WO2000047811A1 - Fibre presentant des proprietes de complexation ameliorees et des proprietes echangeuses de cations - Google Patents
Fibre presentant des proprietes de complexation ameliorees et des proprietes echangeuses de cations Download PDFInfo
- Publication number
- WO2000047811A1 WO2000047811A1 PCT/FR2000/000378 FR0000378W WO0047811A1 WO 2000047811 A1 WO2000047811 A1 WO 2000047811A1 FR 0000378 W FR0000378 W FR 0000378W WO 0047811 A1 WO0047811 A1 WO 0047811A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclodextrin
- acid
- fiber
- poly
- carboxylic
- Prior art date
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 158
- 238000005341 cation exchange Methods 0.000 title abstract description 3
- 238000010668 complexation reaction Methods 0.000 title description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 153
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 98
- 239000000463 material Substances 0.000 claims abstract description 79
- 239000002253 acid Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000004753 textile Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000008247 solid mixture Substances 0.000 claims abstract description 8
- 238000001179 sorption measurement Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000010985 leather Substances 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 30
- 239000001116 FEMA 4028 Substances 0.000 claims description 20
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 20
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 20
- 229960004853 betadex Drugs 0.000 claims description 20
- -1 alkali metal phosphites Chemical class 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 14
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 10
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 7
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 7
- 238000007112 amidation reaction Methods 0.000 claims description 7
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 7
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 7
- 235000019800 disodium phosphate Nutrition 0.000 claims description 7
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 7
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 claims description 4
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 3
- SASYRHXVHLPMQD-UHFFFAOYSA-N 2-(1,2-dicarboxyethylsulfanyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)SC(C(O)=O)CC(O)=O SASYRHXVHLPMQD-UHFFFAOYSA-N 0.000 claims description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 3
- 229940091181 aconitic acid Drugs 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002522 Wood fibre Polymers 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
- 229940018557 citraconic acid Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 2
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002025 wood fiber Substances 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims 3
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 36
- 229920000742 Cotton Polymers 0.000 description 14
- 230000004584 weight gain Effects 0.000 description 12
- 235000019786 weight gain Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 7
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000536 complexating effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229960001673 diethyltoluamide Drugs 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 229920002994 synthetic fiber Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000077 insect repellent Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 2
- 241000531908 Aramides Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920013822 aminosilicone Polymers 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- QAVIDTFGPNJCCX-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;2-(chloromethyl)oxirane;hexanedioic acid Chemical compound ClCC1CO1.NCCNCCN.OC(=O)CCCCC(O)=O QAVIDTFGPNJCCX-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical group OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 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
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or 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
- D06M13/10—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
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or 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
- D06M13/10—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
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives 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
- 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
- D06M2400/00—Specific information on the treatment or the process itself not provided in D06M23/00-D06M23/18
- D06M2400/01—Creating covalent bondings between the treating agent and the fibre
Definitions
- the present invention relates to a process for treating a fiber or a fiber-based material in order to improve its adsorption properties (complexing).
- the present invention also relates to a fiber or a fiber-based material, such as a textile, which has improved adsorption properties.
- the improvement in the complexing properties of the fibers makes it possible to adsorb on a fiber or a material based on fibers, various active compounds such as, for example, fragrances, insecticides, bactericidal, antistatic, anti-bacterial or repellent agents.
- This complexing phenomenon which comes into play at the level of the fibers makes it possible, owing to the subsequent diffusion of the active product adsorbed in the atmosphere surrounding the fiber (release phenomenon), to give this fiber or any material containing it, the different properties. chemicals of the active product adsorbed and this for a determined period which depends on the rate of diffusion of the complexed product (speed of release).
- a known method for improving the adsorbent properties of a fiber is the fixing (grafting) of cyciodextrin (s) molecules on the fiber.
- Cyciodextrins ( ⁇ -cyclodextrin, ⁇ -cydodextrin and ⁇ -cyclodextrin) have long been described as molecules with complexing properties, that is to say as molecules capable of reversibly trapping certain other small molecules of nature hydrophobic, in particular aliphatic or aromatic molecules, from solutions, vapors, or solid mixtures of these molecules.
- the adsorbed molecules are linked with cyclodextrin by the formation of inclusion complexes.
- the fibers functionalized by the cyciodextrins are perfectly suited for producing, on the one hand, materials based on fibers, in particular textiles, which have a stable and long-lasting, the chemical properties of the complexed product and, on the other hand, to make adsorbent materials.
- adsorbent materials find several applications, in particular in the purification of contaminated water and gases.
- Textile materials functionalized with cyciodextrins on which fragrances have been adsorbed, an antistatic agent, an antimicrobial agent, an insect repellant, a bactericidal agent, an insecticide are described, respectively in the documents JP -A-06- 116871, US-5376287, JP-A-09-315920, JP-A-04-263617, JP-A-09-228144, JP-A-05-311509, US-5670456 and JP-A -03-59178.
- EP-A ⁇ 188294 and JP-A-03-59178 disclose a method of fixing using respectively aminosiloxanes and siloxanes reactive.
- Document JP-A-06-322670 relates to a fixing method using a resin based on aminosilicone and / or polyurethane.
- Document JP-A-02-127573 describes a method of fixing using a polymer (Hercosett 57) obtained by crosslinking a polyamide with epichlorohydrin.
- Document JP-A-09-228144 describes a method of fixing by incorporating cyciodextrins or their inclusion complexes in the spinning solution of chemical fibers.
- the document DE-A-4035378 describes a method for fixing cyclodextrin (s) or cyclodextrin derivatives (s) using reagents carrying dimethylol urea groups or derivatives of these groups which react with both a hydroxyl group of cyclodextrin and a functional group of the fiber, thereby binding the cyclodextrin molecule to the fiber.
- the present invention provides a new method of fixing cyclodextrin (s) or cyclodextrin derivatives (s) which makes it possible to permanently fix molecules of cyclodextrin (s) or cyclodextrin derivatives (s) on a fiber or a material. based on fibers, such as, for example, a textile, whatever the nature of the fiber or the material based on fibers considered.
- the present invention relates to a process for treating a fiber or a fiber-based material, such as a yarn, a textile, woven, knitted or non-woven material, paper, leather, or a material based on wood fibers, with a view to improving its adsorption properties, which is characterized by the following successive operations on said fiber or said material: the application of a solid mixture of cyclodextrin (s) and / or derivative (s) ) of cyclodexthne (s) and / or of their inclusion complexes, of at least one poly (carboxylic acid) and / or of at least one poly (carboxylic acid) anhydride and optionally of a catalyst, the heating to a temperature between 150 ° C and 220 ° C, washing with water and drying the product thus obtained.
- a solid mixture of cyclodextrin (s) and / or derivative (s) ) of cyclodexthne (s) and / or of their inclusion complexes of at least one
- inclusion complexes can, for example, be formed from an active agent complexed by a molecule of cyclodextrin or of cyclodextrin derivative.
- a material treated with an inclusion complex offers a better guarantee of the complexing properties of cyclodextrin; the presence of the complexed agent preserving the accessibility of the latter's cavity.
- the process of the present invention is particularly advantageous in that it applies to any natural or artificial fiber and to any type of material based on fibers such as, for example, textile materials, paper or leather, which is able to withstand the heating step without undergoing either physical degradation or chemical degradation.
- the process of the invention applies to fibers and yarns composed of natural and artificial cellulosic fibers, natural and artificial protein fibers, synthetic fibers such as polyesters, polyamides, acrylics, aramides, fluorofibers, or of mineral fibers as well as of materials based on fibers and textiles of the woven, knitted and non-woven textile type and containing one or more types of the abovementioned threads and fibers.
- the fixation of the cyclodextrin (s) molecules on the fiber or the fiber-based material is mainly carried out according to two mechanisms which depend on the chemical nature of the fiber or the fiber-based material.
- the process of the invention firstly makes it possible to form an anhydride of poly (carboxylic) acid which reacts with the fiber or the fiber-based material by forming an amide or ester covalent bond between the fiber or fibers of the treated material and poly (carboxyic) acid.
- a second anhydride of the poly (carboxylic) acid bonded to the fiber is formed; this reacts with a molecule of cyclodextrin or of cyclodextrin derivative by creating an ester bond between the molecule of cyclodextrin or of cyclodextrin derivative and that of poly (carboxylic acid).
- the possible formation of an anhydrous from another carboxyl function of the poly (carboxylic) acid linked to the fiber then allows the reaction with another molecule of cyclodextrin or of cyclodextrin derivative.
- one or more molecules of cyclodextrin (s) or of derivative (s) of cyclodextrin (s) linked by an ester function to a molecule of poly (carboxylic acid) which is itself linked by a covalent bond to a fiber.
- a second type of reaction can occur, either in parallel or independently of the reaction for fixing the cyclodextrin or the cyclodextrin derivative by covalent bond with the fiber.
- the copolymer When the copolymer is formed from a cyclodextrin molecule attached to the fiber by covalent bond, it therefore has at least one covalent bond with a fiber.
- the copolymer When the copolymer is formed from molecules of poly (carboxylic acid) and / or anhydride of poly (carboxylic acid) and of cyclodextrin and / or of derivative (s) of cyclodextri ⁇ e (s) not linked to a fiber , it can nevertheless, if it is crosslinked, that is to say that it forms a three-dimensional network intermingling or coating the fiber or fibers of a fiber-based material, be fixed, mechanically, permanently to the fiber or material under consideration.
- this process is intended to modify the physical properties of a textile material exclusively made up of cellulosic fibers, such as cotton, and not to modify the adsorption properties of a fiber or of a material based on fibers. , by attachment of cyclodextrin (s) or cyclodextrin derivative (s) to the fiber or in the structure of the fiber-based material, regardless of the chemical nature of that fiber or material, as is the case of the present invention.
- certain synthetic fibers or material based on such fibers do not have functional groups capable of reacting according to the mechanism proposed above.
- the fixation of cyclodextrin (s) and / or of cyclodextrin derivatives (s) and / or of their inclusion complexes is carried out by the formation of a crosslinked copolymer obtained by exclusive reaction between the molecules of cyclodextrin ( s) and / or cyclodextrin derivative (s) and at least one poly (carboxylic) acid.
- the crosslinked copolymer thus formed coats the fiber or the fiber-based material permanently.
- the two fixing mechanisms namely fixing by a covalent bond to the fiber and the formation of a crosslinked copolymer sheathing on the fiber coexist.
- carboxylic acid functions which have not reacted by esterification, either with the fiber or with cyclodextrin.
- carboxylic acid functions give the fibers not only odor absorption properties but also cation exchanger.
- these carboxylic acid functions give the fibers a better affinity for water (hydrophilic character) and improve the wettability of the treated material, in particular for materials based on fibers that are not very hydrophilic or hydrophobic.
- the application of the solid mixture is obtained by impregnating the fiber or the fiber-based material with an aqueous solution of cyclodextrin (s) and / or of cyclodextrin derivative (s) and / or their inclusion complexes, of at least one poly (carboxylic acid) and / or at least one anhydride of poly (carboxylic acid) and optionally a catalyst and then drying of the impregnated fiber or of the material based of impregnated fibers.
- an aqueous solution of cyclodextrin (s) and / or of cyclodextrin derivative (s) and / or their inclusion complexes of at least one poly (carboxylic acid) and / or at least one anhydride of poly (carboxylic acid) and optionally a catalyst
- the fiber or the fiber-based material is dried at a temperature between 40 ° C and 150 ° C, preferably substantially equal to or equal to 110 ° C before the actual heating operation, at a temperature between 150 ° C and 220 ° C.
- This preliminary drying is particularly recommended in the case of natural fibers such as wool or cotton in order to avoid their thermal degradation.
- This preliminary drying is advantageously used to obtain a solid mixture incorporated into the fiber or fibers of the fiber-based material treated according to the process of the invention, in the context of the drying which follows the impregnation with an aqueous solution such as previously described.
- the heating itself is intended for the permanent fixation of the molecules of cyclodextrin (s) on the fiber or the fiber-based material, by reaction between the poly (carboxylic acid) and / or the poly (carboxylic acid anhydride) ) and the fiber or the fiber-based material (chemical grafting by covalent bond between the fiber and the molecule of cyclodextrin or of cyclodextrin derivative, or even of copolymer of cyclodextrin (s) and of poly (carboxylic acid (s) ( s)) and / or by reaction between the poly (carboxylic acid) and the cyclodextrin and or the cyclodextrin derivative (s) to form a crosslinked copolymer (mechanical grafting by coating).
- the poly (carboxylic) acid and the anhydride of poly (carboxylic) acid are chosen from the following acids and anhydrides of poly (carboxylic) acids: saturated and unsaturated acyclic poly (carboxylic) acids; saturated and unsaturated cyclics; aromatic, hydroxypoly (carboxylic) acids, preferably citric acid, poly (acrylic) acid, poly (methacrylic) acid, 1, 2, 3, 4-butanetetracarboxylic acid, maleic acid , citraconic acid, itaconic acid, 1, 2, 3-propanetricarboxylic acid, aconitic acid, all-cis-1, 2, 3, 4-cyclopentanetetracarboxylic acid, mellittic acid, l oxidisuccinic acid, thiodisuccinic acid.
- acids and anhydrides of poly (carboxylic) acids are chosen from the following acids and anhydrides of poly (carboxylic) acids: saturated and unsaturated acyclic poly (car
- the mixture contains a catalyst chosen from dihydrogenophosphates, hydrogenophosphates, phosphates, hypophosphites, alkali metal phosphites, alkali metal salts of polyphosphoric acids, carbonates, bicarbonates, acetates, borates, alkali metal hydroxides, aliphatic amines and ammonia, and preferably, among sodium hydrogen phosphate, sodium dihydrogen phosphate and sodium hypophosphite.
- a catalyst chosen from dihydrogenophosphates, hydrogenophosphates, phosphates, hypophosphites, alkali metal phosphites, alkali metal salts of polyphosphoric acids, carbonates, bicarbonates, acetates, borates, alkali metal hydroxides, aliphatic amines and ammonia, and preferably, among sodium hydrogen phosphate, sodium dihydrogen phosphate and sodium hypophosphite.
- the cyclodextrin is chosen from ⁇ -cyclodextrin, ⁇ -cyclodextrin and ⁇ -cyclodextrin and the cyclodextrin derivatives are chosen from the methylated or acetylated hydroxypropyl derivatives of ⁇ -cyclodextrin, of ⁇ -cyclodextrin and ⁇ -cyclodextrin and the inclusion complexes of said cyciodextrins and said cyclodextrin derivatives.
- the present invention also relates to fibers or materials based on fibers which are obtained, preferably, according to the process described above, which are chosen from fibers or materials based on fibers which comprise a hydroxyl function and / or an amino function and which are linked by covalent bond, of the ester or amide type, to at least one molecule of cyclodextrin or of a cyclodextrin inclusion complex or to a linear and / or branched and / or crosslinked copolymer composed of cyclodextrin (s) and / or derivatives of cyclodextrin (s) and / or of an inclusion complex and of at least one poly (carboxylic acid) and the structure of which comprises the repetition of a motif of general formula.
- Cell represents the macromolecular chain of a natural or artificial cellulosic fiber
- [Kér] represents the macromolecular chain of a natural or artificial protein fiber
- O-CO- [Ac] -CO-O represents the molecular chain of a poly (carboxylic) acid in which at least two carboxylic acid functions have undergone an esterification and / or amidation reaction and which preferably comprises at least a carboxylic acid function which has not undergone an esterification or amidation reaction
- [CD] represents the molecular structure of ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, of a cyclodextrin derivative (s), preferably a methylated or acetylated hydroxypropyl derivative of ⁇ -cyclodexthne, ⁇ -cyclodextrin or ⁇ -cyclodextrin or an inclusion complex of said cyciodextrins or cyclodextrin derivatives.
- a cyclodextrin derivative preferably a methylated or acetylated hydroxypropyl derivative of ⁇ -cyclodexthne, ⁇ -cyclodextrin or ⁇ -cyclodextrin or an inclusion complex of said cyciodextrins or cyclodextrin derivatives.
- the ester bond -O-CO- comes from the reaction between the hydroxyl function of the cellulosic fiber and the carboxylic function of the polycarboxylic acid while the amide bond -NH-CO- comes from the reaction between the amino function of keratin fiber and the carboxylic function of poly (carboxylic) acid.
- the poly (carboxylic) acid undergoes an esterification and / or amidation reaction of at least two of its carboxylic acid functions and the cyclodextrin or the cyclodextrin derivative undergoes an esterification with the poly (carboxylic) acid. at least one of its hydroxyl functions.
- the fiber or the material obtained by the process of the invention is simply coated with a crosslinked copolymer of cyclodextrin (s) and poly (carboxylic (s) acid).
- the fiber or the material based on fibers are of cellulosic and / or keratinous origin or comprise hydroxyl and / or amine functions
- the molecules of cyclodextrin (s) are fixed on the fiber or the material based on fibers according to the two methods of attachment described above, namely, direct attachment by covalent bond to the fiber and coating of the fiber with a crosslinked copolymer.
- the present invention relates to these two kinds of fibers or materials, whether or not obtained by the process of the invention.
- the present invention relates to fibers or materials based on fibers on which molecules of cyclodextrin (s) and / or derivatives of cyclodextrin (s) are only fixed by covalent bond, the fibers or materials based on fibers to which molecules of cyclodextrin (s) and / or cyclodextrin derivatives (s) are fixed by covalent bonding and by coating the fiber or fibers of the material with a crosslinked copolymer of cyclodextrin (s) and the fibers or materials based on fibers on which the cyclodextrin is only fixed by coating of crosslinked copolymer, without limitation concerning the nature or the structure of these fibers or of these fiber-based materials.
- These materials can be, for example, knitted, woven or non-woven textiles containing cellulosic and / or keratin and / or synthetic fibers.
- These fibers or materials based on fibers containing carboxylic acid functions have excellent odor adsorption properties and, to a lesser extent, improved water absorption properties.
- Examples 1 to 11 illustrate the process of the present invention.
- Examples 12 and 13 illustrate the adsorbent properties of the materials of the present invention and their possible use, in particular for the manufacture of mosquito repellent clothing and mosquito nets.
- Example 9 5 g of a hydrolyzed polyester fabric with a surface weight of 130 g / m 2 were impregnated using a scarf with an aqueous solution containing ⁇ -cyclodextrin (100 g / l), citric acid (100 g / l) and sodium hydrogen phosphate [12-hydrate] (30 g / l). The take-up rate was 90%. The fabric was dried for 3 minutes at 90 ° C, then treated for 5 minutes at 190 ° C, washed thoroughly with water and dried. The dry weight gain of the fabric was 19%.
- Example 10 5 g of a hydrolyzed polyester fabric with a surface weight of 130 g / m 2 were impregnated using a scarf with an aqueous solution containing ⁇ -cyclodextrin (100 g / l), citric acid (100 g / l) and sodium hydrogen phosphate [12-hydrate] (30 g / l). The take-up rate was 90%. The
- This example illustrates the adsorbent properties of tissues functionalized with ⁇ -cyclodextrin according to the method of the invention.
- Cyciodextrins are known to be capable of forming inclusion complexes with phenolphthalein.
- Six tissue samples functionalized with ⁇ -cyclodextrin according to the method of the invention, of known mass and containing different amounts of ⁇ -cyclodextrin were placed in solutions of phenolphtaleine of known concentration.
- the variation in the concentration of free phenolphthalein in each solution (Ao-Age) was measured by spectroscopy in the visible region at 552.4 nm after 96 hours.
- the changes in phenolphthalein concentration expressed by the variation of the optical density per gram of functionalized tissue are presented in the table below:
- the level of cyclodextrin fixed on textiles was measured by the difference in dry weight gain between a fabric treated with a cyclodextrin / poly (carboxylic acid) / catalyst mixture, and a fabric treated with a poly (carboxylic acid) / catalyst mixture. .
- DEET Diethyltoluamide
- Three cotton fabric samples, of known weight, functionalized with cyciodextrins and obtained according to the process of the invention, using citric acid, sodium hydrogen phosphate [12 hydrate] and ⁇ -, ⁇ - and ⁇ -cyclodextrins were placed in DEET solutions of known concentration.
- the adsorption of DEET on textile materials was determined by measuring the change in absorbance at 270nm of the initial solution after 96 hours. The results are presented in the table below:
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2362534A CA2362534C (fr) | 1999-02-15 | 2000-02-15 | Fibre presentant des proprietes de complexation ameliorees et des proprietes echangeuses de cations |
DE60010055T DE60010055T2 (de) | 1999-02-15 | 2000-02-15 | Fasern mit verbesserten komplexierungs- und kationenaustauscheigenschaften |
AT00905144T ATE264937T1 (de) | 1999-02-15 | 2000-02-15 | Fasern mit verbesserten komplexierungs- und kationenaustauscheigenschaften |
US09/913,448 US7048769B1 (en) | 1999-02-15 | 2000-02-15 | Fiber with improved complexation qualities and cation-exchange properties |
AU26778/00A AU2677800A (en) | 1999-02-15 | 2000-02-15 | Fibre with improved complexation qualities and cation-exchange properties |
EP00905144A EP1157156B8 (fr) | 1999-02-15 | 2000-02-15 | Fibre presentant des proprietes de complexation ameliorees et des proprietes echangeuses de cations |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/01967 | 1999-02-15 | ||
FR9901967A FR2789704B1 (fr) | 1999-02-15 | 1999-02-15 | Procede de traitement d'une fibre ou d'un materiau a base de fibres en vue d'ameliorer ses proprietes adsorbantes et fibre ou materiau a base de fibres presentant des proprietes adsorbantes ameliorees |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000047811A1 true WO2000047811A1 (fr) | 2000-08-17 |
Family
ID=9542174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/000378 WO2000047811A1 (fr) | 1999-02-15 | 2000-02-15 | Fibre presentant des proprietes de complexation ameliorees et des proprietes echangeuses de cations |
Country Status (9)
Country | Link |
---|---|
US (1) | US7048769B1 (fr) |
EP (1) | EP1157156B8 (fr) |
AT (1) | ATE264937T1 (fr) |
AU (1) | AU2677800A (fr) |
CA (1) | CA2362534C (fr) |
DE (1) | DE60010055T2 (fr) |
ES (1) | ES2220402T3 (fr) |
FR (1) | FR2789704B1 (fr) |
WO (1) | WO2000047811A1 (fr) |
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WO2001048025A1 (fr) * | 1999-12-28 | 2001-07-05 | Kimberly-Clark Worldwide, Inc. | Cyclodextrines liees de maniere covalente a des polysaccharides |
WO2002022941A1 (fr) * | 2000-09-14 | 2002-03-21 | Ciba Specialty Chemicals Holding Inc. | Procede de traitement antimicrobien de materiaux fibreux |
WO2002046520A1 (fr) * | 2000-12-07 | 2002-06-13 | Ciba Specialty Chemicals Holding Inc. | Materiau textile muni de cyclodextrines polymeres et procede permettant de le produire |
EP1285988A1 (fr) * | 2001-08-21 | 2003-02-26 | Tharreau Industries | Sustrat non tissé pouvant dégager un arôme et/ou une saveur |
US6861520B1 (en) | 2003-04-30 | 2005-03-01 | Dan River, Inc. | Process for chemically bonding an odor-encapsulating agent to textiles and textiles formed by the process |
FR2908047A1 (fr) * | 2006-11-06 | 2008-05-09 | Perouse Soc Par Actions Simpli | Procede de preparation d'une prothese tubulaire implantable a partir d'un corps tubulaire de base en materiau poreux, et prothese associee |
WO2008068400A2 (fr) * | 2006-11-06 | 2008-06-12 | Laboratoires Perouse | Procede de preparation d'une prothese implantable a partir d'un corps de base en materiau poreux, prothese et utilisation associees |
JP2008519626A (ja) * | 2004-11-15 | 2008-06-12 | ユニヴェルシテ デ シヤーンス エ テクノロジ ドゥ リール エスアーイーセー | 治療用分子の徐放および遅延放出に用いる吸収特性が向上したシクロデキストリンを有する生体材料 |
FR2922774A1 (fr) * | 2007-10-26 | 2009-05-01 | Perouse Soc Par Actions Simpli | Procede de preparation d'une prothese implantable a partir d'un corps de base en materiau poreux, prothese et utilisation associees. |
CN101857908A (zh) * | 2010-06-18 | 2010-10-13 | 四川大学 | 缓释型皮革香味整理剂及其制备方法 |
WO2012131745A1 (fr) | 2011-03-31 | 2012-10-04 | GIANIS S.r.L. | Liant et processus de production de tissus contenant des cyclodextrines fixées par ledit liant |
US8945287B2 (en) | 2006-05-09 | 2015-02-03 | Cocona, Inc. | Active particle-enhanced membrane and methods for making and using the same |
EP2231543B1 (fr) | 2007-12-05 | 2018-09-12 | Saint-Gobain Isover | Composition d'encollage pour laine minerale comprenant un monosaccharide et/ou un polysaccharide et un acide organique polycarboxylique, et produits isolants obtenus |
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DE10051350A1 (de) * | 2000-10-17 | 2002-04-25 | Henkel Kgaa | Reinigungsmaterial |
GB0219281D0 (en) * | 2002-08-19 | 2002-09-25 | Unilever Plc | Fabric care composition |
DE102006010561B4 (de) * | 2006-03-06 | 2009-10-15 | Septana Gmbh | Biozide oder biostatische geruchsmindernde Ausrüstung, ihre Herstellung, Applikation und Verwendung |
US20070270070A1 (en) * | 2006-05-19 | 2007-11-22 | Hamed Othman A | Chemically Stiffened Fibers In Sheet Form |
TWM333909U (en) * | 2007-09-27 | 2008-06-11 | Ct Healthcare Technology Co Ltd | Gauze mask structure |
FR3039840B1 (fr) * | 2015-08-05 | 2021-09-10 | Ajelis Sas | Materiau a base de fibres naturelles hydrophiles et son utilisation pour l'extraction des metaux presents dans un milieu aqueux |
FR3100547B1 (fr) * | 2019-09-11 | 2021-07-30 | Centre Nat Rech Scient | Procédé de modification d’un fil ou d’une surface textile |
CN115075006A (zh) * | 2021-03-11 | 2022-09-20 | 纳米及先进材料研发院有限公司 | 可洗涤的杀灭细菌及杀灭病毒的织物、其制法及其整理的配方套组 |
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US6689378B1 (en) | 1999-12-28 | 2004-02-10 | Kimberly-Clark Worldwide, Inc. | Cyclodextrins covalently bound to polysaccharides |
GB2374345A (en) * | 1999-12-28 | 2002-10-16 | Kimberly Clark Co | Cyclodextrins covalently bound to polysaccharides |
DE10085362B3 (de) * | 1999-12-28 | 2014-01-02 | Kimberly-Clark Worldwide, Inc. | Verfahren zur Herstellung einer Zusammensetzung für die Geruchskontrolle oder die Freisetzung eines Agens, derartige Zusammensetzung und diese umfassender Formkörper und Verfahren zur Herstellung eines Cyclodextrin umfassenden Materials |
WO2001048025A1 (fr) * | 1999-12-28 | 2001-07-05 | Kimberly-Clark Worldwide, Inc. | Cyclodextrines liees de maniere covalente a des polysaccharides |
WO2002022941A1 (fr) * | 2000-09-14 | 2002-03-21 | Ciba Specialty Chemicals Holding Inc. | Procede de traitement antimicrobien de materiaux fibreux |
US7105500B2 (en) | 2000-09-14 | 2006-09-12 | Ciba Specialty Chemicals Corp. | Process for the antimicrobial treatment of fiber materials |
WO2002046520A1 (fr) * | 2000-12-07 | 2002-06-13 | Ciba Specialty Chemicals Holding Inc. | Materiau textile muni de cyclodextrines polymeres et procede permettant de le produire |
EP1285988A1 (fr) * | 2001-08-21 | 2003-02-26 | Tharreau Industries | Sustrat non tissé pouvant dégager un arôme et/ou une saveur |
FR2828896A1 (fr) * | 2001-08-21 | 2003-02-28 | Tharreau Ind | Substrat non tisse pouvant degager un arome et/ou une saveur |
US6861520B1 (en) | 2003-04-30 | 2005-03-01 | Dan River, Inc. | Process for chemically bonding an odor-encapsulating agent to textiles and textiles formed by the process |
JP2008519626A (ja) * | 2004-11-15 | 2008-06-12 | ユニヴェルシテ デ シヤーンス エ テクノロジ ドゥ リール エスアーイーセー | 治療用分子の徐放および遅延放出に用いる吸収特性が向上したシクロデキストリンを有する生体材料 |
US8906403B2 (en) * | 2004-11-15 | 2014-12-09 | Universite Des Sciences Et Technologies De Lille Saic | Biomaterials carrying cyclodextrins having improved absorption properties and used for the progressive and delayed release of therapeutic molecules |
US8945287B2 (en) | 2006-05-09 | 2015-02-03 | Cocona, Inc. | Active particle-enhanced membrane and methods for making and using the same |
WO2008068400A2 (fr) * | 2006-11-06 | 2008-06-12 | Laboratoires Perouse | Procede de preparation d'une prothese implantable a partir d'un corps de base en materiau poreux, prothese et utilisation associees |
WO2008068400A3 (fr) * | 2006-11-06 | 2008-08-21 | Perouse Lab | Procede de preparation d'une prothese implantable a partir d'un corps de base en materiau poreux, prothese et utilisation associees |
FR2908047A1 (fr) * | 2006-11-06 | 2008-05-09 | Perouse Soc Par Actions Simpli | Procede de preparation d'une prothese tubulaire implantable a partir d'un corps tubulaire de base en materiau poreux, et prothese associee |
FR2922774A1 (fr) * | 2007-10-26 | 2009-05-01 | Perouse Soc Par Actions Simpli | Procede de preparation d'une prothese implantable a partir d'un corps de base en materiau poreux, prothese et utilisation associees. |
EP2231543B1 (fr) | 2007-12-05 | 2018-09-12 | Saint-Gobain Isover | Composition d'encollage pour laine minerale comprenant un monosaccharide et/ou un polysaccharide et un acide organique polycarboxylique, et produits isolants obtenus |
CN101857908A (zh) * | 2010-06-18 | 2010-10-13 | 四川大学 | 缓释型皮革香味整理剂及其制备方法 |
CN101857908B (zh) * | 2010-06-18 | 2013-03-20 | 四川大学 | 缓释型皮革香味整理剂及其制备方法 |
WO2012131745A1 (fr) | 2011-03-31 | 2012-10-04 | GIANIS S.r.L. | Liant et processus de production de tissus contenant des cyclodextrines fixées par ledit liant |
Also Published As
Publication number | Publication date |
---|---|
EP1157156A1 (fr) | 2001-11-28 |
AU2677800A (en) | 2000-08-29 |
DE60010055T2 (de) | 2005-03-03 |
EP1157156B1 (fr) | 2004-04-21 |
CA2362534A1 (fr) | 2000-08-17 |
FR2789704A1 (fr) | 2000-08-18 |
US7048769B1 (en) | 2006-05-23 |
EP1157156B8 (fr) | 2008-08-13 |
CA2362534C (fr) | 2011-09-20 |
ES2220402T3 (es) | 2004-12-16 |
ATE264937T1 (de) | 2004-05-15 |
DE60010055D1 (de) | 2004-05-27 |
FR2789704B1 (fr) | 2003-09-26 |
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