CA1110800A - Process for modifying fibrous products containing cellulosic fibers - Google Patents
Process for modifying fibrous products containing cellulosic fibersInfo
- Publication number
- CA1110800A CA1110800A CA262,292A CA262292A CA1110800A CA 1110800 A CA1110800 A CA 1110800A CA 262292 A CA262292 A CA 262292A CA 1110800 A CA1110800 A CA 1110800A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- formula
- solution
- dispersion
- group
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 88
- 230000008569 process Effects 0.000 title claims abstract description 59
- 239000000835 fiber Substances 0.000 title claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 43
- 239000006185 dispersion Substances 0.000 claims abstract description 41
- 239000003377 acid catalyst Substances 0.000 claims abstract description 30
- 239000002689 soil Substances 0.000 claims abstract description 20
- 238000010521 absorption reaction Methods 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920001577 copolymer Polymers 0.000 claims description 85
- 239000000243 solution Substances 0.000 claims description 48
- -1 methacryloyl group Chemical group 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 150000008624 imidazolidinones Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 7
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- LGJMYGMNWHYGCB-UHFFFAOYSA-N 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one Chemical compound CN1C(O)C(O)N(C)C1=O LGJMYGMNWHYGCB-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- CJPKVVXKFYKNAU-UHFFFAOYSA-N (5-acetyloxy-1,3-dimethyl-2-oxoimidazolidin-4-yl) acetate Chemical compound CN1C(OC(C)=O)C(OC(C)=O)N(C)C1=O CJPKVVXKFYKNAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910001510 metal chloride Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- OHXAAEXAEIJDBZ-UHFFFAOYSA-N 1,3-dimethyl-4,5-di(propan-2-yloxy)imidazolidin-2-one Chemical compound CC(C)OC1C(OC(C)C)N(C)C(=O)N1C OHXAAEXAEIJDBZ-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Chemical class 0.000 claims 1
- 150000002462 imidazolines Chemical class 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006243 acrylic copolymer Polymers 0.000 abstract 1
- 239000004744 fabric Substances 0.000 description 44
- 239000000839 emulsion Substances 0.000 description 41
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 36
- 239000000178 monomer Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- 229960004279 formaldehyde Drugs 0.000 description 12
- 235000019256 formaldehyde Nutrition 0.000 description 12
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000011049 filling Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000005299 abrasion Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000002759 woven fabric Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000002075 main ingredient Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910001629 magnesium chloride Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 230000002500 effect on skin Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 101000847066 Homo sapiens Translin-associated protein X Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 241000047703 Nonion Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 102100032834 Translin-associated protein X Human genes 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010721 machine oil Substances 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
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- ILLKMACMBHTSHP-UHFFFAOYSA-N tetradecaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ILLKMACMBHTSHP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- HAEJKWYMBFWXMQ-UHFFFAOYSA-N 1,3-diethyl-4,5-dihydroxyimidazolidin-2-one Chemical compound CCN1C(O)C(O)N(CC)C1=O HAEJKWYMBFWXMQ-UHFFFAOYSA-N 0.000 description 1
- WWVBRUMYFUDEJQ-UHFFFAOYSA-N 1-ethoxyethane-1,2-diol Chemical compound CCOC(O)CO WWVBRUMYFUDEJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- GKMWWXGSJSEDLF-UHFFFAOYSA-N 1-methoxyethane-1,2-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)CO GKMWWXGSJSEDLF-UHFFFAOYSA-N 0.000 description 1
- OAOWPYJFWWOMNQ-UHFFFAOYSA-N 1-methoxypropane-1,2-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)C(C)O OAOWPYJFWWOMNQ-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- NJDRWMQBLVZQRG-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-propoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCOC(O)COCCO NJDRWMQBLVZQRG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- COORVRSSRBIIFJ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCO COORVRSSRBIIFJ-UHFFFAOYSA-N 0.000 description 1
- WBIOHYFEXBPYSK-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCOCCO WBIOHYFEXBPYSK-UHFFFAOYSA-N 0.000 description 1
- WBSXINVZPSZFFL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-1-methoxyethanol Chemical compound COC(O)COCCOCCOCCOCCOCCOCCOCCOCCO WBSXINVZPSZFFL-UHFFFAOYSA-N 0.000 description 1
- RPTPTINIDBZHSA-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-1-methoxyethanol;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.COC(O)COCCOCCOCCOCCOCCOCCOCCOCCO RPTPTINIDBZHSA-UHFFFAOYSA-N 0.000 description 1
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/273—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Landscapes
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50117164A JPS5255797A (en) | 1975-09-30 | 1975-09-30 | Modifying treatment of cellulosic fiber containing article |
| JP117164/75 | 1975-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1110800A true CA1110800A (en) | 1981-10-13 |
Family
ID=14705025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA262,292A Expired CA1110800A (en) | 1975-09-30 | 1976-09-29 | Process for modifying fibrous products containing cellulosic fibers |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4116625A (d) |
| JP (1) | JPS5255797A (d) |
| BE (1) | BE846667A (d) |
| BR (1) | BR7606515A (d) |
| CA (1) | CA1110800A (d) |
| CH (1) | CH618564B (d) |
| DE (1) | DE2643637C2 (d) |
| DK (1) | DK438176A (d) |
| ES (1) | ES451969A1 (d) |
| FI (1) | FI762778A7 (d) |
| FR (1) | FR2326535A1 (d) |
| GB (1) | GB1553999A (d) |
| LU (1) | LU75902A1 (d) |
| NL (1) | NL7610837A (d) |
| NO (1) | NO763327L (d) |
| SE (1) | SE420222B (d) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2036039B (en) * | 1978-09-11 | 1983-04-13 | Unisearch Ltd | Imparting permanent press characteristics to textiles |
| JPS5584985A (en) * | 1978-12-20 | 1980-06-26 | Tokico Ltd | Display unit |
| JPS55116371U (d) * | 1979-02-08 | 1980-08-16 | ||
| JPS55137184U (d) * | 1979-03-16 | 1980-09-30 | ||
| US4269603A (en) * | 1979-05-04 | 1981-05-26 | Riegel Textile Corporation | Non-formaldehyde durable press textile treatment |
| US4269602A (en) * | 1979-05-07 | 1981-05-26 | Riegel Textile Corporation | Buffered non-formaldehyde durable press textile treatment |
| JPS60397U (ja) * | 1983-06-13 | 1985-01-05 | 九州日立マクセル株式会社 | 不織布 |
| FR2606778B1 (fr) * | 1986-11-14 | 1989-02-10 | Charbonnages Ste Chimique | Procede de reticulation |
| DE3723349C1 (de) * | 1987-07-15 | 1988-08-11 | Goldschmidt Ag Th | Mittel zum Ausruesten von Fasern oder Faserprodukten |
| DE3723355A1 (de) * | 1987-07-15 | 1989-01-26 | Goldschmidt Ag Th | Epoxidgruppen aufweisende copolymerisate, deren herstellung und verwendung zur ausruestung von textilfasern oder faserprodukten |
| DE3723350C1 (en) * | 1987-07-15 | 1988-08-25 | Goldschmidt Ag Th | Composition for conferring hydrophilic properties on fibres or fibrous products |
| JP6225518B2 (ja) * | 2013-07-08 | 2017-11-08 | 日油株式会社 | エポキシ樹脂用反応性高分子乳化剤およびこれを含有する水性樹脂組成物 |
| JP6492968B2 (ja) * | 2015-05-25 | 2019-04-03 | 日本ゼオン株式会社 | 不織布用水性組成物、不織布および自動車天井材 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026216A (en) * | 1959-10-05 | 1962-03-20 | Union Carbide Corp | Treatment of textile fabrics with methylglycidyl ethers |
| US3112156A (en) * | 1960-10-07 | 1963-11-26 | Sidney L Vail | Treatment of cellulosic textile material with 1, 3-dimethyl-4, 5-dihydroxy-2-imidazolidinone |
| US3312677A (en) * | 1963-10-29 | 1967-04-04 | Thiokol Chemical Corp | Interpolymers of lower alkyl acrylate esters, olefin-epoxide monomers and polyene monomers |
| US3525721A (en) * | 1967-11-14 | 1970-08-25 | Goodrich Co B F | Copolymers of alkoxy alkyl acrylates,alkyl acrylates and glycidyl acrylate |
| US3758448A (en) * | 1971-10-05 | 1973-09-11 | Union Optics Corp | Copolymers and hydrogels of unsaturated esters |
| US3899289A (en) * | 1972-11-27 | 1975-08-12 | Us Agriculture | Treatment of cotton with glycidyl methacrylate using ionizing radiation |
| US4045172A (en) * | 1973-05-10 | 1977-08-30 | Gaf Corporation | Textile soil release composition and method |
| US4007305A (en) * | 1974-12-23 | 1977-02-08 | Basf Wyandotte Corporation | Method of imparting nondurable soil release and soil repellency properties to textile materials |
-
1975
- 1975-09-30 JP JP50117164A patent/JPS5255797A/ja active Granted
-
1976
- 1976-09-22 US US05/725,621 patent/US4116625A/en not_active Expired - Lifetime
- 1976-09-28 DE DE2643637A patent/DE2643637C2/de not_active Expired
- 1976-09-28 SE SE7610729A patent/SE420222B/xx unknown
- 1976-09-28 BE BE171009A patent/BE846667A/xx not_active IP Right Cessation
- 1976-09-29 BR BR7606515A patent/BR7606515A/pt unknown
- 1976-09-29 LU LU75902A patent/LU75902A1/xx unknown
- 1976-09-29 FR FR7629320A patent/FR2326535A1/fr active Granted
- 1976-09-29 NO NO763327A patent/NO763327L/no unknown
- 1976-09-29 FI FI762778A patent/FI762778A7/fi not_active Application Discontinuation
- 1976-09-29 ES ES451969A patent/ES451969A1/es not_active Expired
- 1976-09-29 DK DK438176A patent/DK438176A/da unknown
- 1976-09-29 CH CH1233576A patent/CH618564B/xx not_active IP Right Cessation
- 1976-09-29 CA CA262,292A patent/CA1110800A/en not_active Expired
- 1976-09-30 NL NL7610837A patent/NL7610837A/xx not_active Application Discontinuation
- 1976-09-30 GB GB40682/76A patent/GB1553999A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7606515A (pt) | 1977-06-28 |
| GB1553999A (en) | 1979-10-17 |
| LU75902A1 (d) | 1977-05-11 |
| JPS5255797A (en) | 1977-05-07 |
| CH618564GA3 (d) | 1980-08-15 |
| CH618564B (de) | 1900-01-01 |
| SE420222B (sv) | 1981-09-21 |
| FI762778A7 (d) | 1977-03-31 |
| DE2643637A1 (de) | 1977-04-14 |
| DE2643637C2 (de) | 1985-02-28 |
| BE846667A (fr) | 1977-01-17 |
| ES451969A1 (es) | 1977-10-16 |
| SE7610729L (sv) | 1977-03-31 |
| NO763327L (d) | 1977-03-31 |
| FR2326535A1 (fr) | 1977-04-29 |
| NL7610837A (nl) | 1977-04-01 |
| US4116625A (en) | 1978-09-26 |
| JPS5337480B2 (d) | 1978-10-09 |
| DK438176A (da) | 1977-03-31 |
| FR2326535B1 (d) | 1978-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |