WO2022216158A1 - 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 PDFInfo
- Publication number
- WO2022216158A1 WO2022216158A1 PCT/NL2022/050198 NL2022050198W WO2022216158A1 WO 2022216158 A1 WO2022216158 A1 WO 2022216158A1 NL 2022050198 W NL2022050198 W NL 2022050198W WO 2022216158 A1 WO2022216158 A1 WO 2022216158A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- fabric
- water
- acrylic ester
- ethylene glycol
- Prior art date
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000002759 woven fabric Substances 0.000 title claims abstract description 16
- 239000004745 nonwoven fabric Substances 0.000 title claims abstract description 15
- 230000002940 repellent Effects 0.000 title description 9
- 239000005871 repellent Substances 0.000 title description 9
- 239000004744 fabric Substances 0.000 claims abstract description 59
- -1 acrylic ester Chemical class 0.000 claims abstract description 54
- 238000010438 heat treatment Methods 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 238000007598 dipping method Methods 0.000 claims description 7
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 claims description 3
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 claims description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 3
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims description 3
- 241000531908 Aramides Species 0.000 claims description 3
- 229920003235 aromatic polyamide Polymers 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 229940051250 hexylene glycol Drugs 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 150000007974 melamines Chemical class 0.000 claims description 3
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 description 17
- 238000005406 washing Methods 0.000 description 17
- 238000000576 coating method Methods 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 13
- 239000000835 fiber Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000010409 ironing Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 239000003599 detergent Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
Definitions
- 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.
- 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.
- EP3919673 describes a special fabric surface that resembles the surface of lotus flower leaves to mimic the water repellence thereof. This artificial lotus-like surface can be treated by commonly known water repellents.
- WO201 6/000831 describes a composition for application on textiles to confer water repellence, wherein three different acrylate monomers, one of which containing fluorine, are polymerized to a polyacrylate by the aid of an azo initiator. Apart from the thus obtained polyacrylate, the composition comprises a wax.
- the present invention provides method for conferring durable water repellence to woven or non-woven fabric and a fibre treatment composition that can impart water repellence having excellent washing durability to a fibre product without the need to incorporate fluor components for water repellence, and without the need for use of silicone, 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.
- 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 comprising at least two functional OH groups, and b. 0.1 - 40 w/w% of an acrylic ester having the formula 1 :
- a 1 is H or CH3
- a 2 is C1-C30 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 120 - 200°C.
- the water miscible solvent participates in a chemical reaction with the acrylic ester through the functional OH groups thereof.
- a (trans)esterification reaction is initiated between a water miscible solvent molecule and the acrylic ester.
- ‘functional OH group’ is therefore meant that the said group is capable of forming the said C-O-C bond.
- the conditions are chosen such, that the above reaction or reactions can take place, e.g. at acid pH.
- the A 2 moiety binds to the fibric fibre by hydrogen bridging of its newly acquired terminal OH group.
- the transesterification reaction results in both, i.e. an incomplete and a complete esterification process, both resulting in the fibre acquiring a hydrophobic A 2 moiety bound thereto through hydrogen bridging. Since the result of the heat treatment is that the A2 moieties become bound to the fabric, this step is also to be regarded as a curing step.
- composition of the present invention does not comprise an acrylate polymer, i.e. a polymer comprising a plurality of acrylate monomers, in particular three or more, polymerized to one another, e.g. by the use of an azo initiator.
- an acrylate polymer i.e. a polymer comprising a plurality of acrylate monomers, in particular three or more, polymerized to one another, e.g. by the use of an azo initiator.
- acrylic ester is free of fluorine groups.
- Suitable acrylic esters as defined above for step i)b. are known in the art, such as Unidyne XF series (Daikin, Japan).
- the heat treatment results in a fabric, the fibres of which comprising hydrophobic A 2 moieties stably bound thereto through hydrogen bridging, therewith acquiring a very strong and sustainable water repellence.
- the water miscible solvent can comprise more than 2 functional OH groups, but the presence of 2 functional OH groups is preferred.
- the water soluble aqueous solvent is preferably an organic water miscible solvent, more 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
- the aqueous solvent preferably comprises at least 0.1 w/w% of the water miscible solvent, preferably at least 0.2 w/w%.
- the aqueous solvent preferably comprises 90 - 99.9 w/w% water and 0.1 - 10 w/w% of the water miscible solvent, more preferably 95 - 99.8 w/w% water and 0.2 - 5 w/w% of the water miscible solvent, or 95 - 99 w/w% water and 1 - 5 w/w% miscible organic solvent.
- the composition preferably comprises 0.2 - 20 w/w% acrylic ester, more preferably 0.5 - 10 w/w%, even more preferably 1 - 6 w/w%.
- the surface tension of the coating should be about 25 mN/m 2 .
- the A 2 moiety is preferably alkyl.
- the A 2 moiety of the acrylic ester preferably has 12 to 24 carbon atoms, more preferably 12 to 21 carbon atoms, even more preferably 18 carbon atoms.
- a -CH2- moiety confers about 31 mN/m 2
- a terminal -CH3 confers 22 mN/m 2 .
- a higher -CH3 content will result in a coating with a lower surface tension and therewith to a stronger water repellence.
- a higher -CH3 content can be obtained by increasing the number of branches in the hydrocarbon chain. Therefore, although the A 2 moiety can be linear, the said moiety is preferably branched.
- the coating could be further improved by including a polyisocyanate having at least 3 crosslinking isocyanate groups in the aqueous composition. It was surprisingly found that the presence of polyisocyanate resulted in a significant increased stability of the coating, without any noticeable wear after 30 washing cycles followed by line drying.
- the functional OH groups of both the water miscible solvent molecules and of the acrylic ester comprising a functional OH group as a result of the above described transesterification reaction, as well as the A2 moiety with a functional OH group obtained this way are covalently bound to the polyisocyanate, resulting in a crosslinked web of hydrophobic carbohydrate moieties, the web being formed by interconnection of the polyisocyanate molecules linked to one another via covalent linkage with the functional OH groups of the water miscible solvent molecules. Since these molecules comprise 2 or more functional OH groups, these function to link polyisocyanate molecules to one another, to form a hydrogen bridge bond with the fabric fibre, and to provide a functional group to the acrylic ester of the A2 moiety, respectively.
- the polyisocyanate can e.g. be aromatic or aliphatic, and suitable polyisocyanates are known in the art. Since the polyisocyanate is in an aqueous composition, e.g. water-based, the polyisocyanate is preferably blocked, e.g. by blocking groups known in the art, such as phenol, nonyl phenol, methylethylketoxime (MEKO), alcohols, e-caprolactam, amides, imidazoles, or pyrazoles.
- JP2020007657 describes a fibre treatment composition containing a water repellent and such a blocked polyisocyanate. In order for the blocked polyisocyanates to become active, i.e.
- a very attractive isocyanate is a trimer based on aliphatic hexamethylene-1 ,6-diisocyanate, in particular HDI trimer (Kowa, NY, US).
- the weight ratio acrylic ester : isocyanate is 100 : 5 - 100, preferably 100 : 30 - 80, more preferably 100 : 50 - 70, most preferably 100 : 60. It was found that a relatively high ratio acrylic ester : isocyanate results in the most stable coating.
- the heating is preferably performed at 130 - 200°C, more preferably 140 - 200°C, more preferably 145 - 200°C 180°C, even more preferably at 145 - 180°C, still even 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 reaction between the components (water miscible solvent, and acrylic ester, and if present, the polyisocyanate) and binding to the fabric. In case of the presence of a blocked polyisocyanate in the composition, the said polyisocyanate becomes unblocked at such a temperature as well.
- the optimal heating temperature may also depend on the treated fabric.
- the heating temperature is preferably kept below 140°C, in particular around 130°C, since above the said temperature, deformation of the material can take place.
- the drying temperature is preferably higher, as described above, most preferably around 160°C.
- 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 fabric as treated in step i) is dried before being subjected to the heating step ii).
- a pre-drying step becomes particularly important in the presence of a polyisocyanate, since the crosslinking reaction is preferably to be performed in a water free environment. In case there is no isocyanate present in the composition, it becomes also possible to combine the heating with the drying. However, drying can usually take place at a lower temperature than heating. Heating is preferably as described above, e.g. between 120°C and 200°C, or at 145 - 200°C, whereas drying preferably takes place preferably between 100 and 140°C, preferably below 140°C. Such a pre-drying step may therefore be more energy saving. Drying is preferably carried out for about 1 - 10 minutes, preferably about 1 - 3 minutes.
- the composition is free of silicon and/or melamine compounds, and for the sole function of water repellence, the composition is preferably fluorine free as well. This means that there are no compounds present in the composition that have fluorine groups in their molecular backbone.
- the composition of the invention comprises in an attractive embodiment a fluorinated C2-C20 alkyl compound comprising a terminal acryl group, as e.g. is described in JP2020153057, and as are known in the art, e.g. The Unidyne TG Series (Daikin, Japan).
- this fluor acrylic ester will be susceptible to the transesterification reaction with the water miscible solvent as the fluorine free acrylic ester of formula 1 as described above, and will therefore result in a fluorinated hydrocarbon moiety bound to the fabric fibre through hydrogen bridging, and be able to participate in the crosslinking with the polyisocyanate, if present.
- the fluorinated alkyl compound is defined as the fluorine free acrylic ester of formula 1 , wherein for the fluorinated compound, the A2 moiety is a C6-C20 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 replaced by a fluorine atom.
- a saturated terminal carbon atom will, when fully substituted, have three fluorine atoms, and a saturated internal carbon, i.e.
- the fluorine groups can be scattered throughout the alkyl backbone.
- Such compounds are e.g. known from WO201 6/096128.
- the A2 of the fluorinated compound is a C 6 alkyl, all 6 of the carbon atoms being fully substituted with fluorine.
- -CF 2 - groups Since the surface tension of -CF 2 - groups is 18 mN/m 2 , and of terminal -CF 2 and -CF 3 groups is 15 mN/m 2 and 6 mN/m 2 , respectively, a branched fluorinated alkyl compound with terminal -CF 2 and -CF 3 groups, in particular -CF 3 groups is preferred.
- the composition preferably comprises in w/w% an equal amount of both non- fluorinated and fluorinated acrylic esters.
- the composition preferably comprises 0.2 - 20 w/w% acrylic ester, more preferably 0.5 - 10 w/w%, even more preferably 1 - 6 w/w% of the fluorinated C2-C20 alkyl compound.
- the weight ratio of isocyanate, if present, to acrylic acid is determined by the sum of both the fluorinated and fluor free acrylic esters present in the composition.
- the method of the invention can also be applied to fabric fibres before being assembled to a fabric or textile, instead of treatment of the fabric or textile.
- a similar water repellence is obtained when a fabric or textile is produced from such treated fibres.
- the fibres and/or the fabric is preferably chosen from polyester, polyamide, acrylate, ultra high molecular weight polyethylene (e.g. Dyneema, DSM, Netherlands), cotton or aramide or a mixture of two or more thereof. It was found that the repellent coating was stably and strongly bonded to these types of fabric.
- the fabric preferably comprises polyester and/or polyamide, more preferably polyester.
- 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.
- the treated fabric is preferably dipped and padded subsequently, in order to remove superfluous liquid composition.
- the invention relates to a composition for conferring durable water repellence to woven or non-woven fabric as described above.
- the invention relates to fibres, woven or non-woven fabric as described herein, treated with the composition, in particular as described herein.
- 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.
- Oil repellence is measure after washing 100 times of samples as described above according to the AATCC118 method 118-1997.
- 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 were 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.
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- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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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 |
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 |
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 |
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 |
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 |
BR112023020680A BR112023020680A2 (en) | 2021-04-08 | 2022-04-08 | METHOD FOR PROVIDING DURABLE WATER REPELLENCE TO FABRICS OR NON-WOVEN AND WATER-REPELLENT 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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NL2027946 | 2021-04-08 | ||
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 |
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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 |
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EP (1) | EP4320306A1 (en) |
JP (1) | JP2024513482A (en) |
KR (2) | KR20240026305A (en) |
CN (1) | CN117295860A (en) |
BR (1) | BR112023020680A2 (en) |
CA (1) | CA3216049A1 (en) |
NL (1) | NL2027946B1 (en) |
WO (1) | WO2022216158A1 (en) |
Citations (7)
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WO2016000831A1 (en) | 2014-07-04 | 2016-01-07 | Archroma Ip Gmbh | Fluorine-containing water-repellent composition |
WO2016096128A1 (en) | 2014-12-19 | 2016-06-23 | Merck Patent Gmbh | Fluorine compounds |
CN109023947A (en) * | 2018-06-22 | 2018-12-18 | 杭州友博纺织品有限公司 | Solution and its production technology and application method for the processing of fabric anti-pollution |
JP2020007657A (en) | 2018-07-05 | 2020-01-16 | 明成化学工業株式会社 | Fiber treatment composition, fiber treatment kit, fiber product and method for manufacturing water-repellent fiber product |
CA3127531A1 (en) * | 2019-01-30 | 2020-08-06 | Toray Industries, Inc. | Water-repellent woven or knitted article, production method for same, and garment |
CN111576043A (en) * | 2020-03-17 | 2020-08-25 | 宁波萌恒线业有限公司 | Processing technology of waterproof yarn |
JP2020153057A (en) | 2019-03-13 | 2020-09-24 | ユニチカトレーディング株式会社 | Woven or knitted fabric and method for producing the same |
Family Cites Families (3)
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JP6209226B2 (en) * | 2014-01-24 | 2017-10-04 | 日華化学株式会社 | Water repellent composition, water repellent fiber product and method for producing water repellent fiber product |
KR20220163534A (en) * | 2017-03-07 | 2022-12-09 | 에이지씨 가부시키가이샤 | Water repellent oil repellent article, method for producing same, and water repellent oil repellent agent composition |
JP6870093B2 (en) * | 2017-07-31 | 2021-05-12 | ダイキン工業株式会社 | Water repellent composition |
-
2021
- 2021-04-08 NL NL2027946A patent/NL2027946B1/en active
-
2022
- 2022-04-08 CA CA3216049A patent/CA3216049A1/en active Pending
- 2022-04-08 EP EP22717944.7A patent/EP4320306A1/en active Pending
- 2022-04-08 WO PCT/NL2022/050198 patent/WO2022216158A1/en active Application Filing
- 2022-04-08 BR BR112023020680A patent/BR112023020680A2/en unknown
- 2022-04-08 JP JP2023561696A patent/JP2024513482A/en active Pending
- 2022-04-08 CN CN202280028780.3A patent/CN117295860A/en active Pending
- 2022-04-08 KR KR1020247005209A patent/KR20240026305A/en active Search and Examination
- 2022-04-08 KR KR1020237036891A patent/KR102638466B1/en active IP Right Grant
Patent Citations (8)
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WO2016000831A1 (en) | 2014-07-04 | 2016-01-07 | Archroma Ip Gmbh | Fluorine-containing water-repellent composition |
WO2016096128A1 (en) | 2014-12-19 | 2016-06-23 | Merck Patent Gmbh | Fluorine compounds |
CN109023947A (en) * | 2018-06-22 | 2018-12-18 | 杭州友博纺织品有限公司 | Solution and its production technology and application method for the processing of fabric anti-pollution |
JP2020007657A (en) | 2018-07-05 | 2020-01-16 | 明成化学工業株式会社 | Fiber treatment composition, fiber treatment kit, fiber product and method for manufacturing water-repellent fiber product |
CA3127531A1 (en) * | 2019-01-30 | 2020-08-06 | Toray Industries, Inc. | Water-repellent woven or knitted article, production method for same, and garment |
EP3919673A1 (en) | 2019-01-30 | 2021-12-08 | Toray Industries, Inc. | Water-repellent woven article, production method for same, and garment |
JP2020153057A (en) | 2019-03-13 | 2020-09-24 | ユニチカトレーディング株式会社 | Woven or knitted fabric and method for producing the same |
CN111576043A (en) * | 2020-03-17 | 2020-08-25 | 宁波萌恒线业有限公司 | Processing technology of waterproof yarn |
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KR20240026305A (en) | 2024-02-27 |
KR20230158624A (en) | 2023-11-20 |
CA3216049A1 (en) | 2022-10-13 |
CN117295860A (en) | 2023-12-26 |
NL2027946B1 (en) | 2022-10-20 |
EP4320306A1 (en) | 2024-02-14 |
BR112023020680A2 (en) | 2023-12-12 |
JP2024513482A (en) | 2024-03-25 |
KR102638466B1 (en) | 2024-02-20 |
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