprising padding the fabric with a compound as in any one of claims 1 to 10 or a DWR system as in any one of claims 11 to 15, and then drying steps. The method of claim 17, further comprising curing, wherein the maximum curing temperature is equal to or lower than 180°C, preferably equal to or lower than 150°C, more preferably equal to or lower than 110°C, and more preferably equal to or lower at 100°C, preferably at or below 80°C. The method of claim 17 or 18, wherein the fiber material is selected from the group consisting of: polyester, polyamide, cotton, blends or variations thereof, preferably polyester or polyamide, or their Blends or variations. The method of any one of claims 17 to 19, wherein the concentration of the compound of any one of claims 1 to 10 in the pad bath is about 2 to about 20 g/L, preferably about 5 to about 15 g/L, optimally about 10 g/L to about 200 g/L.