US2886472A - Treatment of textile materials - Google Patents
Treatment of textile materials Download PDFInfo
- Publication number
- US2886472A US2886472A US580993A US58099356A US2886472A US 2886472 A US2886472 A US 2886472A US 580993 A US580993 A US 580993A US 58099356 A US58099356 A US 58099356A US 2886472 A US2886472 A US 2886472A
- Authority
- US
- United States
- Prior art keywords
- acid
- polyepoxide
- epoxidized
- fabric
- cloth
- 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
- 239000000463 material Substances 0.000 title claims description 55
- 239000004753 textile Substances 0.000 title claims description 32
- 238000011282 treatment Methods 0.000 title description 13
- 229920000647 polyepoxide Polymers 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 34
- 239000012736 aqueous medium Substances 0.000 claims description 10
- 239000004744 fabric Substances 0.000 description 68
- -1 for example Chemical class 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229920000742 Cotton Polymers 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229920000297 Rayon Polymers 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000002964 rayon Substances 0.000 description 6
- 239000002195 soluble material Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- VAJWDZDMPLCJOC-UHFFFAOYSA-N cyclohex-2-en-1-ylmethyl cyclohex-2-ene-1-carboxylate Chemical compound C1CCC=CC1C(=O)OCC1CCCC=C1 VAJWDZDMPLCJOC-UHFFFAOYSA-N 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 229920002689 polyvinyl acetate Polymers 0.000 description 4
- 239000011118 polyvinyl acetate Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- BIOOACNPATUQFW-UHFFFAOYSA-N calcium;dioxido(dioxo)molybdenum Chemical compound [Ca+2].[O-][Mo]([O-])(=O)=O BIOOACNPATUQFW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- XKDLTDLYMCHCAB-UHFFFAOYSA-N 6-[2-(7-oxabicyclo[4.1.0]heptan-6-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C(C)(C)C1(O2)C2CCCC1 XKDLTDLYMCHCAB-UHFFFAOYSA-N 0.000 description 2
- NTUQPJNKERXQPA-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-5-ol Chemical compound OC1CCCC2OC12 NTUQPJNKERXQPA-UHFFFAOYSA-N 0.000 description 2
- FYTJMUYAPJUVHO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-6-ol Chemical compound C1CCCC2OC21O FYTJMUYAPJUVHO-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 239000000025 natural resin Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- YZLCHCSGEUCERU-UHFFFAOYSA-N (3-ethyloxiran-2-yl)methyl 3-[3-[(3-ethyloxiran-2-yl)methoxy]-3-oxopropyl]sulfanylpropanoate Chemical compound CCC1OC1COC(=O)CCSCCC(=O)OCC1C(CC)O1 YZLCHCSGEUCERU-UHFFFAOYSA-N 0.000 description 1
- PZIYGPCHDBRRRW-UHFFFAOYSA-N (3-methyloxiran-2-yl)methyl 2-(3-methyloxiran-2-yl)acetate Chemical compound CC1OC1COC(=O)CC1C(C)O1 PZIYGPCHDBRRRW-UHFFFAOYSA-N 0.000 description 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- GRJURQZMKBRNNH-UHFFFAOYSA-N 1-(6-oxabicyclo[3.1.0]hexan-1-yloxy)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21OC12OC1CCC2 GRJURQZMKBRNNH-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- GFDQTSCNSYVIRM-UHFFFAOYSA-N 2-(3-ethyloxiran-2-yl)ethyl 2-(3-methyloxiran-2-yl)acetate Chemical compound CCC1OC1CCOC(=O)CC1C(C)O1 GFDQTSCNSYVIRM-UHFFFAOYSA-N 0.000 description 1
- IMXTVEPTZXBOEA-UHFFFAOYSA-N 2-(3-propyloxiran-2-yl)ethyl 4-[4-oxo-4-[2-(3-propyloxiran-2-yl)ethoxy]butyl]sulfonylbutanoate Chemical compound CCCC1OC1CCOC(=O)CCCS(=O)(=O)CCCC(=O)OCCC1C(CCC)O1 IMXTVEPTZXBOEA-UHFFFAOYSA-N 0.000 description 1
- VWVDTBDXKCCJOL-UHFFFAOYSA-N 2-hydroxy-4-[(3-methyloxiran-2-yl)methoxy]-2-[2-[(3-methyloxiran-2-yl)methoxy]-2-oxoethyl]-4-oxobutanoic acid Chemical compound CC1OC1COC(=O)CC(O)(C(O)=O)CC(=O)OCC1C(C)O1 VWVDTBDXKCCJOL-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- YFLSTWVANPYCGC-UHFFFAOYSA-N 3-(3-propyloxiran-2-yl)propanoic acid Chemical compound CCCC1OC1CCC(O)=O YFLSTWVANPYCGC-UHFFFAOYSA-N 0.000 description 1
- XOBTWQWSFMZPNQ-UHFFFAOYSA-N 5-(oxiran-2-ylmethyl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC2OC2C1CC1CO1 XOBTWQWSFMZPNQ-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- OULAQVCZRNCPNC-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ol Chemical compound C1C(O)CCC2OC21 OULAQVCZRNCPNC-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose 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
- 229920004934 Dacron® Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
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- 235000009496 Juglans regia Nutrition 0.000 description 1
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- 229920000877 Melamine resin Polymers 0.000 description 1
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- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
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- 239000004902 Softening Agent Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- MWAZVPWTTWPXJF-UHFFFAOYSA-N acetic acid;urea Chemical compound CC(O)=O.NC(N)=O MWAZVPWTTWPXJF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- UTOGBRUNPNKIRC-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] benzene-1,2-dicarboxylate Chemical compound CC1OC1COC(=O)C1=CC=CC=C1C(=O)OCC1C(C)O1 UTOGBRUNPNKIRC-UHFFFAOYSA-N 0.000 description 1
- GISXQQJFNQQWGZ-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] benzene-1,4-dicarboxylate Chemical compound CC1OC1COC(=O)C1=CC=C(C(=O)OCC2C(O2)C)C=C1 GISXQQJFNQQWGZ-UHFFFAOYSA-N 0.000 description 1
- XEUGWLQVJZLDPM-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] hexanedioate Chemical compound CC1OC1COC(=O)CCCCC(=O)OCC1C(C)O1 XEUGWLQVJZLDPM-UHFFFAOYSA-N 0.000 description 1
- RTTKDGLGHLTZJD-UHFFFAOYSA-N bis[(3-methyloxiran-2-yl)methyl] oxalate Chemical compound CC1OC1COC(=O)C(=O)OCC1C(C)O1 RTTKDGLGHLTZJD-UHFFFAOYSA-N 0.000 description 1
- IOPXNFITHWTFFE-UHFFFAOYSA-N bis[(3-pentyloxiran-2-yl)methyl] cyclohex-3-ene-1,2-dicarboxylate Chemical compound CCCCCC1OC1COC(=O)C1C(C(=O)OCC2C(O2)CCCCC)C=CCC1 IOPXNFITHWTFFE-UHFFFAOYSA-N 0.000 description 1
- XJZXAKSDEWDIIR-UHFFFAOYSA-N bis[(3-propyloxiran-2-yl)methyl] butanedioate Chemical compound CCCC1OC1COC(=O)CCC(=O)OCC1C(CCC)O1 XJZXAKSDEWDIIR-UHFFFAOYSA-N 0.000 description 1
- BGJZFLGDPGUOFF-VXPUYCOJSA-N bis[3-(3-heptyloxiran-2-yl)propyl] (z)-but-2-enedioate Chemical compound CCCCCCCC1OC1CCCOC(=O)\C=C/C(=O)OCCCC1C(CCCCCCC)O1 BGJZFLGDPGUOFF-VXPUYCOJSA-N 0.000 description 1
- GYSZJTGMXGDGOW-UHFFFAOYSA-N bis[3-(3-tridecyloxiran-2-yl)propyl] propanedioate Chemical compound CCCCCCCCCCCCCC1OC1CCCOC(=O)CC(=O)OCCCC1C(CCCCCCCCCCCCC)O1 GYSZJTGMXGDGOW-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 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
- LOGBRYZYTBQBTB-UHFFFAOYSA-N butane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)CC(O)=O LOGBRYZYTBQBTB-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- SVGGKWILBMPIJV-UTJQPWESSA-N butyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCCC SVGGKWILBMPIJV-UTJQPWESSA-N 0.000 description 1
- QQNROWCMALTXCD-XQOKXTRKSA-N butyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CCCCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC QQNROWCMALTXCD-XQOKXTRKSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- IHLIVAHFDOAPFC-UHFFFAOYSA-N cyclohex-2-ene-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C=C1 IHLIVAHFDOAPFC-UHFFFAOYSA-N 0.000 description 1
- YVWBQGFBSVLPIK-UHFFFAOYSA-N cyclohex-2-ene-1-carboxylic acid Chemical compound OC(=O)C1CCCC=C1 YVWBQGFBSVLPIK-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- FMMOOAYVCKXGMF-MVKOLZDDSA-N ethyl (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MVKOLZDDSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- SSILHZFTFWOUJR-UHFFFAOYSA-M hexadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCCS([O-])(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-M 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- WFMGDEZKUZALGX-UHFFFAOYSA-N octyl octadeca-9,12-dienoate Chemical compound CCCCCCCCOC(=O)CCCCCCCC=CCC=CCCCCC WFMGDEZKUZALGX-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- UVTBHNQYDPSCPO-UHFFFAOYSA-N pentane-1,1,5-tricarboxylic acid Chemical compound OC(=O)CCCCC(C(O)=O)C(O)=O UVTBHNQYDPSCPO-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- XWKBMOUUGHARTI-UHFFFAOYSA-N tricalcium;diphosphite Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])[O-].[O-]P([O-])[O-] XWKBMOUUGHARTI-UHFFFAOYSA-N 0.000 description 1
- QXILUQNMENFHOJ-UHFFFAOYSA-N tris[(3-methyloxiran-2-yl)methyl] butane-1,2,4-tricarboxylate Chemical compound CC1OC1COC(=O)CCC(C(=O)OCC1C(O1)C)CC(=O)OCC1C(C)O1 QXILUQNMENFHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
- D06M15/55—Epoxy resins
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/08—Oxirane
Definitions
- This invention relates to the treatment of textile materials. More particularly, the invention relates to a method for preparing textile materials that have improved crease and shrink resistance and no chlorine retention.
- the invention further provides improved fabrics prepared by the afore-describe'd process.
- the fabrics treated in the above-described manner have no ability to retainchlor'ine and the coated fabrics may be bleached or otherwise exposed to chlorine without danger of being discolored, charred or weakened during subsequent heat treatments.
- the fabrics have been found to have improved washability and can be washed numeroustimes without danger of losing any substantial amount of the polyepoxide resin.
- the material to be used in the process of the invention includes those having at least one internal epoxy group, i.e., at least one group, and at least one other epoxy group which may be a terminal epoxy group, i.e., may be a Hie-ch orogroup, or an internal epoxy group. These groups may be in an open or closed chain portion of the molecule.
- the polyepoxide is preferably aliphatic and free of elements other than carbon, hydrogen, oxygen and chlorine.
- polyepoxides examples include the epoxysubstituted hydrocarbons, such as, for example, vinyl cyclohexene dioxide, 2,3,5,6-diepoxyoctane, 2,3,6,7-diepoxydodecane, 1,2-epoxy-3-(2,3-epoxypropyl)cyclohexane, 2,2-bis(epoxycyclohexyl)propane, and 1,2-epoxy-4- (3,4-epoxybutyl)cyclohexane.
- epoxysubstituted hydrocarbons such as, for example, vinyl cyclohexene dioxide, 2,3,5,6-diepoxyoctane, 2,3,6,7-diepoxydodecane, 1,2-epoxy-3-(2,3-epoxypropyl)cyclohexane, 2,2-bis(epoxycyclohexyl)propane, and 1,2-epoxy-4- (3,4-epoxybutyl)cyclohexan
- polyepoxides include the ethers of epoxy-substituted cycloalkanol alcohols such as epoxycyclohexanol.
- examples of the group include, among others, di(epoxycyclohexyl) ether, di(epoxycyclopentyl)- ether, glycidyl ether. of t2,3-epoxycyclohexanol, epoxybutyl ether of 2,3-epoxycyclohexanol and epoxyhexyl ether of 3,4-epoxycyclohexanol.
- epoxidized esters of the polyethylenically unsaturated monocarboxylic acids such as epoxidized linseed, soyabean, perilla, oiticia, tung, walnut and dehydrated castor oil, methyl linoleate, butyl linoleate, ethyl 9,12-octadecadienoate, butyl 9,12,15-octadecatrienoate, ethyl elaeostearate, octyl 9,12-octadecadienoate, methyl elaeostearate, monoglycerides of tung oil fatty acids,-monoglycerides of soyabean oil, sunflower, rapeseed, hempseed, sardine, cottonseed oil, and the like.
- Another group of the epoxy-containing materials used in the process of the invention include the epoxidized. esters of unsaturated monohydric alcohols and polycarboxylic acids, such as, f or example, di(2,3-epoxybutyl) adipate, di(2,3-epoxybutyl) oxalate, di(2,3-epoxyhexyl) succinate, di(3,4-epoxybutyi)' maleate, di(2,3-epoxyoctyl) pimelate, di(2,3-epoxybutyl) phthalate, di(2,3-epoxyoctyl) tetrahydrophthalate, di(4,5-epoxydodecyl) maleate, di(2,3-epoxy-butyl) terephthalate, di(2,3-epoxypentyl) thiodipropionate, di(5-,6'- epoxytetradecyl) diphenyldicar
- epoxy-containing materials include those epoxidized esters of unsaturated alcohols and unsaturated carboxylic acids, such as 2,3-epoxycyclohexyl epoxypropionate, 2,3-epoxybutyl 3,4-epoxypentanoate, 3,4-epoxyhexyl 3,4-epoxypentanoate, 3,4-epoxycyclohexyl 3,4-cyclohexanoate, 3,4epoxycyclohexy1 4,5- epoxyoctanoate, and the like.
- Still another group of the epoxy-containing materials include epoxidized derivatives of polyethylenically unsaturated polycarboxylic acids, such as, for example, dimethyl 8,9,12,13-diepoxyeicosanedioate, dibutyl 7,8,11, lZ-diepoxyoctadecanedioate, dioctyl l0,11-diethyl-8,9,12, l3-diepoxyeicosanedioate, dihexyl 6,7,10,11-diepoxyhexa-- decanedioate, didecyl 9-epoxyethyl-10,ll-epoxyoctadecenedioate, dibutyl 3-butyl-3,4,5,6-diepoxycyclohexane-1, 2-dicarboxylate, dicyclohexyl 3 ,4,5 ,6-diepoxycyclohexane- 1,2-dicarboxylate,
- Still another group comprises the epoxidized polyesters obtainedby reacting an unsaturated polyhydric alcohol and/or unsaturated polycarboxylic acid or anhydride groups, such as, for example, the polyester obtained by reacting 8,9,12,13-eicosadienedioic acid with ethylene gly col, the polyester obtained by reacting diethylene glycol with 2-cyclohexene-1,4-dicarboxylic acid and the like, and mixtures thereof.
- an unsaturated polyhydric alcohol and/or unsaturated polycarboxylic acid or anhydride groups such as, for example, the polyester obtained by reacting 8,9,12,13-eicosadienedioic acid with ethylene gly col, the polyester obtained by reacting diethylene glycol with 2-cyclohexene-1,4-dicarboxylic acid and the like, and mixtures thereof.
- Particularly preferred materials to be used according to the process of the invention comprise the epoxy-substituted hydrocarbons, and ethers of epoxy alcohols and epoxy-substituted cyclohexanols, the epoxidized esters of polyethylenically unsaturated monocarboxylic acids containing not more than 22 carbon atoms, the epoxidized esters of polyethylenically unsaturated polycarboxylic acids containing not more than 25 carbon atoms, and the epoxidized esters of ethylenicaly unsaturated monohydric alcohols and ethylenically unsaturated carboxylic acids containing not more than 22 carbon atoms.
- those materials having one or more internal epoxy groups and one or more terminal epoxy groups such as vinyl cyclohexene dioxide, glycidyl ether of epoxy cyclohexanol, epoxidized acrylic acid ester of cyclohexanol and glycidyl ester of epoxycyclohexanecarboxylic acid.
- Many of the above-described epoxy-containing materials are preferably obtained by epoxidizing the corresponding unsaturated compounds.
- the compounds, such as dimethyl 8,9,12,l3-diepoxyeicosanedioate may be obtained by epoxidizing dimethyl 8,9,12,l3-eicosadienedioate.
- the epoxidation may be accomplished by reacting the unsaturated compound with an epoxidizing agent.
- Organic peracids, such as performic, peracetic, perbenzoic acid and the like are preferred agents for this reaction.
- the amount of the epoxidizing agent employed will vary over a considerablerange depending upon the type of product desired. In general, one should employ at least one mole of the oxidizing agent, such as perbenzoic acid, for every ethylenic group to be epoxidized. Thus to produce epoxidized dicrotyl adipate from dicrotyl adipate, one should react the unsaturated ester with at least two moles of perbenzoic acid. In some cases, it is rather difi'icult to effect epoxidation of all of the ethylenic groups and if a completely epoxidized product is required,
- the temperature employed during the epoxidation may vary over a considerable range depending upon the type of reactants and epoxidizing agents selected. It is generally desirable to maintain the temperature between -20 C. to 100 C. Preferred temperatures range from about 10 C. to room temperature, e.g., about 20 C. Atmospheric, superatmospheric, or subatmospheric pressures may be employed as desired.
- the epoxidized product obtained by this method may be recovered from the reaction mixture by any convenient means known to the art, such as distillation, extraction, fractional precipitation and the like.
- the polyepoxides described above are applied to the textile material in the form of an aqueous medium. If the polyepoxides are water-soluble they may be used directly as a water solution. Otherwise, it may be desirable to employ solvents,-emulsifying agents and the like in the aqueous medium in order to obtain the proper concentration of the polyepoxide.
- solvents that may be used in the water solutions include, among others, ethyl alcohol, isopropyl alcohol, methanol, and the like.
- Particularly preferred mediums of this type comprise water-alcohol mixtures having a weight ratio varying from 3 :1 to 1:5.
- Emulsifying agents employed for this purpose are preferably those that are free of nitrogen and strong acidic groups, such as the monooleate of sorbitan polyoxyethylene, the trioleate of sorbitan polyoxyethylene, sorbitan tristearate, sorbitan monolaurate, polyoxyethylene ethers of alkylphenols, carboxymethylcellulose, starch, gum arabic, aryl and alkylated aryl sulfonates, such as cetyl sulfonate, oleyl sulfonate, sulfonated mineral oils, and the like, and mixtures thereof.
- the emulsifying agents are generally employed in amounts varying from 0.1% to 10% by weight and more preferably from 1% to 5% by weight.
- the amount of the polyepoxide in the impregnating solution may vary over a considerable range depending chiefly on the amount of resin to be deposited on the fabric and this in turn will depend on the number of applications and the pick-up allowed per application.
- a concentration ranging from 3% to 25% by weight will ordinarily suffice. If less than 80% pick-up is permitted, the concentration may in some cases go as high as 30% to 50%.
- the hardening or curing agents may be added to the polyepoxide solution before it is applied to the fabric or it may be applied by spraying or other suitable methods to the fabric after it has been impregnated with the poly- .epoxide.
- the curing agents are preferably added to the solution before it is applied to the fabric.
- Preferred curing agents to be used include the acid and acid-acting curing agents, such as the organic and inorganic acids and anhydrides as citric acid, acetic acid, acetic acid anhydride, butyric acid, caproic acid, phthalic acid, phthalic acid anhydride, tartaric acid, aconitic acid, oxalic acid, succinic acid, succinic acid anhydride, lactic acid, maleic acid, maleic acid anhydride, fumaric acid, glutaconic acid, 1,2,4-butanetricarboxylic acid, isophthalic acid, terephthalic acid, malonic acid, 1,1,5-pentanetricarboxylic acid, acetoacetic acid, naphthalic acid, trimallitic acid, phosphoric acid, boric acid, sulfonic acid, phosphinic acid, perchloric acid, persulfuric acid, p-toluenesulfonic acid, ethanesul
- Particularly preferred curing agents comprise the metal salts and preferably salts of metals having an atomic weight between 24 and 210, and preferably in groups I r to IV'and VIII of the periodic table of ele me'nts and inorganic acids the anion portion of which contains at least two dissimilar elementshaving an atomic weight above 2, and particularly inorganic acids of the formula wherein X is a non-metal having an atomic weight above 2, Z is an element which gains from 1 to 2 electrons in its outer orbit, such as oxygen and fluorine, w is an integer, y is an integer greater than 1 and a equals the valency of the radical (X) (Z),,, such as sulfuric acid, fluoboric acid, fluosilicic acid, persulfuric acid, phosphoric acid and the like.
- Examples of these preferred agents include, among others, zinc fluoborate, zinc sulfate, magnesium fluoborate, magnesium perchlorate, potassium persulfate, copper fluoborate, copper persulfate, cobaltic fluoborate, chromic nitrate, magnesium nitrate, calcium phosphite, and the like.
- the above-described curing agents are to be used in sufficient amount to convert the polyepoxide to the desired insoluble infusible state.
- the epoxy groups in the internal position are less reactive to the curing agents under the conditions of the present process than those in the terminal position so the amount of curing agent used must be greater, such as 1.5 times greater, than that used when the compounds have all terminal epoxy groups as the polyglycidyl ethers.
- the organic acids are used .in amounts of from 2% to with the polyglycidyl ethers so in the present invention they are preferably used in amounts varying from about 3% to by weight of polyepoxide.
- the boron-trifluoride complexes are used inamounts from 1.0% to 7.5% with the polyglycidyl ethers so in the present invention they are preferably used in amounts varying from 1.5% to 10% by weight of polyepoxide.
- the metal salts are employed in amounts varying from 0.5% to 40% with the polyglycidyl ethers so in the present invention they are preferably used in amounts varying from 0.75% to 60% by weight of the polyepoxide.
- the solutions employed to treat the textiles may also contain plasticizers to improve their flexibility, though these should not be present in such proportions as to render the finished materials soft or sticky at temperatures and humidities to which they would be exposed. It is found, however, that the substances employed in the present invention yield products which are sufficiently flexible for most purposes without the use of plasticizers.
- organic and inorganic derivatives of phenols for example, diphenylol propane and triphenyl and tricresyl phosphates
- alkyl phthalates for example, diethyl phthalate and glycol phthalates, diethyl tartrate
- derivatives of polyhydric alcohols for example, mono-, diand triacetin, and products obtained by condensing polyhydric alcohols with themselves or with aldehydes or ketones.
- compositions may also contain natural resins, e.g., shellac, rosin, and other natural resins and synthetic or semi-synthetic resins, e.g., ester gum, polyhydroxypolybasic alkyd resins, phenolaldehyde and urea-aldehyde resins.
- natural resins e.g., shellac, rosin, and other natural resins and synthetic or semi-synthetic resins, e.g., ester gum, polyhydroxypolybasic alkyd resins, phenolaldehyde and urea-aldehyde resins.
- Textile softening agents and particularly those of the cationic-type as stearamidoethyl diethyl methyl quaternary ammonium methyl sulphate, trimethyl ammon um methyl sulphate of monostearylmetaphenylenedramme, s-di(1,2-palmitamidoethyl) urea monoacetate, palmityl amine hydrochloride, and the like, and mixtures thereof, may also be added in varying amounts to improve the feel of the treated fabrics.
- the application of the solution containing the polyepoxide to the textile fabric may be effected in any suitable manner, the method selected depending upon the results desired. If it is desired to apply the solution only to one surface of the material, as, for example, when ;it is desired to treat the back only'of a fabric having-a face of artificial or natural silk and a cotton back, the application may be etfected by spraying or by means of rollers, or the composition may be spread upon the surface by means of a doctor blade. When, however, it is desired to coat both surfaces of the material, or if the material is to be thoroughly impregnated with it, the fabrics may be simply dipped in the solution or run through conventional-type padding rollers. The solutions may also be applied locally to the material, for example, by means of printing rollers or by stencilling.
- the amount of the polyepoxides to be deposited on the fabric will vary over a wide range depending upon the degree of wrinkle-resistance and shrink-resistance desired in the finished material. If the fabric is to have a soft feel, such as that intended for use for dresses, shirts, etc., the amount of polyepoxide deposited will generally vary from 3% to'20% by weight of the fabric. If stiffer materials are required such as for shoe fabrics, draperies, etc. still higher amounts of resins, such as of the order of 25% to 50% by weight may be deposited.
- the aqueous medium may be applied again 'or as many times as desired to bring the amount of the polyepoxide resin up to the desired level.
- the treated material is then dried for a short period. This is generally accomplished by exposing the wet sheets to hot gas at temperatures ranging from 50 C. to C. The period of drying will depend largely on the amount of pick-up permitted during the application of thesolution, and the concentration of the polyepoxide. In most instances, drying periods of from 5 to 30 minutes should be suflicient.
- the dried fabric is then exposed to relatively high temperatures to accelerate the cure of the polyepoxides.
- Temperatures used for this purpose generally range from C. to 200 C., and more preferably from 100 C. to C. ,At these preferred temperatures, the cure can usually be accomplished in from 3 to 10 minutes. Exposures of less than 3 minutes, e.g., 1 minute, may probably be used in continuous, commercial processing.
- the process of the invention may be applied to the treatment of any textile material.
- textile materials include those prepared from the natural or artificial textile materials, e.g., cotton, linen, silk, rayon (regenerated cellulose), jute, hemp, animal fibers, such as wool, hair, mohair, nylon, Dacron and terylene mixtures thereof. While the invention has been particularly described with relation to the treatment of Woven fabrics, it may also be applied to other materials, for example, knitted or netted materials. 7
- the materials treated according to the process of the invention will have excellent crease and shrink resistance as well as good resiliency and flexibility and may be used for a wide variety of important applications.
- the woven cotton, rayon and wool fabrics, both colored and white, containing conventional amounts of resin, e.g., 25 to 50% may be used in other applications demanding more crispness and fullness such as the preparation of rugs, carpets, plushes, drapes, upholsteries, shoefabrics, and the like.
- Example I This example illustrates the use of vinyl cyclohexene dioxide in the treatment of cotton.
- the cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine .reten tion, a soft-feel, good color and excellent washability.
- the cloth had a crease recovery value of 111.
- cloth treated with aqueous solution of a polyglycidyl ether using 5 parts of curing agent had a crease recovery of 108.
- Example II This example illustrates the use of 2,2-bis(2,3-epoxycyclohexyl) propane in the treatment of cotton fabric.
- the cloth treated in the above-described manner had good crease and shrink resistance, no chlorine retention, a soft feel, good colorand good washability.
- the cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine retention, a soft feel, good color and excellent washability.
- Example IV This example illustrates the use of epoxidized dimethyl 8,9,11,12-eicosadienedioate in the treatment of cotton fabric.
- One hundred parts of epoxidized dimethyl 8,9,11,12-eicosadienedioate was mixed with water and then 50 parts of a 10% aqueous solution of hydrolyzed polyvinyl acetate was added with stirring. The mixture was then diluted with water to form a 12% aqueous solution of the polyepoxide.
- the cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine retention, a soft feel, good color and excellent washability.
- Example V This example illustrates the use of vinyl cyclohexene dioxide in the treatment of rayon.
- the cloth treated in the above-noted manner had good crease and shrink resistance, soft feel, good color, no chlorine retention and improved washability.
- Example VI This example illustrates the use of epoxidized dicrotyl phthalate in the treatment of cotton fabric.
- the cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine retention, a soft feel, good color and good washability.
- Example VII This example illustrates the use of the glycidyl ether of 2,3-epoxycyclohexanol in the treatment of cotton.
- the impregnated cloth was then dried at 60 C. for 5 minutes and cured at C. The finished product was then washed and rinsed.
- the cloth treated in this manner had good crease and shrink resistance, no chlorine retention, a soft feel, good color and excellent washability.
- a process for treating textile materials made up substantially of cellulosic material to make them creaseresistant and shrink resistant without affecting feel and chlorine-retentive properties which comprises impregnating the textile material with an aqueous medium containing a polyepoxide having at least one group, and from 1.5% to by weight of the polyepoxide of a borontrifiuoride complex, and then heating the treated fabric to cure the polyepoxide.
- a process for treating cellulosic textile materials made up substantially of cellulosic material to make them crease and shrink resistant which comprises impregnating the textile material with an aqueous medium containing a polyepoxide having at least one group, and from 0.75% to 60% by weight of the polyepoxide of a metal salt of a metal having an atomic weight between 24 and 210 and an inorganic acid, and then heating the treated material to cure the polyepoxide.
- a process as in claim 2 wherein the polyepoxide is vinyl cyclohexene dioxide.
- polyepoxide is bis(epoxycyclohexyl)propane.
- a process for treating textile material made up substantially of cellulosic material to make the material crease and shrink resistant which comprises impregnating the textile material with an aqueous medium containing a polyepoxide having at least one 0 -o-o -oogroup, and from 3% to 15% by weight of the polyepoxide of an organic polycarboxylic acid, and then heating the treated material at a temperature between C. and 200 C. for a short period to effect cure of the polyepoxide.
- polyepoxide is an epoxidized polyethylenically unsaturated carboxylic acid ester.
- a process as in claim 8 wherein the textile material is cotton.
Description
United States Patent TREATMENT OF TEXTILE MATERIALS Fred E. Condo, El Cerrito, and Carl W. Schroeder,
Orinda, Calif, assignors to Shell Development Company, New York, N.Y., a corporation-of Delaware No Drawing. Application April 27, 1956 Serial No. 580,993
11 Claims. (Cl. 117-139.4)
This invention relates to the treatment of textile materials. More particularly, the invention relates to a method for preparing textile materials that have improved crease and shrink resistance and no chlorine retention.
Specifically, the invention provides a new process for preparing crease resistant and shrink resistant, textile ma terials having no chlorine retention and improved washability comprises impregnating the textile material with an aqueous medium containing a polyepoxide which has at least one epoxy group in an internal position, i.e., has at least one group, and certain amounts of an epoxy curing agent and then heating to effect cure. The invention further provides improved fabrics prepared by the afore-describe'd process.
This application is a continuation-in-part of our application Ser. No. 259,504, filed December 1, 1951, now US. Patent No. 2,752,269.
Many of the textile fabrics, such as cotton and rayon, have rather poor resilience, i.e., they are easily creased or wrinkled when crushed or otherwise subjected to localized physical force. In addition, many of these fabrics have poor dimensional stability as exemplified by poor resistance to shrinkage. In order to overcome these shortcomings it has been common practice to treat the fabric with a resin, such as a ureaor melamineformaldehyde resin that could be subsequently insolubilized within the fabric fibers. While this method has met with some success with colored fabrics, it has been of little or no use in the treatment of white goods that may be subjected to bleaching. It has been found that during the bleaching process, the added resins retain considerable quantities of the chlorine and when the fabric is subsequently exposed to heat as in ironing or hot-air drying, the cloth is charred or discolored and the strength of the material seriously degraded. In addition, many of the fabrics treated with these resins have poor washability, i.e., the resin is easily lost from the fabric after a few washings with soap and water.
It is an object of the invention, therefore, to provide a new method for treating textile materials. It is a further object to provide a process for rendering textile materials crease .and shrink resistant without giving a harsh feel and undue stiffness to the material. It is a further object to provide a method for making textile materials more resilient. It is a further object to provide a method for preparing crease and shrink-resistant textile materials that have no chlorine retention. It is a further object to provide a'method where the crease and shrink resistant properties will be resistant to washing. It is a further object to provide a method for treating textile materials which, while imparting wrinkle and shrink resistance to the fabrics, has. little if any detrimental elfect on the other desired properties of the fabric.
2,886,472 Patented May 12, 1959 ICC? It is still a further object to provide textile materials having many improved properties. Other objects and advantages of the invention will be apparent from the following detailed description thereof.
It has now been discovered that these and other objects may beaccomplished by the novel process of the invention which comprises impregnating the textile material with an aqueous medium containing a polyepoxide which has at least one epoxy group in an internal position, i.e., has at least one a group, and certain amounts of an epoxy curing agent and then heating to etfect cure. The fabrics treated in this manner, even with relatively small amounts of the polyepoxide, have excellent resistance to creasing and rubbing and still have a soft feel. The fabrics also have improved resistance to shrinkage and are quite resilient.
It'has further been surprisingly found that the fabrics treated in the above-described manner have no ability to retainchlor'ine and the coated fabrics may be bleached or otherwise exposed to chlorine without danger of being discolored, charred or weakened during subsequent heat treatments. In addition, the fabrics have been found to have improved washability and can be washed numeroustimes without danger of losing any substantial amount of the polyepoxide resin.
The material to be used in the process of the invention includes those having at least one internal epoxy group, i.e., at least one group, and at least one other epoxy group which may be a terminal epoxy group, i.e., may be a Hie-ch orogroup, or an internal epoxy group. These groups may be in an open or closed chain portion of the molecule. The polyepoxide is preferably aliphatic and free of elements other than carbon, hydrogen, oxygen and chlorine.
Examples of these polyepoxides include the epoxysubstituted hydrocarbons, such as, for example, vinyl cyclohexene dioxide, 2,3,5,6-diepoxyoctane, 2,3,6,7-diepoxydodecane, 1,2-epoxy-3-(2,3-epoxypropyl)cyclohexane, 2,2-bis(epoxycyclohexyl)propane, and 1,2-epoxy-4- (3,4-epoxybutyl)cyclohexane.
Another group of these polyepoxides include the ethers of epoxy-substituted cycloalkanol alcohols such as epoxycyclohexanol. Examples of the group include, among others, di(epoxycyclohexyl) ether, di(epoxycyclopentyl)- ether, glycidyl ether. of t2,3-epoxycyclohexanol, epoxybutyl ether of 2,3-epoxycyclohexanol and epoxyhexyl ether of 3,4-epoxycyclohexanol.
Other examplesinclude the epoxidized esters of the polyethylenically unsaturated monocarboxylic acids, such as epoxidized linseed, soyabean, perilla, oiticia, tung, walnut and dehydrated castor oil, methyl linoleate, butyl linoleate, ethyl 9,12-octadecadienoate, butyl 9,12,15-octadecatrienoate, ethyl elaeostearate, octyl 9,12-octadecadienoate, methyl elaeostearate, monoglycerides of tung oil fatty acids,-monoglycerides of soyabean oil, sunflower, rapeseed, hempseed, sardine, cottonseed oil, and the like.
Another group of the epoxy-containing materials used in the process of the invention include the epoxidized. esters of unsaturated monohydric alcohols and polycarboxylic acids, such as, f or example, di(2,3-epoxybutyl) adipate, di(2,3-epoxybutyl) oxalate, di(2,3-epoxyhexyl) succinate, di(3,4-epoxybutyi)' maleate, di(2,3-epoxyoctyl) pimelate, di(2,3-epoxybutyl) phthalate, di(2,3-epoxyoctyl) tetrahydrophthalate, di(4,5-epoxydodecyl) maleate, di(2,3-epoxy-butyl) terephthalate, di(2,3-epoxypentyl) thiodipropionate, di(5-,6'- epoxytetradecyl) diphenyldicarboxylate, di(3,4-epoxyheptyl) sulfonyl-dibutyrate, tri(2,3-epoxybutyl) 1,2,4-butanetricarboxylate, di(5,6 epoxypentadecyl) tartarate, di(4,5 epoxytetradecyl) maleate, di(2,3-epoxybutyl) azelate, di(2,3-epoxybutyl) citrate, di(5,6-epoxyoctyl) cyclohexane-l,3-dicarboxylate, di(4,5-epoxyoctadecyl) malonate.
Another group of the epoxy-containing materials include those epoxidized esters of unsaturated alcohols and unsaturated carboxylic acids, such as 2,3-epoxycyclohexyl epoxypropionate, 2,3-epoxybutyl 3,4-epoxypentanoate, 3,4-epoxyhexyl 3,4-epoxypentanoate, 3,4-epoxycyclohexyl 3,4-cyclohexanoate, 3,4epoxycyclohexy1 4,5- epoxyoctanoate, and the like.
Still another group of the epoxy-containing materials include epoxidized derivatives of polyethylenically unsaturated polycarboxylic acids, such as, for example, dimethyl 8,9,12,13-diepoxyeicosanedioate, dibutyl 7,8,11, lZ-diepoxyoctadecanedioate, dioctyl l0,11-diethyl-8,9,12, l3-diepoxyeicosanedioate, dihexyl 6,7,10,11-diepoxyhexa-- decanedioate, didecyl 9-epoxyethyl-10,ll-epoxyoctadecenedioate, dibutyl 3-butyl-3,4,5,6-diepoxycyclohexane-1, 2-dicarboxylate, dicyclohexyl 3 ,4,5 ,6-diepoxycyclohexane- 1,2-dicarboxylate, dibenzyl 1,2,4,S-diepoxycyclohexane- 1,2-dicarboxylate and diethyl 5,6-10,1l-diepoxyoctadecyl succinate.
Still another group comprises the epoxidized polyesters obtainedby reacting an unsaturated polyhydric alcohol and/or unsaturated polycarboxylic acid or anhydride groups, such as, for example, the polyester obtained by reacting 8,9,12,13-eicosadienedioic acid with ethylene gly col, the polyester obtained by reacting diethylene glycol with 2-cyclohexene-1,4-dicarboxylic acid and the like, and mixtures thereof.
Particularly preferred materials to be used according to the process of the invention comprise the epoxy-substituted hydrocarbons, and ethers of epoxy alcohols and epoxy-substituted cyclohexanols, the epoxidized esters of polyethylenically unsaturated monocarboxylic acids containing not more than 22 carbon atoms, the epoxidized esters of polyethylenically unsaturated polycarboxylic acids containing not more than 25 carbon atoms, and the epoxidized esters of ethylenicaly unsaturated monohydric alcohols and ethylenically unsaturated carboxylic acids containing not more than 22 carbon atoms.
Especially preferred are those materials having one or more internal epoxy groups and one or more terminal epoxy groups, such as vinyl cyclohexene dioxide, glycidyl ether of epoxy cyclohexanol, epoxidized acrylic acid ester of cyclohexanol and glycidyl ester of epoxycyclohexanecarboxylic acid. Many of the above-described epoxy-containing materials are preferably obtained by epoxidizing the corresponding unsaturated compounds. Thus, the compounds, such as dimethyl 8,9,12,l3-diepoxyeicosanedioate may be obtained by epoxidizing dimethyl 8,9,12,l3-eicosadienedioate. The epoxidation may be accomplished by reacting the unsaturated compound with an epoxidizing agent. Organic peracids, such as performic, peracetic, perbenzoic acid and the like are preferred agents for this reaction.
The amount of the epoxidizing agent employed will vary over a considerablerange depending upon the type of product desired. In general, one should employ at least one mole of the oxidizing agent, such as perbenzoic acid, for every ethylenic group to be epoxidized. Thus to produce epoxidized dicrotyl adipate from dicrotyl adipate, one should react the unsaturated ester with at least two moles of perbenzoic acid. In some cases, it is rather difi'icult to effect epoxidation of all of the ethylenic groups and if a completely epoxidized product is required,
additional epoxidizing agent and/or longer reaction period may be required.
The temperature employed during the epoxidation may vary over a considerable range depending upon the type of reactants and epoxidizing agents selected. It is generally desirable to maintain the temperature between -20 C. to 100 C. Preferred temperatures range from about 10 C. to room temperature, e.g., about 20 C. Atmospheric, superatmospheric, or subatmospheric pressures may be employed as desired.
The epoxidized product obtained by this method may be recovered from the reaction mixture by any convenient means known to the art, such as distillation, extraction, fractional precipitation and the like.
The polyepoxides described above are applied to the textile material in the form of an aqueous medium. If the polyepoxides are water-soluble they may be used directly as a water solution. Otherwise, it may be desirable to employ solvents,-emulsifying agents and the like in the aqueous medium in order to obtain the proper concentration of the polyepoxide. Examples of solvents that may be used in the water solutions include, among others, ethyl alcohol, isopropyl alcohol, methanol, and the like. Particularly preferred mediums of this type comprise water-alcohol mixtures having a weight ratio varying from 3 :1 to 1:5. Emulsifying agents employed for this purpose are preferably those that are free of nitrogen and strong acidic groups, such as the monooleate of sorbitan polyoxyethylene, the trioleate of sorbitan polyoxyethylene, sorbitan tristearate, sorbitan monolaurate, polyoxyethylene ethers of alkylphenols, carboxymethylcellulose, starch, gum arabic, aryl and alkylated aryl sulfonates, such as cetyl sulfonate, oleyl sulfonate, sulfonated mineral oils, and the like, and mixtures thereof. The emulsifying agents are generally employed in amounts varying from 0.1% to 10% by weight and more preferably from 1% to 5% by weight.
The amount of the polyepoxide in the impregnating solution may vary over a considerable range depending chiefly on the amount of resin to be deposited on the fabric and this in turn will depend on the number of applications and the pick-up allowed per application. When the solution is applied but once, with a to pick-up by weight of the fabric in the dry state, a concentration ranging from 3% to 25% by weight will ordinarily suffice. If less than 80% pick-up is permitted, the concentration may in some cases go as high as 30% to 50%.
The hardening or curing agents may be added to the polyepoxide solution before it is applied to the fabric or it may be applied by spraying or other suitable methods to the fabric after it has been impregnated with the poly- .epoxide. The curing agents are preferably added to the solution before it is applied to the fabric. Preferred curing agents to be used include the acid and acid-acting curing agents, such as the organic and inorganic acids and anhydrides as citric acid, acetic acid, acetic acid anhydride, butyric acid, caproic acid, phthalic acid, phthalic acid anhydride, tartaric acid, aconitic acid, oxalic acid, succinic acid, succinic acid anhydride, lactic acid, maleic acid, maleic acid anhydride, fumaric acid, glutaconic acid, 1,2,4-butanetricarboxylic acid, isophthalic acid, terephthalic acid, malonic acid, 1,1,5-pentanetricarboxylic acid, acetoacetic acid, naphthalic acid, trimallitic acid, phosphoric acid, boric acid, sulfonic acid, phosphinic acid, perchloric acid, persulfuric acid, p-toluenesulfonic acid, ethanesulfonic acid, and the like compounds having at least one sulfonic group linked to a hydrocarbon radical. The borontrifluoride complexes, such as the p-cresol and urea complex, may also be used as curing agents. Amines may be used but are less preferred.
Particularly preferred curing agents comprise the metal salts and preferably salts of metals having an atomic weight between 24 and 210, and preferably in groups I r to IV'and VIII of the periodic table of ele me'nts and inorganic acids the anion portion of which contains at least two dissimilar elementshaving an atomic weight above 2, and particularly inorganic acids of the formula wherein X is a non-metal having an atomic weight above 2, Z is an element which gains from 1 to 2 electrons in its outer orbit, such as oxygen and fluorine, w is an integer, y is an integer greater than 1 and a equals the valency of the radical (X) (Z),,, such as sulfuric acid, fluoboric acid, fluosilicic acid, persulfuric acid, phosphoric acid and the like. Examples of these preferred agents include, among others, zinc fluoborate, zinc sulfate, magnesium fluoborate, magnesium perchlorate, potassium persulfate, copper fluoborate, copper persulfate, cobaltic fluoborate, chromic nitrate, magnesium nitrate, calcium phosphite, and the like.
Coming under special consideration'as curing agents are the above-described organic polycarboxylic acids, boron-trifluoride complexes and the above-described metal salts.
The above-described curing agents are to be used in sufficient amount to convert the polyepoxide to the desired insoluble infusible state. The epoxy groups in the internal position are less reactive to the curing agents under the conditions of the present process than those in the terminal position so the amount of curing agent used must be greater, such as 1.5 times greater, than that used when the compounds have all terminal epoxy groups as the polyglycidyl ethers. The organic acids are used .in amounts of from 2% to with the polyglycidyl ethers so in the present invention they are preferably used in amounts varying from about 3% to by weight of polyepoxide. The boron-trifluoride complexes are used inamounts from 1.0% to 7.5% with the polyglycidyl ethers so in the present invention they are preferably used in amounts varying from 1.5% to 10% by weight of polyepoxide. The metal salts are employed in amounts varying from 0.5% to 40% with the polyglycidyl ethers so in the present invention they are preferably used in amounts varying from 0.75% to 60% by weight of the polyepoxide.
The solutions employed to treat the textiles may also contain plasticizers to improve their flexibility, though these should not be present in such proportions as to render the finished materials soft or sticky at temperatures and humidities to which they would be exposed. It is found, however, that the substances employed in the present invention yield products which are sufficiently flexible for most purposes without the use of plasticizers.
- Among plasticizers that may be used according to the present invention may be mentioned organic and inorganic derivatives of phenols, for example, diphenylol propane and triphenyl and tricresyl phosphates, alkyl phthalates, for example, diethyl phthalate and glycol phthalates, diethyl tartrate, derivatives of polyhydric alcohols, for example, mono-, diand triacetin, and products obtained by condensing polyhydric alcohols with themselves or with aldehydes or ketones. The compositions may also contain natural resins, e.g., shellac, rosin, and other natural resins and synthetic or semi-synthetic resins, e.g., ester gum, polyhydroxypolybasic alkyd resins, phenolaldehyde and urea-aldehyde resins.
Textile softening agents, and particularly those of the cationic-type as stearamidoethyl diethyl methyl quaternary ammonium methyl sulphate, trimethyl ammon um methyl sulphate of monostearylmetaphenylenedramme, s-di(1,2-palmitamidoethyl) urea monoacetate, palmityl amine hydrochloride, and the like, and mixtures thereof, may also be added in varying amounts to improve the feel of the treated fabrics.
The application of the solution containing the polyepoxide to the textile fabric may be effected in any suitable manner, the method selected depending upon the results desired. If it is desired to apply the solution only to one surface of the material, as, for example, when ;it is desired to treat the back only'of a fabric having-a face of artificial or natural silk and a cotton back, the application may be etfected by spraying or by means of rollers, or the composition may be spread upon the surface by means of a doctor blade. When, however, it is desired to coat both surfaces of the material, or if the material is to be thoroughly impregnated with it, the fabrics may be simply dipped in the solution or run through conventional-type padding rollers. The solutions may also be applied locally to the material, for example, by means of printing rollers or by stencilling.
The amount of the polyepoxides to be deposited on the fabric will vary over a wide range depending upon the degree of wrinkle-resistance and shrink-resistance desired in the finished material. If the fabric is to have a soft feel, such as that intended for use for dresses, shirts, etc., the amount of polyepoxide deposited will generally vary from 3% to'20% by weight of the fabric. If stiffer materials are required such as for shoe fabrics, draperies, etc. still higher amounts of resins, such as of the order of 25% to 50% by weight may be deposited. In determining the amount of resin deposited, it should, of course, be remembered that the presence of the polyepoxides in a few instances causes a slight decrease in tear strength of the fabric and the amount deposited should be balanced between the desired wrinkle resistance and the desired tear strength.
If the desired amount of polyepoxide deposited in the fabric is not obtained in one application, the aqueous medium may be applied again 'or as many times as desired to bring the amount of the polyepoxide resin up to the desired level. p v 7 After the textile material has been impregnated with the aqueous medium containing the polyepoxide, the treated material is then dried for a short period. This is generally accomplished by exposing the wet sheets to hot gas at temperatures ranging from 50 C. to C. The period of drying will depend largely on the amount of pick-up permitted during the application of thesolution, and the concentration of the polyepoxide. In most instances, drying periods of from 5 to 30 minutes should be suflicient.
The dried fabric is then exposed to relatively high temperatures to accelerate the cure of the polyepoxides. Temperatures used for this purpose generally range from C. to 200 C., and more preferably from 100 C. to C. ,At these preferred temperatures, the cure can usually be accomplished in from 3 to 10 minutes. Exposures of less than 3 minutes, e.g., 1 minute, may probably be used in continuous, commercial processing.
The process of the invention may be applied to the treatment of any textile material. Such materials include those prepared from the natural or artificial textile materials, e.g., cotton, linen, silk, rayon (regenerated cellulose), jute, hemp, animal fibers, such as wool, hair, mohair, nylon, Dacron and terylene mixtures thereof. While the invention has been particularly described with relation to the treatment of Woven fabrics, it may also be applied to other materials, for example, knitted or netted materials. 7
The materials treated according to the process of the invention will have excellent crease and shrink resistance as well as good resiliency and flexibility and may be used for a wide variety of important applications. The woven cotton, rayon and wool fabrics, both colored and white, containing conventional amounts of resin, e.g., 25 to 50% may be used in other applications demanding more crispness and fullness such as the preparation of rugs, carpets, plushes, drapes, upholsteries, shoefabrics, and the like.
To illustrate the manner in which the invention may be carried out, the following examples are given. It is to be understood, however, that the examples are for the purpose of illustration and the invention is not to be impregnated cloth was-then dried at 60 Example I This example illustrates the use of vinyl cyclohexene dioxide in the treatment of cotton.
100 parts of vinyl cyclohexene dioxide was added to water to form a 9% solution. 10 parts of anhydrous zinc fluoborate was added to the solution with stirring and the resulting mixture padded on cotton fabric by.
. means of a ButterWorth-B-Roll laboratory padder. The
cloth'after padding showed a 65% wet pick-up. The
C. for minutes'and cured at 160 C.'for 5 minutes. The finished product waswashed and rinsed three times in warm water to remove any soluble material.
. The cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine .reten tion, a soft-feel, good color and excellent washability. The cloth had a crease recovery value of 111. For comparison, cloth treated with aqueous solution of a polyglycidyl ether using 5 parts of curing agent had a crease recovery of 108.
Example II This example illustrates the use of 2,2-bis(2,3-epoxycyclohexyl) propane in the treatment of cotton fabric.
100 parts of 2,2-bis(2,3-epoxycyclohexyl) propane was added to water and then 50 parts of a 10% aqueous solution of 85% hydrolyzed polyvinyl acetate added with stirring. The mixture was then diluted with water to form a 10% solution of the polyepoxide.
10 parts of zinc fluoborate was then added to the solution with stirring and the resulting mixture padded on cotton fabric by means of a Butterworth-3-Roll laboratory padder. The cloth after padding showed a 65% wet pick-up. The impregnated cloth was then dried at 60 C. for 5 minutes and cured at 160 C. for 5 minutes. The finished product was washed and rinsed three times in warm water to remove any soluble material.
The cloth treated in the above-described manner had good crease and shrink resistance, no chlorine retention, a soft feel, good colorand good washability.
Ex'ample III This example illustrates the use of epoxidized tetrahydrobenzyl tetrahydrobenzoate in the treatment of cotton fabric.
100 parts of epoxidized tetrahydrobenzyl tetrahydrobenzoate was added to water and then 50 parts of a 10% aqueous solution of hydrolyzed polyvinyl acetate was added with stirring. The mixture was then diluted with water to form a 12% aqueous solution of the polyepoxide.
10 parts of magnesium perchlorate was added to the solution with stirring and the resulting mixture padded on cotton fabric by means of a Butterworth-3-Roll laboratory padder. The cloth after padding showed a 65% wet pick-up. The impregnated cloth was then dried at 60 C. for 5 minutes and cured at 160 C. for 5 minutes. The finished product was washed and rinsed three times in warm water to remove any soluble material.
The cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine retention, a soft feel, good color and excellent washability.
Related results are obtained by replacing the epoxidized tetrahydrobenzyl tetrahydrobenzoate in the above process with equivalent amounts of each of the following: epoxidized 'cyclohexenyl' tetrahydrobenzoate, epoxidized cyclohexenyl aerylate and epoxidized cyclohexenyl octenoate.
Example IV This example illustrates the use of epoxidized dimethyl 8,9,11,12-eicosadienedioate in the treatment of cotton fabric. One hundred parts of epoxidized dimethyl 8,9,11,12-eicosadienedioate was mixed with water and then 50 parts of a 10% aqueous solution of hydrolyzed polyvinyl acetate was added with stirring. The mixture was then diluted with water to form a 12% aqueous solution of the polyepoxide.
10 parts of zinc fiuoborate was added to the solution with stirring and the resulting mixture padded on cotton fabric by means of a Butterworth-3-Roll laboratory padder. The cloth after padding showed a wet pick-up. The impregnated cloth was then dried at 60 C. for 5 minutes and cured at 160C. for 5 minutes. The finished product was washed and rinsed three times in warm water to remove any soluble material.
The cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine retention, a soft feel, good color and excellent washability.
Example V This example illustrates the use of vinyl cyclohexene dioxide in the treatment of rayon.
100 parts of vinyl cyclohexene dioxide was added to water to form a 9% solution. 10 parts of magnesium perchlorate was then added with stirring and the resulting mixture padded on rayon cloth by means of a Butterworth-3-Roll laboratory padder. The cloth was then dried at 60 C. for 5 minutes and cured at 160 C. for 5 minutes. The finished product was washed and rinsed three times in warm water to remove any soluble material.
The cloth treated in the above-noted manner had good crease and shrink resistance, soft feel, good color, no chlorine retention and improved washability.
Example VI This example illustrates the use of epoxidized dicrotyl phthalate in the treatment of cotton fabric.
100 parts of epoxidized dicrotyl phthalate was mixed with water and then 50 parts of a 10% aqueous solution of hydrolyzed polyvinyl acetate was added with stirring. The mixture was then diluted with water to form a 10% aqueous solution of the polyepoxide.
10 parts of zinc fiuoborate was added to the solution with stirring and the resulting mixture padded on cotton fabric by means of a Butterworth-3-Roll laboratory padder. The cloth after padding showed a 65 wet pick-up. The impregnated cloth was then dried at 60 C. for 5 minutes and cured at 160 C. for 5 minutes. The finished product was washed and rinsed three times in warm water to remove any soluble material.
The cloth treated in the above-described manner had excellent crease and shrink resistance, no chlorine retention, a soft feel, good color and good washability.
Related results are obtained by replacing the epoxidized dicrotyl phthalate in the above process with equivalent amounts of each of the following: epoxidized dicrotyl adipate, epoxidized di(3-pentenyl) terephthalate and epoxidized dicrotyl succinate.
Example VII This example illustrates the use of the glycidyl ether of 2,3-epoxycyclohexanol in the treatment of cotton.
stirring and the resulting mixture padded on cotton fabric by means of a Butterworth-3-Roll laboratory padder. The cloth after padding showed a 65% wet pick-up.
. The impregnated cloth was then dried at 60 C. for 5 minutes and cured at C. The finished product was then washed and rinsed. The cloth treated in this manner had good crease and shrink resistance, no chlorine retention, a soft feel, good color and excellent washability.
We claim as our invention:
1. A process for treating textile materials made up substantially of cellulosic material to make them creaseresistant and shrink resistant without affecting feel and chlorine-retentive properties which comprises impregnating the textile material with an aqueous medium containing a polyepoxide having at least one group, and from 1.5% to by weight of the polyepoxide of a borontrifiuoride complex, and then heating the treated fabric to cure the polyepoxide.
2. A process for treating cellulosic textile materials made up substantially of cellulosic material to make them crease and shrink resistant which comprises impregnating the textile material with an aqueous medium containing a polyepoxide having at least one group, and from 0.75% to 60% by weight of the polyepoxide of a metal salt of a metal having an atomic weight between 24 and 210 and an inorganic acid, and then heating the treated material to cure the polyepoxide.
3. A process as in claim 2 wherein the polyepoxide is vinyl cyclohexene dioxide.
4. A process as in claim 2 wherein the polyepoxide is bis(epoxycyclohexyl)propane.
5. A process as in claim 2 wherein the polyepoxide is epoxidized tetrahydrobenzyl tetrahydrobenzoate.
10 6. A process as in claim 2 wherein the textile material is cotton.
7. A process as in claim 2 wherein the textile material is rayon.
8. A process for treating textile material made up substantially of cellulosic material to make the material crease and shrink resistant which comprises impregnating the textile material with an aqueous medium containing a polyepoxide having at least one 0 -o-o -oogroup, and from 3% to 15% by weight of the polyepoxide of an organic polycarboxylic acid, and then heating the treated material at a temperature between C. and 200 C. for a short period to effect cure of the polyepoxide.
9. A process as in claim 8 wherein the polyepoxide is vinyl cyclohexene dioxide.
10. A process as in claim 8 wherein the polyepoxide is an epoxidized polyethylenically unsaturated carboxylic acid ester.
11. A process as in claim 8 wherein the textile material is cotton.
References Cited in the file of this patent UNITED STATES PATENTS
Claims (1)
1. A PROCESS FOR TREATING TEXTILE MATERIALS MADE UP SUBSTANTIALLY OF CELLULOSIC MATERIAL TO MAKE THEN CREASERESISTANT AND SHRINK RESISTAN WITHOUT AFFECTING FEEL AND CHLORINE-RETENTIVE PROPERTIES WHICH COMPRISES IMPREGNATING THE TEXTILE MATERIAL WITH AN AQUEOUS MEDIUM CONTAINING A POLYEPOXIDE HAVING AT LEAST ONE.
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US580993A US2886472A (en) | 1956-04-27 | 1956-04-27 | Treatment of textile materials |
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US580993A US2886472A (en) | 1956-04-27 | 1956-04-27 | Treatment of textile materials |
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US2886472A true US2886472A (en) | 1959-05-12 |
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Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2975149A (en) * | 1959-03-02 | 1961-03-14 | William S Port | Non-terminal epoxy resins |
US3006936A (en) * | 1956-11-30 | 1961-10-31 | Swift & Co | Polyesters from epoxy-containing oleaginous materials and process of making same |
US3012979A (en) * | 1959-04-22 | 1961-12-12 | Standard Oil Co | Compositions from trimellitic anhydride, epoxys and fatty acids |
US3072607A (en) * | 1958-04-03 | 1963-01-08 | Ciba Ltd | Hardenable compositions comprising epoxide compounds and cyclic ethers or thioethers |
US3074973A (en) * | 1958-09-05 | 1963-01-22 | Union Carbide Corp | 4,5-epoxypentyl 4,5-epoxypentanoate and process for its preparation |
US3119711A (en) * | 1960-04-01 | 1964-01-28 | Swift & Co | Pretreatment of glass fibers with epoxidized compounds having an oxirane content above about 8.5 percent |
US3141027A (en) * | 1959-03-12 | 1964-07-14 | Union Carbide Corp | Alkanediol bis |
US3149085A (en) * | 1958-10-20 | 1964-09-15 | West Virginia Pulp & Paper Co | Method of making synthetic resin from lignin and an epoxide and resulting product |
US3155696A (en) * | 1957-04-10 | 1964-11-03 | Swift & Co | Polyesters from epoxy-containing oleaginous materials |
US3190899A (en) * | 1961-06-08 | 1965-06-22 | Staley Mfg Co A E | Reaction of half esters of an alpha, beta-ethylenically unsaturated-al-pha, beta-dicarboxylic acid with a vicinal epoxy compound and products thereof |
US3274129A (en) * | 1959-06-29 | 1966-09-20 | Union Carbide Corp | Polymerization of epoxides |
US3278554A (en) * | 1961-10-11 | 1966-10-11 | Ciba Ltd | Esters containing more than one oxetane group |
US3293073A (en) * | 1964-02-12 | 1966-12-20 | Union Carbide Corp | Process for imparting wash and wear properties to cellulose-containing textile fabric and resulting product |
US3296157A (en) * | 1961-04-13 | 1967-01-03 | Brojer Zbigniew | Method of manufacturing and separating epoxide resins |
US3318659A (en) * | 1962-11-14 | 1967-05-09 | Joel B Bullock | Process of treating cellulose textiles with polyvinyl chloride polymers, a polysiloxane and zirconium acetate and optionally with flame resistant and rot resistant agents |
US3393171A (en) * | 1964-07-06 | 1968-07-16 | Dynamit Nobel Ag | Method of accelerating the hardening of epoxy compounds |
US3404102A (en) * | 1964-04-09 | 1968-10-01 | Union Carbide Corp | Polycyclic epoxide compositions and presins produced therefrom |
US4049851A (en) * | 1975-03-21 | 1977-09-20 | Basf Aktiengesellschaft | Manufacture of bonded textile sheet materials |
US4130511A (en) * | 1976-05-19 | 1978-12-19 | Ciba-Geigy Corporation | Curable epoxide resin compositions |
US4341669A (en) * | 1978-10-02 | 1982-07-27 | Milliken Research Corporation | Cellulose derivative/polyether polyamine/polyepoxide reaction product as antistatic soil release finish for polyester |
US11134686B2 (en) * | 2013-08-29 | 2021-10-05 | Green Impact Holding Ag | Disinfectant composition for textile and related substrates, and method of treating a substrate to provide disinfecting antibacterial, antiviral and antifungal, wash durable, optionally enhanced with multifunctional properties |
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CA490412A (en) * | 1953-02-10 | Canadian Industries Limited | Preparation of vinylcyclohexene dioxide | |
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US2606810A (en) * | 1949-09-28 | 1952-08-12 | American Cyanamid Co | Treatment of wool-containing textile materials and products thereof |
US2752269A (en) * | 1951-12-01 | 1956-06-26 | Shell Dev | Treatment of textile materials |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3006936A (en) * | 1956-11-30 | 1961-10-31 | Swift & Co | Polyesters from epoxy-containing oleaginous materials and process of making same |
US3155696A (en) * | 1957-04-10 | 1964-11-03 | Swift & Co | Polyesters from epoxy-containing oleaginous materials |
US3072607A (en) * | 1958-04-03 | 1963-01-08 | Ciba Ltd | Hardenable compositions comprising epoxide compounds and cyclic ethers or thioethers |
US3074973A (en) * | 1958-09-05 | 1963-01-22 | Union Carbide Corp | 4,5-epoxypentyl 4,5-epoxypentanoate and process for its preparation |
US3149085A (en) * | 1958-10-20 | 1964-09-15 | West Virginia Pulp & Paper Co | Method of making synthetic resin from lignin and an epoxide and resulting product |
US2975149A (en) * | 1959-03-02 | 1961-03-14 | William S Port | Non-terminal epoxy resins |
US3141027A (en) * | 1959-03-12 | 1964-07-14 | Union Carbide Corp | Alkanediol bis |
US3012979A (en) * | 1959-04-22 | 1961-12-12 | Standard Oil Co | Compositions from trimellitic anhydride, epoxys and fatty acids |
US3274129A (en) * | 1959-06-29 | 1966-09-20 | Union Carbide Corp | Polymerization of epoxides |
US3119711A (en) * | 1960-04-01 | 1964-01-28 | Swift & Co | Pretreatment of glass fibers with epoxidized compounds having an oxirane content above about 8.5 percent |
US3296157A (en) * | 1961-04-13 | 1967-01-03 | Brojer Zbigniew | Method of manufacturing and separating epoxide resins |
US3190899A (en) * | 1961-06-08 | 1965-06-22 | Staley Mfg Co A E | Reaction of half esters of an alpha, beta-ethylenically unsaturated-al-pha, beta-dicarboxylic acid with a vicinal epoxy compound and products thereof |
US3278554A (en) * | 1961-10-11 | 1966-10-11 | Ciba Ltd | Esters containing more than one oxetane group |
US3318659A (en) * | 1962-11-14 | 1967-05-09 | Joel B Bullock | Process of treating cellulose textiles with polyvinyl chloride polymers, a polysiloxane and zirconium acetate and optionally with flame resistant and rot resistant agents |
US3293073A (en) * | 1964-02-12 | 1966-12-20 | Union Carbide Corp | Process for imparting wash and wear properties to cellulose-containing textile fabric and resulting product |
US3404102A (en) * | 1964-04-09 | 1968-10-01 | Union Carbide Corp | Polycyclic epoxide compositions and presins produced therefrom |
US3393171A (en) * | 1964-07-06 | 1968-07-16 | Dynamit Nobel Ag | Method of accelerating the hardening of epoxy compounds |
US4049851A (en) * | 1975-03-21 | 1977-09-20 | Basf Aktiengesellschaft | Manufacture of bonded textile sheet materials |
US4130511A (en) * | 1976-05-19 | 1978-12-19 | Ciba-Geigy Corporation | Curable epoxide resin compositions |
US4341669A (en) * | 1978-10-02 | 1982-07-27 | Milliken Research Corporation | Cellulose derivative/polyether polyamine/polyepoxide reaction product as antistatic soil release finish for polyester |
US11134686B2 (en) * | 2013-08-29 | 2021-10-05 | Green Impact Holding Ag | Disinfectant composition for textile and related substrates, and method of treating a substrate to provide disinfecting antibacterial, antiviral and antifungal, wash durable, optionally enhanced with multifunctional properties |
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