GB2028352A - Durable, antistatic, soil release agents and their application to substrates - Google Patents
Durable, antistatic, soil release agents and their application to substrates Download PDFInfo
- Publication number
- GB2028352A GB2028352A GB7927648A GB7927648A GB2028352A GB 2028352 A GB2028352 A GB 2028352A GB 7927648 A GB7927648 A GB 7927648A GB 7927648 A GB7927648 A GB 7927648A GB 2028352 A GB2028352 A GB 2028352A
- Authority
- GB
- United Kingdom
- Prior art keywords
- agent
- substrate
- fabric
- alkyl
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 149
- 239000000758 substrate Substances 0.000 title claims abstract description 49
- 239000002689 soil Substances 0.000 title claims abstract description 42
- 239000004744 fabric Substances 0.000 claims abstract description 119
- 229920000728 polyester Polymers 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000001035 drying Methods 0.000 claims abstract description 10
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 8
- 230000005593 dissociations Effects 0.000 claims abstract description 8
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 229920003180 amino resin Polymers 0.000 claims abstract description 4
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 238000007865 diluting Methods 0.000 claims abstract description 4
- 229910001412 inorganic anion Inorganic materials 0.000 claims abstract description 4
- 150000002891 organic anions Chemical class 0.000 claims abstract description 4
- 229920005989 resin Polymers 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims abstract description 4
- 238000004383 yellowing Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000004753 textile Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- 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 claims description 17
- 239000011734 sodium Substances 0.000 claims description 17
- 229910052708 sodium Inorganic materials 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 229910002651 NO3 Inorganic materials 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 10
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical group [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 10
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 7
- 235000011152 sodium sulphate Nutrition 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229940007076 aluminum cation Drugs 0.000 claims 1
- 229940006486 zinc cation Drugs 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 31
- 235000002639 sodium chloride Nutrition 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 10
- 235000019800 disodium phosphate Nutrition 0.000 description 9
- 229910000397 disodium phosphate Inorganic materials 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010926 purge Methods 0.000 description 9
- 239000002243 precursor Substances 0.000 description 8
- 238000010998 test method Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 229920001966 Qiana Polymers 0.000 description 7
- 229940117927 ethylene oxide Drugs 0.000 description 7
- -1 for example Substances 0.000 description 7
- 238000004900 laundering Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 229920000784 Nomex Polymers 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000002979 fabric softener Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000004763 nomex Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical class [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- 229920004934 Dacron® Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical group 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical class [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000011086 glassine Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical class [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical class [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- YXVFQADLFFNVDS-UHFFFAOYSA-N diammonium citrate Chemical compound [NH4+].[NH4+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O YXVFQADLFFNVDS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 235000016804 zinc Nutrition 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
- 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
A durable, antistatic soil release agent which is resistant to yellowing on the substrate has the formula <IMAGE> X is an aminoplast resin moiety having 4 to 6 methylene groups, each of which is attached to an amino nitrogen atom and to Y1, Y2 or Y3; Y1 is O(C2H4O)5-20R1 wherein R1 is C1-5 alkyl; Y2 is O(C2H4O)5-88R2 wherein R2 is C6-20 alkyl; <IMAGE> wherein R3 is C4-20 alkyl, C4-20 alkenyl or benzyl, R4 is C1-4 alkyl, A<-> is an organic or inorganic anion, each of m and n is at least 1 and the sum of m and n is 12 to 100; each of a and b is 0 to 2 and the sum of a and b is 1 to 2; c is 1 to 2; the sum of a, b and c is 1 to 4; said agent having a specified calculated hydrophile-lipophile balance (HLB), viscosity, electrical resistivity (initially and after 10 washes) and soil release rating on polyester fabric. It is applied by (a) diluting the agent, (b) adding a metal or an ammonium salt to achieve a cloud point of less than 100 DEG C but greater than 25 DEG C, and/or adding sufficient polyacidic compound having a second dissociation constant of greater than 1 x 10<-8> to achieve a pH of 3.0 to 6.0, (c) applying the diluted agent of step (b) to the substrate, and (d) drying and curing the agent on the substrate.
Description
SPECIFICATION
Application of durable, antistatic, soil release agents to substrates
This invention relates to a chemical composition which is useful for imparting durable antistatic and soil release characteristics to a wide variety of substrates, for example, textile fabrics, to a process for durably applying the composition to a substrate, and to substrate durably treated with the chemical composition.
It is an object of this invention to provide a chemical composition which can be used to impart durable, antistatic, soil release and, to some extent, anti-soil redeposition characteristics to a substrate treated therewith. Another object is to provide a process by which the composition can be durably applied to the substrate. A further object is to provide a substrate which exhibits durable, antistatic, soil release and, to some extent, anti-soil redeposition properties. Still another object is to provide such a composition and process which are particularly useful in the textile trade.
Extensive prior art exists in the fields of antistatic agents and soil release agents. Such materials are used extensively to impart antistatic and soil release characteristics to substrates treated therewith, par ticularlytextile materials, such as textile fabrics. A desirable feature of such agents is durability, that is, the ability of the agent to be retained on the substrate during subsequent handling or use thereof. For example, in the case of textile fabrics, such as clothing, it is desirable that any antistatic or soil release property imparted to the fabric be retained thereon through subsequent laundering operations. A need exists for a single substrate treating agent or composition which can impart durable, antistatic soil release properties to the substrate.
The invention resides in a durable antistatic soil release agent which is resistant to yellowing on the substrate treated therewith, to the method of applying the agent to the substrate, and to substrate treated with the agent which is of the formula
wherein Xis an aminoplast resin moiety having amino nitrogen atoms and 4 to 6 methylene groups, each of which methylene groups is attached to an amino nitrogen atom and toY1, Y2 orY3; Y1 is O(C2H4O)s~20R1 wherein R1 is Cis alkyl;
Y2 is O(C2H4O)5~88R2 wherein R2 is CG-20 alkyl;;
wherein R3 is C42o alkyl, C42o alkenyl or benzyl, R4 is C1-4 alkyl, AOis an organic or inorganic anion, each of and n is at least 1 and the sum of m and n is 12 to 100; eachofaandbisOto2andthesumofaandbisO to 2; c is 1 to 2;
the sum ofa, b and c is 1 to 4; said agent having a calculated hydrophile- lipophile balance (HLB) of 14.5 to 18.0, a 20 weight% aqueous solution viscosity, as measured at 20 C on a Brookfield viscometer, of 250 to 16,000 cps (0.250 to 16.000 pascal seconds), an electrical resistivity (Keithley log
R) on polyester fabric, at 20 i 2% relative humidity (R.H.) and 23 + 1 C, of no greaterthan 13.00 initially and no greater than 14.25 after 10 washes, and a soil release rating on polyester fabric of at least 3 initially.Preferably, in the above formula, Y1 is O(C2H40)10--16 and R1 is CH3; Y2 is O(C2H4O)1530 and B2 is C13H27; in Y3, R3 is CB-18 alkyl, or CS-12 alkyl to achieve good waterwettability (drop absorption), R4 is CH3, A0isSO3CH3 and m + n is 20 to 50; the HLB is 15.5 to 17.0; and the 20% aqueous viscosity is 2,000 to 8,000 cps (2.00 to 8.00 pascal seconds).
Although itwill be described in greater detail hereinafter, the process of the invention resides in a process for applying the aforesaid agent to a substrate, which process comprises the steps:
(a) diluting the agent with a normally liquid medium to achieve the desired application liquid viscosity,
(b) adding sufficient salt of a mono-, di- or trivalent metal or of an ammonium cation to achieve a cloud point, of the diluted agent of step (a), of less than 100"C but greater than 25"C, or adding sufficient polyacidic compound having a second dissociation constant of greater than 1 x 10-8 to achieve a pH, of the diluted agent of step (a), or 3.0 to 6.0, or adding both said salt and said polyacidic compound to achieve said cloud point and pH,
(c) applying the diluted agent of step (b) to the substrate to be treated so as to achieve the desired level of agent on the substrate,
(d) drying and curing the agent on the substrate, and
(e) recovering substrate which has been durably treated with the agent of the aforesaid formula.
Finally, the invention herein also resides in substrate which has been durably treated with the aforesaid agent.
The agent of the invention is prepared by conventional techniques by contacting, in appropriate amounts, under appropriate reaction conditions, appropriate precursors of the aforesaid moieties X and V3 and the optional moieties V1 and Y2.
Exemplary of X moiety precursors which can be used to produce the agent of the invention are the melamine methylol derivatives having 4 to 6 methylol groups, which methylol groups can be ether capped with, for example C1-4 alkyl. The optional Y, and Y2 moieties can be provided by the commonly available polyethylene oxides. For example, polyethylene glycol monoethers having 5 to 20 ethyleneoxy moieties and C15 alkyl ether end groups are commercially available under the Car bowaxs designation, thus providing a source of the V1 moiety.Similarly, theY2 moiety is provided by commercially available materials, such as those designated Merpol#, which are polyethylene glycol
monoethers having 5 to 88 ethyleneoxy moieties and C6~20 alkyl ether end groups.
General procedure used to prepare Y2 precursor
One mole of the appropriate C6-C20 alkyl alcohol is dried to 20.2 weight% water, either thermally under nitrogen purge or under reduced pressure (if the
boiling point of the alcohol is high enough). About 0.5 part of sodium hydride (or a similar catalyst) is then added to the alcohol, with stirring, at 80-1 000C, under a nitrogen atmosphere. After 15-60 minutes of agitation, the temperature is increased. When the alcohol temperature is about 140"C, the nitrogen purge is stopped and ethylene oxide is introduced.
The temperature is allowed to reach about 155"C.
The addition of ethylene oxide is continued at this temperature until a total of 5 to 88 moles (depending on the ethyleneoxide content desired) is added per mole of alcohol present. After addition and reaction of the ethylene oxide is complete, any sodium alcoholate formed (from the sodium hydride) is neutralized at about with an equivalent amount of acid, such as p-toluenesulfonic acid. The finished product, if it is not used immediately, can be stored in a sealed container until needed.
General procedure used to prepare Y3 precursor
One mole of the appropriate n-alkylamine is heated under a nitrogen purge to at least 1200C, preferably within the range 185 to 230"C. The nitrogen purge is discontinued and ethylene oxide is introduced and reacted with the amine to produce N, N bis - 2 - hydroxyethyl - n - alkyl amine according to the procedure of H. L. Sanders, J. B. Braunwarth, R.
B. McConnell and R. A. Swenson, J. Am Oil Chem.
Soc., 46 167 (1969). The lower molecular weight bis - hydroxyethyl - n - alkylamines are commercially available. About 1 part of 50-60 weight% sodium hydride in oil is then added to the one mole of the bis - 2 - hydroxyethyl - n - alkylamine under a nitrogen purge at 50-100"C. The mixture is heated with agitation under nitrogen to about 140"C. The nitrogen purge is discontinued, ethylene oxide is introduced and the reaction is run at 140-170"C, preferably at 155-165"C. Ethylene oxide addition is continued until the desired amount has reacted with the bis - 2 hydroxyethyl - n - alkylamine. Then nitrogen purging is resumed while the product is cooled to about 80"C.
An amount of acid, such as dry p-toluenesulfonic acid, equivalenttothe 100% sodium hydride used is then added. The resultant tertiary polyethyleneoxy n - alkylamine is quaternized by the following conventional procedure.
If a commercially available tertiary polyethleneoxy - n - alkylamine is used, it should be dried 2-4 hours at 90-95"C with agitation under reduced pressure (30-50 mm of mercury; 3,999.7 to 6,666.1 pascal). To one mole of the aforesaid tertiary amine is slowly added, with agitation, 0.99-1.0 mole of dimethyl sulfate over a 1-4 hour period while the reaction mixture is kept at 50-60"C, after which the mixture is agitated for an additional 8-20 hours at 50-60"C.
When the reaction is complete, the product can either be used directly in the subsequent condensation step or stored until such use.
General procedure used to prepare agent of the invention
The agent of the invention can be prepared by the following general procedure. Although the procedure given below applies to the preparation of an agent of the aforesaid formula having Y1, V2 and V2 moieties, it will be obvious to one skilled in the art that other agents of said formula wherein one or both of V1 and V2 are absent can similarly be prepared.
A mixture of one mole of the lower alkyl polyethyleneoxy alcohol (V1 precursor) and one mole of the higher alkyl polyethyleneoxy alcohol (Ys precursor) is dried and any peroxides therein are eliminated by heating, with agitation, at 170-190"C for 2 hours under reduced pressure (20-50 mm of mercury; 2,666.4 to 6,666.1 pascal). After cooling to 80-90"C and breaking the vacuum with a nitrogen purge, one mole of the quaternized polyethyleneoxy tertiary amine glycol (V3 precursor), one mole of predried hexakis (methoxymethyl) melamine (X precursor) (Cymels 300) and 0.6 weight%, based on the total weight of the components used, of predried p-toluenesulfonic acid are added.With rapid nitrogen purging of the molten mass, the stirred mixture is heated at 90-95"C. The methanol and small amount of methylal that are evolved can be collected in cold receivers or traps. The total amount of methanol collected should be about three moles.
The condensation is continued until the desired product viscosity is reached. An amount of tertiary amine, preferably having a boiling point above 1200C, for example, triethanolamine, which is 50 mole% greater than the molar amount of p-toluenesulfonic acid used is added immediately to the viscous mass to stop the reaction. The nitrogen flow rate and stirring rate are reduced while the amine neutralizes the acid at85-95 C (10-20 minutes).
Aqueous dilution ofcondensate The above 100% condensate can be stored as is or used directly. However, for most uses, such as the treatment of textile fabrics, it is diluted (by suspending or dispersing or by dissolving in a normally liquid medium) to a manageable viscosity, for example, the desired application liquid viscosity, so that it can be applied by conventional techniques, for example, by padding or exhaust. If the aforesaid 100% condensate has been stored at room temperature, it will be a solid and must be thawed at a temperature of at least 50"C, preferably under a nitrogen atmosphere. The condensate can be diluted with a
normally liquid (at 25"C) medium until the desired
(manageable) viscosity is achieved. The liquid
medium preferably should be miscible with the agent of the invention and the salt andlor polyacidic compounds discussed hereinafter, nonreactive therewith at least up to about the cure temperature, and removable by volatilization at least by the cure temperature. Suitable liquid media include water, alcohols, ketones, esters, ethers and aromatic hyd
rocarbons. A convenient liquid medium for textile treating operations is water. Most of the description
herein relates to the use of water as the normally
liquid medium in connection with the utility of the
agent of the invention as a durable, antistatic, soil
release agent for textile fabrics. It will be readily apparent to one skilled in the art that other substrates can be treated with the agent of the invention to achieve durable antistatic and soil release characteristics.For example, the agent of the invention can be used to treat textile fibers which may or may not subsequently be converted to fabric and to treat substrates which are flexible or nonflexible shaped structures of polymeric materials other than textile fibers and fabrics, for example, molded articles as well as extruded products, such as film and tubing.
If water is used as the normally liquid diluting medium, a weighed portion of the viscous condensate is added slowly to a rapidly stirred quantity of water (the addition of water to the condensate may yield a difficult - to - manage gel-like material). After the condensate dissolves, the mixture is made alkaline, for example, the pH is adjusted to 7.7-8.2, to minimize hydrolysis of the product on storage, by the addition of sodium bicarbonate. If desired, enough water can be added to bring the mass to, for example, a 20 weight% aqueous solution. Such a solution has a Brookfield viscosity of 250 to 16,000 cps (0.250 to 16.000 pascal seconds) at 20"C. In the treatment of fabrics, a more dilute aqueous solution is used, for example, less than 1 weight% in an exhaust application.
The agent of the invention has a calculated hydrophile-lipophile balance (HLB) of 14.5 to 18.0 and a 20 weight% aqueous solution viscosity, as measured on a Brookfield viscometer, of 250 to 16,000 cps (0.250 to 16.000 pascal seconds). In general, all other variables being maintained constant, the higher the viscosity, the better will be the durability achieved with the agent of the invention on the fabric being treated.
The Brookfield viscosity is determined by the
American Society of Testing Materials Test Method
D-1824, modified, with the modifications thereto being as follows:
1. Viscosities are measured at 25 + 0.4 C.
2. Samples are bubble-free when viscosities are determined.
3. Viscosity is determined one to three times, on a given sample, at about the same time.
4. Viscosities are reported in centipoises (cps; pascal seconds).
The hydrophile-lipophile balance (HLB) system is the subject of numerous publications, for example, "Classification of Surface-Active Agents by HLB," W.
C. Griffin,J. Soc. Cosmetic Chemists 1,311(1949); "Calculation of HLB Values of Non-ionic Surfac tants," i ibid. 5, 249 (1954); "The Atlas HLB System," Atlas Chemical Industries, Inc., Wilmington, Delaw are, 4th printing, May, 1971; Proceedings 2nd Int.
Congr. Sur. Act. 1,426 (1957), Academic Press, New
York, N.Y. HLB values reflect the hydrophilic content of the molecule. In accordance with the information available from the aforesaid publications, calculated
HLB values are determined herein by means of the equation:
sum of the molecular weights of all the
hydrophilic moieties of the molecule X20 = molecular weight of the entire molecule
Calculated HLB
The agent of this invention is particularly useful as a textile treating agent for fabrics of synthetic fibers, including woven, nonwoven and knit fabrics of either spun or filamentary type fibers. The fabrics can be of the blended or unblended fiber type. Fabrics treated with the agent exhibit good to excellent antistatic, soil release and, to some extent, anti-soil redeposition characteristics.Moreover, the agent does not substantially affect the hand of the fabric, and the agent appears to be non-toxic, it can be applied topically using pad or exhaust techniques, it is durably retained by the fabric after being applied thereto and it is resistant to yellowing on the fabric.
Fabrics particularly suitable to treatment with the agent of this invention include those of polyester, polyamide, polyacrylic or acetate fibers. Liana, Nomex, Dacron and nylon taffeta fabrics, for example, can be usefully treated by means of this invention.
It is to be understood that the previous discussion of preparative procedures of the agent of the invention and the following examples (within the invention) and experiments (outside the invention) are intended merely as guidelines to enable one skilled in the artto practice the invention. Modifications of the preparative procedures disclosed herein will be readily apparent. It is to be further understood that the parameters set forth above for the agent of the invention are important to achieving the objects of the invention.Control of preparative conditions is important to achieving the requisite parameters of the agent and, although the details given above and hereinafter in the examples are believed to be adequate to practice the invention, ultimate determination of such practice usually is carried out by evaluating the agent, promptly after it is prepared, as to its various characteristics according to the procedures set forth below.
The fabric used in the evaluation of the agent of the invention is produced from commercially available Dacron Polyester Fiber Type 56. The fabric is white, undyed 150/34 (denier/gauge) double-knit fabric. The fabric is scoured at 71"C for 20 minutes with 0.5 gram/litre (0.001 m3) of Merpolo SH nonionic detergent and 1 gram/litre (0.001 m3) of trisodium polyphosphate. After being rinsed well with water the fabric is dried.
The agent to be evaluated is padded onto the fabric so as to give an active ingredient level of 0.8 weight%, based on the weight of dry fabric. A typical pad bath includes the necessary amount of active ingredient, with the bath concentration being adjusted for wet-pickup of the fabric, 0.75 weight% of sodium sulfate, based on the total weight of the bath, and sufficient citric acid to achieve a pH of 4.0.
Pad application can be carried out with a commercially available padder, such as a Spartans II padder, using two passes and two nips. After padding, the fabric is dried and cured at 199"C in a forced hot air oven. Curing conditions may vary depending on the wet pick-up of the fabric. Generally, 60 to 75 seconds are adequate for curing at 199"C. A pin frame is used to hold the fabric.
The cured fabric is rinsed in Permutito water to remove residual salts or acids and then dried, for
example, in a commercially available Sears Roebuck
dryer, at 71 + 5"C. The agent of the invention is tested for its antistatic characteristic on the fabric
using the American Association of Textile Chemists
and Colorists (AATCC) Test Method 76-1975 with
slight modification as described below. Testing of
fabric samples is carried out in a dry box at 20 + 2%
relative humidity and 23 + 1 C, the humidity being
controlled by a commercially available Hygrometer
Indicator Controller (Model 15-3252) with a Model
15-1810 sensing element.Testing equipment includes a Keithley Model 610C Electrometer in combination with a Keithley Model 240A High Voltage Supply and a Model 610S Resistivity Adapter.
Further description of this test may be found in the
AATCC Technical Manual under the aforesaid test method which is entitled "Electrical Resistivity of
Fabrics." Testing of fabric samples is carried out initially (after rinsing) and then after five and ten home laundering/tumble dry cycles, commonly referred to as home wash/tumble dry (HWTD) cycles. The antistatic (A.S.) data appear in the accompanying tables under the heading "A.S.," with the symbols "I, 5W, 10W" being used to indicate the antistatic characteristic initially and after five and ten washes (HWTD cycles), respectively.As indicated above, the agent of the invention must exhibit an electrical resistivity (Keithley Log R), a measure of the antistatic characteristic of the agent, on polyester fabric, at 20 t 2% relative humidity and 23 + 1"C, of no greater than 13.00 initially and no greater than 14.25 after ten washes. For comparison, it may be noted that clean, untreated cotton broadcloth at about 20% relative humidity and about 23"C exhibits a Keithley Log R of 13.65 t 0.05. Untreated synthetic fabrics, in general, exhibit Keithley Log R values of 15.5 to 16.0.
The home launderings are carried out, in general, according to AATCC Test Method 124. Equipment used includes a Sears Roebuck Ken more automatic washer (Model 600) and a Sears Roebuck Kenmore automatic dryer (Model 600). This is the same dryer described above for drying the fabric samples which have been rinsed in Permutit water. Test fabric specimens are cut to 20.3 cm squares and introduced into the washer along with "load fabric" (hemmed pieces of cotton sheeting; 97.4 cm squares) to give a total dry load of 1.81 kilograms. To the washer are added 28 grams of Tides (commercially available) detergent.Washing is carried out under a normal wash cycle (12 minutes), at the high water level setting, using a hotwatertemperature of 60 + 3"C. The temperature of the rinse water used is 41 t 3"C. Soft water (hardness of no more than 5 ppm) is used. For hard water, Calgone is added in an amount sufficient to reduce the hardness to a maximum of 5 ppm. Following washing and spin-drying the fabrics are dried in the dryer at a normal cycle time of 45 minutes, with the temperature dial being set on high to give a maximum stack temperature of 71 + 9"C. This cycle is repeated to achieve the desired number of home launderings.
The soil release (S.R.) characteristic of the agent of this invention is determined, in general, by AATCC
Test Method 130. The treated and cured fabric sam
ples used in the soil release test are prepared in the same manner as those used in the antistatic performance test described above. The soil release test measures the ability of a fabric to release oily stains during home laundering and, as indicated above, the agent of this invention must exhibit a soil release rating on polyester fabric of at least 3 (initial), that is, before being subjected to the home laundering test.
Data relative to this test are provided in the accompanying tables under the heading "S.R.", with data being included to show the soil release ratings initially (I) and after five (5W) and ten (10W) washes (HWTD cycles). Test specimens measuring 10 cm x 20 cm are conditioned for four hours at 21 + 1"C and 65 t 2% relative humidity prior to staining. A single flat thickness of test specimen is placed on AATCC
Textile Blotting Paper on a smooth horizontal surface and five drops (each having a volume of about 0.2 ml; 0.2 x 10-6 m3) of a commercially available oil test liquid (60 weight% Nujols and 40 weight% used piston engine automotive oil) are applied to the test specimen.The oil puddle (total volume, about 1 ml; 1 x 10-6 m3) which is formed is covered by a 7.6 cm x 7.6 cm piece of glassine paper and a 2.28 kilogram weight is placed on the paper. After 60 seconds the weight is removed and the glassine sheet is discarded. The oil-stained fabric specimen is then subjected to washing. Washing is carried out within 15 to 60 minutes of staining with such a number of test specimens that the total number of oil stains in the wash does not exceed thirty. Setting a maximum limit on the number of oil stains provides latitude in selecting the number of test specimens used in the event that it is desirable to place more than one oil stain on each test specimen. The aforesaid Kenmore
Model 600 automatic washer is filled to the high water level with water at a temperature of 60 + 3"C.
To the washer are added 140 + 5 grams of AATCC
Standard Detergent 124, our a known equivalent.
Then the test specimens and cotton sheeting ballast, so as to make a total load of 1.8 t 0.1 kilograms, are introduced. The washer is run through a normal wash cycle (12 minutes). Following completion of the spin-dry cycle, the specimens and ballast are p!aced in the aforesaid Kenmore Model 600 dryer.
Drying is carried outatthe high setting (70 t 6"C), maximum stack temperature, for 45 ~ 5 minutes.
The dried test specimens are rated for residual stains within four hours after drying. Evaluation is made by comparing the residual stains in the test specimen with a standard soil release rating chart. Stains are rated to the nearest whole number from 1 to 5. The higher the number, the less is the residual stain.
As stated above in the formula definition of the agent of this invention, R3 preferably is C8~18 alkyl or, to achieve good waterwettability (drop absorption),
R3 preferably is C8~12 alkyl:The drop absorption test used herein is, in general, based on AATCC Test
Method 39. This test employs the same type of treated/cured fabric specimens described above. Fabric specimens are conditioned at 65 t 2% relative
humidity and 21 + 1 C for at least four hours before testing. Each fabric test specimen is placed over the
mouth of the cap of a 5.1-7.6 cm diameter jar.Water is dropped onto the surface of the fabric in a dropwise fashion from a conventional eye dropper (each drop having a volume of about 0.2 ml; 0.2 x 10-6 m3)
held about 1 cm above the surface of the fabric. The time is measured, using a stop watch, from the
moment that the first drop falls from the dropper
until the wet area of the fabric loses its specular
reflective power. This can best be observed by plac
ing the fabric between the observer and a source of
light, such as an outside window, at such an angle that the specular reflection of light from the surface
of the flattened drop (as the drop hits the surface) can be plainly seen. As the drop is absorbed by the fabric, specular reflection of light ceases and a dull wet spot is formed on the fabric. High drop absorption times, for example, above 5 seconds, indicate poor wettability of the treated fabric.
Additional information on all of the aforesaid test procedures may be found in the AATCC Technical
Manual.
Although the aforesaid testing procedures involve application of the agent of the invention to polyester fabric, optimum benefits from the agent of the invention are achieved using specialized techniques of application that are tailored to the type and characteristics of the fabric being treated. Details of these techniques are discussed below.
The application procedure for the agent of the invention is similarto procedures known in the trade for applying textile treating agents or fabric conditioners of the type disclosed herein. For example, procedures employed in the application of commercially available Zelcon TGF Fabric Conditioner to polyester and certain polyester blend fabrics are similar to the procedure required to applythe agent of this invention to fabric materials. The results achieved with the agent of the invention are readily distinguishable from the results achieved with prior art textile treating agents such as Zelcone TGF Fabric
Conditioner.For example, whereas fabric treated with the latter, using conventional application conditions, does not exhibit durable (to home washes) antistatic behavior, fabric treated with the agent of the invention, using the application procedure described herein, retains its antistatic behavior through numerous home washes (HWTD cycles).
This durability characteristic of the agent of the invention is believed to be related to the waterinsolubilization which takes place during curing of the agent on the fabric.
As already indicated above, the agent of this invention can be applied by pad or exhaust procedures. In either procedure, the dilute aqueous condensate described hereinabove, for example, the 20 weight% aqueous solution, must include certain acids and/or salts before it is applied to the fabric which is to be treated. The addition of an organic polyacidic compound and/or an at least divalent inorganic acid provides antistatic durability of the agent of the invention, when padded onto the fabric, through at least ten washes. The addition of a salt of a mono-, di- ortrivalent metal or of an ammonium cation provides both soil release and antistatic durability of the agent, when either padded or exhausted onto the fabric, through at least ten washes.Preferably, for pad application, both the acid and the salt are present along with the agent qf the invention to achieve maximum effects. It has been found that, in
exhaust application, the salt must be used alone. In
other words, exhaust application cannot be carried
out with acid along or with the combination of acid and salt. Regarding the polyacidic organic compound and the at least diva lent inorganic acid, the second dissociation constant thereof must be greater than 1 x 10-8. Examples of such materials include citric, oxalic, tartaric, succinic, glutaric and phosphoric acids. Boric acid, on the other hand, is unsatisfactory because the second dissociation constant is below the aforesaid minimum value. It has been found that low molecular weight polyacrylic acids also are useful herein.Although such materials are polyacidic, the various dissociation constants of the carboxy groups are not readily determinable because of the polymeric nature of the material. The operability of such an acid herein suggests that it meets the aforesaid requirement on second dissociation constant. Useful polyacrylic acids include those which are readily soluble in water. Such materials include those having molecular weights up to at least 5,000. In using the polyacidic compound, alone or in combination with the salt, the pH of the treating bath should be in the range 3.0 to 6.0, preferably 4.0 to 5.5.The function of the salt of a mono-, di- or trivalent metal or an ammonium salt, including an appropriate quaternary ammonium salt, appears to be related to its ability to lower the cloud point of the dilute aqueous solution of the agent of the invention below 100"C. The salt should have sufficient ionic strength to lower the cloud point below 100"C but it should not be such as to insolubilize the product at ambienttemperature (25"C). Lowering of cloud point is determined using a 0.2 weight% aqueous solution of the agent.Examples of salts which may be employed herein alone or in combination with the organic polyacid include, but are not limited to, calcium, magnesium, zinc and sodium nitrates, the sodium phosphates, such as disodium hydrogen phosphate and trisodium phosphate, sodium, magnesium and calcium chlorides, sodium, magnesium, zinc and aluminum sulfates, sodium and ammonium oxalates, calcium acetate and diammonium citrate.
Salt hydrates are equally useful. The use of the salt permits selective deposition of the agent of the invention during padding or exhaust; it decreases the mobility of the agent of the invention during the cure cycle and, thus, the agent is retained throughout the fabric (i.e., substantial amounts do not migrate); and it enhances the crosslinking which takes place during the drying/curing step as water is evaporated from the treated fabric. In general, it may be said that the cloud point is raised as the HLB increases but is lowered as the Brookfield viscosity is increased.
To exhaust the agent of the invention onto the fabric, the exhaust bath containing the agent, the appropriate salt, in an appropriate amount, and fabric material is heated to within about 5 to 10 C, for example, about 6"C, of the cloud point and held there until exhaust is complete. This is usually effected in no more than 5 to 10 minutes, for example, 6 minutes. The treated fabric is then removed from the exhaust bath, rinses or not rinsed (not rinsing is pre ferred). cooled, extracted of water (using conventional exhaustion techniques to remove excess water) and cured. Curing conditions will vary depending on the moisture content of the fabric, the higher the moisture content, the longer the time and/or the higher the temperature required. In general, for exhaust and pad applications, curing is carried out at 149 to 2040C.A preferred temperature range is 193 to 199"C. Curing at the preferred temperature conveniently can be carried out in less than one minute, for example, in 15 to 30 seconds, depending on moisture content and the weight of the fabric, when the agent of the invention is applied by exhaust techniques. For padding operations wherein moisture levels are higher, longer times usually are required, for examples, 60 to 75 seconds. Durability of the agent of the invention on the fabric requires careful control of curing conditions. Under-curing as well as over-curing will result in diminished durability of the agent. It is to be understood that curing conditions must be determined, for the most part, empirically. For example, a hydrophilic fabric (that is, one retaining moisture readily) will require more rigorous curing conditions than a hydrophobic fabric.
Similarly, selection of salt and/or acid, and the amount thereof, are usually determined empirically.
Evidence of the criticality of the curing conditions, in general, is provided in Table I. The table shows the antistatic and soil release behavior of the agent of the invention on the fabric initially and after five and ten washes. The agent used was that of Example 26 and the fabric to which the agent was applied was the same at that described above for test evaluation of the agent of the invention. The agent was applied to the fabric by padding from a pad bath (of such concentration as to give 0.8 weight % of the agent on the fabric, dry weight) containing 0.75 weight% of sodium sulfate, based on the total weight of the bath, and citric acid to a pH of 4.0. Conditions of drying/curing of the treated fabric are given in the table. As noted, in some instances, curing was preceded by a short drying step at a lower temperature.
TABLE I
Cure Conditions
A.S. S.R.
Time Temp.
(mien) ("CI 1 5W lOW I 5W lOW
3 149 11.62 13.25 13.25 3 3 - 3 163 11.84 13.47 13.25 3 3 - 2 177 11.56 12.91 13.35 3 3 - 2 191 12.43 14.13 14.61 3 3 - 6 149 11.81 13.39 14.17 3 3 - 6 163 12.50 14.73 15.08 3 2 - 6 177 12.59 15.25 15.18 2 1 - 4 177 12.70 15.69 16.03 3 2 - 1 191 11.95 14.35 15.91 3 1
1 193 11.69 12.88 13.25 4 3 1
1 199 11.69 13.08 13.25 3 3 1
1 204 11.62 12.83 13.07 3 3 1
1 204 11.85 13.96 14.73 2 1
1.5 204 11.65 13.13 13.41 3 3
0.75 204 12.10 14.69 16.73 2 1 - 0.75 193 12.63 15.56 15.39 4 1 - 1 193 11.56 13.50 13.65 4 1
1.25 193 11.59 13.08 13.39 4 4
1.5 193 11.62 13.19 13.47 4 3
0.25* 193 11.24 12.81 13.08 3 4 - 0.5* 193 11.65 13.07 13.18 3 3 - 0.5* 193 12.43 13.37 13.56 3 3 - 0.75* 193 14.50 14.43 14.61 4 1 - 1* 193 13.24 14.95 15.53 4 3 *dried 3 minutes at 121"C.
Table II which follows includes data showing the
effect of the addition of a salt and/or an acid to the
agent of the invention in connection with the use of the agent in the pad (except as noted) treatment of fabric of the same type as that described above for test evaluation of the agent of the invention. The
methods used to apply the agent were substantially
the same as those described above. The first column
in Table II refers to the examples (hereinafter) in
which the agent was made. Weight% concentrations
shown are based on the total weight of the pad or exhaust bath.
TABLE 11 Agent
from pHor
Ex. Conc'n. (Conc'n.;
No. Salt (wt%) Acid wt%)
3 Diammonium 0.1 -
citrate
3 " 0.2 -
3 Diammonium 0.1/
citrate/ 0.75
Sodium
sulfate
3 " 0.2/ -
0.75
8 - - Polyacrylic (0.3 /0) M.W. 2,000 8 - - Polyacrylic (0.4%) M.W. 5,000 15 Calcium 0.6 -
chloride
15 Calcium 0.4 Citric 4.0
chloride
15 Sodium 0.3 Polyacrylic 5.5
nitrate M.W. 5,000 17 Calcium 0.6 Citric 4.0
acetate
17 " "
17 " 0.93
17
17 Calcium 0.75
nitrate
17 " 1.25
24 Sodium 0.45 Citric 4.0
nitrate
24 Zinc 1.0
sulfate
24 Zinc 1.0
nitrate
24 Magnesium 0.5 ,,
sulfate
24 Magnesium 0.8
nitrate
26 - - -
TABLE II (Cont'd.)
Agent
From DrylCure
Ex. Temp. Time A.S. S.R.
No. ( C) (min.) @ 5W 10W @ 5W 10W
3 193 1.0 13.06 14.61 15.20 4 2 1
3 ,, " 12.13 13.33 13.23 4 3 2
3 ,, " 13.02 14.43 14.65 4 5 2
3 ,, " 11.97 13.39 13.47 4 4 3
8 " 0.5 11.75 13.59 14.13 4 3 3
8 " " 11.65 13.43 13.61 4 4 3
15 199 " 11.88 13.65 14.25 4 2 2
15 193 1.0 11.84 13.47 13.95 5 4 2
15 " " 11.65 13.03 13.11 5 5 3
17 " " 11.96 13.84 13.20 4 4 1
17 " " 11.69 13.19 13.23 4 4 2
17 " " 12.15 14.18 13.96 4 4 1
17 " " 11.56 13.04 14.01 4 5 2
17 " " 12.37 13.56 13.17 4 5 5
17 " " 12.63 13.96 13.18 4 5 3
24 " " 11.93 13.00 13.61 3 5 5
24 " " 12.31 14.11 14.18 3 4 5
24 " " 13.25 14.39 14.07 3 3 2
24 " " 12.11 13.39 13.73 3 5 5
24 " " 12.23 13.41 13.47 3 3 5
26 - - 12.56 14.69 - 3 1
TABLE II (cont'd)
Agent
from pHor
Ex. Conc'n. (Conc'n.;
No. Salt (Wt%) Acid wt%)
26* Sodium 0.75
sulfate
26 ,, " Tartaric 4.0
26 ,, " Citric 5.5
26 " " Glutaric 4.0
26 ,, " Succinic 4.0
26* Calcium
nitrate
26* Na2HPO4 # 7H2O 1.0
26 " 0.75 Tartaric 4.0
26 ,, " Citric 5.5
26* Na3PO4 # 12H2O 1.25
26* Magnesium 0.5
chloride 6H20 26** Sodium
chloride
26** Sodium
nitrate
26 Aluminum
sulfate
26** Sodium 0.4
oxalate
26 " 0.25 Oxalic 5.0
26 ,, " Citric 5.5
26 - - Succinic 4.0
26 - - Tartaric 4.0
26 - - " 4.5
26 - - " 5.0
26 - - " 5.5
26 - - " 6.0
26 - - Citric 4.0
26 - - " 4.5
26 - - " 5.0
26 5.5 TABLE II (Cont'd.)
Agent from DrylCure
Ex. Temp.Time A.S. S.R.
No. ( C) (min) | 5W lOW | 5W 10W 26* 199 0.5 12.12 12.87 13.43 5 3 2
26 " 1.0 11.65 12.94 13.56 4 4 4
26 " " 12.73 12.73 13.59 4 3 3
26 " 1.25 12.13 13.53 13.59 - - 26 " " 12.12 13.61 15.01 - - 26* " 0.5 12.09 13.01 13.41 4 3 4 26* " " 11.96 13.03 13.61 5 3 4
26 " 1.0 12.27 13.25 14.24 3 4 3
26 " " 11.23 12.73 13.43 3 3 3
26* 193 0.5 12.06 13.13 13.35 4 3 4 26* " " 12.33 13.33 13.73 3 3 2 26** " " 12.56 13.33 14.04 4 3 3 26** " " 12.37 13.59 14.13 4 3 3 26 199 1.25 12.14 13.65 13.95 3 3 26* " 0.5 12.04 13.00 13.61 5 3 2 26 " 1.25 11.93 13.45 13.86 3 4 5 26 " " 11.59 13.39 13.21 4 2 2 26 " " 12.19 13.87 13.73 - - 26 " 1.0 11.65 12.85 13.39 3 1 26 " " 11.83 13.00 13.61 3 1 26 " " 12.17 13.33 14.05 3 1 26 " " 11.84 13.59 14.50 3 1 26 " " 12.21 14.08 14.73 3 1 26 " " 12.81 14.25 15.23 2 1 26 " " 11.96 13.18 13.96 3 1 26 " " 11.97 13.53 14.21 3 1 26 " " 11.69 13.24 13.73 3 1
TABLE II (Cont'd.)
Agent
from pHor
Ex. Conc'n. (Conc'n.; No.Salt (wt %) Acid wt%)
26 - - Citric 6.0
26 - - Oxalic 4.0
26 - - " 4.5
26 - - " 5.0
26 - - " 5.5
26 - - " 6.0
26 - - Boric (0.05%)
26 - - " (0.1%) 26 - - " (0.2%)
26 - - (0.4%) 26 - - " (0.6%) 26 - - 85% H3PO4 4.0
26 - - " 4.5
26 - - " 5.0
27 - - -
27 Calcium 0.75 -
nitrate
28 - - -
TABLE II (Cont'd.)
Agent
From DrylCure
Ex. Temp. Time A.S. S.R.
No. ( C) (min) 1 5W lOW I 5W lOW
26 199 1.0 11.96 13.65 14.47 3 2 1
26 " " 11.84 13.10 13.56 3 2+ - 26 " " 12.01 13.13 13.69 3 2 - 26 " " 11.56 12.84 13.35 3 1 - 26 " " 12.05 11.93 14.43 3 1 - 26 " " 11.98 13.96 14.47 3 1 - 26 " " 12.19 14.21 15.07 3 1 - 26 " " 12.25 14.61 14.98 3 1 - 26 " " 11.88 13.35 13.96 4 1 - 26 " " 13.11 14.59 15.73 3 1 - 26 " " 13.21 15.21 15.95 3 1 -
26 " 1.25 11.85 13.13 13.93 4 4 -
26 " " 12.19 13.33 14.25 4 4 -
26 " " 12.11 13.22 13.90 4 4 -
27 193 1.0 12.87 15.04 15.56 3-4 1 1
27 199 " 11.73 13.99 13.45 4 3 3
28 193 " 13.13 14.69 15.47 3 1 1
*Applied to fabric by exhaust: 10 minutes at 66 C.
**Applied to fabric by exhaust: 10 minutes at 49 C.
Table III which follows includes data showing the effect of the addition of a salt and/or an acid to the agent of the invention in connection with the use of the agent in the treatment of fabrics other than that specified above in connection with the data included in Table II. In all cases, the agent of the invention used was that of Example 26. Thus, the headings of
Tables II and III are the same except that in the latter the Example No. heading has been replaced by the heading to designate the type of substrate fabric.
Application of the agent was carried out by padding as already described above.
TABLE III
pH or
Conc'n. (Conc'n.;
Fabric Salt (wt%) Acid wt%)
Woven calcium 0.25 Citric 4.0 Qiana# nitrate
" " 0.75 " " Ir sodium 0.25
sulfate
" " 0.75 " " Na2HPO4 # 7H2O 1.0 " " " 0.5 "
Knit sodium 0.75 Qiana# sulfate
" " 0.75 Citric 4.0
" - - " "
White sodium 0.75 Qiana# sulfate
" " " " "
" " " " " Nomex# - - Oxalic "
sodium 0.5 Tartaric
sulfate " " Citric "
Red Nylon calcium 0.75
Taffeta nitrate
" " 0.25 " sodium 0.75
sulfate
" " 0.25 " " " Na2HPO4 # H2O 1.0 " " " " 0.25 " "
Dull Spun " 0.5
Acetate
Suiting
" " " Tartaric "
- - Citric
Acetate sodium 0.5
sulfate
' Na2HPO4 # 7H2O " "
TABLE III (Cont'd.)
DrylCure
Temp. Time A.S. S.R.
Fabric ( C) (min) @ 5W 10W @ 5W 10W
Woven 193 0.75 11.5 12.66 13.43 3 4 3 Qiana# " " " 11.89 13.03 14.19 3 3 3
" " " 11.94 13.08 14.10 3 3 2
" " " 11.79 12.70 13.73 3 3 3
" " " 12.25 13.50 14.65 3 3 2
" " " 12.14 13.25 14.39 3 3 2
Knit " " 11.73 12.63 13.25 5 5 3 Qiana# " " " 11.69 13.13 13.25 4 5 5
" " " 12.08 12.90 13.47 3 5 4
White 182 1.0 12.08 13.53 14.19 5 3 3 Qiana# " 193 0.5 11.87 13.99 14.73 5 3 2
" " 0.75 12.06 15.04 14.19 5 4 3 Nomex# 188 1.0 13.28 13.88 14.25 3 3
" " " 13.07 13.43 13.73 3 4 - " " " 13.02 13.73 14.32 3 3 - Red Nylon 193 0.5 11.53 12.35 12.95 5 5
Taffeta
" " " 11.65 12.73 13.45 5 5 - " " " 12.03 12.96 13.65 5 5 - " " " 12.13 13.09 13.65 5 5 - " " " 12.09 13.45 14.24 5 5 - " " " 12.07 13.15 13.23 5 5 - Dull Spun 182 0.75 12.73 13.25 13.73 2 2
Acetate
Suiting
" " " 12.94 13.31 13.96 2 2 - " " " 13.22 13.65 14.00 2 2
Acetate 199 " 12.39 13.41 14.73 3 5
" 182 " 12.45 13.53 14.25 2 5
TABLE III (Cont'd.)
pH or
Conc'n. (Conc'n.; ; Fabric Salt (wt%) Acid wt%) Acrilan# Sodium " " "
Type 16 sulfate
Plain Weave " Na2HPO4 # 7H2O " "
" - - Tartaric Orlon# Na2HPO4 # 7H2O 0.5 Citric
Type 75
Spun Yarn
Plain Weave
" - - Tartaric 5.0 Arnel# Na2HPO4 # 7H2O 0.5 Citric 4.0
Filament
Tricot
" " " Tartaric "
- - - Citric 5.0
Spun Na2HPO4 # 7H2O 0.5 " 4.0 Arnel# Plain Weave
" sodium " Tartaric
sulfate
" Na2HPO4 . 7H2O " " "
TABLEIII (Cont'd.) DrylCure
Temp. Time A.S. S.R.
Fabric ( C) (min) I 5W lOW I 5W 10W
Acrilans 182 0.75 11.87 12.27 13.24 3 2+
Type 16
Plain Weave " " " 12.25 13.00 13.88 3 2+ - " " " 11.97 12.63 13.61 3 3- - Orlon " " 12.31 13.50 14.25 3 2
Type 75
Spun Yarn
Plain Weave
" " " 12.56 14.05 14.35 2 2 Arnel# " " 12.70 13.59 - 3 3
Filament
Tricot " " " 12.73 13.84 - 3 3 - " " " 13.10 14.25 - 3 3 - Spun " " 12.01 13.25 13.61 2 2 Arnel# Plain Weave
" " " 12.13 13.06 13.56 2 2 - " " " 11.98 12.70 13.50 2 2 - " " " 12.17 13.35 13.98 2 2
The amount of agent of the invention applied to the substrate being treated therewith will vary with the substrate and the nature and extent of the effect desired. For most textile applications, however, it has been found that 0.4 to 2.0 weight% of the agent on the fabric, based on the weight of dry fabric, imparts excellent, durable, antistatic soil release characteristics to the fabric. Generally, the preferred amount is 0.8 + 0.1 weight%.
It also has been discovered in connection with this invention that the process of application of the agent of the invention to the substrate, as described herein, need not be followed in its entirety with respect to the treatment of certain substrates. More particularly, if the substrate is of sufficient polyacidic nature, the polyacidic compound described above need not of necessity, be present in the treating bath. For example, fabrics made of fibers of acidmodified polymers, such as the commercially available acid-modified polyamides and acid-modified polyesters, can be usefully treated with the agent of the invention in the absence of the aforesaid requisite salt and/or polyacidic compound, that is, using only conventional aqueous treating bath ingredients, if sufficient acid-function is provided by the acid-modified polymer.
Examples 1 to 45
The following Examples 1 to 45 are intended to show various embodiments of the agent of the invention and the characteristics thereof. The techniques used in the examples to prepare the agents and to apply them to polyester fabric for evaluation are substantially the same as those already described above. More specifically with regard to the application of the agent to fabric, the agent included 0.75 weight%, based on the weight of bath, of sodium sulfate and sufficient citric acid to achieve a pH of 4.0. Dry/cure was affected in 1.0 to 1.25 minutes at 193 to 199 C. Data summarizing Exam ples 1 to 45 are given in Table IV. All oftheembodi- ments of the examples, except as noted below, are of the formula
wherein X is
and V1, Y2, Y3, a, b and care as shown in the table.The various code designations shown in the table for Y1, V2 and V2 are defined as follows: At: O(C5H4O)12CH5 A2: O(C2H40),s straight chain C13H27
A2,: O(C2H40)1s branched chain C13H27
B2: O(C2H4O)a straight chain C13H27
B2,: O(C2H40)s branched chain C13H27
C2: O(C2H40)2s straight chain C13H27 C21: O(C2H40)2s branched chain C13H27
D2:O(C2H40)8 straight chain C13H27 D2': O(C2H40)8 branched chain C13H27
E2: O(C2H40)4s straight chain C13H27
F2: O(C2H4O)aa straight chain C13H27
wherein A#is#OSO3CH3 and for A3 to M5 the following apply:
R3 R4 m + n A3 C18H37 CH3 50
B3: C18H37 CH3 16
C3: C8H37 CH3 50 D3 C18H35 CH3 24
E3: C8H17 CH3 16 F3 C12H25 CH3 42
G3: C4H9 CH2 50
H3: benzyl CH3 50
I3: C8H17 CH3 24
J3: C4H9 C4H9 50 K3 C4H9 CH3 12
L3: C12H25 CH3 30
M3:C8H17 CH3 100
In Example 44, X is
TABLE IV Viscosity
Ex. (pascal
No. (a) Y, (b) V2 (c) V3 HLB seconds)
1 0 - 0 - 1 A3 15.4 1.300
2 1 A, 0 - 1 A2 16.1 1.300
3 2 A, 0 - 1 A2 16.6 0.560
4 0 - 2.3 A2 1 A3 15.6 8.280
5 0 - 2 A2 1 A3 15.6 0.580
6 0 - 2 B2 1 A3 14.5 8.200
7 0 - 1 C2 2 A3 16.7 2.000
8 1 A, 1.2 A2 1 A3 16.1 0.610
9 1 A1 1 A2 1 A3 16.1 4.600
10 1 A, 1 A2 1 A3 16.1 7.680
11 1 A1 1 A2' 1 A3 16.1 1.440
12 1 A, 1 D2 1 A3 15.8 3.200
13 1 A, 1 B2' 1 A3 15.6 0.824
14 1 A, 1 D2' 1 A3 15.8 2,720
15 1 A, 1 C2 1 A3 16.4 8.780
16 1 A, 1 E2 1 A3 17.0 6.180
17 0.8 A, 1.2 A2 1 A3 16.0 7.300
18 0.5 A, 1.5 A2 1 A3 15.8 5.900
19 0.8 A, 1.2 C2 1 A3 16.4 10.800
20 0.8 A, 1.2 C2 1 A3 16.4 5.740
21 0.5 A, 1.5 C2 1 A3 16.4 11.760
22 0.5 A, 1.5 C2 1 A3 16.4 4.120
23 1 A1 1 C2 1 A3 16.5 6.060
24 1 A, 1 C2 1 A3 16.5 8.800
25 1 A, 1 C2 1 A3 16.5 8.960
26 1 A1 1 C2 1 A3 16.5 8.200
27 1 A, 1 C2 1 A3 16.5 2.400
28 1 A, 1 C2 1 A3 16.5 2.400
29 1 A, 1 C2 1 B3 14.9 4.450
30 1 A1 1 C2 1 C3 17.1 1.820
31 1 A, 1 C2 1 C3 17.1 8.050
32 1 A1 1 C2 1 D3 15.5 7.600
TABLE IV (Cont'd.) A.S. S.R.
Ex.No. @ 5W 10W @ 5W 10W
1 11.96 12.07 12.95 3 3 2
2 11.89 - 12.99 4 3 3
3 11.98 14.25 13.47 4 4-5 5
4 11.65 13.33 14.03 4 4 4
5 12.59 13.85 14.13 4 4 3
6 11.69 13.30 13.53 4 3 2
7 11.73 13.18 13.73 4 4 3
8 11.59 13.19 13.08 4 5 3
9 11.78 13.03 13.41 4 3 3
10 11.73 13.08 13.59 3 2 2
11 11.77 12.99 13.98 4 4 3
12 11.79 14.11 - 4 3
13 11.62 12.90 13.61 4 3 2
14 11.91 13.03 13.43 4 4 3
15 11.69 12.95 13.43 4 4 3
16 12.17 13.37 13.56 4 4 3
17 11.79 13.43 13.13 4 4 2
18 11.73 13.19 13.22 4 4 3
19 11.94 12.88 13.13 5 4 3
20 12.04 13.13 13.47 4 4 3+
21 11A5 13.13 13.53 4 2 3
22 11.97 13.18 13.25 3 4 3
23 11.73 13.41 13.95 4 4 3
24 11.84 13.14 13.43 3 4 3
25 12.03 13.25 13.73 4 4 3
26 11.47 12.92 13.45 3 2 - 27 11.41 12.73 13.61 3 3 2
28 11.62 12.83 13.07 3 3 1
29 12.28 13.20 13.49 3 2 2
30 11.81 12.53 13.04 4 4 2
31 11.50 12.39 12.88 4 2 1
32 11.62 13.19 12.95 4 4 3 TABLE IV (Cont'd.) Viscosity
Ex. (pascal
No. (a) Y1 (b) Y2 (c) Y3 HLB seconds)
33 1 A, 1 C2 1 E3 15.7 1.800
34 1 A, 1 C2 1 F3 16.7 0.950
35 1 A1 1 C2 1 F3 16.7 2.700
36 1 A1 1 C2 1 G3 17.3 2.712
37 1 A1 1 C2 1 H3 17.2 2.770
38 1 A1 1 C2 1 13 16.2 12.700
39 1 A1 1 C2 1 J3 17.2 6.200
40 1 A1 1 C2 1 K3 15.8 1.000
41 1 A, 1 C2 1 L3 16.3 2.750
42 1 A1 1 B2 1 A3 15.6 0.420
43 1 A, 1 F2 1 A3 17.8 2.860
44 1 A, 1 C2 1 A3 16.8 4.200
45 1 A1 1 C21 1 A3 16.5 4.360
A.S. S.R.
Ex. No. I 5W lOW 1 5W lOW
33 11.95 13.11 13.98 5 4 4
34 11.30 12.59 12.73 3 1 1
35 11.29 12.59 12.70 3 2 1
36 12.14 13.02 14.20 4 4 2
37 11.86 13.53 13.69 3 2 2
38 12.14 12.70 13.39 4 3 2
39 11.65 13.07 14.03 3 1 - 40 11.56 14.02 - 4 1 1
41 11.69 13.45 13.69 3 4 3
42 11.69 13.33 13.43 4 3 3
43 12.23 13.92 13.98 3 - - 44 11.85 13.37 13.95 3 - - 45 11.65 13.39 13.53 3 - - Example 46
The purpose of this example is to show the antisoil redeposition characteristic of the agent of the invention. Unlike the other advantageous characteristics of the agent, there is no industry-accepted or standard test for measurement of soil redeposition.The test employed herein, in general, is the same as the aforesaid home laundering AATCC Test
Method 124, using Table I, III Machine, except as noted below. The test is carried out using redeposition soil consisting of, on a weight basis:
Germantown Lamp Black 9.7 parts Criscos 29.1 parts Nujols 41.8 parts
Wheat starch (screened 19.4 parts
through a 100-mesh sieve,
U.S. Sieve Series)
Total parts: 100.0
The Criscos and Nujols are heated to 38 C and the
lamp black and starch are added with stirring at this temperature until a homogeneous mixture is
obtained. The redeposition soil is stored under
refrigeration until used. The treated fabric samples,
prepared as described above, are washed, along
with the ballast load fabric.The redeposition soil is
added along with the detergent (10 grams of soil are
admixed with 50 grams of Tides commercially avail
able detergent; a paste is formed by admixing in the presence of 100 ml (0.1 x 10-3 m3) of 82-93 C water).
The soil is uniformly dispersed in the washing machine before the ballast and test samples are introduced. Washing is carried out under the normal wash cycle (12 minutes) using a hotwatertempera- ture of 60 t 3 C. After the test samples are dried, as described hereinabove, they are compared with corresponding unsoiled fabric samples using the
AATCC Gray Scale, the higher the evaluation number, the less is the stain. Table V which follows provides soil redeposition data for untreated and treated (with the agent of the invention) fabrics. The soiling procedure was carried out on fabric samples treated with the agent of the invention and on such samples which had been washed 5X and 10X, that is, washed 5X and 10X after application of the agent before being subjected to the soiling procedure.The agent was applied to the fabric, by the procedure already given, with curing in the presence of sodium sulfate/citric acid being carried out for 1 minute at the temperature indicated in the table.
TABLE V
Cure Gray Scale
Temp. Reading
Agent from Ex. No. ('C) 1 5W lOW 26* 182 4 3 3 27** 199 5/4 5/4 5/4 28** 199 5/4 5/4 5/4
Untreated fabric* (Control) - 3 1 1
Untreated fabrics (Control) - 2 2 2
*white Qiana# **polyester
Experiments 1 to 5
The following Experiments 1 to 5 are intended to show various compositions which fail to meet the aforesaid requirements of the invention and which, therefore, are outside the invention. Data summarizing Experiments 1 to 5 are given in Table VI. The definitions of formula terms and code designations are the same as given above for Examples 1 to 45 (in all cases, X is the same as in said examples, excluding Example 44).
TABLE VI
Viscosity
Expt (pascal
No. (a) Y1 (b) Y2 (c) Y3 HLB seconds)
1 0 - 0 - 1 G3 16.8 0.025
2 1 A1 1.2 A2 1 A3 16.1 0.236
3 1 A1 1.2 A2 1 A3 16.1 0.082
4 1 A1 1 C2 1 M3 18.1 1.570
5 1 A1 1 F2 1 C3 18.2 3.700
Expt. A.S. S.R.
No. I 5W 10W I 5W 10W 1 12.86 14.08 14.43 1 -
2 12.77 15.25 15.73 4 4 3
3 12.41 13.88 14.50 4 2 2
4 12.41 13.61 14.47 3 3 - 5 12.50 13.95 14.96 3 3 2 BESTMODEFOR CARRYING OUT
THE INVENTION
The best mode for carrying out the invention resides in the embodiments described above wherein the agent of Example 26 is applied by pad application to 6 ounce (0.170 kg) doubleknitfabric of 100% polyester filament, using calcium nitrate in the pad bath, with curing of the agent on the fabric being effected in 0.75 minute at 199 C.
INDUSTRIAL APPLICABILITY
The invention disclosed herein is particularly useful for imparting durable, antistatic, soil release characteristics to textile fabric treated with the agent of the invention by the process of the invention.
Claims (46)
1. Process for applying durable, antistatic soil release agent to a substrate, said agent being of the formula
wherein Xis an aminoplast resin moiety having amino nitrogen atoms and 4 to 6 methylene groups, each of which methylene groups is attached to an amino nitrogen atom and to Y1, V2 or V3; V1 is O(C2H4O)a-20B1 wherein R1 is C15 alkyl; V2 is O(C2H4O)5-88R2 wherein R2 is Ca-20 alkyl;
wherein R3 is C4-20 alkyl, C4-20 alkenyl or benzyl, R4 is C,, alkyl, A#is an organic or inorganic anion, each of m and n is at least 1 and the sum of m and n is 12 to 100;; each of a and b is O to 2 and the sum of a and b is
Oto2; c is 1 to 2;
the sum of a, b and c is 1 to 4; said agent having a calculated hydrophile - lipophile balance (HLB) of 14.5 to 18.0, a 20 weight% aqueous solution viscosity, as measured at 20 C on a Brookfield viscometer, of 0.250 to 16,000 pascal seconds, an electrical resistivity (Keithley log R) on polyester fabric, at 20 # 2% relative humidity and 23 + 1 C, of no greater than 13.00 initially and no greater than 14.25 after ten washes, and a soil release rating on polyester fabric of at least 3 initially, said process
comprising the steps::
(a) diluting the agent with a normally liquid
medium to achieve the desired application liquid viscosity,
(b) adding sufficient salt of a mono-, di- or trival
ent metal or of an ammonium cation to achieve a
cloud point (measured as described herein), of the
diluted agent of step (a), of less than 100"C but greates than 25 C, or adding sufficient polyacidic com
pound having a second dissociation constant of greaterthan 1 x 10-8 to achieve a pH of the diluted agent
of step (a) of 3.0 to 6.0, or adding both said salt and said polyacidic compound to achieve said cloud point and pH,
(c) applying the diluted agent of step (b) to the substrate to be treated so as to achieve the desired level of agent on the substrate,
(d) drying and curing the agent on the substrate, and
(e) recovering substrate which has been durably treated with the agent of the aforesaid formula.
2. Process as claimed in Claim 1 wherein the normally liquid medium is water.
3. Process as claimed in Claim 1 or Claim 2 wherein step (b) is carried out by adding only salt and step (c) is an exhaust application step.
4. Process as claimed in Claim 1 or Claim 2 wherein step (b) is carried out by adding only polyacidic compound and step (c) is a pad application step.
5. Process as claimed in Claim 1 or Claim 2 wherein step (b) is carried out by adding salt and polyacidic compound and step (c) is a pad application step.
6. Process as claimed in any of the preceding claims wherein the substrate is a textile fiber.
7. Process as claimed in Claim 6 wherein the substrate is a textile fabric.
8. Process as claimed in Claim 7 wherein the substrate is a polyester textile fabric.
9. Process as claimed in Claim 7 wherein the substrate is a polyamide textile fabric.
10. Process as claimed in Claim 2 wherein the agent in step (a) is diluted as to provide a 220 weight% aqueous solution of agent.
11. Process as claimed in Claim 10 wherein the substrate is a textile fabric and curing in step (d) is carried out at 149 to 204 C.
12. Process as claimed in Claim 11 wherein the substrate is a polyester textile fabric and curing in step (d) is carried out in 0.25 to 6 minutes.
13. Process as claimed in any one of the preceding claims wherein curing is carried out at 193 to 199"C for 0.25 to 1.25 minutes.
14. Process as claimed in any one of the preceding claims wherein the salt is the nitrate, phosphate, chloride, sulfate, oxalate, acetate or citrate of a sodium, magnesium, calcium, zinc, aluminum or ammonium cation.
15. Process as claimed in any one of Claims 1 to
13 wherein the salt is calcium nitrate.
16. Process as claimed in any one of the preced
ing claims wherein the polyacidic compound is
phosphoric, citric, oxalic, tartaric, succinic, glutaric
or polyacrylic acid.
17. Process as claimed in Claim 16 wherein the polyacidic compound is polyacrylic ocid having a molecular weight of up to about 5,000.
18. Process as claimed in any one of claims 1 to 13 wherein the salt is sodium sulfate and the polyacidic compound is citric acid.
19. Process as claimed in any one of Claims 1 to 13 wherein the salt is calcium nitrate and the polyacidic compound is citric acid.
20. Process as claimed in any one of the preceding claims wherein Y, is O(C2H40)1o~,6 and B1 is CH3, wherein V2 is O(C2H40),s~30 and B2 is C,3H2" wherein
R3 is Ca-i8 alkyl, R4 is CH3, AoisOOSO3CH3 and m+n is 20 to 50, and wherein X is
21. Process as claimed in any one of the preceding claims wherein the HLB is 15.5 to 17.0 and the viscosity is 2.000 to 8.000 pascal seconds.
22. Process as claimed in any one of Claims 1 to 19 wherein a is greater than 0 in the first general formula set forth in Claim 1.
23. Process as claimed in any one of Claims 1 to 19 or 22 wherein b is greater than 0 in the first general formula set forth in Claim 1.
24. Process as claimed in Claim 23 wherein each of a and b is greaterthan 0.
25. Process as claimed in any one of the preceding claims wherein the pH in step (b) is 4.0 to 5.5.
26. Process for applying durable, antistatic soil release agent to a substrate substantially as described herein with reference to the Examples.
27. Substrates, including textile fibers and fabrics, whenever treated by the process claimed in any one of the preceding claims.
28. A durable, antistatic soil release agent which is resistant to yellowing on the substrate treated therewith and which is of the formula
wherein
X is an aminoplast resin moiety having amino nitrogen atoms and 4 to 6 methylene groups, each of which methylene groups is attached to an amino nitrogen atom and to V11 V2 orY3; Y, is O(C2H40)5~2oR, wherein R1 is C12 alkyl; V2 is O(C2H4O)a,aR2 wherein R2 is C6~20 alkyl;
wherein R3 is C4--20 alkyl, C420 alkenyl or benzyl, R4 is C1 @4 alkyl, Ao is an organic or inorganic anion, each of m and n is at least 1 and the sum of m and n is 12 to 100; ;
each of a and b is 0 to 2 and the sum of a and b is 0 to2;
c is 1 to 2;
the sum of a, b and c is 1 to 4; said agent having a calculated hydrophile - lipophile balance (HLB) of 14.5 to 18.0, a 20 weight% aqueous solution viscosity, as measured at 20"C on a Brookfield viscometer, of 0.250 to 16.000 pascal seconds, and electrical resistivity (Keithley log R) on polyester fabric, at 20 + 2% relative humidity and 23 + 1"C, of no greater than 13.00 initially and no greater than 14.25 after ten washes, and a soil release rating on polyester fabric of at least 3 initially.
29. An agent as claimed in Claim 28 wherein Y, is O(C2H40)10--16 and R1 is CH3, wherein Y2 is O(C2H40)5~3o and R2 is C13H271 wherein R3 is C818 alkyl, R4 is CH3, A9is)0SO3CH3 and m + n is 20 to 50, and wherein X is
30. An agent as claimed in Claim 28 wherein a is greater than 0.
31. An agent as claimed in Claim 28 wherein b is greater than 0.
32. An agent as claimed in Claim 28 wherein each of a and b is greater than 0.
33. An agent as claimed in any one of Claims 28 to 32 wherein HLB is 15.5 to 17.0 and the viscosity is 2.000 to 8.000 pascal seconds.
34. An agent as claimed in any one of Claims 28 to 33 dispersed or dissolved in a normally liquid medium.
35. An agent as claimed in Claim 34 wherein the normally liquid medium is water.
36. An agent as claimed in Claim 35 dissolved in water to form a a20 weight% aqueous solution.
37. An agent as claimed in Claims 35 or 36 wherein the aqueous solution includes a salt of a mono-, di or trivalent metal or of an ammonium cation.
38. An agent as claimed in Claim 37 wherein the salt is the nitrate, phosphate, chloride, sulfate, oxalate, acetate or citrate of a sodium, magnesium, calcium, zinc, aluminum or an ammonium cation.
39. An agent as claimed in any one of Claims 35 to 38 wherein the aqueous solution includes a polyacidic compound having a second dissociation constant greater than 1 x 10-8.
40. An agent as claimed in Claim 39 wherein the polyacidic compound is phosphoric, citric, oxalic, tartaric, succinic, glutaric or polyacrylic acid.
41. An agent as claimed in Claim 43 wherein the polyacidic compound is polyacrylic acid having a molecular weight of up to about 5,000.
42. An agent as claimed in Claim 35 wherein the aqueous solution includes sodium sulfate and citric acid.
43. An agent as claimed in Claim 35 wherein the aqueous solution includes calcium nitrate and citric acid.
44. A substrate which has been treated with an antistatic soil release agent claimed in any of Claims 28 to 43.
45. A substrate as claimed in Claim 44 which is a polyester textile fabric.
46. A substrate as claimed in Claim 44 which is a polyamide textile fabric.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US93239878A | 1978-08-09 | 1978-08-09 | |
US93239778A | 1978-08-09 | 1978-08-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2028352A true GB2028352A (en) | 1980-03-05 |
GB2028352B GB2028352B (en) | 1983-02-16 |
Family
ID=27130024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7927648A Expired GB2028352B (en) | 1978-08-09 | 1979-08-08 | Durable antistatic soil release agents and their application to substrates |
Country Status (5)
Country | Link |
---|---|
CA (1) | CA1145096A (en) |
DE (1) | DE2932385A1 (en) |
FR (1) | FR2433070A1 (en) |
GB (1) | GB2028352B (en) |
IT (1) | IT1193493B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4346130A (en) | 1981-01-28 | 1982-08-24 | E. I. Du Pont De Nemours And Company | Application of durable, antistatic, soil release agent |
-
1979
- 1979-08-07 CA CA000333324A patent/CA1145096A/en not_active Expired
- 1979-08-08 GB GB7927648A patent/GB2028352B/en not_active Expired
- 1979-08-08 IT IT24998/79A patent/IT1193493B/en active
- 1979-08-09 FR FR7920383A patent/FR2433070A1/en active Granted
- 1979-08-09 DE DE19792932385 patent/DE2932385A1/en not_active Withdrawn
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4346130A (en) | 1981-01-28 | 1982-08-24 | E. I. Du Pont De Nemours And Company | Application of durable, antistatic, soil release agent |
Also Published As
Publication number | Publication date |
---|---|
IT1193493B (en) | 1988-07-08 |
IT7924998A0 (en) | 1979-08-08 |
FR2433070B1 (en) | 1983-11-25 |
GB2028352B (en) | 1983-02-16 |
FR2433070A1 (en) | 1980-03-07 |
DE2932385A1 (en) | 1980-02-21 |
CA1145096A (en) | 1983-04-19 |
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Legal Events
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PCNP | Patent ceased through non-payment of renewal fee |