WO1999039039A1 - Traitement de tissus - Google Patents
Traitement de tissus Download PDFInfo
- Publication number
- WO1999039039A1 WO1999039039A1 PCT/GB1998/002142 GB9802142W WO9939039A1 WO 1999039039 A1 WO1999039039 A1 WO 1999039039A1 GB 9802142 W GB9802142 W GB 9802142W WO 9939039 A1 WO9939039 A1 WO 9939039A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- polycarboxylic
- hydroxy
- catalyst
- crosslinking agent
- Prior art date
Links
- 239000004744 fabric Substances 0.000 title claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 76
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 29
- 229920002678 cellulose Polymers 0.000 claims abstract description 27
- 239000001913 cellulose Substances 0.000 claims abstract description 25
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 230000032050 esterification Effects 0.000 claims abstract description 19
- 238000005886 esterification reaction Methods 0.000 claims abstract description 19
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004132 cross linking Methods 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 3
- 239000004753 textile Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 12
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- DLGBEGBHXSAQOC-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1 DLGBEGBHXSAQOC-UHFFFAOYSA-N 0.000 claims description 3
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 claims description 3
- 229940114055 beta-resorcylic acid Drugs 0.000 claims description 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 description 2
- 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 2
- 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
- 229940090248 4-hydroxybenzoic acid Drugs 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
- 150000001261 hydroxy acids Chemical class 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- AZFVKVWJOGILKI-UHFFFAOYSA-N 2,4-dihydroxy-5-methylbenzoic acid;2-hydroxy-3-methylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O.CC1=CC(C(O)=O)=C(O)C=C1O AZFVKVWJOGILKI-UHFFFAOYSA-N 0.000 claims 2
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical group OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 claims 1
- VWQGSDZXHWPTHJ-UHFFFAOYSA-N 2-hydroxybenzoic acid;2-(2-hydroxyphenyl)acetic acid Chemical compound OC(=O)C1=CC=CC=C1O.OC(=O)CC1=CC=CC=C1O VWQGSDZXHWPTHJ-UHFFFAOYSA-N 0.000 claims 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 32
- 230000037303 wrinkles Effects 0.000 abstract description 12
- -1 alkaline earth metal salts Chemical class 0.000 abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 4
- 239000011574 phosphorus Substances 0.000 abstract description 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 4
- 150000001340 alkali metals Chemical class 0.000 abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 238000001723 curing Methods 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 6
- 229960004025 sodium salicylate Drugs 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 235000019647 acidic taste Nutrition 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 150000003455 sulfinic acids Chemical class 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
- 159000000032 aromatic acids Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 2
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- GOCCREQJUBABAL-UHFFFAOYSA-N 2,2-dihydroxyacetic acid Chemical compound OC(O)C(O)=O GOCCREQJUBABAL-UHFFFAOYSA-N 0.000 description 1
- YLRJQJWRABXQKQ-UHFFFAOYSA-N 2,4-dihydroxy-5-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=C(O)C=C1O YLRJQJWRABXQKQ-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- VHBSECWYEFJRNV-UHFFFAOYSA-N 2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.OC(=O)C1=CC=CC=C1O VHBSECWYEFJRNV-UHFFFAOYSA-N 0.000 description 1
- QKRMFCXDTFLKKT-UHFFFAOYSA-N 2-hydroxyethanesulfonic acid Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O QKRMFCXDTFLKKT-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 229940006015 4-hydroxybutyric acid Drugs 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000005791 algae growth Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005525 durable press finishing Methods 0.000 description 1
- 238000012851 eutrophication Methods 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical class CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical class C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- ZLVSYODPTJZFMK-UHFFFAOYSA-M sodium 4-hydroxybenzoate Chemical group [Na+].OC1=CC=C(C([O-])=O)C=C1 ZLVSYODPTJZFMK-UHFFFAOYSA-M 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical group [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- NTAHVQPVJZSMSA-UHFFFAOYSA-M sodium;2-(2-hydroxyphenyl)acetate Chemical group [Na+].OC1=CC=CC=C1CC([O-])=O NTAHVQPVJZSMSA-UHFFFAOYSA-M 0.000 description 1
- UZLYOWSQVRAOBL-UHFFFAOYSA-M sodium;3-hydroxybenzoate Chemical group [Na+].OC1=CC=CC(C([O-])=O)=C1 UZLYOWSQVRAOBL-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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
- D06M13/203—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
- 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
- D06M13/1845—Aromatic mono- or polycarboxylic acids
-
- 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
- D06M13/207—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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- 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
- D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
-
- 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
- D06M2200/45—Shrinking resistance, anti-felting properties
Definitions
- This invention relates to a method of imparting wrinkle and/or crease and/or shrink resistance and/or smooth drying properties to fabrics made from cellulosic fibres or yarns or blends containing cellulosic fibres or yarns. More particularly it relates to such a method of treatment which does not involve the use of formaldehyde or formaldehyde derivatives or phosphorus containing compounds.
- Such properties can be imparted to cellulosic fabrics by a finishing treatment with resinous compositions.
- the most commonly used resins for such finishing are based on formaldehyde derivatives such as formaldehyde-urea or substituted urea addition products such as DMEU and DMDHEU.
- formaldehyde derivatives such as formaldehyde-urea or substituted urea addition products such as DMEU and DMDHEU.
- Such resins are believed to function by promoting crosslinking of the cellulose in the fabric thereby imparting the desired properties.
- crosslinking agents which do not include formaldehyde or its derivatives to remove the possible evolution of formaldehyde during manufacture, storage and/or use of cellulose, particularly cotton fabrics, treated with formaldehyde addition products.
- Non-formaldehyde crosslinking agents which have been suggested previously include polycarboxylic acids as disclosed by Gaghiardi and Shipee, American Dyestuff Reporter 52, 300 (1963). Rowland et al., Textile Research Journal 37, 393 (1967), disclosed the use of partially neutralized polycarboxylic acids with base prior to the application to the fabric in a pad, dry and heat cure treatment, elaborated US Patent 3526048. Canadian Patent No 2097483 describes rapid esterification and crosslinking of fibrous cellulose in textile form using boric acid or derivatives as crosslinking catalyst.
- the present invention is based on the discovery that certain hydroxycarboxylic acids and/or their salts, particularly alkaii metal salts at lower concentration show accelerating effect on esterification and crosslinking of cellulose by polycarboxylic acids.
- the use of such catalysts can enable the provision of a treatment method that uses neither formaldehyde derivatives or phosphorus compounds, but can give adequately rapid esterification and crosslinking of cellulosic in fibres to provide effective wrinkle, crease or shrink resistance or smooth drying properties to materials made from such cellulosic fibres.
- fibrous cellulosic material is treated with a polycarboxylic acid in the presence of a hydroxycarboxylic acid curing catalyst at elevated temperature.
- the process can be carried out by impregnating the material with a solution containing the polycarboxylic acid and the curing catalyst followed by heat treatment to produce esterification and crosslinking of the cellulose with the polycarboxylic acid.
- the present invention accordingly provides, a method of treating fibrous cellulosic textile material which comprises: a applying to the cellulosic textile material an aqueous solution including at least one polycarboxylic acid as a crosslinking agent for the cellulose and a hydroxycarboxylic acids or a salt as an esterification catalyst, b drying the textile material and heating it to promote crosslinking esterification of the polycarboxylic acid and the cellulose of the cellulosic textile material.
- the material as being “cellulosic” we mean that the major part of the fibre forming components of the material is cellulose.
- the term includes purely cellulosic materials such as cotton and cellulose-rich blends particularly cellulose-rich polyester blends, such as polycotton materials.
- the material contains from 30 to 100% of cellulosic fibres.
- Typical cellulosic fibre materials which can be included in fabrics treated according to this inventions include cotton, flax, rayon, jute, hemp and ramie. It can also be a synthetic cellulosic fibre material such as rayon, particularly viscose rayon or solvent derived rayon commonly called lyocell fibre.
- the cellulosic material can be a blend of fibres of cellulosic materials with non-celiulosic materials and in particular includes blends of cellulosic fibres, particularly cotton, with polyester, particularly polyethylene terephthalate polymer or related copolymers.
- the textile can be a woven (including knitted) or non-woven textile, but as crease resistance is particularly important in clothing, the textile will usually be a clothing textile material.
- the invention uses polycarboxylic acids as cellulose crosslinking agents to improve the wrinkle resistance, shrinkage resistance and smooth drying properties of cellulosic fibre containing textile without the use of formaldehyde or agents that release formaldehyde.
- polycarboxylic acids are known from the literature.
- Suitable polycarboxylic acids for use in the method of this invention include aliphatic, including open chain and alicyclic, polycarboxylic acids, and aromatic polycarboxylic acids. Desirably the polycarboxylic acid includes at least 3, particularly at least 4 and often more carboxylic acid groups per molecule.
- Particularly suitable aliphatic polycarboxylic acids include acids in which at least two carboxylic acid groups are separated by 2 or 3, more usually 2, carbon atoms and desirably where the polycarboxylic acid includes a plurality of such arranged pairs of carboxylic acid groups.
- an aliphatic acid includes an ethylenic double bond, it is very desirable that it is positioned ⁇ , ⁇ - to a carboxylic acid group; such an aliphatic acid may include a hydroxyl group on a carbon atom also carrying a carboxylic acid group; and further the aliphatic chain or ring may include one or more oxygen and/or sulphur atoms.
- Suitable aromatic acids include those where at least two carboxylic acid groups are attached to adjacent aromatic ring carbon atoms.
- Suitable aliphatic polycarboxylic acids include maleic acid, methylmaleic (citraconic) acid, citric acid, itaconic acid, 1 ,2,3-propanetricarboxylic acid, 1,2,3,4-butanetetracarboxylic acid (commonly known as BTCA), all c/s-1 ,2,3,4-cyclopentanetetracarboxylic acid, oxydisuccinic acid, thiodisuccinic acid; oligo- and/or poly-maleic acid and/or anhydride (as described in GB 2295404 A and WO 96/26314 A and abbreviated "OMA”) and suitable aromatic polycarboxylic acids include benzene hexacarboxylic acid and trimellitic acid.
- BTCA 1,2,3,4-butanetetracarboxylic acid
- OMA oligo- and/or poly-maleic acid and/or anhydride
- suitable aromatic polycarboxylic acids include
- the amount of crosslinking agent used will typically be from 1 to 10%, particularly from about 2 to about 7%, by weight based on the dry fabric weight.
- the particular concentration of crosslinking agent used in the treating solution will depend upon the degree of cross linking desired, the proportion of cellulosic fibres in fabric being treated and the solubility of the crosslinking agent. Typically, the concentration is from about 1 to 20%, more usually 2 to 10% particularly from 0.5 to 7 and especially about 5%, by weight of the solution.
- the curing catalyst used in this invention is one or more hydroxycarboxylic acid(s).
- the curing catalyst can be aliphatic, aromatic. Suitable aliphatic compounds include mono-carboxylic 1 2 1 mono-hydroxyl acids, in particular of the formula (I): H-R -CH(OH)-R -COOH (I) where each of R
- R is a direct bond or a C, to C 4 alkylene group, in particular where R is a direct bond, such that the total number of carbon atoms in the acid molecule is from 2 to 6 (??).
- Examples include hydroxyacetic acid (glycollic acid), glyoxalic acid (di-hydroxyacetic acid) and 4-hydroxybutyric acid.
- Suitable aromatic compounds include mono-carboxylic hydroxy acids in which at least one of the carboxyl and hydroxyl groups is directly attached to the aromatic ring. Desirably, the carboxyl group and at least one hydroxyl group are directly attached to the aromatic ring.
- the ring may also carry inert substituents such as one or more C 1 to C alkyl group(s), but desirably, not more than two such groups are attached to the aromatic ring.
- Particular aromatic acids are of the formula (II):
- R 3 is a CH 2 group, or, and desirably, a direct bond; n is from 1 to 3, particularly 1 or 2;
- each R is independently a C, to C 4 alkyl group; and m is 0, 1 or 2.
- aromatic acids those where the carboxylic acid group and a hydroxyl group are directly attached to the aromatic ring and are positioned substituted ortho- to each other on the ring are particularly useful.
- Very desirable such 'ort ⁇ o-acids' are those of the formula (III):
- m and R 4 are independently as defined for formula (II) and n' is 0 or 1.
- suitable ortho-aci ⁇ s include 2-hydroxybenzoic acid (salicylic acid), 2,4-dihydroxybenzoic acid (b-recorcyiic acid), 2,4-dihydroxy- 5-methylbenzoic acid (orcinylic acid) and the cresotic acids, especially 2-hydroxy-3-methylbenzoic acid, 2-hydroxy-4-methylbenzoic acid and 2-hydroxy-5-methylbenzoic acid.
- the hydroxycarboxylic acid catalyst can be used as the free acid or as a salt, particularly an alkali metal, ammonium or alkaline earth metal salt, or a mixture of the free acid and a salt or salt(s).
- the salt forming cations are particularly of potassium, sodium, ammonium, magnesium, calcium or a mixture of these cations. It is not clear whether the free acid form or the salt form of the curing catalyst is the more active component of the catalyst. The form present will depend on the acidity of the solution used for the treatment of the textile and the effect of the drying and heating steps. We have found that the textile is advantageously treated using a moderately acidic solution, typically having a pH of from 2 to 6, usually not more than 4.5, more usually from 2.5 to 4 and especially about 3.
- the curing catalyst may be present as the neutral free acid, as acid anions or a mixture depending on the acidity of the catalyst.
- Aromatic 2-hydroxy- carboxylic acids typically have acidities in aqueous solution such that both the neutral free acid and the acid anions are present at significant concentrations (relative to he overall concentration of the catalyst) at pH values of about 3.
- the amount of hydroxy aromatic acid catalyst used will typically be from 1 to 100%, more usually 1 to 50%, desirably 2 to 30% and especially 5 to 20%, by weight of the polycarboxylic acid crosslinking agent. Expressed as a percentage based on (the dry weight of) the material being treated, the amount will typically be from 0.1 to 10%, more usually from 0.2 to 3%, particularly 0.5 to 2% by weight.
- the concentration used in the treatment solution is typically from 0.1 to 10%, more usually from 0.2 to 5%, particularly from 0.3 to 2%, by weight of the solution.
- hydroxy aromatic acid catalysts used in this invention seems to go beyond the effect that might be expected of a simple catalyst. We do not know why this may be, but suspect that because the hydroxy aromatic acid catalysts have at least two potentially reactive sites, they may be acting to form further cross links by reacting with the cellulose and/or with the polycarboxylic acids used as cellulose crosslinking agents. The precise mechanism by which the effect arises is not critical to the invention.
- the catalysts used in this invention can be used alone or in combination with other catalytic materials. In particular they can be used in combination with organic or inorganic sulphonic or sulfinic acids or salts. In such combinations, suitable organic or inorganic sulphonic or sulfinic acids or their salts include inorganic sulphonic acids i.e. compounds including the group S0 3 H (or
- halosulphonic and amidosuiphonic acids particularly those of the general formula: XS0 2 OH where X is Cl, F or NH 2 , respectively chlorosulphonic and fluorosulphonic acids and amidosuiphonic acid (taurine); and organic sulphonic acids which typically have the general formula: RS0 2 OH where R is an organic group, particularly an alkyl or cycloalkyl group, an unsaturated straight or branched chain hydrocarbyl, particularly alkenyi group, or an unsaturated cyclic or arene group, especially suitable organic catalysts inlcude the alkane sulphonic acids and - 6 -
- alkali metal salts e.g. methane, ethane, propane, butane, pentane and hexane sulphonic acids, camphor sulphonic acid, isethionic acid (2-hydroxyethane sulphonic acid), methane- di-sulphonic acid and trifluoromethanesulphonic acid.
- curing catalysts include arene and alkyl arene sulphonic acids such as benzene, p-hydroxybenzene, p-toluene and dodecylbenzene sulphonic acids, naphthalene-1- and napthalene-2-sulphonic acids and 1 ,3-benzene and 2,6-naphthalene disulphonic acids and benzene sulphinic acid.
- arene and alkyl arene sulphonic acids such as benzene, p-hydroxybenzene, p-toluene and dodecylbenzene sulphonic acids, naphthalene-1- and napthalene-2-sulphonic acids and 1 ,3-benzene and 2,6-naphthalene disulphonic acids and benzene sulphinic acid.
- Sulphonic or sulfinic acid catalysts can be used as the free acids or as salts, particularly an alkali metal, ammonium or alkaline earth metal salts, or a mixture of free acid and salt(s).
- the salt forming cations are particularly of potassium, sodium, ammonium, magnesium, calcium or a mixture of these cations. It is not clear whether the free acid form or the salt form of this type of catalyst is the more active form. The form present will depend on the acidity of the solution used for the treatment of the textile and the effect of the drying and heating steps. At the moderately acid conditions typically used in this invention, it is likely that any sulphonic or sulfinic acid catalysts used will be present mainly as the (electrically) neutral free acid.
- the amount of this additional catalyst used will typically be from 10 to 200%, more usually 25 to 150%, desirably 50 to 120%, by weight of the polycarboxylic acid crosslinking agent. Expressed as a percentage based on the (dry weight of the) textile being treated, the amount will typically be from 1 to 30%, more usually from 2 to 20%, particularly 2.5 to 10% by weight.
- the concentration used in the treatment solution is typically from 0.1 to 20%, more usually from 0.2 to 10%, particularly from 0.5 to 7%, by weight of the solution.
- the treatment is typically carried out by first impregnating the cellulosic or cellulosic containing textile materials with an aqueous treating solution containing the crosslinking agent and the curing catalyst, and removing excess liquid e.g. using wringers, with these steps being repeated, if necessary, to obtain the desired liquid pick up.
- the material is then dried to remove the solvent and then cured, e.g. in an oven, typically at about 150 to 240°C, usually from 160 to 200°C for a time of from 5 seconds to 30 minutes, usually 1 to 5 minutes to promote the esterification and crosslinking of the cellulose by the polycarboxylic acid.
- the pick up of treatment solution is from 30 to 120%, more usually from 50 to 100%, particularly about 80% of the dry weight of the untreated textile.
- FT-IR Fastier transform infra red
- the treatment solution containing the crosslinking agent and the curing catalyst forms part of the • ) 0 invention which accordingly specifically includes an aqueous solution of at least in one polycarboxylic acid cellulose crosslinking agent, particularly at a concentration of from 1 to 20% by weight of the solution, and at least one hydroxycarboxylic acid esterification catalyst, particularly at a concentration of from 0.2 to 10% by weight of the solution.
- the invention further includes an aqueous solution of at least in one polycarboxylic acid cellulose crosslinking agent, particularly at a concentration of from 1 -15 to 20% by weight of the solution, at least one hydroxycarboxylic acid esterification catalyst, particularly at a concentration of from 0.2 to 10% by weight of the solution and at least one organic or inorganic sulphonic or sulfinic acids or a salt esterification catalyst, particularly at a concentration of from 0.2 to 10% by weight of the solution.
- the invention further includes cloth treated by the method of the invention and in particular, a cellulosic textile material, which may be woven (including knitted) or non-woven, which carries residues of at least in one polycarboxylic acid cellulose crosslinking agent esterified to hydroxylic sites in the cellulose and residues of at least one hydroxycarboxylic acid esterification catalyst.
- a cellulosic textile material which may be woven (including knitted) or non-woven, which carries residues of at least in one polycarboxylic acid cellulose crosslinking agent esterified to hydroxylic sites in the cellulose and residues of at least one hydroxycarboxylic acid esterification catalyst.
- the invention also includes a cellulosic textile material, which may be woven (including
- Wrinkle recovery angles were determined by ATCC Test Method 66-1990 Wrinkle recovery of fabrics: Recovery angle method.
- the wrinkle resistance of woven textiles is represented by the wrinkle recovery angles; the greater the WRA the greater the wrinkle resistance of the fabric. Results are reported in degrees.
- Example 1 This Example illustrates the use of salicylic acid (introduced as sodium salicylate) as a curing catalyst for the durable press finishing of cotton fabric using BTCA.
- Cotton cloth test pieces (10 inches square; ca. 25x25 cm;) were thoroughly wetted by immersion in a treatment bath containing an aqueous solution (80 ml) of BTCA (5 g) and sodium salicylate (0.5 g) as curing catalyst at a pH adjusted to 3. The wetted cloth was passed between the rolls of a wringer and the process repeated twice to give an overall pick up 80% by weight of the treatment solution based on the dry weight of the untreated cloth. The test pieces were stretched on a rack and dried in an air forced draft oven at 85°C for 5 minutes. The dried test pieces were then treated in an air draft oven at 180°C for 2 minutes.
- Example 1 was repeated, but substituting sodium benzoate (5 g) for the sodium salicylate used in Example 1 and gave a WRA (before washing) of 261°.
- Example 2 Example 1 was repeated but substituting oligomaieic acid (OMA) for the BTCA used in Example 1 and gave a WRA (before washing) of 255°. - 9 -
- Example 3 Example 1 was repeated, but substituting sodium 3-hydroxybenzoate (1 g) for the sodium salicylate used in Example 1 and gave a WRA (before washing) of 276°.
- Example 4 Example 4
- Example 1 was repeated, but substituting sodium 4-hydroxybenzoate (1 g) for the sodium salicylate used in Example 1 and gave a WRA (before washing) of 276°.
- Example 5 Example 1 was repeated, but substituting sodium 2-hydroxyphenylacetate (1 g) for the sodium salicylate used in Example 1 and gave a WRA (before washing) of 274°.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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KR1020007008298A KR20010034474A (ko) | 1998-01-31 | 1998-07-17 | 직물의 처리 |
EP98935154A EP1051549A1 (fr) | 1998-01-31 | 1998-07-17 | Traitement de tissus |
AU84511/98A AU8451198A (en) | 1998-01-31 | 1998-07-17 | Treatment of fabrics |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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GBGB9802031.6A GB9802031D0 (en) | 1998-01-31 | 1998-01-31 | Treatment of fabrics |
GB9802031.6 | 1998-01-31 | ||
GB9802032.4 | 1998-01-31 | ||
GBGB9802032.4A GB9802032D0 (en) | 1998-01-31 | 1998-01-31 | Treatment of fabrics |
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US08/707,012 Continuation-In-Part US6332029B1 (en) | 1995-09-02 | 1996-09-03 | Acoustic device |
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WO1999039039A1 true WO1999039039A1 (fr) | 1999-08-05 |
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PCT/GB1998/002145 WO1999039040A1 (fr) | 1998-01-31 | 1998-07-17 | Traitement de tissus |
PCT/GB1998/002142 WO1999039039A1 (fr) | 1998-01-31 | 1998-07-17 | Traitement de tissus |
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PCT/GB1998/002145 WO1999039040A1 (fr) | 1998-01-31 | 1998-07-17 | Traitement de tissus |
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EP (2) | EP1051549A1 (fr) |
KR (2) | KR20010034475A (fr) |
CN (2) | CN1284142A (fr) |
AU (2) | AU8451198A (fr) |
WO (2) | WO1999039040A1 (fr) |
Cited By (8)
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WO2001018303A1 (fr) * | 1999-09-10 | 2001-03-15 | Nano-Tex, Llc | Apprets durables pour textiles |
US9546263B2 (en) | 2009-10-09 | 2017-01-17 | Owens Corning Intellectual Capital, Llc | Bio-based binders for insulation and non-woven mats |
US9718729B2 (en) | 2009-05-15 | 2017-08-01 | Owens Corning Intellectual Capital, Llc | Biocides for bio-based binders, fibrous insulation products and wash water systems |
US9957409B2 (en) | 2011-07-21 | 2018-05-01 | Owens Corning Intellectual Capital, Llc | Binder compositions with polyvalent phosphorus crosslinking agents |
US10000666B2 (en) | 2009-10-09 | 2018-06-19 | Owens Corning Intellectual Capital, Llc | Insulative products having bio-based binders |
US10030177B2 (en) | 2011-05-27 | 2018-07-24 | Cargill, Incorporated | Bio-based binder systems |
US10047210B2 (en) | 2011-04-07 | 2018-08-14 | Owens Corning Intellectual Capital, Llc | Bio-based binders including carbohydrates and a pre-reacted product of an alcohol or polyol and a monomeric or polymeric polycarboxylic acid |
US10144902B2 (en) | 2010-05-21 | 2018-12-04 | Cargill, Incorporated | Blown and stripped blend of soybean oil and corn stillage oil |
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CN102995405B (zh) * | 2011-09-19 | 2014-08-13 | 武汉纺织大学 | 一种制备网点免烫纺织品的方法 |
CN102851941B (zh) * | 2012-10-15 | 2014-04-16 | 河北科技大学 | 一种用于牛仔捏皱定型树脂整理的复合催化剂及其使用方法 |
CN107904931A (zh) * | 2017-11-30 | 2018-04-13 | 苏州绣艳天下刺绣工艺有限公司 | 一种免熨棉织物的制备方法 |
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WO2001018303A1 (fr) * | 1999-09-10 | 2001-03-15 | Nano-Tex, Llc | Apprets durables pour textiles |
US6872424B2 (en) | 1999-09-10 | 2005-03-29 | Nano-Tex, Llc | Durable finishes for textiles |
US9718729B2 (en) | 2009-05-15 | 2017-08-01 | Owens Corning Intellectual Capital, Llc | Biocides for bio-based binders, fibrous insulation products and wash water systems |
US9546263B2 (en) | 2009-10-09 | 2017-01-17 | Owens Corning Intellectual Capital, Llc | Bio-based binders for insulation and non-woven mats |
US11286204B2 (en) | 2009-10-09 | 2022-03-29 | Owens Coming Intellectual Capital, LLC | Bio-based binders for insulation and non-woven mats |
US10000666B2 (en) | 2009-10-09 | 2018-06-19 | Owens Corning Intellectual Capital, Llc | Insulative products having bio-based binders |
US10144902B2 (en) | 2010-05-21 | 2018-12-04 | Cargill, Incorporated | Blown and stripped blend of soybean oil and corn stillage oil |
US10851326B2 (en) | 2010-05-21 | 2020-12-01 | Cargill, Incorporated | Blown and stripped blend of soybean oil and corn stillage oil |
US11339347B2 (en) | 2010-05-21 | 2022-05-24 | Cargill, Incorporated | Blown and stripped blend of soybean oil and corn stillage oil |
US11884894B2 (en) | 2010-05-21 | 2024-01-30 | Cargill, Incorporated | Blown and stripped blend of soybean oil and corn stillage oil |
US10047210B2 (en) | 2011-04-07 | 2018-08-14 | Owens Corning Intellectual Capital, Llc | Bio-based binders including carbohydrates and a pre-reacted product of an alcohol or polyol and a monomeric or polymeric polycarboxylic acid |
US11066535B2 (en) | 2011-04-07 | 2021-07-20 | Owens Corning Intellectual Capital, Llc | Bio-based binders including carbohydrates and a pre-reacted product of an alcohol or polyol and a monomeric or polymeric polycarboxylic acid |
US10030177B2 (en) | 2011-05-27 | 2018-07-24 | Cargill, Incorporated | Bio-based binder systems |
US10550294B2 (en) | 2011-05-27 | 2020-02-04 | Cargill, Incorporated | Bio-based binder systems |
US11814549B2 (en) | 2011-05-27 | 2023-11-14 | Cargill, Incorporated | Bio-based binder systems |
US9957409B2 (en) | 2011-07-21 | 2018-05-01 | Owens Corning Intellectual Capital, Llc | Binder compositions with polyvalent phosphorus crosslinking agents |
US12054628B2 (en) | 2011-07-21 | 2024-08-06 | Owens Corning Intellectual Capital, Llc | Binder compositions with polyvalent phosphorus crosslinking agents |
Also Published As
Publication number | Publication date |
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CN1284142A (zh) | 2001-02-14 |
KR20010034475A (ko) | 2001-04-25 |
EP1051549A1 (fr) | 2000-11-15 |
AU8451298A (en) | 1999-08-16 |
AU8451198A (en) | 1999-08-16 |
WO1999039040A1 (fr) | 1999-08-05 |
KR20010034474A (ko) | 2001-04-25 |
EP1051550A1 (fr) | 2000-11-15 |
CN1284143A (zh) | 2001-02-14 |
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