NL2027946B1 - Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition - Google Patents

Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition Download PDF

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Publication number
NL2027946B1
NL2027946B1 NL2027946A NL2027946A NL2027946B1 NL 2027946 B1 NL2027946 B1 NL 2027946B1 NL 2027946 A NL2027946 A NL 2027946A NL 2027946 A NL2027946 A NL 2027946A NL 2027946 B1 NL2027946 B1 NL 2027946B1
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Netherlands
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composition
acrylic ester
fabric
water
fluorinated
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NL2027946A
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Dutch (nl)
Inventor
Bollen-Bouvrie Lucienne
Matheus Maria Verweerden Theodorus
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Lamoral Holding B V
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Priority to NL2027946A priority Critical patent/NL2027946B1/en
Priority to BR112023020680A priority patent/BR112023020680A2/en
Priority to PCT/NL2022/050198 priority patent/WO2022216158A1/en
Priority to CA3216049A priority patent/CA3216049A1/en
Priority to EP22717944.7A priority patent/EP4320306A1/en
Priority to KR1020247005209A priority patent/KR20240026305A/en
Priority to JP2023561696A priority patent/JP2024513482A/en
Priority to CN202280028780.3A priority patent/CN117295860A/en
Priority to KR1020237036891A priority patent/KR102638466B1/en
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Publication of NL2027946B1 publication Critical patent/NL2027946B1/en

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/2246—Esters of unsaturated carboxylic acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06C—FINISHING, DRESSING, TENTERING OR STRETCHING TEXTILE FABRICS
    • D06C7/00—Heating or cooling textile fabrics
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/08—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with halogenated hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/236—Esters of carboxylic acids; Esters of carbonic acid containing halogen atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/395—Isocyanates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2331/00—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products
    • D10B2331/04—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products polyesters, e.g. polyethylene terephthalate [PET]
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2401/00—Physical properties
    • D10B2401/02—Moisture-responsive characteristics
    • D10B2401/021—Moisture-responsive characteristics hydrophobic

Abstract

Disclosed is a method for conferring durable water repellence to woven or nonwoven fabric, comprising the steps of: (1) treating the fabric with an aqueous composition, the composition comprising (a) an aqueous solvent comprising at least 80 w/w% water, and 20 w/w% or less of a water miscible organic solvent, and (b) 0.1 — 40 w/w% of an acrylic ester having the formula 1: '.“ ‘.? cuzzc—c—o-A2 wherein A1 is H or CH3, and A2 is 01-030 linear or branched, saturated or unsaturated hydrocarbon that may have an alicyclic or aromatic ring, the acrylic ester being dissolved, emulsified or dispersed in the aqueous solvent, (2) heating the treated fabric to 145 - 200°C. Further such a composition and fabric treated with such a composition are disclosed.

Description

Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition The invention relates to a method for conferring durable water repellence to woven or non-woven fabric, to a composition for conferring durable water repellence to woven or non-woven fabric and to woven or non-woven fabric treated with the said composition.
Method for conferring durable water repellence to woven or non-woven fabric are known in the art.
Up to now, the provision of durable water repellence to fabric has relied on fluorocarbon-based treatments that are highly effective and extraordinarily durable.
However, the by-products such as fluor surfactants and derivatives based on C8 and C6 fluor surfactants are toxic and persist in the environment, a combination that makes it unacceptable despite its excellent performance.
Many coatings that are fluor-free today have a short life span.
A water repellent rain shell functionally degrades into a wind shell long before the garment itself wears out.
JP2020153057 describes a vinyl-based polymerisation of a specific divinyl compound with a molecular weight of 600 or more involving chemical bonding of the vinyl polymer to polyester fabric.
An additional film is applied, comprising a fluorinated copolymer or an acrylic monomer that is polymerized with a perfluoroalkyl group having 6 or less carbon atoms.
The additional film is crosslinked by a melamine resin.
JP2020007657 describes a fibre treatment composition containing a water repellent and a polyisocyanate.
The present invention provides method for conferring durable water repellence to woven or non-woven fabric and a fiber treatment composition that can impart water repellency having excellent washing durability to a fiber product without fluor components and without the use of isocyanates or melamine boosters.
The present method for conferring durable water repellence to woven or non-woven fabric results in a highly durable and sustainable water repellent coating on the fabric, that remains unaffected even after 100 or more rounds of machine washing.
To this end, the method comprises the following steps: i) treating the fabric with an aqueous composition, the composition comprising: a. an aqueous solvent comprising at least 80 w/w% water, and 20 w/w% or less of a water miscible organic solvent, and b. 0.1 — 40 w/w% of an acrylic ester having the formula 1: Ao CHC dga? , wherein A' is H or CHs, and A? is C:-C39 linear or branched, saturated or unsaturated hydrocarbon that may have an alicyclic or aromatic ring, the acrylic ester being dissolved, emulsified or dispersed in the aqueous solvent, ii) heating the treated fabric to 145 - 200°C.
It has been found that the acrylic esters as defined is capable of binding to the fabric and to polymerize in the aqueous solvent by heat treatment. Without being bound to any scientific explanation, it is believed that the presence of a water miscible organic solvent functions in polymerisation of the acrylic ester. Such acrylic esters are known in the art, such as Unidyne XF series (Daikin, Japan) and Neoseed NR series (Nicca Chemicals, Japan).
The fabric is first treated with the composition comprising the acrylic ester in an aqueous solvent, the solvent comprising both water and a water miscible solvent. After treatment the treated fabric is subjected to a heat treatment.
By the heat treatment, the acrylic ester polymerized and binds to the fabric, resulting in a very strong and sustainable water repellence.
It is preferred that the fabric as treated in step i) is dried before being heated. It is however also possible to combine the heating with the drying. However, drying can take place at a lower temperature than heating. Heating is between 145 and 200°C, whereas drying takes place preferably between 100 and 140°C, preferably below 140°C. Drying is carried out for about 1 — 10 minutes, preferably about 1 — 3 minutes.
The water miscible solvent preferably comprises at least two functional OH groups. It is believed that the OH groups are capable of forming a covalent C-O-C bond with the oxygen of the C=O group of the acrylic ester of formula 1, and thus resulting in polymerisation of the acrylic ester. With ‘functional OH group’ is therefore meant that the said group is capable of forming the said C-O-C bond.
Accordingly, the water miscible solvent is preferably chosen from the group, consisting of: ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol dimethyl ether, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol, tripropylene glycol monomethyl ether, polypropylene glycol and hexylene glycol. Most preferred is tripropylene glycol.
The aqueous solvent preferably comprises 95 — 99 w/w% water and 1 — 5 w/w% miscible organic solvent.
For optimal water repellence, the A? moiety of the acrylic ester has 12 to 24 carbon atoms, preferably 12 to 21 carbon atoms. The A? moiety is preferably alkyl and/or linear.
The composition preferably comprises 0.2 - 20 w/w% acrylic ester, more preferably 0.5 — 10 w/w%.
In a very attractive embodiment, the composition is fluorine free. This means that there are no compounds present in the composition that have fluorine groups in their molecular backbone.
However, in another attractive embodiment, the composition comprises a fluorinated C:-C29 alkyl compound having a functional terminal group, capable of forming a covalent bond with the oxygen of the C=O group of the acrylic ester of formula 1. By the addition of such a compound, the said compound can be linked to the acrylic ester via the C=O group thereof. This linkage can e.g. take place during the heating step. By the provision of such a fluorinated acrylic ester, not only water repellence, but also oil repellence is obtained, still without the need for isocyanates or melamine boosters. The fluorinated alkyl compound is preferably linear.
In an attractive embodiment, the fluorinated alkyl compound is a Cs-Cz9 alkyl, 1 to 6 of the carbon atoms being fully substituted with fluorine. The term ‘fully substituted with fluorine’ means that all the H atoms of the respective carbon atom have been replace by a fluorine atom. A saturated terminal carbon atom will, when fully substituted, have three fluorine atoms, and a saturated internal carbon, i.e. flanked by two adjacent carbon atoms by a single bond, will have two fluorine atoms. This means that the fluorine groups can be scattered throughout the alkyl backbone. Such compounds are e.g. known from WO2016/096128.
The fluorinated C:-Cz9 alkyl compound preferably comprises a terminal acryl group for linkage to the acrylic ester of formula 1, as e.g. is described in
JP2020153057, and as are known in the art, e.g. The Unidyne TG Series (Daikin, Japan). The composition preferably comprises 0.2 — 10 w/w%, more preferably 0.5 — 5 w/w% of the fluorinated C:-C29 alkyl compound.
In a particular embodiment, the fluorinated C2-C29 alkyl compound is allowed to be covalently linked to the oxygen of the C=O group of the acrylic ester of formula 1 before the treatment of the fabric. In that case, the composition comprises a fluorinated acrylic ester instead of a non-fluorinated acrylic ester as would be the case in the above described embodiments.
In step ii), the heating is preferably performed at 140 — 180°C, more preferably at 150 - 170°C and most preferably around 160°C. It has been found that such a heating step result in an excellent polymerisation and binding to the fabric. The temperature also depends on the treated fabric. The heating step can be performed by exposure of the treated fabric to a hot air stream, or by residing in a heat chamber, or e.g. by ironing. The skilled person will be aware of the proper temperature choice. The heating step is preferably performed for 30 seconds to 10 minutes, preferably for 1 — 3 minutes.
The treatment of step i) is preferably chosen from dipping the fabric in the composition, or spraying the composition onto the fabric. Dipping means that the fabric is immersed in the composition. Dipping is preferred, but spraying is a very attractive home appliance, where the fabric can be sprayed from an aerosol comprising the composition, whereafter the heat treatment can be performed by ironing. In an industrial setting, the treated fabric is preferably dipped and padded subsequently, in order to remove superfluous liquid composition.
In another aspect, the invention relates to a composition for conferring durable water repellence to woven or non-woven fabric as described above.
In still another aspect, the invention relates to woven or non-woven fabric as described herein, treated with the composition, in particular as described herein. The invention will now be further illustrated by way of examples and figure, showing a possible industrial set up for the method of the invention.
The arrows reflect the transportation direction of the fabric 1, guided by guidance rollers 2. The process is continuous, e.g. without interruption. Fabric 1 is immersed in a bath 3 comprising the composition 4 of the invention. After leaving the bath 3, the fabric 4 passes through two padding rolls 5, squeezing the superfluous liquid composition from the fabric. The fabric is dried with hot air in drying chamber 6, where the temperature is e.g. 130°C, and eventually enter a heating chamber, where the temperature is e.g. 160°C. 5 Examples Water repellence Samples of PES 1 fabric 135 gr/m? and PES 2 fabric 190 gr/m? (MB Sportswear, Eindhoven Netherlands) were washed 100 times according to the method of Iso 6330 3G or 4H. After washing, the water repellence is measured by the ISO 4920 (version 2012- 12) spray method Commercial washing cycles: The water repellence measured by the Iso 4920 spray method after washing 120 times according to the method of using a commercial washing machine of the type Miele Twindos (Germany) using the program Express 2.0 and the detergent Colour Reus extra strong against stains, extra clean (Henkel, Germany). The program specifications and the contents of the detergent are given in tables 1 and 2, respectively.
Table 1: Washing program load |2-3kg
Table 2: Ingredients detergent anionic surface active agents (5-15%) soap (< 5 %) non ionic surface active agents phoshonates hexl cynnamal methylisothiazolinone benzisothiazolinone Oil repellence Oil repellence is measure after washing 100 times of samples as described above according to the AATCC118 method 118-1997.
Sample preparation The fabric sample was cut 15 x 15 cm from the reel and by dipping the fabric for 1 minute in the coating emulsion. The uncoated fabric was weighed in duplo. After dipping, the coated sample was placed on a rubber sleeve of a manual coating unit (RK prints) for the padding process. With a smooth roller with a weight of 10 kg the excess of emulsion was squeezed out by 2 times rolling the roller over the fabric.
The samples was dried in an oven with forced air ventilation for 3 minutes at 130°C ; subsequently the sample was cured for 1 minute at 160°C. After curing, the sample was weighted in duplo again.
The compositions as used in examples 1 — 4 are given in table 3.
Table 3: Compositions ~ Compositions | cee leon he . Unidyne XF5000 6.0 - Water miscible Tripropylene glycol solvent (Sigma Aldrich US) 0.1-0.5 0.5-10 | 0.1-0.5 0.5-1.0 . Unidyne TG Series | Demiwater | | 97-99 | 88-93 | 97-99 | 79-875 | Crowe | Jw | 8 [we [man
11.0 In examples 1 and 3, a polyester woven fabric PES 135 gr/m? (‘pique’) (MB Sportswear, Eindhoven Netherlands) was used, whereas in examples 2 and 4, 195 gr/m2 ‘smooth’ (MB Sportswear, Eindhoven Netherlands) was used. It was observed that all examples, after the washing cycles retained their water repellence. Grade iso 5 was measured for all samples before the first washing and after 100 or 120 times washing. Grade 5 means that no sticking or wetting of the upper surface was observed. The same was true for examples 1 and 3 when the dipping was replaced by spraying and the padding was replaced by tumbling in a tumble dryer (AEG Lavatherm protex plus, AEG, Germany) with the program setting ‘cotton extra dry’. Heating was performed by ironing at 150°C (level **) for example 1 and at 200°C (level **“*) for example 2, in conformity with the ironing prescriptions of the fabric manufacturer. Also for these samples, Grade iso 5 was measured for all samples before the first washing and after 100 or 120 times washing.
The oil repellence for examples 2 and 4 as measured according to AATCC118 was grade 5 - 6 after 100 — 120 times washing.

Claims (42)

CONCLUSIESCONCLUSIONS 1. Werkwijze voor het duurzaam waterafstotend maken van geweven of niet-geweven stof, welke werkwijze de volgende stappen omvat: a. behandeling van de stof met een waterige samenstelling, waarbij de samenstelling omvat: i. een waterig oplosmiddel dat ten minste 80 gew.% water en 20 gew.% of minder met water mengbaar organisch oplosmiddel omvat , en i. 0,1 - 40 gew.% van een acrylester met formule 1: wo Ohra? ; waarin A! staat voor H of CH: is en A? staat voor een C:-C: lineaire of vertakte, verzadigde of onverzadigde koolwaterstof met eventueel een alicyclische of aromatische ring, waarbij de acrylester in het waterige oplosmiddel opgelost, geëmulgeerd of gedispergeerd is, b. verhitting van de behandelde stof tot 145 - 200°C.A method for making woven or non-woven fabric permanently water-repellent, which method comprises the following steps: a. treating the fabric with an aqueous composition, wherein the composition comprises: i. an aqueous solvent comprising at least 80 wt% water and 20 wt% or less water-miscible organic solvent, and i. 0.1 - 40% by weight of an acrylic ester of formula 1: wo Ohra? ; where A! stands for H or CH: is and A? represents a C:-C: linear or branched, saturated or unsaturated hydrocarbon optionally containing an alicyclic or aromatic ring, wherein the acrylic ester is dissolved, emulsified or dispersed in the aqueous solvent, b. heating the treated substance to 145 - 200°C. 2. Werkwijze volgens conclusie 1, waarbij de samenstelling vrij is van isocyanaat- en melamineverbindingen.A method according to claim 1, wherein the composition is free of isocyanate and melamine compounds. 3. Werkwijze volgens conclusie 1 of 2, waarbij de behandelde stof van stap i) voorafgaand aan stap ii) wordt gedroogd.A method according to claim 1 or 2, wherein the treated substance of step i) is dried prior to step ii). 4. Werkwijze volgens conclusie 1, waarbij het weefsel bij 100 - 140°C wordt gedroogd.The method of claim 1, wherein the fabric is dried at 100-140°C. 5. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij het met water mengbare oplosmiddel ten minste twee functionele OH-groepen omvat.A method according to any one of the preceding claims, wherein the water-miscible solvent comprises at least two OH functional groups. 6. Werkwijze volgens conclusie 5, waarbij het met water mengbare oplosmiddel wordt gekozen uit de groep, bestaande uit: ethyleenglycol, ethyleenglycol monomethylether, ethyleengiycol monoëthylether, ethyleenglycol monobutylether, ethyleenglycol monomethyletheracetaat, ethyleenglycol monoéthyletheracetaat, ethyleenglycol monobutyletheracetaat, propyleenglycol, propyleenglycol monomethylether, propyleenglycol monoëthylether, propyleenglycol dimethylether, dipropyleenglycol, dipropyleengiycol monomethylether, dipropyleenglycol dimethylether, dipropyleenglycol monoéthylether, tripropyleenglycol, tripropyleenglycol monomethylether, polypropyleenglycol en hexyleenglycol.The method of claim 5, wherein the water-miscible solvent is selected from the group consisting of: ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol dimethyl ether, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol, tripropylene glycol monomethyl ether, polypropylene glycol and hexylene glycol. 7. Werkwijze volgens conclusie 6, waarbij het met water mengbaar oplosmiddel tripropyleenglycol omvat.The method of claim 6, wherein the water-miscible solvent comprises tripropylene glycol. 8. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij het waterig oplosmiddel 95 - 99 gewichtsprocent water en 1 - 5 gewichtsprocent een mengbaar organisch oplosmiddel omvat.A method according to any one of the preceding claims, wherein the aqueous solvent comprises 95-99% by weight of water and 1-5% by weight of a miscible organic solvent. 9. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij A2 van de acrylester 12 tot 24 koolstofatomen, bij voorkeur 12 tot 21 koolstofatomen heeft.A method according to any one of the preceding claims, wherein A 2 of the acrylic ester has 12 to 24 carbon atoms, preferably 12 to 21 carbon atoms. 10. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij A2 van de acrylester alkyl is.A method according to any one of the preceding claims, wherein A 2 of the acrylic ester is alkyl. 11. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij A2 van de acrylester lineair is.A method according to any one of the preceding claims, wherein A2 of the acrylic ester is linear. 12. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij de samenstelling 0,2 - 20 w/w% acrylester omvat, bij voorkeur 0,5 - 10 w/w®%.A method according to any one of the preceding claims, wherein the composition comprises 0.2 - 20 w/w% acrylic ester, preferably 0.5 - 10 w/w%®. 13. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij de samenstelling fluorvrij is.A method according to any one of the preceding claims, wherein the composition is fluorine free. 14. Werkwijze volgens willekeurig welke van de voorgaande conclusies 1 - 12, waarbij de samenstelling voorts een gefluoreerde C:C2 alkylverbinding met een functionele eindgroep omvat, die een covalente verbinding kan vormen met de zuurstof van de C=O groep van de acrylester van formule 1.The method of any one of claims 1 to 12, wherein the composition further comprises a fluorinated C:C2 alkyl compound having a functional end group capable of forming a covalent bond with the oxygen of the C=O group of the acrylic ester of formula 1. 15. Werkwijze volgens conclusie 14, waarbij de gefluoreerde alkylverbinding lineair is.The method of claim 14, wherein the fluorinated alkyl compound is linear. 16. Werkwijze volgens conclusie 14 of 15, waarbij de gefluoreerde alkylverbinding een Ce-C2 alkyl is waarvan 1 tot 6 koolstofatomen volledig met fluor gesubstitueerd zijn.The method according to claim 14 or 15, wherein the fluorinated alkyl compound is a C 6 -C 2 alkyl having 1 to 6 carbon atoms fully substituted with fluorine. 17. Werkwijze volgens willekeurig welke van de voorgaande conclusies 14 - 16, waarbij de gefluoreerde C=:-C» alkylverbinding een eindstandige acrylgroep omvat.A method according to any one of claims 14 to 16, wherein the fluorinated C=:-C1 alkyl compound comprises a terminal acrylic group. 18. Werkwijze volgens willekeurig welke van de voorgaande conclusies 14 - 17, waarbij de samenstelling 0,2 - 10 gewichtsprocent, bij voorkeur 0,5 - 5 gewichtsprocent van de gefluoreerde C2-C29 alkylverbinding omvat.A method according to any one of the preceding claims 14-17, wherein the composition comprises 0.2-10% by weight, preferably 0.5-5% by weight of the fluorinated C2-C29 alkyl compound. 19. Werkwijze volgens willekeurig welke van de voorgaande conclusies 14 - 18, waarbij men de gefluoreerde C:-Cx alkylverbinding voorafgaand aan de behandeling van de stof covalent aan de zuurstof van de C=O groep van de acrylester volgens formule 1 laat binden.A method according to any one of claims 14 to 18, wherein the fluorinated C:-Cx alkyl compound is allowed to covalently bond to the oxygen of the C=O group of the formula 1 acrylic ester prior to treatment of the substance. 20. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij in stap ii) de verhitting wordt uitgevoerd bij 140 - 180°C, bij voorkeur bij 150 - 170°C.A method according to any one of the preceding claims, wherein in step ii) the heating is carried out at 140-180°C, preferably at 150-170°C. 21. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij de verhittingsstap wordt uitgevoerd gedurende 30 seconden tot 10 minuten.A method according to any one of the preceding claims, wherein the heating step is carried out for 30 seconds to 10 minutes. 22. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij de stof wordt gekozen uit polyester, polyamide, acrylaat of een mengsel van twee of meer van deze stoffen.A method according to any one of the preceding claims, wherein the substance is selected from polyester, polyamide, acrylate or a mixture of two or more of these substances. 23. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij voor de behandeling van stap i} wordt gekozen uit onderdompeling van het weefsel in de samenstelling of verstuiving van de samenstelling op het weefsel.A method according to any one of the preceding claims, wherein the treatment of step i} is selected from immersing the fabric in the composition or spraying the composition onto the fabric. 24. Werkwijze volgens willekeurig welke van de voorgaande conclusies, waarbij de behandelde stof wordt uitwrongen voordat deze wordt gedroogd of verhit.A method according to any one of the preceding claims, wherein the treated fabric is wrung out before being dried or heated. 25. Samenstelling voor het duurzaam waterafstotend maken van geweven of niet-geweven stof, omvattende: i. een waterig oplosmiddel dat ten minste 80 gew.% water en 20 gew.% of minder met water mengbaar organisch oplosmiddel omvat , en i. 0,1 - 40 gew.% van een niet gefluoreerde acrylester met formule 1: CH Oe Oe AX waarin A! staat voor H of CH: is en A? staat voor een C1-C30 lineaire of vertakte, verzadigde of onverzadigde koolwaterstof eventueel met een alicyclische of aromatische ring, waarbij de acrylester in het waterige oplosmiddel is opgelost, geëmulgeerd of gedispergeerd.25. Composition for making woven or non-woven fabric permanently water repellent, comprising: i. an aqueous solvent comprising at least 80 wt% water and 20 wt% or less water-miscible organic solvent, and i. 0.1 - 40% by weight of a non-fluorinated acrylic ester of formula 1: CHOe Oe AX where A! stands for H or CH: is and A? denotes a C1-C30 linear or branched, saturated or unsaturated hydrocarbon optionally containing an alicyclic or aromatic ring, wherein the acrylic ester is dissolved, emulsified or dispersed in the aqueous solvent. 26. Samenstelling volgens conclusie 25, waarbij de samenstelling vrij is van isocyanaat- en melamineverbindingen.The composition according to claim 25, wherein the composition is free of isocyanate and melamine compounds. 27. Samenstelling volgens conclusie 25 of 26, waarbij het met water mengbaar oplosmiddel ten minste twee functionele OH-groepen bevat.A composition according to claim 25 or 26, wherein the water-miscible solvent contains at least two OH functional groups. 28. Samenstelling volgens conclusie 27, waarbij het met water mengbare oplosmiddel gekozen is uit de groep, bestaande uit: ethyleenglycol, ethyleenglycol monomethylether, ethyleenglycol monoëthylether, ethyleenglycol monobutylether, ethyleenglycol monomethyletheracetaat, ethyleenglycol monoéthyletheracetaat, ethyleenglycol monobutyletheracetaat, propyleenglycol, propyleenglycol monomethylether, propyleenglycol monoëthylether, propyleenglycol dimethylether, dipropyleenglycol, dipropyleenglycol monomethylether, dipropyleenglycol dimethylether, dipropyleenglycol monoéthylether, tripropyleenglycol, tripropyleenglycol monomethylether, polypropyleenglycol en hexyleenglycol.The composition of claim 27, wherein the water-miscible solvent is selected from the group consisting of: ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol dimethyl ether, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol, tripropylene glycol monomethyl ether, polypropylene glycol and hexylene glycol. 29. Samenstelling volgens conclusie 28, waarbij het met water mengbaar oplosmiddel tripropyleenglycol omvat.The composition of claim 28, wherein the water-miscible solvent comprises tripropylene glycol. 30. Samenstelling volgens willekeurig welke van conclusies 25 - 29, waarbij A? van de acrylester 12 tot 24 koolstofatomen, bij voorkeur 12 tot 21 koolstofatomen heeft.A composition according to any one of claims 25 to 29, wherein A? of the acrylic ester has 12 to 24 carbon atoms, preferably 12 to 21 carbon atoms. 31. Samenstelling volgens willekeurig welke van conclusies 25 - 30, waarbij A? van de acrylester alkyl is.A composition according to any one of claims 25 to 30, wherein A? of the acrylic ester is alkyl. 32. Samenstelling volgens willekeurig welke van conclusies 25 - 31, waarbij A? van de acrylester lineair is.A composition according to any one of claims 25 to 31, wherein A? of the acrylic ester is linear. 33. Samenstelling volgens willekeurig welke van conclusies 25 - 32, waarbij de samenstelling 0,2 - 20 w/w®% acrylester omvat, bij voorkeur 0,5 — 10 w/w%.A composition according to any one of claims 25 - 32, wherein the composition comprises 0.2 - 20 w/w% acrylic ester, preferably 0.5 - 10 w/w%. 34. Samenstelling volgens willekeurig welke van conclusies 25 - 33, waarbij de samenstelling fluorvrij is.A composition according to any one of claims 25 to 33, wherein the composition is fluorine free. 35. Samenstelling volgens willekeurig welke van conclusies 25 - 33, waarbij de samenstelling voorts een gefluoreerde C:-C>2 alkylverbinding omvat met een functionele eindstandige groep, welke groep een covalente binding kan aangaan met de zuurstof van de C=0 groep van de acrylester volgens formule 1.A composition according to any one of claims 25 to 33, wherein the composition further comprises a fluorinated C:-C>2 alkyl compound having a functional terminal group, which group can form a covalent bond with the oxygen of the C=0 group of the acrylic ester of formula 1. 36. Samenstelling volgens conclusie, waarbij de gefluoreerde alkyl lineair is.The composition of claim wherein the fluorinated alkyl is linear. 37. Samenstelling volgens conclusie 35 of 36, waarbij de gefluoreerde alkylverbinding een Ce- Coo alkyl is waarvan 1 tot 6 koolstofatomen volledig met fluor gesubstitueerd zijn.A composition according to claim 35 or 36, wherein the fluorinated alkyl compound is a C 6 -C 0 alkyl having 1 to 6 carbon atoms fully substituted with fluorine. 38. Samenstelling volgens willekeurig welke van conclusies 35 — 37, waarbij de gefluoreerde C2-C alkylverbinding een eindstandige acrylgroep omvat.A composition according to any one of claims 35-37, wherein the fluorinated C2-C alkyl compound comprises a terminal acrylic group. 39. Samenstelling volgens willekeurig welke van conclusies 35 — 38, waarbij de samenstelling 0,2 - 10 gewichtsprocent, bij voorkeur 0,5 - 5 gewichtsprocent van de gefluoreerde C2-C2 alkylverbinding omvat.A composition according to any one of claims 35-38, wherein the composition comprises 0.2-10% by weight, preferably 0.5-5% by weight of the fluorinated C2-C2 alkyl compound. 40. Samenstelling volgens willekeurig welke van conclusies 35 — 39, waarbij de gefluoreerde Cs-C20 alkylverbinding covalent aan de zuurstof van de C=O groep van de acrylester volgens formule 1 is gebonden.A composition according to any one of claims 35-39, wherein the fluorinated C 8 -C 20 alkyl compound is covalently bonded to the oxygen of the C=O group of the acrylic ester of formula 1. 41. Geweven of niet geweven stof, die is behandeld met de samenstelling volgens willekeurig welke van conclusies 25 - 40.A woven or nonwoven fabric treated with the composition of any one of claims 25-40. 42. Geweven of niet geweven stof volgens conclusie 41, waarbij de stof is gekozen uit polyester, polyamide, acrylaat of een mengsel van wee of meer daarvan.The woven or nonwoven fabric of claim 41, wherein the fabric is selected from polyester, polyamide, acrylate or a mixture of two or more thereof.
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NL2027946A NL2027946B1 (en) 2021-04-08 2021-04-08 Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition
BR112023020680A BR112023020680A2 (en) 2021-04-08 2022-04-08 METHOD FOR PROVIDING DURABLE WATER REPELLENCE TO FABRICS OR NON-WOVEN AND WATER-REPELLENT COMPOSITION
PCT/NL2022/050198 WO2022216158A1 (en) 2021-04-08 2022-04-08 Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition
CA3216049A CA3216049A1 (en) 2021-04-08 2022-04-08 Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition
EP22717944.7A EP4320306A1 (en) 2021-04-08 2022-04-08 Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition
KR1020247005209A KR20240026305A (en) 2021-04-08 2022-04-08 Method for conferring durable water repellence to woven or non-woven fabric and water repellent composition
JP2023561696A JP2024513482A (en) 2021-04-08 2022-04-08 Method and water-repellent composition for imparting durable water repellency to woven or non-woven fabrics
CN202280028780.3A CN117295860A (en) 2021-04-08 2022-04-08 Method for imparting durable water repellency to woven or nonwoven fabrics and water repellency composition
KR1020237036891A KR102638466B1 (en) 2021-04-08 2022-04-08 Method and water-repellent composition for imparting sustained water repellency to fabrics or non-woven fabrics

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