US3206328A - Process for imparting anti-static properties to hydrophobic textile materials and product thereof - Google Patents
Process for imparting anti-static properties to hydrophobic textile materials and product thereof Download PDFInfo
- Publication number
- US3206328A US3206328A US11973A US1197360A US3206328A US 3206328 A US3206328 A US 3206328A US 11973 A US11973 A US 11973A US 1197360 A US1197360 A US 1197360A US 3206328 A US3206328 A US 3206328A
- Authority
- US
- United States
- Prior art keywords
- diglycidyl ether
- fabric
- textile
- acid
- treated
- 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.)
- Expired - Lifetime
Links
- 230000002209 hydrophobic effect Effects 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 16
- 239000004753 textile Substances 0.000 title description 49
- 239000000463 material Substances 0.000 title description 36
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 36
- 230000005611 electricity Effects 0.000 claims description 18
- 230000003068 static effect Effects 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 13
- 150000005846 sugar alcohols Polymers 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229920003002 synthetic resin Polymers 0.000 claims description 10
- 239000000057 synthetic resin Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 3
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 69
- 239000004744 fabric Substances 0.000 description 58
- 239000000758 substrate Substances 0.000 description 22
- 239000004677 Nylon Substances 0.000 description 21
- 229920001778 nylon Polymers 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- 239000000835 fiber Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- -1 molecule Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 9
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 8
- 230000035508 accumulation Effects 0.000 description 8
- 238000009825 accumulation Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920002972 Acrylic fiber Polymers 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 229920002994 synthetic fiber Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BKKCHPZQDBOJLI-UHFFFAOYSA-N 3-amino-6-[2-(4-aminophenyl)ethenyl]cyclohexa-2,4-diene-1,1-disulfonic acid Chemical compound NC1=CC(C(C=C1)C=CC1=CC=C(C=C1)N)(S(=O)(=O)O)S(=O)(=O)O BKKCHPZQDBOJLI-UHFFFAOYSA-N 0.000 description 4
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- AMTOHUZYCNNVHB-UHFFFAOYSA-N 1,5-dihydroxy-2,2-bis(hydroxymethyl)pentan-3-one Chemical compound OCCC(=O)C(CO)(CO)CO AMTOHUZYCNNVHB-UHFFFAOYSA-N 0.000 description 3
- XDVZFVQLRRGUKX-UHFFFAOYSA-N 5,5-diamino-2-[2-(2-sulfophenyl)ethenyl]cyclohexa-1,3-diene-1-sulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)=C1C=CC1=CC=CC=C1S(O)(=O)=O XDVZFVQLRRGUKX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002956 ash Substances 0.000 description 3
- 238000005282 brightening Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000009988 textile finishing Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZTGKHKPZSMMHNM-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=CC=2C=CC=CC=2)=C1S(O)(=O)=O ZTGKHKPZSMMHNM-UHFFFAOYSA-N 0.000 description 2
- ADBRRRQVCURCTK-UHFFFAOYSA-N 5,5-diamino-2-(2-sulfophenyl)cyclohexa-1,3-diene-1-sulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)=C1C1=CC=CC=C1S(O)(=O)=O ADBRRRQVCURCTK-UHFFFAOYSA-N 0.000 description 2
- WTRVMTQZFCLTOR-UHFFFAOYSA-N 5,5-diamino-2-phenylcyclohex-2-ene-1,1-disulfonic acid Chemical compound OS(=O)(=O)C1(S(O)(=O)=O)CC(N)(N)CC=C1C1=CC=CC=C1 WTRVMTQZFCLTOR-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000019504 cigarettes Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
- YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000001846 repelling effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004758 synthetic textile Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- IYDYVVVAQKFGBS-UHFFFAOYSA-N 2,4,6-triphenoxy-1,3,5-triazine Chemical compound N=1C(OC=2C=CC=CC=2)=NC(OC=2C=CC=CC=2)=NC=1OC1=CC=CC=C1 IYDYVVVAQKFGBS-UHFFFAOYSA-N 0.000 description 1
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- BFUGAHPTVMZLAC-UHFFFAOYSA-N 2,4-dichloro-6-methyl-1,3,5-triazine Chemical compound CC1=NC(Cl)=NC(Cl)=N1 BFUGAHPTVMZLAC-UHFFFAOYSA-N 0.000 description 1
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 1
- FEHVKHFORSHUKE-UHFFFAOYSA-N 2-butyl-4,6-dichloro-1,3,5-triazine Chemical compound CCCCC1=NC(Cl)=NC(Cl)=N1 FEHVKHFORSHUKE-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 description 1
- ABSXMLODUTXQDJ-UHFFFAOYSA-N 4-(4-sulfophenyl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=C(S(O)(=O)=O)C=C1 ABSXMLODUTXQDJ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
- DWEQVNFWAKJCEY-UHFFFAOYSA-N 4-methylimidazolidin-2-one Chemical compound CC1CNC(=O)N1 DWEQVNFWAKJCEY-UHFFFAOYSA-N 0.000 description 1
- MBJAPGAZEWPEFB-UHFFFAOYSA-N 5-amino-2-(4-amino-2-sulfophenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O MBJAPGAZEWPEFB-UHFFFAOYSA-N 0.000 description 1
- VAANUEHPYNAMQR-UHFFFAOYSA-N 5-amino-2-(4-aminophenyl)cyclohexa-2,4-diene-1,1-disulfonic acid Chemical compound OS(=O)(=O)C1(S(O)(=O)=O)CC(N)=CC=C1C1=CC=C(N)C=C1 VAANUEHPYNAMQR-UHFFFAOYSA-N 0.000 description 1
- BNDRECGBDISUAI-UHFFFAOYSA-N 6-(2-phenylethenyl)cyclohexa-2,4-diene-1,1-disulfonic acid Chemical compound OS(=O)(=O)C1(S(O)(=O)=O)C=CC=CC1C=CC1=CC=CC=C1 BNDRECGBDISUAI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- JUQPZRLQQYSMEQ-UHFFFAOYSA-N CI Basic red 9 Chemical compound [Cl-].C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)=C1C=CC(=[NH2+])C=C1 JUQPZRLQQYSMEQ-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000529895 Stercorarius Species 0.000 description 1
- 241000282840 Vicugna vicugna Species 0.000 description 1
- 241000933336 Ziziphus rignonii Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000010006 anti-felting Methods 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- BIOOACNPATUQFW-UHFFFAOYSA-N calcium;dioxido(dioxo)molybdenum Chemical compound [Ca+2].[O-][Mo]([O-])(=O)=O BIOOACNPATUQFW-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004855 creaseproofing Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Substances [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000012612 static experiment Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 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
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/11—Compounds containing epoxy groups or precursors thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
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- D—TEXTILES; PAPER
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/335—Amines having an amino group bound to a carbon atom of a six-membered aromatic ring
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0056—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0056—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
- D06P1/0064—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres by using reactive polyfunctional compounds, e.g. crosslinkers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S260/15—Antistatic agents not otherwise provided for
- Y10S260/19—Non-high polymeric antistatic agents/n
- Y10S260/20—Antistatic agent contains pentavalent nitrogen
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
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- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2385—Improves shrink resistance
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2418—Coating or impregnation increases electrical conductivity or anti-static quality
- Y10T442/2459—Nitrogen containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2582—Coating or impregnation contains an optical bleach or brightener or functions as an optical bleach or brightener [e.g., it masks fabric yellowing, etc.]
Definitions
- the present invention relates to novel compositions, processes for durably modifying textile materials and the so modified materials.
- durable modification is intended to include dyeing, the impartation of an anti-static finish, the impartat-ion of a durable fluorescent or brightening effect, the impartation of shrinkage resistance and animalization of cellulosic substrates and numerous other changes or modifications in suitable substrates.
- substrate as that term is employed herein, is meant a base material which may either be a formed fabric and preferably, is or may be molded or extruded articles containing or made from hydrophobic synthetic resins.
- the substrate or base is a formed textile material and may be knitted, woven, non-woven, felted, or otherwise formed.
- textile material as that term is employed herein, it is meant fibers, filaments, two, or fabrics which, as noted above, may be Woven, non-woven, knitted felted or otherwise formed, prepared from natural fibers of either vegetable or animal origin, synthetic fibers or combinations and mixtures of natural and synthetic fibers.
- natural fibers contemplated are cotton, linen, hemp, ramie, jute and the like, and among the natural fibers of animal origin are Wool, vicuna and the like.
- synthetic fibers are nylon, viscose rayon, cellulose acetate, polyester fibers and acrylic fibers. It will be noted that the present invention results in imparting durable anti-static properties to fabrics composed of synthetic hydrophobic fibers which are subject to the accumulation of static electricity.
- Such materials include nylon, the acrylic fibers, polyester fibers and the like.
- the textile material is preferably cellulosic in origin or contains at least 50% of cellulose fiber, as for example cotton.
- Still further objects of the present invention relate to novel compositions, methods of employing the same on suitable substrates and the substrates so finished, whereby improved durable dyeing, the impartatio-n of fluorescent brightening, the animalization of the fiber, the impartation of an anti-static finish, and numerous other modifications thereof may be readily and easily accomplished. Often more than one desirable modification is imparted to a substrate in a single finishing step.
- novel polymeric reaction products are prepared by reacting two diiferent compounds having the following general formulae:
- R and R are organic nuclei and X and X and Y and Y are functional elements which can react, the Xs and with the Ys.
- the novel compounds or polymers are preferably formed in situ on the suitable substrate and particularly on textile material. This may be accomplished by way of illustration through the application of a polyfunctional textile agent, together with a second polyfunctional compound.
- the illustrative textile agent contains two or more groups which can react with two or more groups of the polyfunctional compound to form a polymer in the fibers and/ or on the fibers of the textile material.
- textile agent is principally a term of convenience in that many of the hereinafter illustrative X-RX polyfunctional compounds are dyes, brighteners, etc., which have known utility in the textile field.
- R is an organic nucleus of a. homogeneous or heterogeneous organic chain or organic ring compound, as for example of a dye, molecule, anti-static agent, a water or grease repellent, an ultraviolet absorber, a softener, a fire retardant, a bactericide, a moth repellent, a brightener, or other suitable agent which may impart a desirable property to a substrate and in particular, to a textile fiber or fabric.
- R is the nucleus of a homogeneous or heterogeneous organic chain or organic ring compound.
- R may be alkyl, aryl, alkaryl and aralkyl.
- Y and Y may be isothiocyanato (MCS), isocyanato (NCO) or l-aziridinyl CH (I CH2
- YR --Y may be methylene-bis-acrylamide, (CH CHCONH) CH
- the preferred polyfunctional textile agents (XRX are those having the following general formulae:
- Z is a monovalent anion such as halide, and n is or 1, and
- polyglycidyl ethers dibutyl carbonate, hexamethylene diisocyanate, triethylene melamine, divinyl sulfone, epichlor-ohydrin, 2,4-dichloros-triazine, 2,4,6-trichloro-s-triazine, 2,4-dichloro-6-methyl-s-triazine, 2,4-dichloro-6-butyl-s-triazine, 2,4-dichloro-6-phenyl-s-triazine, 2,4 dichloro o-benzyl-striazine, methylene-bishcrylamide, tetramethylol acetone and triphenyl cyanurate are illustrative compounds.
- the textile agents and the polyfunctional organic compounds capable of reacting with each other to form the novel reaction products of this invention may be applied to suitable substrates and in particular, textile materials by conventional methods as for example by padding, dipping, spraying, immersion and the like.
- the two components, i.e., the textile agents as they are classified herein and the polyfunctional compounds, may be applied individually from separate baths or advantageously simultaneously from the same bath.
- the polyfunctional compounds may be applied in amounts varying over a comparatively wide range of from between .5% to about 25% based on the dry weight of the textile material.
- the amount may vary from between .5% and 15% based on the dry weight of the fabric.
- the finish is essentially for purposes of optical brightening or dyeing, the polyfunctional compounds may be employed in amounts of from between .5% and 5% of the fabric. Shrinkage control usually requires between 2% and 20% and so on depending upon the particular finishes to be effected.
- the textile agent and second polyfunctional compound may be employed in comparatively wide molecular ratio one to the other and still achieve very satisfactory results. Preferably they are employed in approximately equal molar quantities or with an excess of the second polyfunctional compound. As a general rule, they are employed in mole ratios of between about .01 mole to about 1 mole of the textile agent to about 1 mole of the second polyfunctional compound and preferably from between about .1 to about 1 mole of the former to 1 mole of the latter.
- a suitable alkaline catalyst may be applied separately, with one of the components, or in combination with each of the components and simultaneously therewith as from a single bath.
- a catalyst may be an alkaline agent, such as alkali metal hydroxide used as sodium, potassium, lithium or ammonium hydroxide or the alkaline earth metal oxides and hydroxides; in addition, tertiary amines and triethyl amine, tributyl amine, dimethyl aniline and the like.
- alkali metal hydroxide used as sodium, potassium, lithium or ammonium hydroxide or the alkaline earth metal oxides and hydroxides
- tertiary amines and triethyl amine, tributyl amine, dimethyl aniline and the like in some instances, as when the reactants are definitely basic and a sufiicient alkaline medium is obtained, added catalyst is not required to effect polymerization.
- polymerization is effected at a pH of between about 8 and about 13.
- the polyfunctional compounds may be both water soluble and, as will be apparent, for many applications they are preferably so.
- solvent soluble polyfunctional compounds are fully contemplated as is the use of water soluble and solvent soluble compounds in a single application. Suitable'solvents will readily suggest themselves depending on the application to be effected. Thus, solvents such as benzene, xylene, carbon tetrachloride, acetone and the like may be employed.
- the polymerization reaction preferably carried out in situ on the substrate to be durably modified, is brought about by the application of heat to the treated fabric.
- the temperature required for the polymerization is usually from between about 125 F. and about 400 F.
- the time required to complete the polymerization varies inversely with the temperature used. That is, atthe lower curing temperature, the longer time is required and vice versa.
- the finishes applied in accordance with the present invention to textile materials have improved durability to washing and particularly to washing under alkaline conditions.
- Nylon talfeta was treated with the above solutions by padding, obtaining a 50% wet-pickup. After drying at 225 F. for 2 minutes, the fabrics were heated at 300 F. for 3 minutes.
- the treated fabrics contained the amounts of'4,4-diamino-2,2-stilbenedisulfonic acid shown in the Table I, and 5% of the diglycidyl ether of ethylene glycol on the weight of the fabric.
- the treated fabrics were treated for their anti-static properties by the cigarette ash test, which may be described as follows: i
- the treated fabric is exposed to an atmosphere of 40% relative humidity for four hours. Afterbeing stroked rapidly and heavily several times with a glass rod, the
- the fabric is held close to cigarette ashes. If the ashes do not jump and cling to the fabric, the fabric is considered to have good anti-static properties.
- Table I demonstrates that the use of an accelerator of the type normally employed with epoxy resins tends to adversely affect the durability of the finish in accordance with this invention. More importantly, Table I demonstrates that outstanding and durable anti-static properties may be imparted to nylon in accordance with the present invention.
- Nylon taffeta was treated with the above solution by padding, obtaining a wet-pickup. After drying at 225 F. for 2 minutes, the fabric was heated at 300 F. for 3 minutes. The treated fabric contained 5% of each of the above agents on the weight of the fabric.
- Example 1 The test for anti-static properties and the Washes were carried out as in Example 1. The treated fabric showed good anti-static properties for 7 washes.
- the treated fabric showed good anti-static properties for 5 washes.
- EXAMPLE 5 Application of 8-amin0-1-naphthol-5sulfonic acid and diglycidyl ether of ethylene glycol on nylon as an anti-static An aqueous solution was prepared containing 5% of S-amino-l-naphthol-S-sulfonic acid, 20% of sodium hydroxide on the weight of the naphtholsulfonic acid, and 10% of diglycidyl ether of ethylene glycol (pH:11.8).
- Nylon taffeta was treated with the above solution by padding, obtaining a 50% wet-pickup. After drying at 225 F. for 2 minutes, the fabric was heated at 300 F. for 3 minutes. The treated fabric contained 2.5% of S-amino-l-naphthol-S-sulfonic acid and 5% of the diglycidyl ether of ethylene glycol.
- Nylon taffeta was treated with the above solution by padding, obtaining a 50% wet-pickup. After drying at 225 F. for 2 minutes, the fabric was heated at 300 F. for 3 minutes. The treated fabric contained 5% of each of the above agents on the weight of the fabric.
- Example 1 The test for anti-static properties and the washes were carried out as in Example 1. The treated fabric showed good anti-static properties for 10 washes.
- EXAMPLE 7 Application of disodiurn salt of 4,4-bis[2-amin0-4-(psulfoanilino)-s-triazin 6 ylamino]-stilbene-2,2-disulfonic acid and diglycidyl ether on nylon as an optical brightener A. 0.1% of 4,4-bis[2-amino-4-(p-sulfoanilino)-s-t1iazin-6-ylaminol]-stilbene-2,2'-disulfonic acid as the di sodium salt and 5% of diglycidyl ether on the Weight of the fabric were applied to nylon fabric from a single aqueous bath. The fabric was dried and cured for 3 minutes at 300 F.
- EXAMPLE 8 Application of homofuchsine and diglycidyl ether of ethylene glycol 0n polyester fiber Aqueous solution A contained 0.5% of Cl. Basic Violet 14 (Cl. 42,510), i.e., homofuchsine, and 5% of diglycidyl ether of ethylene glycol.
- Solution B contained 0.5% of (3.1. Basic Violet 14 alone.
- Fabrics formed of polyester fibers were immersed in each of the above solutions at room temperature for three minutes. The excess solution was removed from each of the fabrics by squeezing to give a 70% wetpickup. After the fabrics were dried at 194 F. for 15 minutes, they were heated at 290 F. for three minutes.
- the fabric treated with solution A contained notably more color than that treated with solution B.
- the fabrics treated with solution A were more strongly dyed with a violet color than those treated with solution B, and the difference was greater when the fabrics were dried at 290 F.
- a textile material may be finished with an aminoplast textile finishing resin, as for example, the formaldehyde condensates of urea, thiourea, ethylene urea, ethylene thiourea, 1,2 propylene urea, 1,3 propylene urea, guanamines, melamine, thiobisamides such as thiobispropionamide and the alkylated derivatives of these methylol compounds and then subsequently modified in accordance with the present invention.
- an aminoplast textile finishing resin as for example, the formaldehyde condensates of urea, thiourea, ethylene urea, ethylene thiourea, 1,2 propylene urea, 1,3 propylene urea, guanamines, melamine, thiobisamides such as thiobispropionamide and the alkylated derivatives of these methylol compounds and then subsequently modified in accordance with the present invention.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto at least two polyfunctional compounds capable of reacting with each other, one of said polyfunctional compounds being a member of the group consisting of 4,4- diamino-2,2-stilbenedisulfonic acid, 4,4'-diaminodibenzyl- 2,2-disulfonic acid, 4,4-diaminobiphenyl-2,2'-disulfonic acid, S-amino-l-naphthol 5 sulfonic acid, 4,4-bis(2- amino-4-(p-sulfanilino)-s-triazin 6 ylamino) stilbene- 2,2-disulfonic acid and homofuchsine and the other of said polyfunctional compounds being a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1, and thereafter combining said compounds on the article by heating the article containing them at reaction temperatures.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4-diamino-2,2'-stilbenedisulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the so treated article to reaction temperatures.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diaminodibenzyl-2,2-disulfonic acid, and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the so treated article to reaction temperatures.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diaminobiphenyl-2,2-'disulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the so treated article to reaction temperatures.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 8-amino-l-naphthol-S-sulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the treated article to reaction temperatures.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diamino-2,2'-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol and thereafter subjecting the treated article to reaction temperatures.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diamino-2,2'-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol and thereafter subjecting the treated article to a temperature of from about F. to about 400 F.
- a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4-diam-ino 2,2. stil-benedisulfonic acid and diglycidyl ether and thereafter subjecting the treated article to reaction temperatures.
- a process for treating textile material containing hydrophobic synthetic fibers, which textile material is subject to the accumulation of static electricity which comprises applying thereto at least two polyfunctional compounds capable of reacting with each other, one of said polyfunctional compounds being a member of the group consist-ing of 4,4-diamino-2,-2'-stilbenedisulfonic acid, 4,4 diamino-dibenzyl 2,2 :di-sul-fonic acid, 4,4- diamino-biphenyl-Z,2'-disulfonic acid, S-amino-l-naphthol 5 sulfonic acid, 4,4-bis(2-amino-4-(p-sulfanilino)- s triaZin-6-ylamino)-stilbene-2,2 disulfonic acid and homofuchsine and the other of said polyfunctional compounds being a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1, and thereafter combining said compounds on
- a process for reducing the tendency of nylon fabric to accumulate surface charges of static electricity and to optically brighten said fabric which comprises applying thereto 4,4'-diamino-2,2'-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol and thereafter subjecting the treated fabric to reaction temperatures.
- Synthetic hydrophobic textile material having thereon in an amount sulficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4-diamino-2,2'-stilbenedisulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
- Synthetic hydrophobic textile material having thereon in an amount sufficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4-diaminodibenzyl-2, 2-disulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
- Synthetic hydrophobic textile material having thereon in an amount suflicient to reduce the accumulat-ion of surface charges of static electricity a polymeric reaction product of 4,4-diaminobiphenyl-2,2-disulfonic acid and a :diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
- Synthetic hydrophobic textile material having thereon in an amount suificient to reduce the accumula tion of surface charges of static electricity a polymeric reaction product of 8-amino-l-naphthol-S-sulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
- Synthetic hydrophobic textile material having thereon in an amount sufficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4-diamino-2,2-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol.
- Synthetic hydrophoblic textile material having thereon in an amount sufficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4'-diamino-2,2-stilbenedisulfonic acid and diglycidyl ether.
- Nylon material having thereon a polymeric reaction product of 4,4'-diamino-2,2-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE600676D BE600676A (xx) | 1960-03-01 | ||
NL261845D NL261845A (xx) | 1960-03-01 | ||
US11973A US3206328A (en) | 1960-03-01 | 1960-03-01 | Process for imparting anti-static properties to hydrophobic textile materials and product thereof |
FR853726A FR1281706A (fr) | 1960-03-01 | 1961-02-24 | Agent polymère de traitement des textiles et procédé pour sa préparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11973A US3206328A (en) | 1960-03-01 | 1960-03-01 | Process for imparting anti-static properties to hydrophobic textile materials and product thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
US3206328A true US3206328A (en) | 1965-09-14 |
Family
ID=21752764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11973A Expired - Lifetime US3206328A (en) | 1960-03-01 | 1960-03-01 | Process for imparting anti-static properties to hydrophobic textile materials and product thereof |
Country Status (3)
Country | Link |
---|---|
US (1) | US3206328A (xx) |
BE (1) | BE600676A (xx) |
NL (1) | NL261845A (xx) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3337288A (en) * | 1963-05-06 | 1967-08-22 | Dainichiseika Color Chem | Reactive coloring matter, processes for producing the same and processes for coloring articles with the same |
US3391019A (en) * | 1964-02-21 | 1968-07-02 | Ici Ltd | Process for coating shaped hydrophobic polymeric materials with reaction product of halogenotriazine and polymer containing hydroxyl, amino or mercapto group |
US3563375A (en) * | 1967-08-08 | 1971-02-16 | Auby Prod Chim | Method of selectively separating solid particles by electrostatic sorting in fluidized bed |
US3705877A (en) * | 1967-08-30 | 1972-12-12 | Asahi Chemical Ind | Antistatic synthetic resin compositions containing trazine derivatives |
US3743477A (en) * | 1967-07-03 | 1973-07-03 | Sandoz Ltd | Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes |
US3852029A (en) * | 1970-10-22 | 1974-12-03 | Ciba Geigy Ag | Stable concentrated solutions of direct dyes and process for their manufacture |
US3952128A (en) * | 1971-09-01 | 1976-04-20 | Kao Soap Co., Ltd. | Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same |
US4418164A (en) * | 1982-07-19 | 1983-11-29 | E. I. Du Pont De Nemours And Company | Aramid fiber coated with polyfunctional aziridine |
US5057371A (en) * | 1985-06-14 | 1991-10-15 | Minnesota Mining And Manufacturing Company | Aziridine-treated articles |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB453431A (en) * | 1935-03-06 | 1936-09-07 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of condensation products |
US2506486A (en) * | 1948-04-21 | 1950-05-02 | Union Carbide & Carbon Corp | Thermosetting resin from a diphenol and a diglycidyl ether of a diphenol |
US2730427A (en) * | 1952-08-13 | 1956-01-10 | American Cyanamid Co | Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds |
US2752269A (en) * | 1951-12-01 | 1956-06-26 | Shell Dev | Treatment of textile materials |
US2839431A (en) * | 1955-08-26 | 1958-06-17 | Du Pont | Antistatic agents for hydrophobic fiber |
US2846397A (en) * | 1949-10-14 | 1958-08-05 | Ciba Ltd | Water-soluble salts of derivatives of 4:4'-diaminostilbene-2:2'-disulfonic acid for enhancing the brightness of organic fibrous material |
US2885388A (en) * | 1952-08-29 | 1959-05-05 | Ciba Ltd | Polymerizable amide-like condensation products and process for their manufacture |
US2892674A (en) * | 1955-05-27 | 1959-06-30 | Ici Ltd | Treatment of cellulosic materials |
US2903381A (en) * | 1954-09-03 | 1959-09-08 | Shell Dev | Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups |
US2933473A (en) * | 1956-07-09 | 1960-04-19 | Gen Electric | Mercaptans as catalysts for polymerization of ethoxyline resins |
US2980676A (en) * | 1957-07-24 | 1961-04-18 | Ciba Ltd | Glycidyl ethers of n-methylolamino-1:3:5-triazines |
US3018287A (en) * | 1958-11-05 | 1962-01-23 | Fidelity Union Trust Company | Optical brighteners for use with paper |
US3026216A (en) * | 1959-10-05 | 1962-03-20 | Union Carbide Corp | Treatment of textile fabrics with methylglycidyl ethers |
US3030247A (en) * | 1955-07-28 | 1962-04-17 | Minnesota Mining & Mfg | Stable heat-curing epoxy resin compositions |
US3046075A (en) * | 1962-07-24 | Dyeing and finishing textile materials | ||
US3066005A (en) * | 1958-02-01 | 1962-11-27 | Bayer Ag | Process for the treatment of hydroxyl group-containing textile materials |
US3073662A (en) * | 1963-01-15 | Process for the production of fast dye- |
-
0
- BE BE600676D patent/BE600676A/xx unknown
- NL NL261845D patent/NL261845A/xx unknown
-
1960
- 1960-03-01 US US11973A patent/US3206328A/en not_active Expired - Lifetime
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3073662A (en) * | 1963-01-15 | Process for the production of fast dye- | ||
US3046075A (en) * | 1962-07-24 | Dyeing and finishing textile materials | ||
GB453431A (en) * | 1935-03-06 | 1936-09-07 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of condensation products |
US2506486A (en) * | 1948-04-21 | 1950-05-02 | Union Carbide & Carbon Corp | Thermosetting resin from a diphenol and a diglycidyl ether of a diphenol |
US2846397A (en) * | 1949-10-14 | 1958-08-05 | Ciba Ltd | Water-soluble salts of derivatives of 4:4'-diaminostilbene-2:2'-disulfonic acid for enhancing the brightness of organic fibrous material |
US2752269A (en) * | 1951-12-01 | 1956-06-26 | Shell Dev | Treatment of textile materials |
US2730427A (en) * | 1952-08-13 | 1956-01-10 | American Cyanamid Co | Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds |
US2885388A (en) * | 1952-08-29 | 1959-05-05 | Ciba Ltd | Polymerizable amide-like condensation products and process for their manufacture |
US2903381A (en) * | 1954-09-03 | 1959-09-08 | Shell Dev | Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups |
US2892674A (en) * | 1955-05-27 | 1959-06-30 | Ici Ltd | Treatment of cellulosic materials |
US3030247A (en) * | 1955-07-28 | 1962-04-17 | Minnesota Mining & Mfg | Stable heat-curing epoxy resin compositions |
US2839431A (en) * | 1955-08-26 | 1958-06-17 | Du Pont | Antistatic agents for hydrophobic fiber |
US2933473A (en) * | 1956-07-09 | 1960-04-19 | Gen Electric | Mercaptans as catalysts for polymerization of ethoxyline resins |
US2980676A (en) * | 1957-07-24 | 1961-04-18 | Ciba Ltd | Glycidyl ethers of n-methylolamino-1:3:5-triazines |
US3066005A (en) * | 1958-02-01 | 1962-11-27 | Bayer Ag | Process for the treatment of hydroxyl group-containing textile materials |
US3018287A (en) * | 1958-11-05 | 1962-01-23 | Fidelity Union Trust Company | Optical brighteners for use with paper |
US3026216A (en) * | 1959-10-05 | 1962-03-20 | Union Carbide Corp | Treatment of textile fabrics with methylglycidyl ethers |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3337288A (en) * | 1963-05-06 | 1967-08-22 | Dainichiseika Color Chem | Reactive coloring matter, processes for producing the same and processes for coloring articles with the same |
US3391019A (en) * | 1964-02-21 | 1968-07-02 | Ici Ltd | Process for coating shaped hydrophobic polymeric materials with reaction product of halogenotriazine and polymer containing hydroxyl, amino or mercapto group |
US3743477A (en) * | 1967-07-03 | 1973-07-03 | Sandoz Ltd | Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes |
US3563375A (en) * | 1967-08-08 | 1971-02-16 | Auby Prod Chim | Method of selectively separating solid particles by electrostatic sorting in fluidized bed |
US3705877A (en) * | 1967-08-30 | 1972-12-12 | Asahi Chemical Ind | Antistatic synthetic resin compositions containing trazine derivatives |
US3852029A (en) * | 1970-10-22 | 1974-12-03 | Ciba Geigy Ag | Stable concentrated solutions of direct dyes and process for their manufacture |
US3952128A (en) * | 1971-09-01 | 1976-04-20 | Kao Soap Co., Ltd. | Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same |
US4418164A (en) * | 1982-07-19 | 1983-11-29 | E. I. Du Pont De Nemours And Company | Aramid fiber coated with polyfunctional aziridine |
US5057371A (en) * | 1985-06-14 | 1991-10-15 | Minnesota Mining And Manufacturing Company | Aziridine-treated articles |
Also Published As
Publication number | Publication date |
---|---|
NL261845A (xx) | 1900-01-01 |
BE600676A (xx) | 1900-01-01 |
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